Researcher Profile and Settings

Affiliation

• Faculty of Fisheries Sciences　Marine Life Science　Marine Food Science and Technology

Job Title

• Professor

Degree

• March, 1990, M. Agr. (Hokkaido University); December, 1995, Ph.D. (Fisheries Science)（Hokkaido University）

URL

http://bioresutffshu.web.fc2.com/

J-Global ID

• 200901056110568391

Research Interests

• アルギン酸   フコイダン   多糖類   NMR   酵素阻害   ブロモフェノール   リポキシゲナーゼ   フロロタンニン   α-グルコシダーゼ   構造解析   海藻   MS   褐藻   天然物有機化学   食品化学   海洋天然物化学   水産化学   Food Chemistry.   Natural Product Chemistry   Marine Organic Chemistry   

Research Areas

• Life sciences / Bioorganic chemistry
• Life sciences / Food sciences
• Life sciences / Marine/Aquatic life sciences

Educational Organization

•  Bachelor's degree program　School of Fisheries Sciences
•  Master's degree program　Graduate School of Fisheries Sciences
•  Doctoral (PhD) degree program　Graduate School of Fisheries Sciences

Academic & Professional Experience

• 2022/09 - Today Hokkaido University, Faculty of Fisheries Sciences Division of Marine Life Science, Group of Marine Food Science and Technology Professor
• 2013/04 - 2022/08 Faculty of Fisheries Sciences, Hokkaido University Associate Professor
• 2005/04 - 2013/03 Faculty of Fisheries Sciences, Hokkaido University Associate Professor
• 2000/04 - 2005/03 Graduate School of Fisheries Sciences, Hokkaido University Associate Professor
• 2000 - 2005 Associate Professor
• 2005 - Associate Professor
• 1997/04 - 2000/03 Faculty of Fisheries, Hokkaido University Associate Professor
• 1997 - 2000 Associate Professor
• 1995/04 - 1997/03 Faculty of Fisheries, Hokkaido University Research Associate
• 1995 - 1997 Research Associate
• 1991/04 - 1995/03 Faculty of Fisheries, Hokkaido University Research Associate
• 1990/04 - 1991/03 Mitsubishi Kasei Corporation Researcher
• 1990 - 1991 Technical Staff,Mitsubishi Kasei Corporation

Education

• 1988/04 - 1990/03  Hokkaido University
•        - 1990  Hokkaido University  Graduate School, Division of Agriculture
• 1984/04 - 1988/03  Hokkaido University  Faculty of Agriculture
•        - 1988  Hokkaido University  Faculty of Agriculture

Association Memberships

• JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY   北海道海洋生物科学研究会   日本水産学会   日本農芸化学会   and Agrochemistry; Japanese Society of Nutrition and Food Science.   Biotechnology   The Japanese Society of Fisheries Science; Japan Society for Bioscience   

Research Activities

Published Papers

• Acid extraction enzymatic method to measure laminaran in edible brown algae.

  Momochika Kumagai, Keigo Ogasawara, Masahiro Ide, Hideyuki Kurihara, Sanae Kato

  Fisheries Science 89 (3) 409 - 414 0919-9268 2023/03/25 [Refereed][Not invited]
  
• Classification of Marine Algae–Derived Compounds by the Mechanism Responsible for Decreasing Lipoxygenase-Catalyzed Lipid Hydroperoxides

  Hideyuki Kurihara, Kenta Yachiyama, Chihiro Morimoto

  Natural Product Communications 17 (8) 1 - 6 1934-578X 2022/08 [Refereed][Not invited]
   

  Lipoxygenase (LOX)-mediated lipid hydroperoxides (LHPOs) are converted to physiologically active mediators. Thus, decreasing hydroperoxides is important for diminishing various health-related risks. In this study, decreasing compounds of LOX-catalyzed LHPOs were investigated and classified by mechanism using a modified triple LOX-indamine dye formation (IDF) method. The compounds 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (1) and fucoxanthin (2) were isolated from algae as compounds that can decrease hydroperoxides. Along with previously isolated pheophytin a (3), a chlorophyll-related compound, and purchased nordihydroguaiaretic acid (4), a well-known lipoxygenase inhibitor, all the compounds were examined to determine the mechanisms responsible for decreasing LHPOs by using a modified triple LOX-IDF method. Compounds 1 and 4 were found to be LOX inhibitors, compound 2 was a decomposer of the produced LHPOs, and compound 3 was both an inhibitor and a decomposer of the produced LHPOs.
• Kinetic study of mushroom tyrosinase inhibition using naturally occurring bromophenols and comparison with related phenolic compounds

  MD. Reazul Islam, Hideyuki Kurihara

  Journal of Pharmacognosy and Phytochemistry 10 (6) 61 - 65 2278-4136 2021/11/01 [Refereed][Not invited]
  
• Phlorotannins Derived From the Brown Alga Colpomenia bullosa as Tyrosinase Inhibitors

  Hideyuki Kurihara, Kazuki Kujira

  Natural Product Communications 16 (7) 1 - 5 1934-578X 2021/07 [Refereed][Not invited]
   

  Tyrosinase catalyzes hydroxylation of L-tyrosine and dehydrogenation of L-DOPA in the melanin biosynthesis pathway. Tyrosinase inhibitors have potential use as cosmetic whitening agents and for preventing seafood deterioration. In this report, tyrosinase inhibitors extracted from brown alga Colpomenia bullosa (Scytosiphonaceae, Scytosiphonales) were investigated. Inhibitory principles were isolated from the extract and identified as phlorotannins, phloroglucinol (1), diphlorethol (2), triphlorethol C (3), which have not been isolated in a free form previously, and fucophlorethol C (4). Compounds 3 and 4 have not been reported previously as tyrosinase inhibitors. Triphlorethol C (3) was the most potent tyrosinase inhibitor among the phlorotannins isolated, whereas isomeric fucophlorethol C (4) displayed the weakest inhibitory activity. The results suggest that molecular structures of phlorotannins strongly affect their tyrosinase inhibitory activity.
• Evaluation of non-volatile key taste compounds of air-dried herring (Clupea pallasii) fillet.

  A. K. M. Azad Shah, Masashi Ogasawara, Makoto Egi, Hideyuki Kurihara, Koretaro Takahashi

  Journal of Microbiology, Biotechnology and Food Sciences 10 (6) e2970  2021/06 [Refereed][Not invited]
  
• Lipid Composition of Liposomal Membrane Largely Affects Its Transport and Uptake through Small Intestinal Epithelial Cell Models

  Keisuke Konishi, Lei Du, Grégory Francius, Michel Linder, Tomoaki Sugawara, Hideyuki Kurihara, Koretaro Takahashi

  Lipids 55 (6) 671 - 682 0024-4201 2020/11 [Refereed][Not invited]
  
• Health beneficial food emulsifier produced from fishery byproducts

  Toshihiro Nagao, Shu Takahashi, Hideyuki Kurihara, Koretaro Takahashi

  Journal of Oleo Science 69 (10) 1231 - 1240 1345-8957 2020/10 [Refereed][Not invited]
  
• Preparation of phosphatidyl-panthenol by phospholipase D-mediated transphosphatidylation and its anti-inflammatory activity on macrophage-like RAW264.7 cells

  Yukihiro Yamamoto, Kounosuke Suzuri, Tasuku Kunii, Hideyuki Kurihara, Kazuo Miyashita, Masashi Hosokawa

  Biocatalysis and Agricultural Biotechnology 26 101629 - 101629 1878-8181 2020/07 [Refereed][Not invited]
   

  Panthenol is known to be pro-vitamin B-5 and show several functions such as wound-healing, anti-oxidative, and anti-inflammatory activities. In this study, panthenol was phosphatidylated via phospholipase D (PLD)-mediated transphosphatidylation and its anti-inflammatory effects were investigated on macrophage-like RAW264.7 cells. By PLD-mediated transphosphatidylation from phosphatidylcholine (PC), hydroxy group of p1 position in panthenol molecule was alternatively formed phosphate ester bond even though panthenol has three of hydroxy groups in the molecule. The yield was 96 mol% under optimum reaction conditions: 50 umol of PC, 1.6 U of PLD, 500 umol of panthenol, 1.6 mL/1.6 mL of ethyl acetate/0.2 M acetate buffer (pH 5.6) ratio, 10 mM of CaCl2 in the buffer, 37 degrees C for 24 h. Phosphatidyl-panthenol (P-panthenol) suppressed mRNA expression level of pro-inflammatory mediators such as IL-6, IL-1 beta, TNF-alpha and COX-2 more than precursor compounds, PC and panthenol, in activated RAW264.7 cells. P-panthenol also suppressed protein secretion levels of IL-6 and IL-1 beta in the culture medium of RAW264.7 cells. These results demonstrate that P-panthenol, which is easily synthesized in high yield, is potential compound for novel anti-inflammatory phospholipid.
• Isogloiosiphone B, a novel acetal, and hydrophobic compounds as β-glucuronidase inhibitors derived from the red alga Neodilsea yendoana

  Duo Zhang, Hideyuki Kurihara

  Bioscience, Biotechnology and Biochemistry 82 (1) 46 - 48 1347-6947 2018 [Refereed][Not invited]
   

  A novel acetal named isogloiosiphone B was isolated from the red alga Neodilsea yendoana, along with three known hydrophobic compounds as β-glucuronidase inhibitors. The acetal was determined as a naturally occurring compound from the extraction experiments with several kinds of solvent. The acetal showed the highest inhibition against β-glucuronidase among the compounds examined.
• Two new algal bromophenols from Odonthalia corymbifera

  Md. Reazul Islam, Daisuke Mikami, Hideyuki Kurihara

  TETRAHEDRON LETTERS 58 (43) 4119 - 4121 0040-4039 2017/10 [Refereed][Not invited]
   

  Two new algal bromophenols, odonthalol and odonthadione, were isolated from the alga Odonthalia corymbifera. Odonthalol was determined as a trimer of brominated hydroxylated benzyl (BHB) units. Three units were connected via ether and methylene bridges. Odonthadione was identified as a hybrid compound of the BHB unit and a unique cyclopentenedione. The cyclopentenedione unit has not been reported from natural origin. (C) 2017 Elsevier Ltd. All rights reserved.
• Production of a Health-Beneficial Food Emulsifier by Enzymatic Partial Hydrolysis of Phospholipids Obtained from the Head of Autumn Chum Salmon

  A. K. M. Azad Shah, Toshihiro Nagao, Hideyuki Kurihara, Koretaro Takahashi

  JOURNAL OF OLEO SCIENCE 66 (2) 147 - 155 1345-8957 2017/02 [Refereed][Not invited]
   

  Phospholipids and their partial hydrolysates, namely lysophospholipids (LPLs), have been widely used in food, pharmaceutical, and cosmetic products as highly efficient emulsifiers. This study was conducted to produce docosahexaenoic acid (DHA)-esterified LPLs by enzymatic modification of phospholipids obtained from the head of autumn chum salmon (Oncorhynchus keta). The emulsifying properties of the obtained LPLs were also evaluated. Two different types of substrates of salmon head phospholipids were prepared via silica gel and cold acetone precipitation. Enzymatic partial hydrolysis was carried out using immobilized phospholipase Al (PLA(1)) and Lipozyme RM IM. Results showed that the increase in DHA in the LPLs was much higher in the silica-separated phospholipids than in the acetone precipitated phospholipids. When silica-separated phospholipids were used as the substrate, the DHA content of the LPLs increased from 23.1% to 40.6% and 42.6% after 8 h of partial hydrolysis with Lipozyme RM IM and immobilized PLA respectively. The yield of the LPLs was comparatively higher in the Lipozyme RM IM than in the immobilized PLA, hydrolysis reaction. The critical micelle concentration values of the LPLs and purified lysophosphatidylcholine (LPC) were 100 mg/L and 5 mg/L, respectively. The surface tension values of the LPLs and LPC were reduced to 30.0 mN/m and 30.5 mN/m, respectively. The hydrophilic-lipophilic balance of the LPLs and LPC were 6.0 and 9.4, respectively. Based on the emulsifying properties observed, we conclude that LPLs derived from the phospholipids of salmon head lipids could be used as a health-beneficial emulsifier in the food industry.
• Tyrosinase inhibitory and antioxidant activity by bromophenols from the alga Odonthalia corymbifera.

  Md. Reazul Islam, Daisuke Mikami, Hideyuki Kurihara

  Natural Products: an Indian Journal 13 (2) 110 - 110 0974-7508 2017 [Refereed][Not invited]
   

  In the course of our search for tyrosinase inhibitors and antioxidants, six known bromophenol dimers were purified from methanol extract of the red alga Odonthalia corymbifera. The compounds were identified by comparison with published spectroscopic data. These bromophenols were categorized into symmetric and asymmetric dimers. Among them, the tetrabrominated dimers displayed more potent tyrosinase inhibition than the tribrominated ones. Especially, the asymmetric tetrabrominated compound showed strong inhibition. These results suggest that number of bromine substitution and orientation of bromine and phenolic hydroxy groups are important factors of tyrosinase inhibitory potency. The bromophenols were also investigated for antioxidant activities by using DPPH and ABTS radical scavenging, CUPRAC and FRAP metal reducing and copper chelation assays. All dimers showed comparable antioxidant activities to the positive controls examined. Symmetric dimers displayed relatively higher antioxidant activities than asymmetric ones.
• Transport and uptake effects of marine complex lipid liposomes in small intestinal epithelial cell models

  Lei Du, Yu-Hong Yang, Jie Xu, Yu-Ming Wang, Chang-Hu Xue, Hideyuki Kurihara, Koretaro Takahashi

  FOOD & FUNCTION 7 (4) 1904 - 1914 2042-6496 2016 [Refereed][Not invited]
   

  Nowadays, marine complex lipids, including starfish phospholipids (SFP) and cerebrosides (SFC) separated from Asterias amurensis as well as sea cucumber phospholipids (SCP) and cerebrosides (SCC) isolated from Cucumaria frondosa, have received much attention because of their potent biological activities. However, little information is known on the transport and uptake of these lipids in liposome forms in small intestinal cells. Therefore, this study was undertaken to investigate the effects of these complex lipid liposomes on transport and uptake in Caco-2 and M cell monolayer models. The results revealed that SFP and SCP contained 42% and 47.9% eicosapentaenoic acid (EPA), respectively. The average particle sizes of liposomes prepared in this study were from 169 to 189 nm. We found that the transport of the liposomes across the M cell monolayer model was much higher than the Caco-2 cell monolayer model. The liposomes consisting of SFP or SCP showed significantly higher transport and uptake than soy phospholipid (soy-PL) liposomes in both Caco-2 and M cell monolayer models. Our results also exhibited that treatment with 1 mM liposomes composed of SFP or SCP for 3 h tended to increase the EPA content in phospholipid fractions of both differentiated Caco-2 and M cells. Moreover, it was also found that the hybrid liposomes consisting of SFP/SFC/cholesterol (Chol) revealed higher transport and uptake across the M cell monolayer in comparison with other liposomes. Furthermore, treatment with SFP/SFC/Chol liposomes could notably decrease the trans-epithelial electrical resistance (TEER) values of Caco-2 and M cell monolayers. The present data also showed that the cell viability of differentiated Caco-2 and M cells was not affected after the treatment with marine complex lipids or soy-PL liposomes. Based on the data in this study, it was suggested that marine complex lipid liposomes exhibit prominent transport and uptake in small intestinal epithelial cell models.
• Inhibition of algal bromophenols and their related phenols against glucose 6-phosphate dehydrogenase

  Daisuke Mikami, Hideyuki Kurihara, Momoka Ono, Sang Moo Kim, Koretaro Takahashi

  FITOTERAPIA 108 20 - 25 0367-326X 2016/01 [Refereed][Not invited]
   

  A novel bromophenol, n-butyl 2,3-dibromo-4,5-dihydroxybenzyl ether, and known bromophenols were isolated from Rhodomelaceae algae as glucose 6-phosphate dehydrogenase (G6PD) inhibitors. Among them, bromophenol dimers showed stronger inhibitory activity against Leuconostoc mesenteroides and Saccharomyces cerevisiae G6PDs than the corresponding monomers. The dibenzyl ether-type dimers had lower IC50 values than the diarylmethane-type dimers against L. mesenteroides G6PD among the bromophenols examined. In contrast, the inhibitory activities of diarylmethane-type dimers against S. cerevisiae G6PD were stronger than those of dibenzyl ether-type dimers. Especially, 3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyI)-4,5-dihydroxybenzyl methyl ether selectively inhibited S. cerevisiae G6PD compared to L mesenteroides G6PD. (C) 2015 Elsevier B.V. All rights reserved.
• Antitumour activity of EPA-enriched phospholipids liposomes against S180 ascitic tumour-bearing mice

  Lei Du, Yu-Hong Yang, Yu-Ming Wang, Chang-Hu Xue, Hideyuki Kurihara, Koretaro Takahashi

  JOURNAL OF FUNCTIONAL FOODS 19 970 - 982 1756-4646 2015/12 [Refereed][Not invited]
   

  The health benefits of eicosapentaenoic acid (EPA)-enriched phospholipids (PL) have witnessed a recent upsurge. In the present study, PL from starfish Asterias amurensis (SFP) and sea cucumber Cucumaria frondosa (SCP) were extracted and the liposomes were prepared. Both SFP and SCP liposomes showed antitumour effects in vitro and exhibited high transport and uptake effects in small intestinal epithelial cell models. The results also demonstrated that dietary SFP and SCP liposomes prolonged the life span and ameliorated oxidative stress status of S180 ascitic tumour-bearing mice. Results also showed that dietary SFP and SCP liposomes up-regulated the expression of Bax and down-regulated Bcl-2 level in tumour cells, then induced release of cytochrome c from mitochondria to cytosol, thus the activation of caspase 9 and caspase 3. Taken together, these findings suggest that SFP and SCP liposomes exert antitumour effects mainly via activation of mitochondrial apoptotic pathways in tumour-bearing mice. (C) 2015 Elsevier Ltd. All rights reserved.
• Fucophlorethol C, a phlorotannin as a lipoxygenase inhibitor

  Hideyuki Kurihara, Remi Konno, Koretaro Takahashi

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 79 (12) 1954 - 1956 0916-8451 2015/12 [Refereed][Not invited]
   

  Fucophlorethol C, a phlorotannin, was isolated from the brown alga Colpomenia bullosa (Scyto-siphonaceae) as a novel lipoxygenase (LOX) inhibitor. It was obtained as a free form from natural origin for the first time. The compound inhibited a soybean LOX to the same extent as the known inhibitor nordihydroguaiaretic acid.
• EPA-enriched phospholipids ameliorate cancer-associated cachexia mainly via inhibiting lipolysis

  Lei Du, Yu-Hong Yang, Yu-Ming Wang, Chang-Hu Xue, Hideyuki Kurihara, Koretaro Takahashi

  FOOD & FUNCTION 6 (12) 3652 - 3662 2042-6496 2015 [Refereed][Not invited]
   

  Excessive loss of fat mass is considered as a key feature of body weight loss in cancer-associated cachexia (CAC). It affects the efficacy and tolerability of cancer therapy and reduces the quality and length of cancer patients' lives. The aim of the present study was to evaluate the effects of EPA-enriched phospholipids (EPA-PL) derived from starfish Asterias amurensis on cachectic weight loss in mice bearing S180 ascitic tumor, and TNF-alpha-stimulated lipolysis in 3T3-L1 adipocytes and to elucidate the possible mechanisms involved. Our findings revealed that oral administration of EPA-PL at 100 mg per kg body weight (BW) per day for 14 days prevented body weight loss in CAC mice by preserving the white adipose tissue (WAT) mass. We found that serum levels of nonesterified fatty acid (NEFA) and pro-inflammatory cytokines such as tumor necrosis factor a (TNF-alpha) and interleukin (IL)-6 increased in CAC mice but decreased significantly after oral treatment of EPA-PL. In addition, EPA-PL treatment also suppressed the overexpression of several key lipolytic factors and raised the mRNA levels of some adipogenic factors in the WAT of CAC mice. Moreover, treatment of EPA-PL (200 and 400 mu M) markedly inhibited TNF-alpha-stimulated lipolysis in adipocytes. Furthermore, the antilipolytic effects of EPA-PL were stimulated by the extracellular signal-regulated kinase 1/2 (ERK 1/2) inhibitor PD 98059 and blocked via the AMP-activated protein kinase (AMPK) inhibitor compound C and the phosphoinositide-3-kinase (PI3K) inhibitor LY 294002. Taken together, these data suggest that the dietary EPA-PL ameliorates CAC mainly via inhibiting lipolysis and at least in part for recovering the function of adipogenesis.
• Supercritical Fluid Extraction of "Koku" Enhancing Compounds from Fish and Fishery by-Products

  Munehisa Shibata, Kei Onodera, Momochika Kumagai, A. K. M. Azad Shah, Masashi Ogasawara, Hideyuki Kurihara, Tatsufumi Okino, Koretaro Takahashi

  FOOD SCIENCE AND TECHNOLOGY RESEARCH 20 (6) 1199 - 1205 1344-6606 2014/11 [Refereed][Not invited]
   

  The potential of supercritical carbon dioxide (SC-CO2) extraction of "koku" enhancing compounds from dried herring fillet ("Migaki-nishin" in Japanese) and sturgeon liver was explored. "Koku" enhancing compounds from a water-soluble extract and a mixed water miscible SC-CO2 extract were isolated and evaluated for their effects on sensory perception. Results showed that only select compounds were found in the mixed water miscible SCCO, extract compared to the complicated composition of the water-soluble extract. A notable feature was that the mixed water miscible SC-CO2 extract contained "koku" enhancing compounds, e.g., nicotinamide, glycerol and creatine. This study revealed for the first time that these compounds were extracted by SC-CO2 extraction and that nicotinamide enhances "koku". We also extracted "koku" enhancing compounds from sturgeon liver using the SCCO, extraction technique. Instrumental analysis revealed that the sturgeon liver contained relatively large amounts of nicotinamide and glycerol. Thus, it is suggested that this technique might be applicable to the extraction of select compounds from fish and fishery by-products.
• Lipoxygenase inhibitors derived from marine macroalgae

  Hideyuki Kurihara, Yoshio Kagawa, Remi Konno, Sang Moo Kim, Koretaro Takahashi

  BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 24 (5) 1383 - 1385 0960-894X 2014/03 [Refereed][Not invited]
   

  The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z, 9Z, 12Z, 15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z, 9Z, 12Z, 15Z, 18Z)-1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O. corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance. (C) 2014 Elsevier Ltd. All rights reserved.
• Red Algal Bromophenols as Glucose 6-Phosphate Dehydrogenase Inhibitors

  Daisuke Mikami, Hideyuki Kurihara, Sang Moo Kim, Koretaro Takahashi

  MARINE DRUGS 11 (10) 4050 - 4057 1660-3397 2013/10 [Refereed][Not invited]
   

  Five bromophenols isolated from three Rhodomelaceae algae (Laurencia nipponica, Polysiphonia morrowii, Odonthalia corymbifera) showed inhibitory effects against glucose 6-phosphate dehydrogenase (G6PD). Among them, the symmetric bromophenol dimer (5) showed the highest inhibitory activity against G6PD.
• Seasonal variations of lipid content and composition in starfish Asterias amurensis L?tken.

  A. K. M. Azad Shah, Hideyuki Kurihara, Koretaro Takahashi

  Eurasian Chemico-Technological Journal. 15, 45-50 15 (1) 45 - 50 2013 [Refereed][Not invited]
  
• Effects of metal ions on the activity and stability of peroxidase in Tartary buckwheat shoots

  Daisuke Mikami, Hideyuki Kurihara, Koretaro Takahashi, Tatsuro Suzuki, Toshikazu Morishita

  Journal of Agricultural Chemistry and Environment 02 (03) 59 - 64 2325-7458 2013 [Refereed][Not invited]
  
• Effect of drying on creatine/creatinine ratios and subsequent taste of herring (Clupea pallasii) fillet

  A. K.M. Azad Shah, Masashi Ogasawara, Hideyuki Kurihara, Koretaro Takahashi

  Food Science and Technology Research 19 (4) 691 - 696 1344-6606 2013 [Refereed][Not invited]
   

  This study was conducted to investigate the effect of drying time on creatine/creatinine ratios, and subsequently taste of herring fillet. Creatine and creatinine contents were quantified during drying of herring fillet by hydrophilic interaction liquid chromatography (HILIC) and their effect on sensory perception was determined. Results showed that creatine content decreased significantly (p < 0.05), while creatinine content increased during the drying period. Creatinine/creatine ratio of herring fillet increased significantly (p < 0.05) up to the eighth day of drying and plateaued out thereafter. Sensory evaluation revealed that addition of a mixture of creatine and creatinine (at the ratio between 95:5 and 75:25) to the Japanese noodle soup resulted in optimum flavor enhancement of soup characteristics such as thickness, mouthfulness and continuity. These results suggest that for dried herring fillet, optimum creatinine/creatine ratios are reached after 10 days of drying.
• Synthesis of novel phospholipids that bind phenylalkanols and hydroquinone via phospholipase D-catalyzed transphosphatidylation

  Yukihiro Yamamoto, Hideyuki Kurihara, Kazuo Miyashita, Masashi Hosokawa

  NEW BIOTECHNOLOGY 28 (1) 1 - 6 1871-6784 2011/01 [Refereed][Not invited]
   

  Phenylalkanols such as tyrosol and hydroxytyrosol (h-tyrosol), which possess antioxidant and anticancer properties, were phosphatidylated by phospholipase D (PLD)-catalyzed transphosphatidylation. After a 24-hour reaction of phosphatidylcholine (PC) and tyrosol with PLD, a new product was detected by TLC and identified to phosphatidyl-tyrosol by high-resolution MS and NMR analyses. The optimum reaction conditions were as follows: soyPC 50 mu mol, tyrosol 500 mu mol, ethyl acetate 1.6 ml, PLD 1.6 U, 0.2 M sodium acetate buffer (pH 5.6) 0.8 ml, 37 degrees C for 24 hours. Under the optimum reaction conditions, the yields of phosphatidyl-tyrosol, hydroquinone (HQ), 2-(4-aminophenyl) ethanol (4APE), h-tyrosol and 2-phenylethanol (PEA) were 87 +/- 3.7, 13 +/- 1.3, 90 +/- 2.3, 64 +/- 5.5 and 85 +/- 1.0 mol%, respectively. Furthermore, from the results of transphosphatidylation of soyPC with several phenylethanols and phenylpropanols, we established the following details about the reaction specificity of transphosphatidylation by PLD from Streptomyces sp.: (1) para-amino and para-hydroxyl groups in the benzene ring of PEA derivatives do not affect the transphosphatidylation by PLD, whereas meta-hydroxyl group slightly inhibits the transphosphatidylation. (2) Meta- and ortho-methyl groups in the benzene ring of PEA derivatives also slightly inhibit the transphosphatidylation. (3) Secondary and tertiary alcohols and hydroquinone are difficult to transphosphatidylate by PLD.
• Identification and sensory evaluation of flavour enhancers in Japanese traditional dried herring (Clupea pallasii) fillet

  A. K. M. A. Shah, Masashi Ogasawara, Makoto Egi, Hideyuki Kurihara, Koretaro Takahashi

  FOOD CHEMISTRY 122 (1) 249 - 253 0308-8146 2010/09 [Refereed][Not invited]
   

  Flavour-enhancing components of dried herring fillet (migaki-nishin in Japanese) were isolated and evaluated for their effects on sensory perception. Sensory evaluation revealed that addition of dried herring fillet water-soluble extracts to Japanese noodle soup significantly (P<0.05) enhanced soup flavour characters, such as thickness, mouthfulness and continuity. The extracts were fractionated by dialysis and chromatography. Fractions containing flavour enhancers were isolated by sensory perception. Results from instrumental analyses showed that the kokumi flavour enhancers in dried herring fillet were creatine and creatinine. (C) 2010 Elsevier Ltd. All rights reserved.
• alpha-Glucosidase Inhibitory Activity of Bromophenol Purified from the Red Alga Polyopes lancifolia

  Keun Young Kim, The Han Nguyen, Hideyuki Kurihara, Sang Moo Kim

  JOURNAL OF FOOD SCIENCE 75 (5) H145 - H150 0022-1147 2010/06 [Refereed][Not invited]
   

  A bromophenol, bis(2,3-dibromo-4,5-dihydroxybenzyl) ether, was purified from the red alga Polyopes lancifolia. Its IC(50) values were 0.098 and 0.120 mu M against Saccharomyces cerevisiae and Bacillus stearothermophilus alpha-glucosidases, respectively, and 1.00 and 1.20 mM against rat-intestinal sucrase and maltase. This bromophenol competitively inhibited S. cerevisiae alpha-glucosidase with a K(I) value of 0.068 mu M and was very stable at pH 2 for 60 min at 37 degrees C. Therefore, this P. lancifolia bromophenol may have potential as natural nutraceutical for the management of type 2 diabetes.
• Microbiota during fermentation of chum salmon (Oncorhynchus keta) sauce mash inoculated with halotolerant microbial starters: Analyses using the plate count method and PCR-denaturing gradient gel electrophoresis (DGGE)

  Shuji Yoshikawa, Daisuke Yasokawa, Koji Nagashima, Koji Yamazaki, Hideyuki Kurihara, Tomoki Ohta, Yuji Kawai

  FOOD MICROBIOLOGY 27 (4) 509 - 514 0740-0020 2010/06 [Refereed][Not invited]
   

  Nine different combinations of mugi koji (barley steamed and molded with Aspergillus oryzae) and halotolerant microorganisms (HTMs), Zygosaccharomyces rouxii, Candida versa fills, and Tetragenococcus halophilus, were inoculated into chum salmon sauce mash under a non-aseptic condition used in industrial fish sauce production and fermented at 35 +/- 2.5 degrees C for 84 days to elucidate the microbial dynamics (i.e., microbial count and microbiota) during fermentation. The viable count of halotolerant yeast (HTY) in fermented chum salmon sauce (FCSS) mash showed various time courses dependent on the combination of the starter microorganisms. Halotolerant lactic acid bacteria (HTL) were detected morphologically and physiologically only from FCSS mash inoculated with T halophilus alone or with T halophilus and C. versatilis during the first 28 days of fermentation. Only four fungal species, Z. rouxii, C versatilis, Pichia guilliermondii, and A. oryzae, were detected throughout the fermentation by PCR-denaturing gradient gel electrophoresis (PCR-DGGE). In FCSS mash, dominant HTMs, especially eumycetes, were nonexistent. However, under the non-aseptic conditions, undesirable wild yeast such as P. guilliermondii grew fortuitously. Therefore, HTY inoculation into FCSS mash at the beginning of fermentation is effective in preventing the growth of wild yeast and the resultant unfavorable flavor. (C) 2009 Elsevier Ltd. All rights reserved.
• Effect of Halotolerant Starter Microorganisms on Chemical Characteristics of Fermented Chum Salmon (Oncorhynchus keta) Sauce

  Shuji Yoshikawa, Hideyuki Kurihara, Yuji Kawai, Koji Yamazaki, Akira Tanaka, Takafumi Nishikiori, Tomoki Ohta

  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 58 (10) 6410 - 6417 0021-8561 2010/05 [Refereed][Not invited]
   

  Chum salmon sauce mash was inoculated with barley koji (barley steamed and molded with Aspergillus oryzae) and halotolerant microorganisms (HTMs), Zygosaccharomyces rouxii, Candida versatilis, and Tetragenococcus halophilus, in nine different combinations under non-aseptic conditions similar to the industrial fish sauce production and fermented at 35 +/- 2.5 degrees C for 84 days. The changes in the chemical components, color, and sensory properties during fermentation were investigated. Free amino acid content was increased, and the browning of fish sauce was enhanced by the usage of barley koji during fermentation. The halotolerant yeast (HTY) produced ethanol and repressed the browning by consumption of reducing sugar. Inoculated Z. rouxii in the fish sauce mash produced 2-phenylethanol (2-PE) and 4-hydoxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF), and C. versatilis in the fish sauce mash produced 4-ethylguaiacol (4-EG), known as characteristic flavor compounds in soy sauce, adding soy-sauce-like flavor to the fish sauce. Thus, inoculation of HTMs and barley koji was effective for conferring the soy-sauce-like flavor and increasing free amino acid and ethanol contents in fish sauce product.
• Mechanism Involved in the Formation of Characteristic Taste and Flavor during the Production of Dried Herring (Clupea pallasii) Fillet

  A. K. M. Azad Shah, Tomoe Ishihara, Masashi Ogasawara, Hideyuki Kurihara, Naomichi Baba, Koretaro Takahashi

  FOOD SCIENCE AND TECHNOLOGY RESEARCH 16 (3) 201 - 208 1344-6606 2010/05 [Refereed][Not invited]
   

  The objective of this study was to identify the mechanisms responsible for the characteristic taste and flavor of dried herring fillet (DHF, migaki-nishin in Japanese). Dialyzed water-soluble fractions (DWSF) obtained from herring fillet were dried for 4 days, mixed with fatty acids, and the reaction products were evaluated for their effects on sensory perception. To clarify the mechanisms of in situ chemical changes in DHF lipid, ESI-MS analysis was done using a phosphatidylcholine probe. Sensory evaluation revealed that addition of the reaction products of DWSF with docosahexaenoic acid to Japanese noodle soup significantly (P < 0.05) enhanced soup flavor characteristics, such as thickness, mouthfulness, and continuity, compared to the reaction products of DWSF with linoleic acid or capric acid. ESI-MS analyses showed that lyso-derivatives were the most abundant compounds in the lipid fraction of DHF. A small amount of lipid oxidation products and their reaction products were also observed in DHF. This study demonstrated that during the drying period, partial hydrolysis of lipids released free fatty acids. These free fatty acids, or their oxidation products, might react with amino acid-related compounds to generate the characteristic taste and flavor of DHF.
• Changes in Chemical and Sensory Properties of Migaki-Nishin (Dried Herring Fillet) during Drying

  A. K. M. A. Shah, C. Tokunaga, M. Ogasawara, H. Kurihara, K. Takahashi

  JOURNAL OF FOOD SCIENCE 74 (7) S309 - S314 0022-1147 2009/09 [Refereed][Not invited]
   

  Migaki-nishin is a Japanese term that refers to dried herring fillets. It is widely consumed in Japan due to its characteristic flavor enhancing properties. This study was conducted to investigate the changes in chemical and sensory properties of migaki-nishin during drying. Chemical analyses showed that extractive nitrogen and amount of peptides increased significantly (P < 0.05) up to the 8th day of drying and then slightly decreased by the 10th day. Glutamic acid, alanine, glycine, and histidine were the most abundant free amino acids and the largest increase was found in samples dried for 10 d. A decrease in Hunter's L* value (lightness) and increase in b* value (yellowness) as well as browning intensity suggested that nonenzymatic browning occurred in migaki-nishin during drying. Fluorescence spectrophotometric determination also revealed that Maillard reactions progressed throughout the drying period. In addition, available lysine content and free amino groups decreased significantly (P < 0.05) as drying progressed. Sensory evaluation showed that addition of water-soluble extracts to Japanese noodle soup (mentsuyu) linearly enhanced the flavor characteristics such as thickness, mouthfulness, and continuity with the increased length of drying time. These results suggest that during the drying period, proteolysis as well as Maillard reaction products increased markedly, which might contribute to the characteristic taste and flavor of migaki-nishin.
• Changes in lipids and their contribution to the taste of migaki-nishin (dried herring fillet) during drying

  A. K. M. Azad Shah, Chikara Tokunaga, Hideyuki Kurihara, Koretaro Takahashi

  FOOD CHEMISTRY 115 (3) 1011 - 1018 0308-8146 2009/08 [Refereed][Not invited]
   

  This study was conducted to investigate the changes in lipids and their effect on the taste of nigaki-nishin during drying. Lipid was extracted from herring fillets following different drying stages to measure the degree of lipid oxidation and changes in lipid composition, and fatty acid profile. Peroxide value, carbonyl value and acid value of the lipids were significantly increased (P < 0.05) during the drying period. Marked increase in free fatty acids, with decreases in triglyceride and phospholipid content were observed in proportion to drying time and this result suggested that hydrolysis was induced by lipases and phospholipases. The decreases in polyunsaturated fatty acids (PUFAs), especially eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), were observed in the total lipids and phospholipid fraction. In addition, significant increase in PUFAs especially DHA was found in the free fatty acid fraction. Sensory evaluation showed that an addition of DHA to mentsuyu significantly (P < 0.05) enhances the intensities of thickness. mouthfulness and continuity. These results suggest that during drying period lipid oxidation was not only occurred but also lipolysis predominantly released DHA, which might have a contribution to kokumi enhancement of migaki-nishin. (C) 2009 Elsevier Ltd. All rights reserved.
• Potent alpha-glucosidase inhibitors purified from the red alga Grateloupia elliptica

  K. Y. Kim, K. A. Nam, H. Kurihara, S. M. Kim

  PHYTOCHEMISTRY 69 (16) 2820 - 2825 0031-9422 2008/11 [Refereed][Not invited]
   

  Diabetes mellitus is a most serious and chronic disease whose incidence rates are increasing with incidences of obesity and aging of the general population over the world. One therapeutic approach for decreasing postprandial hyperglycemia is to retard absorption of glucose by inhibition of alpha-glucosidase. Two bromophenols, 2,4,6-tribromophenol and 2,4-dibromophenol, were purified from the red alga Grateloupia elliptica. IC(50) values of 2,4,6-tribromophenol and 2,4-dibromophenol were 60.3 and 110.4 mu M against Saccharomyces cerevisiae alpha-glucosidase, and 130.3 and 230.3 mu M against Bacillus stearothermophilus alpha-glucosidase, respectively. In addition, both mildly inhibited rat-intestinal sucrase (IC(50) of 4.2 and 3.6 mM) and rat-intestinal maltase (IC(50) of 5.0 and 4.8 mM). Therefore, bromophenols of G. elliptica have potential as natural nutraceuticals to prevent diabetes mellitus because of their high ot-glucosidase inhibitory activity. (C) 2008 Elsevier Ltd. All rights reserved.
• beta-Glucuronidase Inhibitory Activity of Bromophenols Purified from Grateloupia elliptica

  Keun Young Kim, Kwan Sik Choi, Hideyuki Kurihara, Sang Moo Kim

  FOOD SCIENCE AND BIOTECHNOLOGY 17 (5) 1110 - 1114 1226-7708 2008/10 [Refereed][Not invited]
   

  beta-Glucuronidases of intestinal bacteria are capable of retoxifying compounds that have been detoxified by liver glucuronidation, which is one of the most important detoxication processes in the liver. Therefore, this enzyme is known to accelerate colon cancer invasion and metastasis. Two bromophenols, 2,4,6-tribromophenol (I) and 2.4-dibromophenol (II), were Purified from the red alga Grateloupia elliptica. IC50 values of bromophenol I and II against Escherichia coli beta-glucuronidase were 5.4 and 8.5 mg/mL, respectively. Hence, bromophenols of G. elliptica, a potent beta-glucuronidase inhibitor, can be used as a novel pharmaceutical agent for the prevention and treatment of colon cancer.
• Glycosylceramides Obtain from the Starfish Asterias amurensis Lutken

  A. K. M. Azad Shah, Mikio Kinoshita, Hideyuki Kurihara, Masao Ohnishi, Koretaro Takahashi

  JOURNAL OF OLEO SCIENCE 57 (9) 477 - 484 1345-8957 2008/09 [Refereed][Not invited]
   

  Complex lipids in the starfish Asterias amurensis were characterized and the influence of sphingoid bases on human colon carcinoma Caco-2 cells was also investigated. Lipid content of gonad and viscera were 3.3% and 6.8%, respectively, in wet basis. The main lipid class in gonad was ceramide monohexoside (CMH) while triglyceride (TG) was predominant in the viscera. The most abundant fatty acid in the polar lipid was eicosapentaenoic acid (EPA, C20:5n-3), with the gonad and viscera samples having the highest proportion of 41.5% and 32.7%, respectively, of total fatty acids. Starfish internal organ contained enormous amount (0.7% in wet base) of glycosylceramide. Sphingoid bases of the glycosylceramide were mainly consisted of d22:2, d22:1 and d18:3. This sphingoid base exerted an apoptotic activity on Caco-2 cells. Thus, starfish could be used as a potential source of precious and useful complex lipids.
• Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells

  Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita

  BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 18 (14) 4044 - 4046 0960-894X 2008/07 [Refereed][Not invited]
   

  In order to prepare functional phospholipids in the medical and pharmaceutical fields, perillyl alcohol, myrtenol, and nerol were transphosphatidylated via phospholipase D in an aqueous system. The yields of phosphatidyl-perillyl alcohol, -myrtenol, and -nerol were 79 mol %, 87 mol %, and 91 mol %, respectively. The synthetic phosphatidylated monoterpenes showed a markedly antiproliferative effect on human prostate PC-3 and human leukemia HL-60 cells at 100 mu M, while the free monoterpene alcohols had no effect at 400 mu M. (c) 2008 Elsevier Ltd. All rights reserved.
• Preparation of phosphatidylated terpenes via phospholipase D-mediated transphosphatidylation

  Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Kazuo Miyashita

  JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 85 (4) 313 - 320 0003-021X 2008/04 [Refereed][Not invited]
   

  Terpenes such as geraniol, geranylgeraniol, farnesol, and phytol are known as functional compounds which exhibit anticancer effects and activate nuclear receptors. For the application of functional terpenes in various fields, including the cosmetic and food industries, we attempted to synthesize phosphatidylated terpenes (terpene-PLs) by using phospholipase D (PLD). Transphosphatidylation of phosphatidylcholine with terpenes was carried out using PLD in a biphasic system containing ethyl acetate/water or in an aqueous system without organic solvent. The yield of terpene-PL increased with the reaction time and the amount of PLD in both the biphasic and aqueous systems. Further, the yield of terpene-PL in the aqueous system was higher than that in the biphasic system. In addition, among four PLDs from Streptomyces sp., Streptomyces chromofuscus, cabbage, and peanut, only the PLD from Streptomyces sp. could synthesize terpene-PL. The reaction yield, based on substrate phospholipid, of phosphatidylgeraniol reached 90 mol% under the following optimal reaction conditions: 50 mu mol soyPC; 2,000 mu mol geraniol; 1.6 U PLD; 0.8 ml of 0.2 M sodium acetate buffer (pH 5.6); temperature, 37 degrees C ; and reaction time, 24 h. The reaction yields of phosphatidylfarnesol, phosphatidylgeranylgeraniol, and phosphatidylphytol were 73, 54, and 17 mol%, respectively.
• Characterization of molecular species of collagen in scallop mantle

  Xuan Ri Shen, Hideyuki Kurihara, Koretaro Takahashi

  FOOD CHEMISTRY 102 (4) 1187 - 1191 0308-8146 2007 [Refereed][Not invited]
   

  Pepsin-solubilized collagen (SMPC) extracted from scallop mantle was first subjected to amino acid analysis and molecular weight determination. The SMPC was rich in hydroxylysine. After salting out, the SMPC showed two different profiles in molecules, amino acids and peptide maps. The two different collagen molecules had different uronic acid contents and gel-forming abilities. SMPC may be applicable to a variety of usage, including functional foods. (c) 2006 Elsevier Ltd. All rights reserved.
• beta-Glucosidase inhibitory activities of phenylpropanoid glycosides, vanicoside A and B from Polygonum sachalinense rhizome

  Y. Kawai, H. Kumagai, H. Kurihara, K. Yamazaki, R. Sawano, N. Inoue

  FITOTERAPIA 77 (6) 456 - 459 0367-326X 2006/09 [Refereed][Not invited]
   

  The phenylpropanoid glycosides, vanicoside A and B, isolated from rhizomes of giant knotweed (Polygonum sachalinense) showed p-glucosidase inhibitory activity, with IC50 values of 59.8 and 48.3 mu g/ml (59.9 and 50.5 mu M), respectively. In contrast, p-coumaric acid and ferulic acid, corresponding to phenylpropanoyl moieties of vanicosides, exhibited very little inhibition. (c) 2006 Elsevier B.V. All rights reserved.
• Docosahexaenoic acid and eicosapentaenoic acid-enriched phosphatidylcholine liposomes enhance the permeability, transportation and uptake of phospholipids in Caco-2 cells

  Z Hossain, H Kurihara, M Hosokawa, K Takahashi

  MOLECULAR AND CELLULAR BIOCHEMISTRY 285 (1-2) 155 - 163 0300-8177 2006/04 [Refereed][Not invited]
   

  The influence of docosahexaenoic acid (DHA)- and eicosapentaenoic acid (EPA)-enriched phosphatidylcholine (PC) on the permeability, transport and uptake of phospholipids was evaluated in Caco-2 cells. The cells were grown on permeable polycarbonate transwell filters, thus allowing separate access to the apical and basolateral chambers. The monolayers of the cells were used to measure lucifer yellow permeability and transepithelial electrical resistance (TEER). Transcellular transportation of diphenylhexatriene (DPH) labeled-PC small unilamellar vesicles (SUV) from the apical to basolateral chamber, and uptake of the same SUV was monitored in the cell monolayers. Cell-membrane perturbation was evaluated to measure the release of lactate dehydrogenase and to determine the cell viability with sodium 2-(4-iodophenyl)-3-(4-nitrophenyl) -5-(2, 4-disulfophenyl)-2H-tetrazolium dye reduction assay. The lucifer yellow flux was 1.0 and 1.5 nmol/h/cm(2)with 50 mu M PC, and 17.0 and 23.0 nmol/h/cm(2) with 100 mu M PC when monolayers of Caco-2 cells were treated with DHA- and EPA-enriched PC, respectively. TEER decreased to 24 and 27% with 50 and 100 mu M DHA-enriched PC, and to 25 and 30% with 50 and 100 mu M EPA-enriched PC, respectively. Our results show that DHA- and EPA-enriched PC increases tight junction permeability across the Caco-2 cell monolayer whereas soy PC has no effect on tight junction permeability. Transportation and uptake of DHA- and EPA-enriched PC SUV differed significantly (P < 0.01) from those of soy PC SUV at all doses. We found that PC SUV transported across Caco-2 monolayer and was taken up by Caco-2 cells with very slight injury of the cell membrane up to 100 mu M PC. Lactate dehydrogenase release and cell viability did not differ significantly between the treatment and control, emphasizing that injury was minimal. Our results suggest that DHA- and EPA-enriched PC enhance the permeability, transport and uptake of PC SUV across monolayers of Caco-2 cells.
• Separation of the alpha chains of scallop mantle collagen.

  Xuan Ri Shen, Hideyuki Kurihara, Koretaro Takahashi

  Bulletin of Fisheires Sciences, Hokkaido University 北海道大学 56 (3) 67 - 74 1346-1842 2005/12 [Not refereed][Not invited]
  
• Growth inhibition and induction of differentiation and apoptosis mediated by sodium butyrate in Caco-2 cells with algal glycolipids

  Z Hossain, H Kurihara, M Hosokawa, K Takahashi

  IN VITRO CELLULAR & DEVELOPMENTAL BIOLOGY-ANIMAL 41 (5-6) 154 - 159 1071-2690 2005/05 [Refereed][Not invited]
   

  Glycolipids should have potential effects as antitumor agents. However. very few studies have examined this property of digalactosyl diacylglycerol (DGDG) and sulfoquinovosyl diacylglycerol (SQDG) on colon cancer cells. Cell viability was determined every 24 h with sodium 2-(4-iodophenyl)-3-(4 -nitrophenyl)-5-(2, 4-disulfophenyl)-2H-tetrazolium dye reduction assay up to 72 h. Alkaline phosphalase activity was measured for assessing cell differentiation. Apoptosis was tested with enzyme-linked immunosorbent assay analysis. Growth of Caco-2 cells was inhibited apparently at 48 h after addition of SQDG and at 72 h with DGDG. Alkaline phosphalase activity of Caco-2 cells obviously increased in combination with DGDG or SQDG and sodium butyrate (NaBT) at 72 h, indicating that DGDG and SQDG enhanced cell differentiation induced with NaBT. An increased enrichment factor was found when the cell was treated in combination with DGDG or SQDG and NaBT. These results Strongly suggest that DGDG and SQDG should he considered as the leading compounds of potentially useful colon cancer Chemotherapy agents when NaBT is combined.
• Characterization of pepsin-solubilized collagen from scallop mantle

  XR Shen, S Ono, H Kurihara, K Takahashi

  JOURNAL OF THE JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY-NIPPON SHOKUHIN KAGAKU KOGAKU KAISHI 52 (9) 398 - 405 1341-027X 2005 [Refereed][Not invited]
   

  Pepsin-solubilized collagen was prepared from scallop mantle. The scallop mantle pepsin solubilized collagen (SMPC) was subjected to analyses of amino acid composition, digestive pattern by protease, electron microscopic view of collagen fibers, and moisture absorption to evaluate its characteristics in comparison with bovine skin type I and bovine placental type V collagens. The amino acid composition of SMPC coincided with that of bovine type V collagen. The SDS-PAGE analysis showed that two a-chains were similar in molecular weight to those of bovine placental type V collagen. However, SMPC was more susceptible than bovine placental type V collagen to Staphylococcus aureus V8 protease digestion. The diameter of the SMPC gel fibril was about half of the bovine type I collagen gel fibril. Gel formation ability of the bovine type I collagen was higher than that of SMPC. SMPC showed a higher moisture absorption isotherm under high humidity than bovine skin type I collagen. Electron microscopic view of SMPC showed in part a sponge-like structure.
• Performance of scallop mantle collagen and hydrolysate as hair cere materials.

  Xuan Ri Shen, Yusuke Jin, Kensaku Kawakami, Hideyuki Kurihara, Koretaro Takahashi

  Fragrance Journal フレグランスジャーナル社 33 (8) 86 - 89 0288-9803 2005 [Not refereed][Not invited]
   

  Pepsin solubilized collagen, hot water extracted collagen, and collagen peptite were prepared from scallop mantle. They were subjected to the measurements of moisture sorption ability, denaturation temperature, foaming ability, restoration of hair cuticles, and breaking strength of the individual hair, in contrast to bovine skin collagen,gelatin and peptide, respectively to evaluate the rationality using them as raw materials as hair care goods and cosmetic products.
• Butyrate-Induced Growth Inhibition and Differentiation in Caco-2 Cells with Hybrid Liposomes

  Zakir Hossain, Hideyuki Kurihara, Masashi Hosokawa, Koretaro Takahashi

  Journal of Oleo Science 54 (5) 281 - 288 1347-3352 2005 [Refereed][Not invited]
   

  Hybrid liposomes were prepared by mixing glycerophospholipids with glyceroglycolipids. The effects of hybrid liposomes on Caco-2 cells were investigated. Growth inhibition of cells was determined with sodium 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-(2, 4-disulfophenyl)-2H-tetrazolium dye reduction assay. Alkaline phosphatase activity was measured for assessing the cell differentiation induced by sodium butyrate (NaBT). Growth of Caco-2 cells was inhibited at 48 h after addition of all four types hybrid liposomes (PC/DGDG, PC/SQDG, PS/DGDG and PS/SQDG) while at 72 h growth inhibition was significant for all treatments except the hybrid liposome of phosphatidylcholine and digalactosyldiacylglycerol under concentrations of 50 μM glycerophospholipids with 50 μM glyceroglycolipids. Alkaline phosphatase activity of Caco-2 cells increased significantly when cells were treated in combination of hybrid liposomes and NaBT at 72 h, indicating that hybrid liposomes enhanced cell differentiation induced with NaBT. © 2005, Japan Oil Chemists' Society. All rights reserved.
• Anticancer benefit of Sargassum horneri extract.

  Taichi Matsuda, Jinichi Sasaki, Hideyuki Kurihara, Mutsuo Hatano, Koretaro Takahashi

  Bulletin of Fisheries Sciences, Hokkaido University 北海道大学 56 (3) 75 - 86 1346-1842 2005 [Not refereed][Not invited]
  
• Antimicrobial substances from rhizomes of the giant knotweed Polygonum sachalinense against the fish pathogen Photobacterium damselae subsp piscicida

  H Kumagai, Y Kawai, R Sawano, H Kurihara, K Yamazaki, N Inoue

  ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES 60 (1-2) 39 - 44 0939-5075 2005/01 [Refereed][Not invited]
   

  The antimicrobial compounds against the fish pathogen Photobacterium damselae subsp. piscicida were isolated from Polygonum sachalinense rhizomes. The structures of the antimicrobial compounds I and 2 were determined by H-1 and C-13 NMR, 2D-NMR (COSY, HSQC, HMBC and ROESY) and FAB-MS to be phenylpropanoid glycosides, vanicoside A and B, respectively. Both compounds have feruloyl and p-coumaroyl groups bonded to a sucrose moiety in their structures. Vanicoside A also has an acetyl group in the sucrose moiety. The MIC values for vanicoside A and B against Ph. damselae subsp. piscicida DPp-1 were 32 and 64 mu g/ml, respectively. The antimicrobial activities of these vanicosides were modest, in contrast to higher activities (MICs at < 4 mu g/ml) of antibiotics, florphenicol, ampicillin and amoxicillin, which have been generally used for treating pasteurellosis. The activities of the vanicosides, however, were higher than those (MICs at 256 mu g/ml) of ferulic acid and p-coumaric acid. It was suggested that the structure of phenylpropanoids esterified with sucrose was essential for higher antimicrobial activity of vanicosides and also acetylation of sucrose might affect the activity against the bacterium.
• Authority and Responsibility of Teaching Assistants in Laboratry Work, Field Practice and Computational Training in the Faculty of Fisheries, Hokkaido University : From the Joint Workshop of the Faculty Staff and Teaching Assistants

  KURIHARA Hideyuki, INOUE Norio

  Journal of higher education and lifelong learning 北海道大学 12 11 - 22 1341-9374 2004/03
• Biochemical Composition and Lipid Compositional Properties of the Brown Alga Sargassum horneri.

  Zakir Hossain, Hideyuki Kurihara, Koretaro Takahashi

  Pakistan Journal of Biological Sciences Asian Network for Scientific Information 6 (17) 1497 - 1500 1028-8880 2003 [Refereed][Not invited]
   

  Biochemical composition of brown alga Sargassum horneri was investigated by determination of moisture, protein, carbohydrate, ash, simple lipids and glycolipids. Fatty acid composition of simple lipids and glycolipids was determined by gas chromatography. The algal specimens were collected in two different months, January (sample-1) and February (sample-2). Moisture contents were 86.94 and 87.00% in sample-1 and sample-2, respectively. Protein, carbohydrate and ash contents were 22.94, 19.93 and 32.00% of the dry sample-1, respectively, while the contents of the dry sample-2 were 21.96, 20.81 and 33.58%, respectively. Glycolipids were 1.38 and 1.96% of the dry sample-1 and sample-2, respectively, whereas 2.45 and 2.75% when the samples were digested with the abalone Haliotis discus enzyme. Of the glycolipids obtained, MGDG, DGDG and SQDG were nearly 15, 15 and 68%, respectively. The major fatty acids in simple lipids were 16:0, 18:1 and 22:0. The major fatty acids in individual lipid class were 16:0, 18:1, 20:1, 20:4 and 20:5 in MGDG, 16:0, 20:0, 20:4 and 20:5 in DGDG and 16:0, 18:0, 18:1, 18:2 and 20:4 in SQDG. S. horneri is a potential source of valuable glycolipids.
• Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga

  H Harada, U Yamashita, H Kurihara, E Fukushi, J Kawabata, Y Kamei

  ANTICANCER RESEARCH 22 (5) 2587 - 2590 0250-7005 2002/09 [Refereed][Not invited]
   

  In a previous report, we discussed an extract from a marine red alga, Amphiroa zonata, which shows selective cytotoxic activity to human leukemic cells, but no cytotoxicity to normal human dermal fibroblast (HDF) cells in vitro. In this study, we identified palmitic acid, a selective cytotoxic substance from the marine algal extract, and investigated its biological activities. At concentrations ranging from 12.5 to 50 mug/ml, palmitic acid shows selective cytotoxicity to human leukemic cells, but no cytotoxicity to normal HDF cells. Furthermore, palmitic acid induces apoptosis in the human leukemic cell line MOLT-4 at 50 mug/ml. Palmitic acid also shows in vivo antitumor activity in mice. One molecular target of palmitic acid in tumor cells is DNA topoisomerase I, however, interestingly, it does not affect DNA topoisomerase II, suggesting that palmitic acid may be a lead compound of anticancer drugs.
• alpha-glucosidase inhibitory activity of a 70% methanol extract from ezoishige (Pelvetia babingtonii de Toni) and its effect on the elevation of blood glucose level in rats

  T Ohta, S Sasaki, T Oohori, S Yoshikawa, H Kurihara

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 66 (7) 1552 - 1554 0916-8451 2002/07 [Refereed][Not invited]
   

  The 70% methanol extract from ezoishige (Pelvetia babingtonii de Toni) inhibited the rat-intestinal alpha-glucosidase, sucrase and maltase activities, with IC50 values of 2.24 and 2.84 mg/ml. Sucrose was orally administered with or without the extract to rats at 1000 mg/kg. The postprandial elevation in the blood glucose level at 15 and 30 min after the administration of sucrose with the extract was significantly suppressed when compared with the control. These results suggest that the extract from ezoishige has potent a-glucosidase inhibitors and would be effective for suppressing postprandial hyperglycemia.
• Enzyme inhibitors obtained from macroalgae

  Hideyuki Kurihara

  Fisheries Science 68 (Suppl. II) 1589 - 1592 1444-2906 2002 [Not refereed][Not invited]
   

  Inhibitors obtained from macroalgae against α-glucosidase and urease were investigated. Alpha-glucosidase inhibitors obtained from the red algae of Rhodomelaceae family were identified as bromophenols. Symmetric bisbenzyl ethers strongly inhibited Saccharomyces cerevisiae α-glucosidase, compared with the others. Inhibitors against α-glucosidase and urease were obtained from the brown algae Pelvetia babingtonii (Fucaceae) and Alaria crassifolia (Alariaceae). The inhibitors were identified as phlorotannins. P. babingtonii phlorotannin decreased blood glucose levels in sucrose-loaded rats. © 2002, The Japanese Society of Fisheries Science. All rights reserved.
• Inhibition of beta-glucuronidase by extracts of Chondria crassicaulis.

  Chisato Sekikawa, Hideyuki Kurihara, Keiichiro Goto, Koretaro Takahashi

  Bulletin of Fisheries Sciences, Hokkaido University 北海道大学 53 (1) 27 - 30 1346-1842 2002 [Not refereed][Not invited]
  
• Inhibition of beta-glucuronidase by purine nucleotides

  H Tohda, H Kurihara, M Hosokawa, K Takahashi

  FISHERIES SCIENCE 65 (4) 667 - 668 0919-9268 1999/08 [Refereed][Not invited]
  
• Two new bromophenols from the red alga Odonthalia corymbifera

  H Kurihara, T Mitani, J Kawabata, K Takahashi

  JOURNAL OF NATURAL PRODUCTS 62 (6) 882 - 884 0163-3864 1999/06 [Refereed][Not invited]
   

  Two novel bromophenols (1 and 2) were isolated fi om an extract of a red alga, Odonthalia corymbifera, together with a known bromophenol (3). The novel bromophenols were determined as 4-bromo-2,3-dihydroxy-6-hydroxymethylphenyl 2,5-dibromo-6-hydroxy-3-hydroxymethylphenyl ether (1) and bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (2), from spectroscopic evidence. Compounds 1-3 were found to be inactivators of or-glucosidase.
• Inhibitory potencies of bromophenols from rhodomelaceae algae against alpha-glucosidase activity

  H Kurihara, T Mitani, J Kawabata, K Takahashi

  FISHERIES SCIENCE 65 (2) 300 - 303 0919-9268 1999/04 [Refereed][Not invited]
   

  Inhibitory potencies against alpha-glucosidase activities were compared among bromophenols obtained from extracts of three Rhodomelaceae red algae, Symphyocladia latiuscula, Odonthalia corymbifera, and Polysiphonia morrowii. The bromophenols from these species are characterized by a number of Pr atoms per benzene ring: S. latiuscula, three Br atoms (1 and 2); O. corymbifera, two Br atoms (3-7); and P. morrowii, one Br atom (8 and 9). The bromophenols exhibited mixed inhibition against yeast alpha-glucosidase reaction. In particular, symmetric dibenzyl ethers, bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether (2) and bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (5), exhibited about 10(3) fold smaller K-i values than the other bromophenols. Their inhibition modes are disclosed to be mixed inhibition closed to competitive inhibition. Inhibitory potencies of the bromophenols increased with the increasing degree of bromo-substitution per benzene ring and the decreasing degree of methyl-substitution. In contrast to the strong inhibitory activity against yeast alpha-glucosidase activity, the bromophenols moderately inhibited rat-intestinal sucrase and maltase activity. The inhibitory potencies were all comparative among the bromophenols examined.
• Antibacterial activity against cariogenic bacteria and inhibition of insoluble glucan production by free fatty acids obtained from dried Gloiopeltis furcata

  H Kurihara, Y Goto, H Aida, M Hosokawa, K Takahashi

  FISHERIES SCIENCE 65 (1) 129 - 132 0919-9268 1999/02 [Refereed][Not invited]
   

  Antibacterial substance for mutans streptococci was obtained from dried Gloiopeltis furcata by chromatographic separation. The substance was determined to be a mixture of free fatty acids (FFAs), from the results of instrumental analyses. The FFAs obtained showed moderate antibacterial activity against mutans streptococci, with minimal inhibitory concentration values between 25 and 50 mu g/ml. These FFAs also inhibited insoluble glucan production catalyzed by glucosyltransferase of Streptococcus sobrinus. Experiments carried out by using commercially available fatty acids indicated that unsaturated fatty acids showed more potent inhibition against insoluble glucan production than saturated fatty acids.
• Apoptosis-Inducing Effect of Fucoxanthin on Human Leukemia Cell Line HL-60

  Masashi Hosokawa, Satoshi Wanezaki, Kozue Miyauchi, Hideyuki Kurihara, Hiroyuki Kohno, Jun Kawabata, Shizuo Odashima, Koretaro Takahashi

  Food Science and Technology Research 5 (3) 243 - 246 1344-6606 1999 [Refereed][Not invited]
   

  The apoptosis-inducing effect of fucoxanthin on human leukemic HL-60 cells was investigated. Fucoxanthin, which was obtained from the brown alga Undaria pinnatifida, inhibited the proliferation of HL-60 cells and induced DNA fragmentation on agarose gel electrophoresis, a typical characteristic feature of apoptotic cells. The results of sandwich ELISA using anti-biotin-antibody and anti-DNA-antibody also demonstrated DNA fragmentation in accordance with the increase in fucoxanthin concentration and incubation time. Since the level of DNA fragmentation did not increase after 24 h incubation, fucoxanthin appeared to have some effect on cell cycle. In contrast, β-carotene did not show an apoptosis-inducing effect on HL-60 cells. These results suggested that a carotenoid structure might be crucial for inducing apoptosis.
• Screening of seafood for inhibition of glucosidases

  H Kurihara, T Saiki, M Hatano

  NIPPON SUISAN GAKKAISHI 63 (4) 634 - 635 0021-5392 1997/07 [Refereed][Not invited]
  
• Inhibitory effect on the alpha-glucosidase reaction by the aggregated state of sulfoquinovosyldiacylglycerol

  H Kurihara, T Mitani, J Kawabata, M Hatano

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 61 (3) 536 - 538 0916-8451 1997/03 [Refereed][Not invited]
   

  The inhibitory activity of aggregated SQDG toward the alpha-glucosidase reaction decreased,vith increasing turbidity of the SQDG suspension, Dideacylated derivatives of SQDG, sulfoquino-vosylglycerol and sulfoquinovose, showed no inhibition toward the reaction, The expression of inhibition by the SQDG family would require a hydrophobic acyl group(s) to produce an aggregate and/or interact with a hydrophobic site in the enzyme.
• Isolation and identification of alpha-glucosidase inhibitors from tochu-cha (Eucommia ulmoides)

  J Watanabe, J Kawabata, H Kurihara, R Niki

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 61 (1) 177 - 178 0916-8451 1997/01 [Refereed][Not invited]
   

  alpha-Glucosidase inhibitory activity was found in aqueous methanol extracts of tochu-cha, dried leaves of Eucommia ulmoides (Eutommiaceae). Five active principles against yeast enzyme were isolated and characterized. Among them, quercetin (1, K-i: 8.5 x 10(-6) hi) was considered to contribute mostly to the activity of the tochu leaves. In regard to an animal alpha-glucosidase, rat intestinal sucrase activity was also inhibited by 1.
• Effects of Phospholipids Containing Docosahexaenoic Acid on Differentiation and Growth of HL-60 Human Promyelocytic Leukemia Cells.

  Kaoru Tochizawa, Masashi Hosokawa, Hideyuki Kurihara, Hiroyuki Kohno, Shizuo Odashima, Koretaro Takahashi

  Journal of Japanese Oil Chemists' Society Japan Oil Chemists' Society 46 (4) 383 - 390 1341-8327 1997 [Refereed][Not invited]
   

  Effects of docosahexaenoic acid (DHA) -containing phospholipids (DHA-PLs) on retionic acid (RA) -induced cell differentiation and growth inhibition of the human promyelocytic leukemia cell line, HL-60 were investigated. Cell differentiation judged from NBT reduction assay reached to 5060% by incubation with 12.5μM DHA-containing phosphatidylcholines (DHA-PCs) prior to the addition of RA. Differentiation without DHA-PCs remained at 39.2%. By prior incubation with DHA-containing phosphatidylethanolamines (DHA-PEs), differentiation was 70% at 12.5μM. DHA-PEs induced NBT reducing activity to as much as 2030%, and inhibited cell growth in the absence of RA. Activity for promoting cell differentiation differed according to DHA-PL molecular species. 1-Palmitoyl (or oleoyl)- 2-docosahexaenoyl-sn-glycero-3-phosphocholine (or phosphoethanolamine) was found most effective molecular species for enhancing RA-induced cell differentiation.
• Digalactosyldiacylglycerol suppression of inhibition by sulfoquinovosyldiacylglycerol of alpha-glucosidase

  H Kurihara, S Tada, K Takahashi, M Hatano

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 60 (5) 932 - 933 0916-8451 1996/05 [Refereed][Not invited]
   

  Digalactosyldiacylglycerol (DGDG) suppressed the inhibition by sulfoquinovosyldiacylglycerol (SQDG) of an alpha-glucosidase reaction. Suppressing was considered to be an apparent decrease in inhibitory activity of SQDG ascribed to direct interaction between SQDG and DGDG, This suppression was presumed to be caused by less access of SQDG to the enzyme because SQDG and DGDG formed mixed micelles.
• Inhibition of glycosidase reactions by constituents of the bivalves composing chemosynthetic communities in Sagami Bay, central Japan.

  Hideyuki Kurihara, Hiroyuki Tohda, Mutsuo Hatano, Jun Hashimoto

  VENUS (Japanese Journal of Malacology) 日本貝類学会 55 (4) 299 - 305 0042-3580 1996 [Refereed][Not invited]
   

  In order to obtain useful metabolites from bivalves composing chemosynthetic communities, their constituents were screened for inhibitory activities toward biologically important glycosidase, α-glucosidase, β-glucosidase, and β-glucuronidase, reactions. The bivalves examined included a vesicomyid clam Calyptogena soyoae and a deep-sea mussel Bathymodiolus platifrons collected around cold seeps in Sagami Bay, central Japan. Inhibition assays for glycosidase reactions were performed using an agar plate method. The constituents of C. soyoae showed potent inhibition toward all glycosidase reactions examined, however those of B. platifrons showed no inhibition. These results suggest that C. soyoae would have more potent metabolic activity of organic compounds than B. platifrons and would contain useful chemical compounds.
• Effects of NaCl on oxidaion of fish oil containing defatted-muscles under higher water activity conditions.

  Koretaro Takahashi, Kazuaki Sogo, Hideyuki Kurihara, Kozo Takama

  Nippon Yukagaku Kaishi 日本油化学会 = Japan Oil Chemists' Society 45 (12) 1359 - 1361 1341-8327 1996 [Refereed][Not invited]
   

  Effects of NaCl on fish oil oxidation under higher water activity conditions were investigated using a model system consisting of a mixture of sardine oil and chloroform-methanol-defatted sardine muscles. Oxidation rates were determined based on the induction period of oxidation at 20°C in oxygen absorption analysis. Increase in NaCl concentration or water activity shortened the induction period. NaCl may possibly hinder interactions of metal ions with proteins so that interactions between metal ions and oils become greater. In such a situation, higher water activity may enhance the mobility of metal ions with considerable accelerations of lipid oxidation.
• Inhibition of Sulfoquinovosylmonoacylglycerol against alpha-Glucosidase Reaction.

  Hideyuki Kurihara, Junichi Ando, Jun Kawabata, Mutsuo Hatano

  Journal of Japanese Oil Chemists' Society Japan Oil Chemists' Society 45 (4) 347 - 349 1341-8327 1996 [Refereed][Not invited]
   

  A new α-glucosidase inhibitor was isolated from an edible brown alga Hizikia fusiformis along with the known α-glucosidase inhibitor 6-sulfo-α-D-quinovopyranosyldiacylglycerol (SQDG), and was identified as 6-sulfo-α-D-quinovopyranosylmonoacylglycerol (SQMG). SQMG inhibited α-glucosidase more potently than SQDG.
• 海産生物に含まれる有用生化学資源に関する研究―特に海藻のα-グルコシダーゼ阻害性糖脂質について―

  Hideyuki Kurihara

  Hokkaido University 1995/12 [Not refereed][Not invited]
  
• STEREOCHEMISTRY OF TWO TETRASTILBENES FROM CAREX SPECIES

  J KAWABATA, M MISHIMA, H KURIHARA, J MIZUTANI

  PHYTOCHEMISTRY 40 (5) 1507 - 1510 0031-9422 1995/11 [Refereed][Not invited]
   

  The stereochemistry of two tetrastilbenes, miyabenols A and B, was determined by NOE measurements. Their biogenetic relationship with other oligostilbenes and the absolute configuration are also presented.
• SULFOQUINOVOSYLDIACYLGLYCEROL AS AN ALPHA-GLUCOSIDASE INHIBITOR

  H KURIHARA, J ANDO, M HATANO, J KAWABATA

  BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 5 (12) 1241 - 1244 0960-894X 1995/06 [Refereed][Not invited]
   

  SulfoquinovosyldiacyIglycerol isolated from an edible brown alga Hizikia fusiforme inhibited yeast alpha-glucosidase.
• Cadmium elimination from mid-gut gland of the Japanese scallop and liver of the Japanese common squid.

  栗原秀幸, 谷端信孝, 羽田野六男

  Hideyuki Kurihara, Nobutaka Tanibata, Mutsuo Hatano 北海道大学 45 (4) 120 - 125 0018-3458 1994 [Not refereed][Not invited]
  
• A New Screening Method for Glucosidase Inhibitors and its Application to Algal Extracts

  Hideyuki Kurihara, Masayoshi Sasaki, Mutsuo Hatano

  Fisheries Science 60 (6) 759 - 761 1444-2906 1994 [Refereed][Not invited]
   

  A screening method for α- and jS-D-glucosidase inhibitors was developed by using agar plates. An enzyme agar plate containing either α- or β-D-glucosidase was used in combination with a substrate agar plate containing p-nitrophenyl α- or β-D-glucopyranoside. Paper disks impregnated with algal extracts were placed on the enzyme agar plate, then preincubated for 2.5 h at 25°C. The substrate agar was layered on the enzyme agar. Inhibitory zones appeared colorless in the yellow background of p-nitrophenol. Extracts of algae collected in southern Hokkaido were screened for α- and β-D-glucosidase inhibitors by the proposed agar plate method. Among nine algal species examined, seven species inhibited α-D-glucosidase, whereas five species inhibited β-D-glucosidase. © 1994, The Japanese Society of Fisheries Science. All rights reserved.
• GERANIIN, A HYDROLYZABLE TANNIN FROM NYMPHAEA-TETRAGONA GEORGI (NYMPHAEACEAE)

  H KURIHARA, J KAWABATA, M HATANO

  BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 57 (9) 1570 - 1571 0916-8451 1993/09 [Refereed][Not invited]
   

  Geraniin, an antimicrobial hydrolyzable tannin against fish pathogenic bacteria, was isolated from Nymphaea tetragona (Nymphaeaceae).
• Concentration of cadmium in the livers of several kinds of squids and an approach to its elimination.

  Hideyuki Kurihara, Hatsuyo Togawa, Mutsuo Hatano

  Bulletin of the Faculty of Fisheries, Hokkaido University 北海道大学 44 (1) 32 - 38 0018-3458 1993 [Not refereed][Not invited]
  
• Concentration of cadmium in the mid-gut gland of the scallop, Pactinopecten yessoensis, and an approach to its elimination.

  Hideyuki Kurihara, Shintaro Arai, Mutsuo Hatano

  Bulletin of the Faculty of Fisheries, Hokkaido University 北海道大学 44 (1) 39 - 45 0018-3458 1993 [Not refereed][Not invited]
  
• OLIGOSTILBENES FROM CAREX-KOBOMUGI

  H KURIHARA, J KAWABATA, S ICHIKAWA, M MISHIMA, J MIZUTANI

  PHYTOCHEMISTRY 30 (2) 649 - 653 0031-9422 1991 [Refereed][Not invited]
   

  A novel tetrastilbene, kobophenol A was isolated from subterranean parts of Carex kobomugi together with the previously known miyabenol C and (-)-epsilon-viniferin. The stereochemistry of kobophenol A and miyabenol C was elucidated as (7aR,8aR,7bS,7cS,8cS,7dS,8dR) and (7aR,8aR,7bS,8bS), respectively. The biogenetic relationship of all the above compounds is briefly discussed.
• KOBOPHENOL B, A TETRASTILBENE FROM CAREX-PUMILA

  J KAWABATA, M MISHIMA, H KURIHARA, J MIZUTANI

  PHYTOCHEMISTRY 30 (2) 645 - 647 0031-9422 1991 [Refereed][Not invited]
   

  A novel antimicrobial tetrastilbene, made up of two epsilon-viniferin units, was isolated from the subterranean parts of Carex pumila. Its complex polycyclic structure was elucidated by 1D and 2D NMR analyses.
• (-)-EPSILON-VINIFERIN AND RELATED OLIGOSTILBENES FROM CAREX-PUMILA THUNB (CYPERACEAE)

  H KURIHARA, J KAWABATA, S ICHIKAWA, J MIZUTANI

  AGRICULTURAL AND BIOLOGICAL CHEMISTRY 54 (4) 1097 - 1099 0002-1369 1990/04 [Refereed][Not invited]
  
• コウボウムギ（Carex kobomugi)の抗菌性オリゴスチルベン類の立体構造解析

  Hideyuki Kurihara

  Graduate School of Agriculture, Hokkaido University 1990/03 [Not refereed][Not invited]
  
• 77(P2-7) KOBOPHENOL A, AN ANTIBACTERIAL TETRASTILBENE FROM CAREX KOBOMUGI OHWI (CYPERACEAE)

  Kawabata J., Kurihara H., Ichikawa S., Mizutani J.

  Symposium on the Chemistry of Natural Products, symposium papers 天然有機化合物討論会 (31) 585 - 592 1989/09/17 

  In the course of our search for antibacterial oligostilbenes in Carex spp. (Cyperaceae), a novel tetrastilbene named kobophenol A (5), having a unique 2,3,4,5-tetraaryltetrahydrofuran unit, has been isolated from subterranean parts of C. kobomugi Ohwi. Methanol extracts of fresh roots and rhizoma of C. kobomugi were fractionated by a series of solvent partitions followed by column and thin layer chromatography to afford a major active principle, kobophenol A (5), as a pale yellow oil along with previously known oligostilbenes, miyabenol C (3) and ε-viniferin (4). All isolates showed antibacterial activity against Staphylococcus aureus. Kobophenol A (5) has a molecular formula of C_<56>H_<44>O_<13>, which corresponds to a tetrastilbene. Permethylation of 5 yielded a decamethyl ether (6). The plane structure of 5 was elucidated principally with the aid of 2D-NMR (HH-, CH- and long range CH-COSY) as well as the UV and 1D-NMR results. The EI-MS fragmentation pattern of 6 well supports this structure. The relative stereochemistry of 5 has been assigned from results of 2D PSNOESY and 1D NOE difference spectrum experiments as rel-(7aR,8aR,7bS,8bS,7cS,8cS,7dS,8dR).
• KOBOPHENOL-A, A UNIQUE TETRASTILBENE FROM CAREX-KOBOMUGI OHWI (CYPERACEAE)

  J KAWABATA, S ICHIKAWA, H KURIHARA, J MIZUTANI

  TETRAHEDRON LETTERS 30 (29) 3785 - 3788 0040-4039 1989 [Refereed][Not invited]
  

Conference Activities & Talks

• Decreasing Mechanism of lipoxygenase-mediated peroxides by seaweed constituents.  [Not invited]

  Hideyuki Kurihara, Kenta Yachiyama

  International symposium “Fisheries Science for future generations”  2017/09
• Bromophenols as antioxidants and tyrosinase inhibitors  [Not invited]

  Md. Reazul Islam, Daisuke Mikami, Hideyuki Kurihara

  International symposium “Fisheries Science for future generations”  2017/09
• ホタテガイ副次産物由来油脂（ホタテオイル）の3ヶ月間給餌による安全性及び機能性の確認試験  [Not invited]

  谷崎俊文, 森翔平, 栗原秀幸, 高橋是太郎, 吉岡武也, 細見亮太, 福永健治

  2nd ACOS & 第56回日本油化学会年会  2017/09
• Beta-glucuronidase inhibitors from Neodilsea yendoana  [Not invited]

  ○Duo Zhang, Hideyuki Kurihara

  平成29年度日本水産学会春季大会  2017/03
• Radical scavenging activity and tyrosinase inhibition of bromophenols  [Not invited]

  Md. Reazul Islam, Hideyuki Kurihara

  平成29年度日本水産学会春季大会  2017/03
• 新規ブロモフェノールの構造及び4JCHカップリング観測  [Not invited]

  栗原秀幸, Md. レアズル イスラム, 三上大輔

  平成29年度日本水産学会春季大会  2017/03
• クロハギンナンソウ由来ミコスポリン様化合物と機能の検討  [Not invited]

  紺野智太, 栗原秀幸, 林裕也, 高橋是太郎

  日本食品科学工学会2017年北海道支部大会  2017/02
• リポキシゲナーゼ反応に影響を与える海藻成分の作用メカニズム  [Not invited]

  谷内山健太, 栗原秀幸, 高橋是太郎

  日本食品科学工学会2017年北海道支部大会  2017/02
• Antioxidant activity and tyrosinase inhibition of marine-derived bromophenols  [Not invited]

  ○Md. Reazul ISLAM, Momoka ONO, Hideyuki KURIHARA

  日本農芸化学会2016年度大会  2016/03
• 海藻抽出物のβ-グルクロニダーゼ阻害成分  [Not invited]

  張 鐸, 今井 雅志, 栗原 秀幸

  日本農芸化学会2016年度大会  2016/03
• イカミール由来リゾリン脂質の製造およびその食品応用  [Not invited]

  狩野栄詩, 永尾寿浩, 栗原秀幸, 高橋是太郎

  日本食品科学工学会2016年北海道支部大会  2016/02
• Effects of EPA-enriched Phospholipids on Basal and Tumor Necrosis Factor-α-induced Lipolysis in 3T3-L1 Adipocytes  [Not invited]

  杜 磊, 王 玉明, 栗原秀幸, 高橋是太郎

  日本食品科学工学会2016年北海道支部大会  2016/02
• ハケサキノコギリヒバから得られたブロモフェノール三量体  [Not invited]

  三上大輔, 栗原秀幸

  平成27年度日本水産学会北海道支部大会  2015/12
• 紅藻ウラソゾに含まれるリポキシゲナーゼ阻害活性物質  [Not invited]

  森本千尋, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会北海道支部大会  2015/12
• 海藻由来ブロモフェノールの抗酸化活性  [Not invited]

  小野桃香, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会北海道支部大会  2015/12
• Antitumour activity of eicosapentaenoic acid-enriched phospholipid liposomes against S180 ascites tumour-bearing mice  [Not invited]

  杜 磊, 王 玉明, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会秋季大会  2015/09
• 3T3-L脂肪細胞におけるTNF-α誘導性脂質分解に及ぼすEPAリン脂質とDHAリン脂質の抑制効果の比較  [Not invited]

  杜 磊, 栗原秀幸, 高橋是太郎, 王 玉明

  日本油化学会第54回年会  2015/09
• ヒトデセレブロシドの高純度化及びセレブロシド除去後の複合脂質のリポソーム化  [Not invited]

  安部孝彰, 栗原秀幸, 高橋是太郎

  日本油化学会第54回年会  2015/09
• EPA-enriched phospholipids ameliorates cancer-associate cachexia by attenuating adipose atrophy  [Not invited]

  杜磊, 王玉明, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会春季大会  2015/03
• サケ頭部リン脂質の酵素的部分加水分解によるDHAの濃縮  [Not invited]

  狩野栄詩, Azad Shah, 鷹橋秀, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会春季大会  2015/03
• ヒトデセレブロシドの高純度化及びリポソーム化  [Not invited]

  安部孝彰, 栗原秀幸, 高橋是太郎

  平成27年度日本水産学会春季大会  2015/03
• 褐藻多糖類分別法の問題点とその改善  [Not invited]

  栗原秀幸, 大原麻友美, 石井沙也加, 高橋是太郎

  日本食品科学工学会2015年北海道支部大会  2015/02
• ヒトデセレブロシドの高純化及びリポソーム化  [Not invited]

  安部孝彰, 高橋是太郎, 栗原秀幸

  日本食品科学工学会2015年北海道支部大会  2015/02
• 水産副次産物由来リゾリン脂質の調製  [Not invited]

  狩野栄詩, Azad Shah, 栗原秀幸, 高橋是太郎

  日本食品科学工学会2015年北海道支部大会  2015/02
• EPA-enriched Phospholipids Ameliorates Cancer-associated Cachexia by Attenuating Adipose Atrophy  [Not invited]

  杜磊, 王玉明, 栗原秀幸, 高橋是太郎

  日本食品科学工学会2015年北海道支部大会  2015/02
• 水産複合脂質リポソームの腸管モデルにおける透過及び取り込み  [Not invited]

  杜磊, 小西慶典, Adrien Jacquot, Michel Linder, 栗原秀幸, 高橋是太郎

  日本油化学会第53回年会  2014/09
• 水産複合脂質リポソームの腸管透過および吸収動態  [Not invited]

  小西慶典, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2014/03  函館市  日本水産学会
  
• ヒトデ複合脂質の高機能リポソーム化  [Not invited]

  相澤亮太, 栗原秀幸, 高橋是太郎, 清水佳?, 力村信吾

  日本水産学会春季大会  2014/03  函館市  日本水産学会
  
• 海藻由来のリポキシゲナーゼ阻害物質  [Not invited]

  紺野玲未, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2014/03  函館市  日本水産学会
  
• フジマツモ科海藻由来ブロモフェノールのグルコース6-リン酸デヒドロゲナーゼ阻害活性  [Not invited]

  三上大輔, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2014/03  函館市  日本水産学会
  
• 水産複合脂質リポソームの腸管透過および吸収動態  [Not invited]

  小西慶典, 栗原秀幸, 高橋是太郎

  日本食品科学工学会北海道支部大会  2014/03  帯広市  日本食品科学工学会北海道支部
  
• 紅藻フジマツモ由来のキサンチンオキシダーゼ阻害物質の探索  [Not invited]

  原田真, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2013/12  札幌市  日本水産学会北海道支部
  
• ヒトデ複合脂質の高機能リポソーム化  [Not invited]

  相澤亮太, 栗原秀幸, 高橋是太郎, 清水佳隆, 力丸信吾

  日本水産学会北海道支部大会  2013/12  札幌市  日本水産学会北海道支部
  
• 各種水産複合脂質リポソームの腸管透過及び吸収動態  [Not invited]

  小西慶典, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2013/12  札幌市  日本水産学会北海道支部
  
• 海藻由来α-グルコシダーゼ阻害活性物質に関する研究  [Not invited]

  三浦葉奈子, 栗原秀幸, 高橋是太郎

  日本農芸化学会北海道支部会  2013/11  札幌市  日本農芸化学会北海道支部
  
• 逆相ポリメックODSカラムHPLCを用いた飽和型トリアシルグリセロール位置異性体の分析  [Not invited]

  横地恵一, 溝部帆洋, 栗原秀幸, 高橋是太郎

  日本食品科学工学会北海道支部大会  2013/03  網走市  日本食品科学工学会北海道支部
  
• スギノリ目海藻由来のカテプシンB 阻害物質  [Not invited]

  岡本純, 栗原秀幸, 栗原秀幸

  日本水産学会北海道支部大会  2012/12  網走市  日本水産学会北海道支部
  
• 褐藻多糖類定量法の改良  [Not invited]

  大原麻友美, 石浦政浩, 中井陽介, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  2012/09  下関市  日本水産学会
  
• 北海道産海藻抽出物のリポキシゲナーゼ阻害成分  [Not invited]

  紺野玲未, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  2012/09  下関市  日本水産学会
  
• 超臨界二酸化炭素を応用した肝からのこく附与物質の選択的抽出  [Not invited]

  小野寺敬, 沖野龍文, 栗原秀幸, 高橋是太郎

  日本食品科学工学会年次大会  2012/08  札幌市  日本食品科学工学会
  
• 紅藻クシベニヒバのbeta-グルクロニダーゼ阻害物質  [Not invited]

  今井雅志, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2012/03  東京都  日本水産学会
  
• 紅藻由来グルコース-6-リン酸デヒドロゲナーゼ阻害剤の探索  [Not invited]

  三上大輔, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2012/03  東京都  日本水産学会
  
• 海洋および陸上植物由来モノガラクトシルジアシルグリセロールのリポキシゲナーゼとα-キモトリプシンに対する阻害性  [Not invited]

  野崎仁崇, 栗原秀幸, 高橋是太郎

  日本食品科学工学会北海道支部大会  2012/02  札幌市  日本食品科学工学会北海道支部
  
• 海洋植物及び陸上植物MGDG のリポキシゲナーゼとα-キモトリプシンに対する阻害性  [Not invited]

  野崎仁崇, 佐々木茂文, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2011/11  函館市  日本水産学会北海道支部
  
• セイヨウハバノリ由来α-キモトリプシン阻害活性成分  [Not invited]

  小林奈未, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2011/11  函館市  日本水産学会北海道支部
  
• 北海道産海藻抽出物のβ‐グルクロニダーゼ阻害活性成分  [Not invited]

  今井雅志, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2011/11  函館市  日本水産学会北海道支部
  
• Glucose-6-phosphate dehydrogenase and alpha-glucosidase inhibitors derived from marine algae.  [Not invited]

  ○Daisuke Mikami, Tsuyoshi Ayaki, Hideyuki Kurihara, Koretaro Takahashi

  International Conference and Exhibition on Neutraceuticals and Functional Foods  2011/11  札幌市
• 北海道産海藻及び水産食品の機能成分―酵素阻害，多糖類，フレーバー成分―  [Invited]

  栗原秀幸

  第17回水産油脂技術懇話会  2011/06  東京都  財団法人日本水産油脂協会
  
• ドコサヘキサエン酸結合型リゾおよびジアシルリン脂質の取り込み動態  [Not invited]

  小野山一輝, 大久保剛, 対馬忠広, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2011/03  東京都  日本水産学会
  
• EPA 結合型及びDHA 結合型ホスファチジルコリンの悪液質緩和作用  [Not invited]

  池亀啓太, 石田裕紀, 栗原秀幸, 高橋是太郎

  日本食品科学工学会北海道支部大会  2011/02  札幌市  日本食品科学工学会北海道支部
  
• ドコサヘキサエン酸結合型リゾおよびジアシルリン脂質の取り込み動態に関する研究  [Not invited]

  小野山一輝, 大久保剛, 対馬忠広, 栗原秀幸, 高橋是太郎

  日本食品科学工学会北海道支部大会  2011/02  札幌市  日本食品科学工学会北海道支部
  
• 紅藻ノコギリヒバ属由来のキサンチンオキシダーゼ阻害物質  [Not invited]

  上本倉平, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  2010/09  京都市  日本水産学会
  
• 水産複合脂質リポソームの耐消化性及び腸管における吸収に関する研究  [Not invited]

  廣内勇二, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  2010/09  京都市  日本水産学会
  
• 数種類の褐藻由来硫酸化フカンの化学的特性の比較  [Not invited]

  中井陽介, 藤田太陽, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  2010/09  京都市  日本水産学会
  
• 身欠きニシンの超臨界二酸化炭素抽出物の性状について―コク附与物質について―  [Not invited]

  芝田宗久, 栗原秀幸, 高橋是太郎, 小笠原正志

  日本水産学会春季大会  2010/03  藤沢市  日本水産学会
  
• 身欠きニシンの超臨界二酸化炭素抽出物の性状について―コク附与物質について―  [Not invited]

  芝田宗久, 栗原秀幸, 高橋是太郎, 小笠原正志

  日本食品科学工学会北海道支部大会  2010/02  札幌市  日本食品科学工学会北海道支部
  
• 海藻成分の機能性や活用に関する最近の動き  [Invited]

  栗原秀幸

  日本水産学会北海道支部大会シンポジウム  2009/11  函館市  日本水産学会北海道支部
  
• Health-sustainable compounds derived from the marine organisms around Hokkaido, Japan.  [Invited]

  栗原秀幸

  First Symposium between Dong-eui University and Hokkaido University on “Engineering & Material and Bio Related Research “  2009/11  韓国釜山広域市  韓国東義大学校
  
• 水産複合リン脂質の膜組成が腸管における透過に及ぼす影響  [Not invited]

  廣内勇二, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2009/11  函館市  日本水産学会北海道支部
  
• 海藻由来のリポキシゲナーゼ阻害物質  [Not invited]

  石田裕紀, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2009/11  函館市  日本水産学会北海道支部
  
• 海藻由来カテプシンB阻害物質  [Not invited]

  吉川知孝, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2009/11  函館市  日本水産学会北海道支部
  
• Changes in chemical composition and sensory properties of migaki-nishin (dried herring fillet) during processing.  [Not invited]

  ○A. K. M. Azad Shah, Chikara Tokunaga, Hideyuki Kurihara, Koretaro Takahashi

  5thWorld Fisheries Congress  2008/10  横浜市  日本水産学会
  
• Changes in lipid composition and their contribution to the taste of migaki-nishin during processing.  [Not invited]

  ○A. K. M. Azad Shah, Chikara Tokunaga, Hideyuki Kurihara, Koretaro Takahashi

  日本油化学会年会  2008/09  東京都  日本油化学会
  
• 北海道産植物のポリフェノール類及び機能性物質に関する研究  [Invited]

  栗原秀幸

  日本農芸化学会北海道支部会  2008/08  札幌市  日本農芸化学会北海道支部
  
• 海藻由来のリポキシゲナーゼ阻害活性物質  [Not invited]

  栗原秀幸, 香川吉央, 高橋是太郎

  日本農芸化学会北海道支部会  2008/08  札幌市  日本農芸化学会北海道支部
  
• Chemical and sensory changes in Migaki-nishin” (dried herring fillet) during processing.  [Not invited]

  ○A. K. M. Azad Shah, Chikara Tokunaga, Hideyuki Kurihara, Koretaro Takahashi

  日本水産学会春季大会  2008/03  静岡市  日本水産学会
  
• Chemical and sensory changes in Migaki-nishin” (dried herring fillet) during processing.  [Not invited]

  ○A. K. M. Azad Shah, Chikara Tokunaga, Hideyuki Kurihara, Koretaro Takahashi

  日本食品科学工学会北海道支部大会  2008/03  札幌市  日本食品科学工学会北海道支部
  
• クロハギンナンソウ由来のMAA＆gadusol類について  [Not invited]

  佐野優, 林裕也, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2007/09  函館市  日本水産学会北海道支部
  
• 各種酵素に対する海藻抽出物の阻害活性  [Not invited]

  門馬大介, 香川吉央, 会田雅彦, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2007/09  函館市  日本水産学会北海道支部
  
• 三種の褐藻由来硫酸化フカンの化学的特性  [Not invited]

  藤田太陽, 山村一生, 田中利幸, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2007/09  函館市  日本水産学会北海道支部
  
• ガゴメ粘性多糖類の抽出条件の検討  [Not invited]

  吉野博之, 李永, 清水健志, 栗原秀幸, 安井肇

  日本水産学会春季大会  2007/03  東京都  日本水産学会
  
• Biologically active compounds obtained from macroalgae collected in Hokkaido, Japan.  [Not invited]

  Hideyuki Kurihara

  The XIXth International Seaweed Symposium  2007/03  神戸市
• 褐藻フシスジモク由来のα-グルコシダーゼ阻害活性成分  [Not invited]

  籠島美由紀, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2006/12  札幌市  日本水産学会北海道支部
  
• フジマツモ由来のリポキシゲナーゼ阻害活性成分  [Not invited]

  香川吉央, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2006/12  札幌市  日本水産学会北海道支部
  
• フジマツモ属海藻の成分について  [Not invited]

  奥田大貴, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2006/12  札幌市  日本水産学会北海道支部
  
• 水産未活用素材の酵素阻害活性スクリーニング  [Not invited]

  栗原秀幸, 香川吉央, 籠島美由紀, 小林由起子, 高橋是太郎

  日本水産学会北海道支部大会  2006/12  札幌市  日本水産学会北海道支部
  
• 超臨海二酸化炭素中の部分加水分解反応を応用した高度不飽和リゾ型リン脂質の調製  [Not invited]

  内藤裕久, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2006/03  高知市  日本水産学会
  
• 北海道産海藻抽出物のリポキシゲナーゼ阻害活性  [Not invited]

  香川吉央, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2006/03  高知市  日本水産学会
  
• 褐藻・紅藻の機能性物質―多糖類・フェノール性化合物・UV吸収性物質―  [Invited]

  栗原秀幸

  北海道海洋生物科学研究会第4回シンポジウム  2005/12  札幌市  北海道海洋生物科学研究会
  
• 褐藻ガゴメに含まれる硫酸化多糖の特性  [Not invited]

  山村一生, 栗原秀幸, 高橋是太郎

  日本水産学会東北・北海道合同支部大会  2005/12  仙台市  日本水産学会東北・北海道支部
  
• ホタテガイ外套膜ペプシン由来可溶化コラーゲンの特性  [Not invited]

  申鉉日, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2005/04  東京都  日本水産学会
  
• アカモク（Sargassum horneri）熱水抽出物の繊維芽肉腫に対する抗腫瘍活性  [Not invited]

  松田太一, 佐々木甚一, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2005/04  東京都  日本水産学会
  
• エゾイシゲから得られた多糖類に関する化学的研究  [Not invited]

  田中利幸, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2005/04  東京都  日本水産学会
  
• ホタテ外套膜コラーゲンの分子構造の部分特性  [Not invited]

  申鉉日, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部大会  2004/11  函館市  日本水産学会北海道支部
  
• Function of Seaweeds in Hokkaido, Japan  [Invited]

  栗原秀幸

  2004 International Life Science Symposium for the Gangwondo Industry Innovation.  2004/10  韓国江陵市  韓国江陵大学校
  
• アカモク熱水抽出物の抗腫瘍活性  [Not invited]

  松田太一, 佐々木甚一, 穂刈勝利, 栗原秀幸, 高橋是太郎

  日本食品科学工学会大会  2004/09  盛岡市  日本食品科学工学会
  
• アンジオテンシンI変換酵素阻害ペプチドの腸管上皮細胞の透過性  [Not invited]

  小野世吾, 細川雅史, 栗原秀幸, 宮下和夫, 高橋是太郎

  日本食品科学工学会大会  2004/09  盛岡市  日本食品科学工学会
  
• クロハギンナンソウの代謝産物  [Not invited]

  林裕也, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2004/04  鹿児島市  日本水産学会
  
• スジメに含まれるβ-グルクロニダーゼ阻害活性成分  [Not invited]

  関川千里, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2003/04  東京都  日本水産学会
  
• コラーゲン生合成に対する海洋生物抽出物の効果  [Not invited]

  野間葉子, 栗原秀幸, 高橋是太郎

  日本水産学会北海道・東北合同支部大会  2002/11  余市町  日本水産学会北海道・東北支部
  
• スジメに含まれるβ-グルクロニダーゼ阻害活性成分  [Not invited]

  関川千里, 栗原秀幸, 高橋是太郎

  日本水産学会北海道・東北合同支部大会  2002/11  余市町  日本水産学会北海道・東北支部
  
• 紅藻カレキグサ（Tichocarpus crinitu）に含まれるフェノール性化合物の検索  [Not invited]

  本大介, 栗原秀幸, 高橋是太郎

  日本水産学会北海道・東北合同支部大会  2002/11  余市町  日本水産学会北海道・東北支部
  
• 海藻由来の機能性物質  [Invited]

  栗原秀幸

  北海道海洋生物科学研究会第1回シンポジウム  2002/10  札幌市  北海道海洋生物科学研究会
  
• サクラマスにおける成熟雄誘引フェロモンの分画  [Not invited]

  山家秀信, 栗原秀幸, 荒井克俊, 山崎文雄

  日本水産学会春季大会  2002/04  奈良市  日本水産学会
  
• Bromophenols and other constituents as enzyme inhibitors from Rhodomelaceae algae.  [Not invited]

  Hideyuki Kurihara, Takeshi Mitani, Chisato Sekikawa, Koretaro Takahashi, Jun Kawabata

  10th International symposium on marine natural products  2001/06  名護市
• 分離海洋細菌Bacillus megaterium AP22株由来の抗真菌物質MC17の単離と構造ならびに活性  [Not invited]

  貞閑智範, 川端潤, 福士江里, 栗原秀幸, 亀井勇統

  日本水産学会春季大会  2001/04  藤沢市  日本水産学会
  
• 日本における海藻の高付加価値利用  [Invited]

  栗原秀幸

  韓国江陵大学東海岸海洋生物資源研究センター国際シンポジウム  2000/10  韓国江陵市  韓国江陵大学校
  
• 褐藻エゾイシゲ由来フロロタンニンのラット小腸α-グルコシダーゼ阻害活性  [Not invited]

  栗原秀幸, 綾木毅, 高橋是太郎, 佐々木茂文, 太田智樹

  日本農芸化学会北海道支部会  2000/07  帯広市  日本農芸化学会北海道支部
  
• チガイソに含まれるフロロタンニン類のウレアーゼ阻害活性  [Not invited]

  会田雅彦, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2000/04  東京都  日本水産学会
  
• ユナに含まれるβ-グルクロニダーゼ阻害成分  [Not invited]

  関川千里, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2000/04  東京都  日本水産学会
  
• 海藻付着微生物由来のβ-グルクロニダーゼ阻害物質  [Not invited]

  東田裕之, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  2000/04  東京都  日本水産学会
  
• 海藻のβ-グルクロニダーゼ阻害成分のスクリーニングと精製  [Not invited]

  関川千里, 後藤慶一郎, 栗原秀幸, 高橋是太郎

  日本水産学会北海道支部例会  1999/12  札幌市  日本水産学会北海道支部
  
• 褐藻エゾイシゲ由来のα-グルコシダーゼ阻害成分  [Not invited]

  綾木 毅, 栗原秀幸, 太田智樹, 加藤 剛, 石井善晴, 高橋是太郎

  日本水産学会春季大会  1999/04  東京都  日本水産学会
  
• チガイソ胞子葉に含まれるウレアーゼ阻害成分  [Not invited]

  会田雅彦, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1999/04  東京都  日本水産学会
  
• スルメイカ墨汁嚢に含まれるウレアーゼ阻害成分  [Not invited]

  栗原秀幸, 道津大輔, 高橋是太郎

  日本水産学会春季大会  1999/04  東京都  日本水産学会
  
• 海藻に含まれる健康維持に有効な成分  [Invited]

  栗原秀幸

  第１４回北海道バイオ・ステージ〜バイオテクノロジーが見つけた海の幸〜やさしいバイオ講座  1998/11  函館市  北海道バイオフォーラム
  
• DHA結合型リン脂質を膜素材とするリポソームの基本的性状  [Not invited]

  森田直樹, 細川雅史, 栗原秀幸, 高橋是太郎

  日本水産学会秋季大会  1998/09  函館市  日本水産学会
  
• 加工残滓のホタテガイ中腸腺に含まれるβ-グルクロニダーゼ阻害成分  [Not invited]

  関口健, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1998/04  東京都  日本水産学会
  
• かつお節に含まれるヌクレオシドのβ-グルクロニダーゼ阻害性について  [Not invited]

  東田裕之, 栗原秀幸, 高橋是太郎, 川端潤

  日本水産学会春季大会  1998/04  東京都  日本水産学会
  
• ワカメ由来フコキサンチンのヒト白血病細胞に対する分化およびアポトーシス誘導能  [Not invited]

  和根崎智, 細川雅史, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1998/04  東京都  日本水産学会
  
• 紅藻類海藻から得られた各種ブロモフェノール類のα-グルコシダーゼ阻害性  [Not invited]

  三谷健, 栗原秀幸, 高橋是太郎, 川端潤

  日本水産学会春季大会  1998/04  東京都  日本水産学会
  
• 水産食品に含まれるう蝕抑制因子  [Not invited]

  栗原秀幸, 後藤百合江, 会田雅彦, 高橋是太郎

  日本水産学会秋季大会  1997/09  東広島市  日本水産学会
  
• フジマツモ科紅藻から得られたブロモフェノール類のα-グルコシダーゼに対する阻害性  [Not invited]

  栗原秀幸, 三谷健, 高橋是太郎, 川端潤

  日本農芸化学会北海道支部会  1997/07  札幌市  日本農芸化学会北海道支部
  
• 紅かつお節のβ-グルクロニダーゼ阻害物質  [Not invited]

  東田裕之, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1997/04  東京都  日本水産学会
  
• 紅藻ハケサキノコギリヒバに含まれるα-グルコシダーゼ阻害物質  [Not invited]

  三谷健, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1997/04  東京都  日本水産学会
  
• ヒト前骨髄性白血病細胞の分化に及ぼすDHA結合型リン脂質の促進効果  [Not invited]

  栃澤馨, 細川雅史, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1997/04  東京都  日本水産学会
  
• ヒト前骨髄性白血病細胞の分化と増殖に及ぼす水産物由来低極性成分の影響  [Not invited]

  細川雅史, 宮内こずえ, 栗原秀幸, 高橋是太郎

  日本水産学会春季大会  1997/04  東京都  日本水産学会
  
• 高水分活性域で起こる魚油の酸化に及ぼす食塩の影響  [Not invited]

  高橋是太郎, 十河和明, 栗原秀幸

  油化学討論会  1996/10  つくば市  日本油化学会
  
• 会合状態の異なるSQDGおよびその脱アシル分解物の酵母α-グルコシダーゼに対する阻害性  [Not invited]

  栗原秀幸, 三谷健, 羽田野六男, 川端潤

  日本農芸化学会東北北海道合同支部会  1996/09  弘前市  日本農芸化学会東北・北海道支部
  
• 化学合成生物群集に属する生物成分の酵素阻害性  [Not invited]

  栗原秀幸, 東田裕之, 羽田野六男, 橋本惇

  日本水産学会春季大会  1996/04  東京都  日本水産学会
  
• 杜仲葉のα-グルコシダーゼ阻害物質  [Not invited]

  渡辺 純, 川端 潤, 仁木良哉, 栗原秀幸

  日本農芸化学会大会  1995/08  札幌市  日本農芸化学会
  
• グリセロ糖脂質ＳＱＤＧのα-グルコシダーゼに対するＤＧＤＧの影響  [Not invited]

  栗原秀幸, 多田純彦, 羽田野六男

  日本農芸化学会大会  1995/08  札幌市  日本農芸化学会
  
• ヒジキの糖脂質スルホキノボシルジアシルグリセロール（ＳＱＤＧ）のαーグルコシダーゼ阻害性  [Not invited]

  安藤淳一, 栗原秀幸, 羽田野六男, 川端潤

  日本水産学会春季大会  1995/04  東京都  日本水産学会
  
• アセトニドと魚油トリグリセリドを基質とした低温アルコリシスによるＤＨＡおよびＥＰＡの濃縮  [Not invited]

  大西優摩, 高橋是太郎, 栗原秀幸, 羽田野六男

  日本水産学会春季大会  1995/04  東京都  日本水産学会
  
• ヒジキから得られたαーグルコシダーゼ阻害性グリセロ糖脂質について  [Not invited]

  栗原秀幸, 安藤淳一, 川端潤, 羽田野六男

  日本農芸化学会北海道支部会  1994/07  江別市  日本農芸化学会北海道支部
  
• ヒジキに含まれるαーグルコシダーゼ阻害物質について  [Not invited]

  安藤淳一, 栗原秀幸, 羽田野六男, 川端潤

  日本水産学会春季大会  1994/04  東京都  日本水産学会
  
• グルコシダーゼ阻害物質の検索法と水産物への適用  [Not invited]

  栗原秀幸, 佐々木政昌, 羽田野六男, 川端潤

  日本水産学会春季大会  1994/04  東京都  日本水産学会
  
• ホスホリパーゼＤによるホスファチジルカルニチンの合成  [Not invited]

  斎藤一繁, 高橋是太郎, 細川雅史, 栗原秀幸, 羽田野六男

  日本水産学会春季大会  1993/04  東京都  日本水産学会
  
• イカ肝膵臓に含まれるCd結合物質の精製  [Not invited]

  新井信太郎, 栗原秀幸, 羽田野六男

  日本水産学会春季大会  1993/04  東京都  日本水産学会
  
• イカ肝膵臓中のCd含量及びその除去法  [Not invited]

  栗原秀幸, 渡川初代, 谷端信孝, 羽田野六男

  日本水産学会春季大会  1993/04  東京都  日本水産学会
  
• ホタテガイ中腸腺中のCd含量及びその除去法  [Not invited]

  栗原秀幸, 新井信太郎, 谷端信孝, 羽田野六男

  日本水産学会春季大会  1993/04  東京都  日本水産学会
  
• 北方水生生物の二次代謝産物ーＩヒツジグサの抗菌物質について  [Not invited]

  栗原秀幸, 川端潤, 羽田野六男

  日本水産学会春季大会  1992/04  東京都  日本水産学会
  
• コウボウシバの抗菌性オリゴスチルベン類の構造解析  [Not invited]

  川端潤, 三島学, 市川聡, 栗原秀幸, 原正人, 福士江里, 水谷純也

  天然有機化合物討論会  1991/10  大阪市  日本化学会、日本薬学会、日本農芸化学会
  
• コウボウシバ(Carex pumila)に含まれる新規多環性テトラスチルベン，Kobophenol Bの構造  [Not invited]

  川端潤, 三島学, 栗原秀幸, 水谷純也

  日本農芸化学会北海道支部会  1990/07  札幌市  日本農芸化学会北海道支部
  
• スゲ属植物の抗菌性テトラスチルベンmiyabenol A及びBの立体化学  [Not invited]

  川端潤, 三島学, 栗原秀幸, 水谷純也

  日本農芸化学会大会  1990/04  福岡市  日本農芸化学会
  
• カヤツリグサ科コウボウムギに含まれる抗菌性テトラスチルベンKobophenol Aの構造  [Not invited]

  川端潤, 栗原秀幸, 市川聡, 水谷純也

  天然有機化合物討論会  1989/10  名古屋市  日本化学会、日本薬学会、日本農芸化学会
  
• コウボウシバに含まれる抗菌性オリゴスチルベンについて  [Not invited]

  栗原秀幸, 市川聡, 川端潤, 水谷純也

  日本農芸化学会大会  1989/04  新潟市  日本農芸化学会
  
• コウボウムギの抗菌性テトラスチルベンKobophenol Aの立体化学  [Not invited]

  栗原秀幸, 川端潤, 水谷純也

  日本農芸化学会北海道支部会  1988/07  帯広市  日本農芸化学会北海道支部
  
• スゲ属抗菌性スチルベノイドmiyabenol Cの立体化学に関する考察  [Not invited]

  川端潤, 栗原秀幸, 水谷純也

  日本農芸化学会大会  1988/04  名古屋市  日本農芸化学会
  

MISC

• 分離海洋細菌Bacillus megaterium AP22株由来の抗真菌物質MC17の単離と構造ならびに活性

  貞閑智範, 川端潤, 福士江里, 栗原秀幸, 亀井勇統  日本水産学会大会講演要旨集  2001-  34  2001/04/01  [Not refereed][Not invited]
  
• 褐藻エゾイシゲ由来フロロタンニンのラット小腸α-グルコシダーゼ阻害活性

  栗原秀幸, 綾木毅, 高橋是太郎, 佐々木茂文, 太田智樹  日本農芸化学会誌  74-  (11)  2000
• 褐藻エゾイシゲ由来フロロタンニンのラット小腸α-グルコシダーゼ阻害活性

  栗原秀幸, 綾木毅, 高橋是太郎, 佐々木茂文, 太田智樹  日本農芸化学会北海道支部・日本土壌肥料学会北海道支部・日本生物工学会北日本支部・日本応用糖質科学会北海道支部・北海道農芸化学協会合同学術講演会講演要旨  2000-  2000
• 褐藻エゾイシゲ由来のα-グルコシダーゼ阻害成分

  綾木毅, 栗原秀幸, 太田智樹, 加藤剛, 石井善晴, 高橋是太郎  日本水産学会大会講演要旨集  1999-  1999
• .BETA.-glucuronidase inhibition of nucleoside contained in dried bonito.

  HIGASHIDA HIROYUKI, KURIHARA HIDEYUKI, TAKAHASHI KORETARO, KAWABATA JUN  日本水産学会大会講演要旨集  1998-  175  1998/04  [Not refereed][Not invited]
  
• .ALPHA.-glucosidase inhibition of various bromophenols obtained from red algae seaweeds.

  MITANI TAKESHI, KURIHARA HIDEYUKI, TAKAHASHI KORETARO, KAWABATA JUN  日本水産学会大会講演要旨集  1998-  172  1998/04  [Not refereed][Not invited]
  
• Inhibition for .ALPHA.-glucosidase of bromophenol obtained from Rhodomelaceae red alga.

  KURIHARA HIDEYUKI, MITANI TAKESHI, TAKAHASHI KORETARO, KAWABATA JUN  日本農芸化学会北海道支部・日本土壌肥料学会北海道支部・日本生物工学会北日本支部・日本応用糖質科学会北海道支部・北海道農芸化学協会合同学術講演会講演要旨  1997-  9  1997  [Not refereed][Not invited]
  
• Interference activity of the SQDG different in assembly condition and its deacylation fragments against yeast .ALPHA.-glucosidase.

  KURIHARA HIDEYUKI, MITANI KEN, HATANO MUTSUO, KAWABATA JUN  日本農芸化学会東北支部大会プログラム・講演要旨集  1996-  (Godo Gakujutsu Koenkai)  60  1996/09  [Not refereed][Not invited]
  
• SULFOQUINOVOSYLDIACYLGLYCEROL AS AN ALPHA-GLUCOSIDASE INHIBITOR (VOL 5, PG 1241, 1995)

  H KURIHARA, J ANDO, M HATANO, J KAWABATA  BIOORGANIC & MEDICINAL CHEMISTRY LETTERS  5-  (15)  1757  -1757  1995/08  [Not refereed][Not invited]
  
• 杜仲葉のα-グルコシダーゼ阻害物質 : 食品

  渡辺 純, 川端 潤, 仁木 良哉, 栗原 秀幸  日本農藝化學會誌  69-  172  -172  1995/07/05
• グリセロ糖脂質SQDGのα-グルコシダーゼ阻害に対するDGDGの影響 : 食品

  栗原 秀幸, 多田 純彦, 羽田野 六男  日本農藝化學會誌  69-  172  -172  1995/07/05
• ヒジキの糖脂質スルホキノボシルジアシルグリセロール(SQDG)α‐グルコシダーゼ阻害性

  安藤淳一, 栗原秀幸, 羽田野六男, 川端潤  日本水産学会大会講演要旨集  1995-  307  1995/04  [Not refereed][Not invited]
  
• ヒジキから得られたα‐グルコシダーゼ阻害性グリセロ糖脂質について

  栗原秀幸, 安藤淳一, 川端潤, 羽田野六男  日本農芸化学会北海道支部・日本土壌肥料学会北海道支部・日本生物工学会北日本支部・日本応用糖質科学会北海道支部・北海道農芸化学協会合同学術講演会講演要旨  1994-  6  1994  [Not refereed][Not invited]
  
• Structural studies on oligostilbenes in Carex pumila Thunb.

  川端潤, 三島学, 市川聡, 栗原秀幸, 原正人, 福士江里, 水谷純也  天然有機化合物討論会講演要旨集  33rd-  581  -588  1991/09  [Not refereed][Not invited]
  
• スゲ属植物の抗菌性スチルベノイドmiyabenol Cの立体化学に関する考察(有機化学・天然物化学-抗生物質生理活性物質(微生物)-)

  川端 潤, 栗原 秀幸, 水谷 純也  日本農藝化學會誌  62-  (3)  569  -569  1988/03/15

Industrial Property Rights

• 特開2012-115167:魚介エキスの製造方法  2012/06/21

  高 橋, 是太郎, 栗 原, 秀 幸, 芝 田, 宗, 久, 小野寺, 敬, 小笠原, 正  キリン協和フーズ株式会社  201203088422116350
• 特開2011-125315:こく味増強剤  2011/06/30

  小笠原, 正 志, 仲久木, 裕, 子, 高 橋, 是太郎, エイ・ケイ・エム・アザド・シャー, 栗 原, 秀  キリン協和フーズ株式会社  201103017519107787
• 特開2011-125316:風味増強剤  2011/06/30

  小笠原, 正 志, 仲久木, 裕, 子, 高 橋, 是太郎, 芝 田, 宗 久, 栗 原 秀  キリン協和フーズ株式会社  201103079977471426
• 特開2005-289858:抗菌組成物、及び、魚病類結節症の予防剤及び/又は治療剤  2005/10/20

  猪上 徳雄, 川合 祐史, 山▲崎▼ 浩司, 栗原 秀幸, 熊谷 光倫, 澤野 亮  川合祐史, 明治製菓株式会社  200903028595649592
• 特開2004-215506:海藻抽出物  2004/08/05

  栗原 秀幸, 倉又 一成  歯舞漁業協同組合  200903055649348671
• 特許第3543175号:α−グルコシダーゼ阻害物質  2004/04/16

  栗原 秀幸, 綾木 毅, 高橋 是太郎, 佐々木 茂文, 太田 智樹, 大堀 忠志, 吉川 修司  北海道  200903096703610288
• 特開2000-342224:エゾイシゲからの肥満及び糖尿病予防を目的とする食品素材  2000/12/12

  太田 智樹, 栗原 秀幸, 石井 善晴  北海道  200903039639156965

Awards & Honors

• 2015/08 Japanese Society for Food Science and Technology Food Science and Technology Research Award
   Supercritical Fluid Extraction of "Koku"Enhancing Compounds from Fish and Fishery By-products 

  受賞者: SHIBATA Munehisa;ONODERA Kei;KUMAGAI Momochika;SHAH A.K.M. Azad;OGASAWARA Masashi;KURIHARA Hideyuki;OKINO Tatsufumi;TAKAHASHI Koretaro
• 2008 日本農芸化学会北海道支部奨励賞
  

Research Grants & Projects

• Enzymatic conversion of kelp biomass for biofuels and health beneficial products.

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research

  Date (from‐to) : 2020/04 -2024/03 

  Author : FOX BRIAN, 細川 雅史, 栗原 秀幸, 高須賀 太一

   

  Our aim of the current project is to develop an efficient method to depolymerize natural kelps available in the Hokkaido ocean by a combination of several enzyme functions, including laminarin-degrading enzymes and alginate-degrading enzymes. A set of kelp spp. were obtained and ready to analytically evaluate their chemical compositions for the next fiscal year. Regarding a laminarin-degrading enzyme, we had picked up a glycoside hydrolase 55 enzyme (GH55) from a highly cellulolytic insect symbiont bacterium (Bianchetti and Takasuka et al., 2015, Journal of Biological Chemistry). 7 polysaccharide lyases 18 enzymes (PL18s), which function in alginate degradation, were selected from 7 different bacterial species, and four PL18s had been recombinantly expressed and subjected to the initial enzyme screening by using pure alginic acid substrate. Moreover, two polysaccharide lyase 17 enzymes (PL17s), were gene synthesized and cloned into the bacterial expression vector. From the previous studies, PL18 is shown to be the endo-type polysaccharide lyase, which produces oligoalginic acids (>3 degrees of polymerization (DP)), while PL17 should catalyze an exo-type reaction. In the FY2021, collected kelps will be tested to be hydrolyzed by at least three different enzymes, GH55, PL17, and PL18, and end products will be analyzed.
• 北海道産カヤモノリ目褐藻由来リポキシゲナーゼ阻害活性物質の解明

  公益財団法人北水協会：北海道の水産に関する学術及び技術開発に係る試験研究、調査を支援し，その振興に寄与する事業

  Date (from‐to) : 2013/04 -2014/03 

  Author : 栗原 秀幸
• フコイダンの迅速新規測定法の確立に関する研究事業

  公益財団法人南北海道学術振興財団：助成事業「先端的な学術研究」

  Date (from‐to) : 2013/04 -2013/11 

  Author : 栗原 秀幸
• イオン交換ミニカラムを用いた褐藻多糖類の迅速分別定量法の最適化

  （独法）科学技術振興機構：研究成果展開事業 研究成果最適展開支援プログラム（A-STEP）フィージビリティスタディ【ＦＳ】ステージ 探索タイプ

  Date (from‐to) : 2011/12 -2012/06 

  Author : 栗原 秀幸
• 新規機能性物質としての海藻由来酵素阻害物質の精製と利用

  日本学術振興会：二国間交流事業 韓国との共同研究

  Date (from‐to) : 2004/07 -2006/06 

  Author : 栗原 秀幸
• 海藻機能性多糖の微細構造解析による腫瘍予防型食品開発の差別化

  財団法人北海道科学技術総合振興センター：研究開発助成事業 研究開発シーズ育成補助金

  Date (from‐to) : 2002/06 -2003/03 

  Author : 栗原 秀幸
• 未利用海藻を利用した健康食品等の開発技術プロジェクト

  財団法人北海道科学技術総合振興センター：産学共同研究

  Date (from‐to) : 2002/06 -2003/03 

  Author : 栗原 秀幸
• 海藻多糖類の化学的特性の解明

  Date (from‐to) : 2003
• Elucidation of chemical properties of algal polysaccharides

  Date (from‐to) : 2003
• 褐藻の機能性ポリフェノールである高分子フロロタンニンの精密構造解析法の確立

  文部科学省：科学研究費補助金(奨励研究(A), 若手研究(B))

  Date (from‐to) : 2001 -2002 

  Author : 栗原 秀幸

   

  フロロタンニンは褐藻類に特有のフロログルシノールの酸化的重合物であり、重合のしかたによってさまざまな構造をとりうる。本研究はそれらの詳細な構造解析を行う予定で以下の成果を得た。エゾイシゲ(Silvetia babintonii、ヒバマタ科,8.00kg)を70%メタノールで抽出した。抽出物を水と酢酸エチルで溶媒分画したところ、両画分にフロロタンニンが検出された。構造解析が容易な低分子量フロロタンニンの含まれる酢酸エチル可溶部をセルロースカラムクロマトグラフィーで分画して、水で溶出する画分を集めた。本画分はフロロタンニン以外の低極性不純物を含んでいたため、酢酸エチルと水で再度溶媒分画して精製をおこなった。水可溶画分がフロロタンニン混合物と同定できた。得られたフロロタンニン混合物の分子量を測定するために本年度は質量分析(MS)を行った。まず、ESI-MS(-)を測定したところ、高マスユニット側にm/z919を与えた。フェルラ酸をマトリックスとしてMALDI-TOF-MS(+)を測定したところ、m/z984を与えた。これらはフロログルシノールのヘキサマーあるいはヘプタマー程度の大きさである。しかし、単純なフロログルシノールの酸化的カップリングに対応するマスユニットを与えておらず、何らかの置換基が存在するようである。この置換基の解明には至らなかった。解明に至らなかった原因に得られたフ...
• 砂利石のある河川流水環境下で放出されるウグイオスのメス誘引フェロモンの同定

  文部科学省：科学研究費補助金(特定領域研究(A))

  Date (from‐to) : 2000 -2000 

  Author : 栗原 秀幸

   

  ウグイ産卵成熟期(6月)に捕獲したオス・メスを砂利石を敷いた人工水路に収容すると、一部の個体で産卵成熟の状態になる(オスでは膀胱の尿量が増え、メスでは卵成熟・抱卵して、誘引フェロモン感受性が高くなる)。このときにオスはメス誘引フェロモンを放出する。そこで、成熟したオスから採集した尿を用いて、室内試験水槽に収容した成熟メスの誘引行動を観察した。誘引活性を指標にして誘引フェロモンの分画を行った。6月に千曲川水系で捕獲したウグイのオス・メスを砂利石を敷き詰めた人工水路に収容し、河川水を流した。収容したウグイのうち、成熟したオスから尿を採集した。フェロモン感受性の高いことが知られている卵成熟・抱卵したメスを触診で判断して選抜した。室内試験水槽はパーティションで3室に区切り、魚が通り抜けられるような穴を開けた。両外側の部屋に水を注入、中央の部屋から排水して「水の流れ」をつくった。中央の部屋にメスを収容して、どちらか一方の外側の部屋にオス尿を添加したときの誘引活性を調べたところ、メスが鋭敏な誘引活性を示した。オス(約30匹分)の尿9.4mLを凍結乾燥して乾燥物29.0mgを得た。凍結乾燥物を脱イオン交換水に溶解してゲルろ過クロマトグラフィーに供し、脱イオン交換水で溶出した。各画分を215nmでモニターしたところ、最大極大吸収をもつ画分に強い誘引活性が観察された。活性画分を集め、弱陽イオン...
• H.pylori制圧を期待できるチガイソ科海藻胞子葉のウレアーゼ阻害成分

  文部科学省：科学研究費補助金(奨励研究(A))

  Date (from‐to) : 1999 -2000 

  Author : 栗原 秀幸

   

  本年度は、チガイソ科海藻チガイソ(Alaria crassiforia)の胞子葉に含まれているウレアーゼ阻害成分であるフロロタンニンの分子量の検討した。さらにフロロタンニンの微生物由来酸性ウレアーゼに対する阻害活性の検討を行った。チガイソを含水アセトンで抽出した後に、溶媒分画を行い、セルロースカラムクロマトグラフィーに供してフロロタンニンを得た。得られたフロロタンニンの分子量測定には、疎水性高分子化合物の分子量測定用のゲル浸透高速液体クロマトグラフィー(HPLC)法を用いた。フロロタンニンはフェノール性水酸基が多数存在するために、多数の分子が会合対を形成していると推定できる。よって、フロロタンニンをそのままゲルろ過クロマトグラフィーに供すると見かけの分子量が高値を示すと予想できる。そこで、フェノール性水酸基のアセチル化を行い分子間相互作用を抑えた。フロロタンニンアセチル化物をゲル浸透HPLCに供した結果、アセチル化物の分子量は3000〜7000と見積もられた。昨年度はJack beans由来の中性ウレアーゼを用いて阻害活性を検討した。今年度は胃内のような低pH条件下でのフロロタンニンのウレアーゼに対する阻害活性を検討した。乳酸菌Lactobacillus fermentumの生産する酸性ウレアーゼに対する阻害活性を調べた結果、pH4の条件下でもフロロタンニンは酵素阻害活性を示...
• Molecular basis for establishing the environment in digestive tract by food components

  Ministry of Education, Culture, Sports, Science and Technology：Grants-in-Aid for Scientific Research(基盤研究(B))

  Date (from‐to) : 1998 -1999 

  Author : Jun KAWABATA, 石塚 敏, 栗原 秀幸

   

  As the inhibitory principles against rat intestinal maltase, two ellagitannins, eugeniin and casuarictin, were isolated from the methanolic extracts of Clove buds. Structure-activity relationship study of the isolates together with synthetic pentagalloylglucose (PGG), which showed the highest activity , revealed that the inhibitory activity depended on the number of uncoupled galloyl residues in the molecule. These tannins also inhibited maltase expressed on a human carcinoma cell line, Caco-2. On the other hand, the acetone extracts of roselle tea, dried flower buds of Hibiscus sabdariffa,...
• 毒物暴露予防を期待できる水産加工食品かつお節のβ-グルクロニダーゼ阻害性成分

  秋山記念生命科学振興財団：研究助成 奨励助成

  Date (from‐to) : 1997/09 -1998/03 

  Author : 栗原 秀幸
• 食後高血糖抑制を期待できる海藻グリセロ糖脂質のα-グルコシダーゼ阻害様式の検討

  文部科学省：科学研究費補助金(奨励研究(A))

  Date (from‐to) : 1995 -1995 

  Author : 栗原 秀幸

   

  グリセロ糖脂質のスルホキノボシルジアシルグリセリド(SQDG)と類縁体の酵母α-グルコシダーゼに対する阻害様式を検討した。SQDGの阻害活性試験を改めて行なったところ、阻害活性にばらつきがあった。SQDG溶液が白濁したときに阻害活性が低く、SQDG溶液が透明なときに阻害活性が強くなる傾向があった。そこで、反応系内のSQDG濃度を一定にして、超音波処理により濁度の異なるSQDG溶液を調製した。各濁度における1/v〜1/sプロットは阻害物質濃度を変化させたときと同様なプロットを与えた。SQDGが大きな会合体を形成(濁度が高い)する割合の高いときには、「阻害に有効な」(小さな会合体または単一分子と考えられる)SQDG濃度が低いので阻害活性が低くなり、濁度が低く小さな会合体の割合が高いときには、「阻害に有効な」SQDG濃度が高いので、阻害活性が高くなると考えられる。SQDGに0.03 N NaOH/MeOHを加えて、室温で2時間反応を行い、スルホキノボシルグリセロール(SQG)を調製した。また、SQDGに1N HClを加え、還流加熱を2時間行い、スルホキノボ-ス(SQ)を調製した。SQGやSQの終濃度0〜100μMで 酵素活性を検討したところ、両者はほとんど阻害効果を示さなかった。よって、スルホキノボシルグリセリド類が酵母α-グルコシダーゼに対して阻害効果を示すためには疎水性部分(ア...
• 食後高血糖抑制を期待できる海藻食品ヒジキ中のα-グルコシダーゼ阻害物質の構造

  文部科学省：科学研究費補助金(奨励研究(A))

  Date (from‐to) : 1994 -1994 

  Author : 栗原 秀幸

   

  食後高血糖抑制効果を期待できるα-グルコシダーゼ阻害物質を水産食品中に見いだす研究はほとんどなされていない。その萌芽的研究として、本研究により海藻食品のヒジキからα-グルコシダーゼ阻害物質を初めて単離し、構造、阻害活性および様式を明らかにした。まず、寒天平板を用いたα-グルコシダーゼ阻害性試験を指標として、阻害成分の分画をおこなった。市販乾燥ヒジキの含水メタノール抽出物から各種クロマトグラフィーにより分画し、二種類の阻害物質を単離した。得られた両阻害物質はともに糖および含硫化合物呈色試験に陽性で、GCにより脂肪酸残基の存在が明らかとなった。各種臓器分析(IR、UV、MS、NMR)の結果から、両阻害物質の構造を植物の主要な糖脂質である6-スルホ-α-キノボビラノシルジアシルグリセロール(SQDG)およびそのリゾ型の6-スルホ-α-キノボビラノシルモノアシルグリセロール(SQMG)と決定した。速度論的解析により、SQDGの酵母α-グルコシダーゼに対する阻害物質定数(Ki)を3.0μMと、阻害様式を拮抗型阻害とそれぞれ明らかにした。SQMGの単離量が少なく、Kiを求めることができなかったので、SQMGとSQDGの同濃度での酵素阻害率を比較したところ、SQMGの阻害活性が2.5倍強かった。以上のように、ヒジキから新タイプのα-グルコシダーゼ阻害物質として糖脂質を得た。本研究では、SQ...
• Elucidation of marine-derived functional constituents in oraganisms

  Date (from‐to) : 1990

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