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Okino Tatsufumi
| Faculty of Environmental Earth Science Integrated Environmental Science Environmental Adaptation Science | Professor |
| Center for Environmental and Health Sciences | Professor |
Researcher basic information
■ Degree■ URL
researchmap URLホームページURL■ Various IDs
ORCID IDJ-Global ID■ Research Keywords and Fields
Research KeywordResearch Field
- Life Science, Aquatic life science
- Nanotechnology/Materials, Bio chemistry
- Nanotechnology/Materials, Chemistry and chemical methodology of biomolecules
- Bachelor's degree program, School of Science
- Master's degree program, Graduate School of Environmental Science
- Doctoral (PhD) degree program, Graduate School of Environmental Science
Research activity information
■ Papers- Observations of vertical body orientations of Serrivomer eels in the mesopelagic zone along the West Mariana Ridge
Michael J. Miller; Tetsuya Miwa; Shun Watanabe; Mari Kuroki; Takatoshi Higuchi; Aya Takeuchi; Tatsufumi Okino; Katsumi Tsukamoto
MARINE AND FRESHWATER BEHAVIOUR AND PHYSIOLOGY, 58, 5, 99, 120, 03 Sep. 2025
English, Scientific journal - Isolation and Computer-Based Structural Determination of Madangolide B
Masahiro Hagihara; Jakia Jerin Mehjabin; Charles S. Vairappan; Tatsufumi Okino; Kiyotake Suenaga; Arihiro Iwasaki
ORGANIC LETTERS, 27, 25, 6807, 6811, 17 Jun. 2025
English, Scientific journal - Identification and Characterization of Bioactive Compounds from a Marine Bivalve Clam Marcia hiantina via Mass Spectrometry Techniques
Rhoda Mae C. Simora; Andrea Roxanne J. Anas; Nandani Balloo; Zhengyi Ling; Karmelie Jane M. Monaya; Yoshiaki Takaya; Tatsufumi Okino
CURRENT ANALYTICAL CHEMISTRY, 22, 4, 715, 731, 24 Apr. 2025
English, Scientific journal - Carotenoids identified from slipper-shaped oyster Magallana bilineata powder residue exhibit potent biological activities
Rhoda Mae C. Simora; Raymund B. Parcon; Andrea Roxanne J. Anas; Tatsufumi Okino
JOURNAL OF FOOD AND DRUG ANALYSIS, 33, 4, 2025
English, Scientific journal - Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis
Chin-Soon Phan; Zhengyi Ling; Jakia Jerin Mehjabin; Kenichi Matsuda; Nurcahyo Iman Prakoso; Taiki Umezawa; Toshiyuki Wakimoto; Tatsufumi Okino
Journal of Natural Products, American Chemical Society (ACS), 30 Oct. 2024
Scientific journal - Evaluation of the cytotoxicity, genotoxicity, and antifungal activities of race-index compounds from the red alga Laurencia nipponica
Kensuke Kaneko; Miyu Shinke; Takashi Kamada; Tatsufumi Okino; Ayumi Yamamoto
Journal of Applied Phycology, Springer Science and Business Media LLC, 26 Sep. 2024
Scientific journal - Chemotherapeutic prospects of organic extracts of Bornetella nitida from Selayar Island
Nunuk Hariani Soekamto; Bahrun; Tatsufumi Okino; Herlina Rasyid; Pratiwi Pudjiastuti; Yuni Elsa Hadisaputri; Rahadian Zainul
KUWAIT JOURNAL OF SCIENCE, 51, 3, Jul. 2024
English, Scientific journal - Noducyclamides A1–A4, B1, and B2 from the Cyanobacterium Nodularia sp. NIES-3585
Jakia Jerin Mehjabin; Chin-Soon Phan; Tatsufumi Okino
Journal of Natural Products, American Chemical Society (ACS), 08 Apr. 2024
Scientific journal - Cyanoremediation of heavy metals (As(v), Cd(ii), Cr(vi), Pb(ii)) by live cyanobacteria (Anabaena variabilis, and Synechocystis sp.): an eco-sustainable technology.
Md Sabbir Hossain; Tatsufumi Okino
RSC advances, 14, 15, 10452, 10463, 26 Mar. 2024, [International Magazine]
English, Scientific journal, The cyanoremediation technique for heavy metal (HM) removal from wastewater using live cyanobacteria is promising to reduce the pollution risk both for the environment and human health. In this study, two widely recognized freshwater cyanobacteria, Anabaena variabilis and Synechocystis sp., were used to explore their efficacy in HM (As(v), Cd(ii), Cr(vi), Pb(ii)) removal. The different optimum adsorption conditions were pH 8 and 7.5 for A. variabilis and Synechocystis sp., respectively, but the temperature (25 °C) and contact time (48 hours) were the same for both strains. Under these specified conditions, A. variabilis exhibited the capability to remove 25% of As(v), 78% of Cd(ii), 54% of Cr(vi), and 17% of Pb(ii), whereas Synechocystis sp. removed 77% of As(v), 57% of Cd(ii), 91% of Cr(vi), and 77% of Pb(ii) at different initial concentrations. Metal diversity interfered negatively with cyanobacterial growth, especially Cd(ii) and As(v), as measured by OD730, dry biomass, chlorophyll a, and carotenoid production for both strains. Fourier transform infrared spectrum (FT-IR) analysis revealed the existence of diverse surface binding sites for HM adsorption, stemming from proteins and polysaccharides. Scanning Electron Microscopy (SEM) and Energy Dispersive X-ray Spectroscopy (EDS) confirmed the presence of HMs on the surface of the cyanobacterial cells. Finally, the zeta potential results indicating alterations in the surface negative charges elucidated the adsorption mechanisms involved in the HM removal by both cyanobacteria. These results provided a comprehensive understanding of the HM adsorption mechanism by cyanobacteria, offering valuable theoretical insights that can be extrapolated to enhance our comprehension of the cyanoremediation mechanisms by various other cyanobacterial strains. - Antimicrobial and Cytotoxic Effect of Bornetella Nitida Green Algae Isolate on MCF-7 Breast Cancer.
Yuni Elsa Hadisaputri; Nunuk Hariani Soekamto; Pratiwi Pudjiastuti; Aria Aristokrat; Bahrun Bahrun; Fajar Fauzi Abdullah; Tatsufumi Okino
Breast cancer (Dove Medical Press), 16, 555, 565, 2024, [International Magazine]
English, Scientific journal, INTRODUCTION: Marine algae are increasingly becoming a potential resource for new drugs. In recent decades, including Bornetella nitida (B. nitida). Meanwhile, antimicrobial and anticancer agents are the first line of choice for developing alternative compounds, considering the annually increasing resistant events. Therefore, this study aimed to examine the antimicrobial and cytotoxic potential of B. nitida isolate compounds. METHODS: The B. nitida resulted in 2 compounds, sitosterol 3β tetracosanoate and (E)-17-(8-ethyl-4,5,9-trimethyldec-6-en-2-yl)-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol. Both compounds were tested to have antibacterial effects against Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Methicillin-resistant Staphylococcus Aureus (MRSA). Proliferation assay was conducted using the PrestoBlue™ Cell Viability Reagent, which was also used to measure the IC50 against MCF-7 breast cancer cells. RESULTS: The results showed that (E)-17-(8-ethyl-4,5,9-trimethyldec-6-en-2-yl)-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol had antimicrobial activity against Staphylococcus aureus and IC50 value of 142.18 µg/mL against MCF-7 cells, while sitosterol 3β tetracosanoate does not have any antimicrobial activity and IC50 value of 681.65 µg/mL. Moreover, the mechanism prediction using docking with caspase-3 receptor to induce apoptosis was also evaluated. CONCLUSION: Based on the results, (E)-17-(8-ethyl-4,5,9-trimethyldec-6-en-2-yl)-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol of B. nitida has great potential as an antimicrobial and anticancer agent. - Heat shock and iron limitation modulate the metabolic profile of the cyanobacterium
Microcystis aeruginosa NIES ‐88
Nandani Balloo; Jakia Jerin Mehjabin; Chin‐Soon Phan; Tatsufumi Okino
Phycological Research, Wiley, 25 Jul. 2023, [Peer-reviewed]
Scientific journal, Abstract
The freshwater cyanobacterium Microcystis aeruginosa NIES‐88, which can produce microcystins, micropeptins, and argicyclamides, was subjected to a one strain many compounds (OSMAC) analysis. We report its response to two environmental stressors, temperature and iron limitation, by means of untargeted and targeted metabolomics. The results demonstrated a slower specific growth rate of 0.20 per day and 0.16 per day in adverse conditions of 37°C and iron limitation, respectively. The metabolic signature of M. aeruginosa was highly dependent on incubation temperatures. Production of microcystins LR and RR was severely downregulated while that of argicyclamide B was significantly upregulated, with a highest 10‐fold increase on day 14 of heat shock treatment. M. aeruginosa NIES‐88 was found to produce a new compound, argicyclamide D (1), in iron limited medium, which has the same macrocyclic structure as the previously reported analogs. Hence, it is proposed that acclimation of M. aeruginosa to environmental stressors might be mediated by a change in the metabolic pathways as well as modulation of the levels of their expressed metabolites. - Syntheses and Biological Activities of Danicalipin A Derivatives.
Taiki Umezawa; Takeshi Maeda; Takuya Akiyama; Nurcahyo Iman Prakoso; Jakia Jerin Mehjabin; Tatsufumi Okino; Fuyuhiko Matsuda
Chemistry & biodiversity, 20, 6, e202300400, Jun. 2023, [International Magazine]
English, Scientific journal, Synthesis of three derivatives of danicalipin A, tetrachloride, trisulfate and a fluorescent probe was achieved through Wittig reaction strategy. Toxicity of the derivatives against brine shrimp (Artemia salina) as also investigated to provide useful information for the biological activity; i) less chloride derivative showed similar toxicity to danicalipin A, ii) the amphiphilic property, a characteristic feature of danicalipin A, was crucial because trisulfate considerably decreased the toxicity and iii) fluorescent derivative kept brine shrimp toxicity of danicalipin A. - Gene cloning and characterization of a vanadium-dependent bromoperoxidase from the red alga Laurencia saitoi, a producer of brominated diterpenoids and triterpenoids
Kensuke Kaneko; Daiki Kobayashi; Shiro Masaki; Kenji Washio; Masaaki Morikawa; Tatsufumi Okino
JOURNAL OF APPLIED PHYCOLOGY, Apr. 2023
English, Scientific journal - Occurrence and Distribution of Shipworms (Mollusca: Bivalvia: Teredinidae) and Two New Records of <i>Bankia</i> species along the Coast of Hokkaido, Japan
Angem Librando-Descallar; Zhengyi Ling; Takuma Haga; Tatsufumi Okino
Sessile Organisms, 40, 1, 1, 12, The Sessile Organisms Society of Japan, 14 Mar. 2023, [Peer-reviewed], [Last author, Corresponding author]
Scientific journal - Biological evaluation and molecular docking of Indonesian Gracilaria salicornia as antioxidant agents
BAHRUN; Tatsufumi OKINO; Herlina RASYID; Nunuk Hariani; SOEKAMTO
Journal of Research in Pharmacy, 27, 1, 207, 220, Jan. 2023, [Peer-reviewed]
English, Scientific journal - Characterization of vanadium-dependent bromoperoxidases involved in the production of brominated sesquiterpenes by the red alga Laurencia okamurae
Takafumi Ishikawa; Kenji Washio; Kensuke Kaneko; Xiao Rong Tang; Masaaki Morikawa; Tatsufumi Okino
Applied Phycology, 3, 1, 120, 131, Informa UK Limited, 31 Dec. 2022, [Peer-reviewed], [Last author]
Scientific journal - Marine Algal and Cyanobacterial Surface-Active Compounds
J.J. Mehjabin; T. Okino
Marine Surfactants, 201, 211, CRC Press, 21 Nov. 2022, [Last author]
In book - Nostosin G and Spiroidesin B from the Cyanobacterium Dolichospermum sp. NIES-1697
Chin-Soon Phan; Jakia Jerin Mehjabin; Andrea Roxanne J. Anas; Masahiro Hayasaka; Reiko Onoki; Juting Wang; Taiki Umezawa; Kenji Washio; Masaaki Morikawa; Tatsufumi Okino
Journal of Natural Products, American Chemical Society (ACS), 10 Aug. 2022, [Peer-reviewed], [Last author, Corresponding author]
Scientific journal - Environmental DNA detects a possible Japanese eel spawning event near a video-recorded anguillid eel in the open ocean
A Takeuchi; T Higuchi; M Kuroki; S Watanabe; MJ Miller; T Okino; T Miwa; K Tsukamoto
Marine Ecology Progress Series, Inter-Research Science Center, 2022, [Peer-reviewed]
Scientific journal - Argicyclamides A-C Unveil Enzymatic Basis for Guanidine Bis-prenylation
Chin-Soon Phan; Kenichi Matsuda; Nandani Balloo; Kei Fujita; Toshiyuki Wakimoto; Tatsufumi Okino
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 143, 27, 10083, 10087, Jul. 2021, [Peer-reviewed], [Last author, Corresponding author]
English, Scientific journal - Several possible spawning sites of the Japanese eel determined from collections of their eggs and preleptocephali
Aya Takeuchi; Takatoshi Higuchi; Shun Watanabe; Michael J. Miller; Ritsuno Yama; Tatsuhiro Fukuba; Akihiro Okamura; Tatsufumi Okino; Tetsuya Miwa; Katsumi Tsukamoto
FISHERIES SCIENCE, 87, 3, 339, 352, May 2021, [Peer-reviewed]
English, Scientific journal - Bioactivities of Lyngbyabellins from Cyanobacteria ofMooreaandOkeaniaGenera
Imam Fathoni; Julie G. Petitbois; Walied M. Alarif; Ahmed Abdel-Lateff; Sultan S. Al-Lihaibi; Erina Yoshimura; Yasuyuki Nogata; Charles S. Vairappan; Eti Nurwening Sholikhah; Tatsufumi Okino
MOLECULES, 25, 17, Sep. 2020, [Peer-reviewed], [Last author, Corresponding author], ［Internationally co-authored］
English, Scientific journal - Biosurfactants from Marine Cyanobacteria Collected in Sabah, Malaysia
Jakia Jerin Mehjabin; Liang Wei; Julie G. Petitbois; Taiki Umezawa; Fuyuhiko Matsuda; Charles S. Vairappan; Masaaki Morikawa; Tatsufumi Okino
Journal of Natural Products, 83, 6, 1925, 1930, American Chemical Society (ACS), 20 May 2020, [Peer-reviewed], [Last author, Corresponding author], ［Internationally co-authored］
Scientific journal - Cytotoxicity and Antibacterial Potential of Halogenated Chamigrenes from Malaysian Red Alga, Laurencia majuscula
Takashi Kamada; Chin-Soon Phan; Tatsufumi Okino; Charles Santhanaraju Vairappan
Planta Medica International Open, 6, 02, e36, e40, Georg Thieme Verlag KG, Nov. 2019, [Peer-reviewed], ［Internationally co-authored］
English, Scientific journal,Abstract Red algae of the genus Laurencia have been known to produce a wide array of bioactive secondary metabolites. Here, we report the isolation of two new halogenated chamigrenes, lauremantanones A (1) and B (2), along with seven known compounds, dendroidiol (3), (+)-elatol (4), cartilagineol (5), obtusol (6), (+)-laurencenone B (7), 2-chloro-3-hydroxy-α-chamigren-9-one (8), and puertitol A (9), from a population of Laurencia majuscula (Harvey) Lucas from Mantanani Island (North Borneo). The structures of the two new metabolites were determined based on spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds isolated from this alga exhibited potent cytotoxic (HeLa, MCF-7, P-388) and antibacterial (against antibiotic-resistant clinical bacteria) activities. The major metabolite of this population has significant importance in the geographical distribution of this species globally. - Environmentally Friendly Antifouling Metabolites from Red Sea Organisms
Sultan Semran Al-Lihaibi; Ahmed Abdel-Lateff; Walied Mohamed Alarif; Hajer Saeed Alorfi; Yasuyuki Nogata; Tatsufumi Okino
Journal of Chemistry, 2019, 1, 15, Hindawi Limited, 30 Oct. 2019, [Peer-reviewed], [Last author], ［Internationally co-authored］
English, Scientific journal, Seventy-one marine organisms representing different classes of marine fauna and flora were collected from the Red Sea. They include sponges, hydrozoan, soft corals, sea cucumber, ascidian, cyanobacteria, and macroalgae. The methanolic extracts were evaluated for their toxicity and settlement inhibition effects by using culturedBalanus amphitrite. Thirty-three extracts displayed antifouling effects: four samples were highly potent at 1μ g/mL with a percentage of settlement inhibition above 31%, twenty-two were potent at 10μ g/mL with a percentage of settlement inhibition between 16 and 30%, and seven were active at 10μ g/mL with a percentage of settlement inhibition between 0 and 15%. Two promising extracts were purified by employing several chromatographic techniques, leading to the isolation of 12 known compounds. The isolated compounds were evaluated for their antifouling activities and demonstrated potent antifouling effects with EC50 values of less than 10μ g/mL. - Parthenogenetic female populations in the brown alga Scytosiphon lomentaria (Scytosiphonaceae, Ectocarpales): decay of a sexual trait and acquisition of asexual traits
Hoshino Masakazu; Okino Tatsufumi; Kogame Kazuhiro
JOURNAL OF PHYCOLOGY, 55, 1, 204, 213, Feb. 2019, [Peer-reviewed]
English, Scientific journal - First use of oceanic environmental DNA to study the spawning ecology of the Japanese eel Anguilla japonica
Takeuchi Aya; Watanabe Shun; Yamamoto Satoshi; Miller Michael J; Fukuba Tatsuhiro; Miwa Tetsuya; Okino Tatsufumi; Minamoto Toshifumi; Tsukamoto Katsumi
MARINE ECOLOGY PROGRESS SERIES, 609, 187, 196, 17 Jan. 2019, [Peer-reviewed]
Scientific journal - In vitro cytotoxic anticancer potential of bioactive fraction isolated from Indonesian tidal sponge Calthropella sp.
Fitria Susilowti; Respati Tri Swasono; Tatsufumi Okino; Winarto Harya
Asian Journal of Pharmaceutical and Clinical Research, 12, 1, 380, 383, 2019, [Peer-reviewed], ［Internationally co-authored］
English, Scientific journal - Synthesis and Structure-Activity Relationship of Omaezallene Derivatives.
Taiki Umezawa; Nurcahyo Iman Prakoso; Miho Kannaka; Yasuyuki Nogata; Erina Yoshimura; Tatsufumi Okino; Fuyuhiko Matsuda
Chemistry & biodiversity, 16, 1, e1800451, Jan. 2019, [Peer-reviewed], [International Magazine]
English, Scientific journal - Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium Moorea bouillonii
Fumiaki Nakamura; Hiroshi Maejima; Midori Kawamura; Daisuke Arai; Tatsufumi Okino; Meng Zhao; Tao Ye; Jungyeol Lee; Young-Tae Chang; Nobuhiro Fusetani; Yoichi Nakao
Bioorganic and Medicinal Chemistry Letters, 28, 12, 2206, 2209, 01 Jul. 2018, [Peer-reviewed], ［Internationally co-authored］
English, Scientific journal - Observation of a Gelatinous Octopod, Haliphron atlanticus, along the Southern West Mariana Ridge: A Unique Cephalopod of Continental Slope and Mesopelagic Communities
Michael J. Miller; Tetsuya Miwa; Shun Watanabe; Mari Kuroki; Takatoshi Higuchi; Aya Takeuchi; Kenta Serizawa; Tatsufumi Okino; Katsumi Tsukamoto
Journal of Marine Biology, 2018, Hindawi Limited, 2018, [Peer-reviewed]
English, Scientific journal - Antioxidants from the brown alga dictyopteris undulata
Momochika Kumagai; Keisuke Nishikawa; Hiroshi Matsuura; Taiki Umezawa; Fuyuhiko Matsuda; Tatsufumi Okino
Molecules, 23, 5, 2018, [Peer-reviewed], [Last author, Corresponding author]
English, Scientific journal - Serinolamides and Lyngbyabellins from an Okeania sp Cyanobacterium Collected from the Red Sea
Julie G. Petitbois; Loida O. Casalme; Julius Adam V. Lopez; Walied M. Alarif; Ahmed Abdel-Lateff; Sultan S. Al-Lihaibi; Erina Yoshimura; Yasuyuki Nogata; Taiki Umezawa; Fuyuhiko Matsuda; Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 80, 10, 2708, 2715, Oct. 2017, [Peer-reviewed]
English, Scientific journal - New Marine Antifouling Compounds from the Red Alga Laurencia sp.
Yuko Oguri; Mami Watanabe; Takafumi Ishikawa; Takashi Kamada; Charles S. Vairappan; Hiroshi Matsuura; Kensuke Kaneko; Takahiro Ishii; Minoru Suzuki; Erina Yoshimura; Yasuyuki Nogata; Tatsufumi Okino
MARINE DRUGS, 15, 9, Sep. 2017, [Peer-reviewed]
English, Scientific journal - Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia
Julius Adam V. Lopez; Julie G. Petitbois; Charles S. Vairappan; Taiki Umezawa; Fuyuhiko Matsuda; Tatsufumi Okino
ORGANIC LETTERS, 19, 16, 4231, 4234, Aug. 2017, [Peer-reviewed]
English, Scientific journal - A quantitative shRNA screen identifies ATP1A1 as a gene that regulates cytotoxicity by aurilide B
Shohei Takase; Rumi Kurokawa; Daisuke Arai; Kind Kanemoto Kanto; Tatsufumi Okino; Yoichi Nakao; Tetsuo Kushiro; Minoru Yoshida; Ken Matsumoto
SCIENTIFIC REPORTS, 7, May 2017, [Peer-reviewed]
English, Scientific journal - Total synthesis and biological activity of dolastatin 16
Loida O. Casalme; Arisa Yamauchi; Akinori Sato; Julie G. Petitbois; Yasuyuki Nogata; Erina Yoshimura; Tatsufumi Okino; Taiki Umezawa; Fuyuhiko Matsuda
ORGANIC & BIOMOLECULAR CHEMISTRY, 15, 5, 1140, 1150, Feb. 2017, [Peer-reviewed]
English, Scientific journal - Total Synthesis of Natural Antifouling Products
Taiki Umezawa; Keisuke Nishikawa; Tatsufumi Okino; Fuyuhiko Matsuda
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 74, 7, 689, 699, Jul. 2016, [Peer-reviewed]
Japanese - Wewakazole B, a Cytotoxic Cyanobactin from the Cyanobacterium Moorea producens Collected in the Red Sea
Julius Adam V. Lopez; Sultan S. Al-Lihaibi; Walied M. Alarif; Ahmed Abdel-Lateff; Yasuyuki Nogata; Kenji Washio; Masaaki Morikawa; Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 79, 4, 1213, 1218, Apr. 2016, [Peer-reviewed]
English, Scientific journal - Potent antifouling metabolites from red sea organisms
Sultan S. Al-Lhaibi; Ahmed Abdel-Lateff; Waled M. Alarif; Yasuyuki Nogata; Seif-Eldin N. Ayyad; Tatsufumi Okino
Asian Journal of Chemistry, 27, 6, 2252, 2256, Chemical Publishing Co., 01 Jun. 2015, [Peer-reviewed]
English, Scientific journal - 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, Nov. 2014, [Peer-reviewed]
English, Scientific journal - cDNA cloning and characterization of vanadium-dependent bromoperoxidases from the red alga Laurencia nipponica
Kensuke Kaneko; Kenji Washio; Taiki Umezawa; Fuyuhiko Matsuda; Masaaki Morikawa; Tatsufumi Okino
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 78, 8, 1310, 1319, Aug. 2014, [Peer-reviewed]
English, Scientific journal - Omaezallene from Red Alga Laurencia sp.: Structure Elucidation, Total Synthesis, and Antifouling Activity
Taiki Umezawa; Yuko Oguri; Hiroshi Matsuura; Shohei Yamazaki; Masahiro Suzuki; Erina Yoshimura; Takeshi Furuta; Yasuyuki Nogata; Yukihiko Serisawa; Kazuyo Matsuyama-Serisawa; Tsuyoshi Abe; Fuyuhiko Matsuda; Minoru Suzuki; Tatsufumi Okino
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53, 15, 3909, 3912, Apr. 2014, [Peer-reviewed]
English, Scientific journal - Alnuheptanoid A: a new diarylheptanoid derivative from Alnus japonica
Sabrin R. M. Ibrahim; Mostafa A. Fouad; Ahmed Abdel-Lateff; Tatsufumi Okino; Gamal A. Mohamed
NATURAL PRODUCT RESEARCH, 28, 20, 1765, 1771, 2014, [Peer-reviewed]
English, Scientific journal - Bouillonamide: A Mixed Polyketide-Peptide Cytotoxin from the Marine Cyanobacterium Moorea bouillonii
Lik Tong Tan; Tatsufumi Okino; William H. Gerwick
MARINE DRUGS, 11, 8, 3015, 3024, Aug. 2013, [Peer-reviewed]
English, Scientific journal - Sesquiterpenes from the marine algicolous fungus Drechslera sp.
Ahmed Abdel-Lateff; Tatsufumi Okino; Walied M. Alarif; Sultan S. Al-Lihaibi
JOURNAL OF SAUDI CHEMICAL SOCIETY, 17, 2, 161, 165, Apr. 2013, [Peer-reviewed]
English, Scientific journal - Thrombin Inhibitors from the Freshwater Cyanobacterium Anabaena compacta
Andrea Roxanne J. Anas; Takaya Kisugi; Taiki Umezawa; Fuyuhiko Matsuda; Marc R. Campitelli; Ronald J. Quinn; Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 75, 9, 1546, 1552, Sep. 2012, [Peer-reviewed]
English, Scientific journal - Stevioside enhances apoptosis induced by serum deprivation in PC12 cells
Kumiko Takahashi; Yongkun Sun; Ikumi Yanagiuchi; Toshiyuki Hosokawa; Takeshi Saito; Miyako Komori; Tatsufumi Okino; Masaaki Kurasaki
TOXICOLOGY MECHANISMS AND METHODS, 22, 4, 243, 249, May 2012, [Peer-reviewed]
English, Scientific journal - Synthesis and Biological Activity of Kalkitoxin and its Analogues
Taiki Umezawa; Manabu Sueda; Takao Kamura; Teppei Kawahara; Xuerong Han; Tatsufumi Okino; Fuyuhiko Matsuda
JOURNAL OF ORGANIC CHEMISTRY, 77, 1, 357, 370, Jan. 2012, [Peer-reviewed]
English, Scientific journal - Chlorosulfolipids
Teppei Kawahara; Tatsufumi Okino
Studies in Natural Products Chemistry, 36, 219, 247, 2012, [Peer-reviewed]
English, Scientific journal - Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities
Keisuke Nishikawa; Hiroshi Nakahara; Yousuke Shirokura; Yasuyuki Nogata; Erina Yoshimura; Taiki Umezawa; Tatsufumi Okino; Fuyuhiko Matsuda
JOURNAL OF ORGANIC CHEMISTRY, 76, 16, 6558, 6573, Aug. 2011, [Peer-reviewed]
English, Scientific journal - A Stereoselective Vanadium-Dependent Chloroperoxidase in Bacterial Antibiotic Biosynthesis
Peter Bernhardt; Tatsufumi Okino; Jaclyn M. Winter; Akimasa Miyanaga; Bradley S. Moore
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 133, 12, 4268, 4270, Mar. 2011, [Peer-reviewed]
English, Scientific journal - Asymmetric Total Synthesis of Danicalipin A and Evaluation of Biological Activity
Taiki Umezawa; Masayuki Shibata; Kensuke Kaneko; Tatsufumi Okino; Fuyuhiko Matsuda
ORGANIC LETTERS, 13, 5, 904, 907, Mar. 2011, [Peer-reviewed]
English, Scientific journal - Total Synthesis of 10-Isocyano-4-cadinene and Determination of Its Absolute Configuration
Keisuke Nishikawa; Hiroshi Nakahara; Yousuke Shirokura; Yasuyuki Nogata; Erina Yoshimura; Taiki Umezawa; Tatsufumi Okino; Fuyuhiko Matsuda
ORGANIC LETTERS, 12, 5, 904, 907, Mar. 2010, [Peer-reviewed]
English, Scientific journal - Anti-Mycobacterium phlei Activity of the Bark of Ziziphus talanai (Blanco) Merrill
Andrea Roxanne J. Anas; Irene M. Villasenor; Hiroshi Matsuura; Tatsufumi Okino
PHILIPPINE AGRICULTURAL SCIENTIST, 92, 4, 388, 391, Dec. 2009, [Peer-reviewed]
English, Scientific journal - Modulation of carcinogen metabolizing enzymes by chromanone A; a new chromone derivative from algicolous marine fungus Penicillium sp.
Amira M. Gamal-Eldeen; Ahmed Abdel-Lateff; Tatsufumi Okino
ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY, 28, 3, 317, 322, Nov. 2009, [Peer-reviewed]
English, Scientific journal - Synthesis and Biological Activity of Kalkitoxin and its Analogues
Umezawa Taiki; Kamura Takao; Kawahara Teppei; Sueda Manabu; Kan Setsuyo; Okino Tatsufumi; Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 51, 329, 334, Symposium on the chemistry of natural products, 01 Sep. 2009
Japanese, Kalkitoxin (1) was isolated from cyanobacterium Lyngbya majuscule in the Caribbean Sea. It is reported that 1 posssesses some intersting biological activities. For example, 1 shows a strong ichtyotoxic activity toward the common gold fish and brine shrimp. Also, kalkitoxin has a strong neurotoxicity (LC_<50>=3.86nM) in cerebellar granule neouron (CGN) as an inhibitor N-methyl-D-aspartate (NMDA) receptor antagonists and is a highly potent blocker of the voltage-depending sodium channel in mouse neuro-2a cells (EC_<50>=1nM). We have been attracted by the structure-activity relationship of kalkitoxins. In present paper, we describe the synthesis of kalkitoxin and its analogues (epimer and demethylated kalkitoxins (nor form) and their biological activity with brine shrimp. The synthesis was started from 15, which was converted to α,β-unsaturaed imide 14 with phosphonate 17. 1,4-Addition reaction to 14 with methyl curprate gave imide 18 as 10 : 1 mixture of diastereomers. The imide 18 was transformed into second 1,4-addition precursor 11 in 9 steps. The conjugate addition reaction of 11 proceeded smoothly to give imide 26 as a single diastereomer, which was derived to 1 via condensation with amine 10, synthesize without racemization by novel method, and highly efficient thiazoline formation with TiCl_4. Kalkitoxin analogues 2-7 were synthesized in the similar manner by simply changing the chiral auxiliary or chiral building block. Finally, the biological activity with 1-7 was evaluated as LC_<50> toward brine shrimp. - Absolute Configuration of Chlorosulfolipids from the Chrysophyta Ochromonas danica
Teppei Kawahara; Yasuhiro Kumaki; Takashi Kamada; Takahiro Ishii; Tatsufumi Okino
JOURNAL OF ORGANIC CHEMISTRY, 74, 16, 6016, 6024, Aug. 2009, [Peer-reviewed]
English, Scientific journal - Induction of larval metamorphosis in the sea cucumber Apostichopus japonicus by neurotransmitters
Hiroshi Matsuura; Ikuko Yazaki; Tatsufumi Okino
FISHERIES SCIENCE, 75, 3, 777, 783, May 2009, [Peer-reviewed]
English, Scientific journal - Micropeptins from the Freshwater Cyanobacterium Microcystis aeruginosa (NIES-100)
Takaya Kisugi; Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 72, 4, 777, 781, Apr. 2009, [Peer-reviewed]
English, Scientific journal - Aureobasidin, New Antifouling Metabolite from Marine-Derived Fungus Aureobasidium sp.
Ahmed Abdel-Lateff; Ehab S. Elkhayat; Mostafa A. Fouad; Tatsufumi Okino
NATURAL PRODUCT COMMUNICATIONS, 4, 3, 389, 394, Mar. 2009, [Peer-reviewed]
English, Scientific journal - Antifouling alkaloids from Crinum augustum (Amaryllidaceae)
Pharmacog. Res., 1, 43, 52, 2009 - Chemical Composition and Hepato-protective activity of Imperata cylindrica Beauv.
Gamal A. Mohamed; Ahmed Abdel Lateff; Mostafa A. Fouad; Sabrin R. M. Ibrahim; Ehab S. Elkhayat; Tatsufumi Okino
PHARMACOGNOSY MAGAZINE, 5, 17, 28, 36, Jan. 2009
English, Scientific journal - Chemical Composition and Hepato-protective activity of Imperata cylindrica Beauv.
Gamal A. Mohamed; Ahmed Abdel Lateff; Mostafa A. Fouad; Sabrin R. M. Ibrahim; Ehab S. Elkhayat; Tatsufumi Okino
PHARMACOGNOSY MAGAZINE, 5, 17, 28, 36, Jan. 2009, [Peer-reviewed]
English, Scientific journal - Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp.
Charles Santhanaraju Vairappan; Minoru Suzuki; Takahiro Ishii; Tatsufumi Okino; Tsuyoshi Abe; Michio Masuda
PHYTOCHEMISTRY, 69, 13, 2490, 2494, Oct. 2008, [Peer-reviewed]
English, Scientific journal - P-43 Stereochemistry of Chlorosulfolipids from the Chrysophyta Ochromonas danica(Poster Presentation)
Kawahara Teppei; Okino Tatsufumi
Symposium on the Chemistry of Natural Products, symposium papers, 50, 391, 396, Symposium on the chemistry of natural products, 01 Sep. 2008
Japanese, Chlorosulfolipids (CSLs) are unusual naturally occurring compounds, which were first isolated at the end of the 1960s from freshwater microalgae such as Chrysophyceae Ochromonas danica and Poterioochromonas malhamensis. They constitute 15% of total lipids. The preparation of the CSLs in sufficient purity for structural characterization has proven to be difficult because the polar lipids were extremely hydroscopic and viscously. Therefore, any bioassays have not taken in nature form and structural elucidation was not satisfied with stereochemical analysis. Herein, we report successful isolation and determination of relative and absolute configuration of eight chlorosulfolipids. The Chrysophyta O. danica (IAM CS-2) was cultured at 25℃ for 1 week in a medium containing 0.1% glucose, 0.1% tryptone, 0.1% yeast extract and 0.05% meat extract with aeration. The cells were collected by continuous centrifugation, and freeze dried. The freeze-dried cells were homogenized and extracted with 1L of MeOH (three times) and 1L of EtOAc. The combined extracts were evaporated in vacuo and sequentially extracted with hexane, CHCl_3, EtOAc, BuOH and water. The active fractions (EtOAc, BuOH) of brineshrimp assay were applied repeatedly to silica gel and flash ODS column chromatography. Finally reverse phase-HPLC using a C_<30> column and an ELSD detector yielded four known CSLs (1,6-8) and four new compounds (2-5). Compound 1 was a major component of CSL from O. danica. Planar structure of 1 was established by HR-ESI-MS, 1D, 2D NMR and ESI-MS/MS. By using the JBCA method, relative configurations of 1 were determined by measuring ^<23>_J_ - Late Pleistocene changes in terrestrial biomarkers in sediments from the central Arctic Ocean
Masanobu Yamamoto; Tatsufumi Okino; Saiko Sugisaki; Tatsuhiko Sakamoto
ORGANIC GEOCHEMISTRY, 39, 6, 754, 763, 2008, [Peer-reviewed]
English, Scientific journal - Plant-growth regulators from common starfish (Asterias amurensis Lutken) waste
Takahiro Ishii; Tatsufumi Okino; Yosuke Mino; Hiroaki Tamiya; Fuyuhiko Matsuda
PLANT GROWTH REGULATION, 52, 2, 131, 139, Jun. 2007, [Peer-reviewed]
English, Scientific journal - P-19 New sphingolipids from the starfish Asterias amurensis Lutken and their plant-growth promotion activity
Ishii Takahiro; Okino Tatsufumi; Mino Yosuke; Tamiya Hiroaki; Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 48, 295, 300, Symposium on the chemistry of natural products, 15 Sep. 2006
Japanese, A large number of studies on the isolation and structure elucidation of sphingolipids from starfish have been reported. These compounds are the predominant metabolites of starfish and include a broad variety of pharmacological activities. In recent years, outbreak of starfish in Hokkaido causes serious damage to the fishery and aquacultural grounds for benthic shellfish. Although such starfish is a nuisance to fishermen, the collected starfish can be used as fertilizer. In our preliminary growth test, starfish compost mix showed plant-growth promoting effect to the plant Brassica campestris (Komatsuna). Thus, we investigated Asterias amurensis Lutken as a source of plant-growth promoters. A bioassay-guided separation of both hot water and methanol extracts from A. amurensis gave several active fractions which showed plant-growth promoting effect. A new glucocerebroside, asteriacerebroside G (1) and a new ceramide, asteriaceramide A (2), together with two known compounds, asteriacerebrosides A and B were isolated from the lipophilic fractions from the methanol extract. Three asteriacerebrosides had promotive effect on the entire plant body of B. campestris. On the other hand, asteriaceramide A (2) exhibited a root growth promoting effect. Moreover, the aqueous fraction from the water extract contained a sulfur-containing guanidine derivative, asterubine. In order to study the effect of active asterubine, we produced synthetic asterubine. The promotive activity of natural asterubine was equivalent to that of the synthesized product. These active compounds from unutilized natural resource A. amurensis could be employed as useful plant-growth regulators in a number of agricultural technologies in the future. - A ceramide and cerebroside from the starfish Asterias amurensis Lutken and their plant-growth promotion activities
Takahiro Ishii; Tatsufumi Okino; Yosuke Mino
JOURNAL OF NATURAL PRODUCTS, 69, 7, 1080, 1082, Jul. 2006, [Peer-reviewed]
English, Scientific journal - Tichocarpols A and B, two novel phenylpropanoids with feeding-deterrent activity from the red alga Tichocarpus crinitus
T Ishii; T Okino; M Suzuki; Y Machiguchi
JOURNAL OF NATURAL PRODUCTS, 67, 10, 1764, 1766, Oct. 2004
English, Scientific journal - Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: Application of catalytic asymmetric phase-transfer reaction
Y Fukuta; T Ohshima; Gnanadesikan, V; T Shibuguchi; T Nemoto; T Kisugi; T Okino; M Shibasaki
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 101, 15, 5433, 5438, Apr. 2004
English, Scientific journal - Li, W. I., Marquez, B. L. ., Okino, T., Yokokawa, F., Shioiri, T., Gerwick, W. H. & Murray, T. F., Characterization of the preferred stereochemistry for the neuropharmacologic actions of antillatoxin. J. Nat. Prod., 67 (4), 559-568.*
2004 - Yokokawa, F., Asano, T., Okino, T., Gerwick, W. H., & Shioiri, T., An expeditious total synthesis of kalkitoxins: determination of the absolute stereoctructure of natural kalkitoxin. Tetrahedron, 60 (32), 6859-6880.*
2004 - Ishii, T., Okino, T., Suzuki, M., Kuramata, K. & Machiguchi, Y., Feeding-deterrent activity of phenylpropanoids from the red alga Tichocarpus crinitus against the sea urchin Strongylocentrotus intermedius, Mar. Biotechnol., 6, S247-S251.*
2004 - New antifouling kalihipyrans from the marine sponge Acanthella cavernosa
Tatsufumi Okino; Erina Yoshimura; Hiroshi Hirota; Nobuhiro Fusetani
Journal of Natural Products, 59, 11, 1081, 1083, Nov. 1996, [Peer-reviewed]
English, Scientific journal - 76(P61) SETTLEMENT INDUCING AND INHIBITING SUBSTANCES FOR LARVAE OF SESSILE MARINE ORGANISMS
HIROTA Hiroshi; TSUKAMOTO Sachiko; OKINO Tatsufumi; TOMONO Yasuhiko; KATO Haruko; YOSHIMURA Erina; FUSETANI Nobuhiro
Symposium on the Chemistry of Natural Products, symposium papers, 38, 451, 456, Symposium on the chemistry of natural products, 02 Sep. 1996
Japanese, As a part of our study on larval settlement (attachment and metamorphosis) of sessile marine invertebrates, we are searching the settlement inducing and inhibiting substances from various marine organisms. Here we present our new findings on the metamorphosis inducing compounds on ascidian Halocynthia roretzi larvae and the antifoulants against barnacle Balanus amphitrite larvae. Metamorphisis of ascidian larvae has been thought to be induced by some chemical cues. a) We found the conditioned medium with the ascidian H. roretzi larvae induced the larval metamorphosis of the conspecies. The metamorphosis-inducer has been isolated, and the strucutre was identified as lumichrome (1). b) From various marine organisms, we have isolated almost 40 compounds including 24 new ones as the metamorphosis-inducers on the ascidian. For example, from a marine sponge Callyspongia sp. (to be), ten acyclic polyacetylene derivatives were obtained (e.g. 2 and 3). A marine sponge Stelletta sp. afforded a norsesequiterpenamide with two guanidium moieties, stellettadine A (4), the absolute stereochemistry of which was determined by degradation into 2-methylglutaric acid. From the marine sponge Anthosigmella aff. raromicrosclera, two pipecolate derivatives (5 and 6) were obtained. On MeOH extracts of more than 300 marine invertebrates, we have performed antifouling screening against barnacle larvae (B. amphitrite). Following the screening result, we attempted the isolation and structure determination of antifoulants to afford more than 60 compounds including almost 30 new ones. a) From the marine sponge Acanthella cavernosa, 26 antifoulants were obtained. Kalihinane-type compounds with isocyano, formamino, and/or isothiocyano group(s) showed prominent antifouling activities, some of which were stronger than that of cupric sulfate. Steroids with epidioxy group (e.g. 7) delayed the timing of larval settlement. b) Nudibranchs of the family Phillidiidae afforded 11 sesquiterpenoid antifoulants (e.g. 8). c) From the marine sponge Pseudoceratina purpurea, seven antifoulants (9 - 15) including a unique cyanoformamide derivative (14) were obtained. d) The marine sponge Agelas mauritiana afforded oroidin and its unique dimer (16). e) From a marine sponge Axinyssa sp., three new sesquiterpenoids with dichloromethyleneamino group (17-19) were obtained. f) A soft coral Dendronephthya sp. afforded four new D-seco-steroids (e.g. 20). These research results will become important on understanding the more concise mechanism of larval settlement and for development of commercial antifouling agents. - Antifouling activity isocyanoterpenoids and related compounds isolated from a marine sponge and nudibranchs
Nobuhiro Fusetani; Hiroshi Hiroto; Tatsufumi Okino; Yasuhiko Tomono; Erina Yoshimura
Journal of Natural Toxins, 5, 2, 249, 261, Jun. 1996
English, Scientific journal - P-12 ANTIFOULING TERPENOIDS AGAINST BARNACLE LARVAE FROM MARINE ORGANISMS
OKINO Tatsufumi; HIROTA Hiroshi; TOMONO Yasuhiko; YOSHIMURA Erina; FUSETANI Nobuhiro
Symposium on the Chemistry of Natural Products, symposium papers, 37, 337, 342, Symposium on the chemistry of natural products, 01 Sep. 1995
Japanese, It is widely believed that sessile marine organisms possess chemical defenses against fouling organisms. Therefore, these secondary metabolites might be potential non-toxic antifouling agents. During our search for antifouling agents from Japanese marine organisms, we found that extracts of nudibranchs of the genus Phyllidia and of sponges of the genus Acanthella inhibited larval settlement and metamorphosis of Balanus amphitrite. Bioassay-guided isolation afforded sixteen new along with sixteen known terpenoids. Extracts of sponges and nudibranchs were subjected to solvent partitioning, silica-gel column chromatographies and HPLC. Five new kalihinenes and kalihipyrans have been isolated from a sponge Acanthella collected off Yakushima island, while 4 new kalihinols, a new diterpene hydrocarbon, and two new sesquiterpenes have been obtained from a sponge Acanthella collected off Hachijo-jima island. Four new sesquiterpenes have been obtained from 3 nudibranchs of the genus Phyllidia collected in the southern Kyushu. Molecular formulas of kalihinane diterpenes were established by high resolution MS. IR spectra suggested their functionalities; isonitrile, isothiocyanate, or isocyanate. Extensive 2D NMR analyses were applied to elucidate their structures. Especially, stereochemistries were determined by NOESY experiments and values of coupling constants. Compounds 1-3 were the first examples of kalihinene-type diterpenes in tetrahydropyran series, while 12 was a rare compound possessing an isocyanate functionality as a natural product. Structures of six new sesquiterpenes were elucidated mainly by 2D NMR analyses. A compound 32 had a new carbon skeleton. Most of these compounds showed strong antifouling activity against the barnacle Balanus amphitrite larvae. Especially, 15-formamidokalihinene (6), 10-formamidokalihinene (7), kalihinol A (8), 3-isocyanotheonellin (28), and 10-isocyano-4-cadinene (30) showed potent antifouling activity, more active than CuSO_4. - 63 POTENT TRYPSIN INHIBITORS FROM FRESHWATER BLUE-GREEN ALGA MICROCYSTIS AERUGINOSA
Okino Tatsufumi; Matsuda Hisashi; Haraguchi Ryo; Murakami Masahiro; Yamaguchi Katsumi
Symposium on the Chemistry of Natural Products, symposium papers, 34, 486, 493, Symposium on the chemistry of natural products, 10 Sep. 1992
Japanese, Microalgae are rich sources of structurally-novel and biologically-active compounds. In the course of our screening program of enzyme inhibitors from microalgae, we found potent trypsin-inhibitory activity in the extract of cultured freshwater blue-green alga Microcystis aeruginosa. Microcystis aeruginosa (NIES-100) was obtained from the National Institute for Environmental Studies, Japan. The 80% methanol extract of lyophilized alga (248g) harvested from 810L culture was subjected to solvent partition, DEAE, SiO_2 and ODS column chromatography, finally to reversed-phase HPLC using ODS column to obtain trypsin inhibitors named micropeptin A (1) and micropeptin B (2). Molecular formula of micropeptin A was decided as C_<49>H_<78>N_8O_<13> from HRFABMS and NMR data. Amino acid analysis of the acid hydrolyzate gave Thr, Glu, Val, Leu, Lys and N-MeTyr. ^1H-^1H COSY, HOHAHA, HMQC-HOHAHA and HMBC spectra showed the presence of these six amino acids, octanoic acid and 3-amino-6-hydroxy-2-piperidone. Interpretation of HMBC and ROESY spectra revealed the cyclic structure of 1. The structure of 2 only differs from 1 in having hexanoic acid in place of octanoic acid. Chiral GC and LC analyses indicated all the usual amino acids to be in L-form. The IC_<50> of 1 against trypsin and plasmin was 0.071; 0.026μg/mL, respectively.
- Up to Date of Cyanobacterial Natural Products
Okino Tatsufumi, YAKUGAKU ZASSHI, 144, 1, 27, 32, 01 Jan. 2024
More than 2000 compounds have been reported from cyanobacteria. The most successful example is dolastatin 10, of which a related compound monomethylauristatin E is used as antibody-drug conjugate (ADC) for Hodgkin lymphoma and systemic anaplastic large cell lymphoma. Recently genome-based analyses by Piel led to the discovery of novel compounds from cyanobacteria. W. H. Gerwick found a potential as anti-SARS-CoV-2 agent in gallinamide A, which was reported as a cathepsin L inhibitor. In our group columbamides were isolated from the marine cyanobacterium Moorena bouillonii. The geometry of the double bond was determined by the coupling constant obtained using non-decoupled heteronuclear single quantum coherence (HSQC). The configuration of chloromethine in a long-chain acyl moiety was determined by the Ohrui method at room temperature using a chiral HPLC column. Columbamide D showed biosurfactant activity. One strain many compounds (OSMAC) is a method to discover new compounds by changing culture conditions. Prior to our experiments, attempts to apply OSMAC in cyanobacteria resulted in the induction or up-regulation of only known compounds. The heat shock culture of the freshwater cyanobacterium Microcystis aeruginosa up-regulated a ribosomal peptide argicyclamide C. At the same time, we discovered bis-prenylated and monoprenylated argicyclamides A and B. More recently iron-limited culture produced hydroxylated argicyclamide A. OSMAC and genome-based screening could lead the discovery of unique biologically active compounds from cyanobacteria., The Pharmaceutical Society of Japan, Japanese - Antifouling Research Against Marine Organisms: A Long Battle against Barnacles
OKINO Tatsufumi, KAGAKU TO SEIBUTSU, 59, 1, 16, 22, 01 Jan. 2021
船底防汚塗料への有機スズ化合物の使用が世界的に禁止されてから13年が経過した．その間新規の防汚剤は2種だけである．表面の微細構造や物性による防汚技術開発も進む一方で，防汚剤の有効性・必要性は確かである．しかしながら，結局化学物質を海洋に放出することと化学物質の環境規制の強化のため，新規の防汚剤の開発は困難を極めている．そのなかで，最近，フジツボのオクトパミンレセプターに作用する化合物が新規防汚剤として上市された．一方，天然物からの探索研究も活発であり，非常に活性の高い化合物も発見されているし，生分解性や低毒性に着目しながら開発フェーズが進んでいる化合物もある．, Japan Society for Bioscience, Biotechnology, and Agrochemistry, Japanese - 海洋生物由来の天然有機物質による付着生物阻害効果
沖野 龍文, 塗装工学, 54, 452, 456, 2019 - ウナギの産卵生態に関する研究 2)
渡邊俊; 塚本勝巳; 三輪哲也; 黒木真理; MILLER M. J; 樋口貴俊; 竹内綾; 芹澤健太; 沖野龍文; 滝川一雅; 石原徹也; 栗本穂高; 押谷俊吾; 奈須俊勝, 日本水産学会大会講演要旨集, 2018, 38, 26 Mar. 2018
Japanese - ウナギの産卵生態に関する研究 1)
渡邊俊; 塚本勝巳; 三輪哲也; 黒木真理; MILLER M. J; 樋口貴俊; 竹内綾; 芹澤健太; 沖野龍文; 滝川一雅; 石原徹也; 栗本穂高; 押谷俊吾; 奈須俊勝, 日本水産学会大会講演要旨集, 2018, 38, 26 Mar. 2018
Japanese - ウナギの産卵生態に関する研究
塚本勝巳; 渡邊俊; 三輪哲也; 黒木真理; MILLER M. J; 樋口貴俊; 竹内綾; 芹澤健太; 沖野龍文; 滝川一雅; 石原徹也; 栗本穂高; 押谷俊吾; 奈須俊勝, ブルーアース要旨集, 2018, 20, 2018
Japanese - Anti-fouling Effects of Natural Compounds from Marine Organisms
G. Petitbois Julie; 沖野 龍文, Marine engineering : journal of the Japan Institute of Marine Engineering = マリンエンジニアリング :日本マリンエンジニアリング学会誌, 52, 1, 33, 37, Jan. 2017
日本マリンエンジニアリング学会, Japanese - 海洋生物由来の天然有機化学物質による付着生物阻害効果
PETITBOIS Julie G; 沖野龍文, マリンエンジニアリング, 52, 1, 33‐37, 37, 01 Jan. 2017
日本マリンエンジニアリング学会, Japanese - Accumulation of allelochemicals in sweet vernal grass (Anthoxanthum odoratum)and impact to pasture renovation
毛糠智子; 平田聡之; 沖野龍文; 山田敏彦, 日本育種学会・日本作物学会北海道談話会会報(Web), 58, 30‐31(J‐STAGE), 31, 2017
Hokkaido Branch, the Japanese Society of Breeding and Hokkaido Branch, the Crop Science Society of Japan, Japanese - 紅藻マギレソゾLaurencia saitoi由来ブロモペルオキシダーゼの臭素化反応
正木志良; 金子賢介; 小林大毅; 石川高史; 西川慶祐; 森本善樹; 鷲尾健司; 森川正章; 沖野龍文, 日本農芸化学会大会講演要旨集(Web), 2016, 4B032 (WEB ONLY), 05 Mar. 2016
Japanese - Acyl amides from Okeania sp. collected from the Red Sea, and Moorea bouillonii from Malaysia
Petitbois Julie Gabrielle; Lopez Julius Adam Velasco; Al-lihaibi Sultan; Alarif Walied; Abdel-Lateff Ahmed; Vairappan Charles; Okino Tatsufumi, Symposium on the Chemistry of Natural Products, symposium papers, 58, Poster34, 2016
Marine cyanobacteria are bountiful sources of novel bioactive compounds, including metabolites composed of an acyl chain bonded to an amine moiety. In this presentation, the isolation and structure elucidation of three acyl amides, serinolamide C (1), columbamide D (2) and E (3), from genetically close cyanobacteria, Okeania sp. collected from the Red Sea and Moorea bouillonii from Malaysia, are reported.
The two filamentous cyanobacteria were collected by SCUBA, near Jeddah, Saudi Arabia, for Okeania sp., and near Kota Kinabalu, Malaysia, for Moorea bouillonii. They were identified by 16S rRNA gene sequencing analysis using cyanobacteria-specific primers. Both samples were extracted with MeOH followed by liquid/liquid partition using EtOAc and H2O and subsequently n-BuOH. The obtained fractions were tested against Amphibalanus amphitritebarnacle larvae for antifouling activities, and against MCF-7 breast cancer cells for cytotoxicity. A series of open column chromatographies and HPLCs afforded 11.9 mg of 1, 1.5 mg of 2 and 0.5 mg of 3.
The molecular formulae of 1, 2, and 3 were determined by MS as C21H41NO3, C23H43Cl2NO3 and C23H42Cl3NO3respectively, suggesting two unsaturations. Dereplication using 1H NMR data showed serinolamides (Gutierrez et al., 2011) and columbamides (Kleigrewe et al., 2015) as the nearest candidates. Several techniques of NMR allowed elucidating their planar structure. Partial synthesis of 1 yielded to the determination of its stereochemistry by comparison with the two synthesized enantiomers. Similar study is in progress concerning 2 and 3, in parallel with further investigation of their bioactivities., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 紅藻ミツデソゾLaurencia okamurae由来ブロモペルオキシダーゼの性状解析
石川高史; 金子賢介; 湯暁蓉; 鷲尾健司; 森川正章; 沖野龍文, 化学系学協会北海道支部冬季研究発表会講演要旨集(CD-ROM), 2016, ROMBUNNO.1B17, 2016
Japanese - Total synthesis of natural antifouling products
Taiki Umezawa; Keisuke Nishikawa; Tatsufumi Okino; Fuyuhiko Matsuda, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 74, 7, 689, 699, 2016
Society of Synthetic Organic Chemistry, Japanese, Book review - ニホンウナギの産卵回遊生態の解明に向けて
渡邊俊; 三輪哲也; 福場辰洋; 沖野龍文; 丸山奏子; 岡村明浩; 佐藤優太; 水品亜由菜; 樋口貴俊; 竹内綾; 宮尾萌莉; 加来剛; 坂本洋平; MILLER Michael J; 塚本勝巳, 日本水産学会大会講演要旨集, 2015, 48, 27 Mar. 2015
Japanese - 紅藻ソゾ属3種のブロモペルオキシダーゼの活性評価
金子賢介; 小林大毅; 鷲尾健司; 森川正章; 沖野龍文, 日本化学会講演予稿集, 95th, 4, 1409, 11 Mar. 2015
Japanese - Wewakazole B, A New Cyclic Dodecapeptide from the Red Sea Cyanobacterium Moorea producens
Lopez Julius Adam Velasco; Al-Lihaibi Sultan S.; Alarif Walied M.; Abdel-Lateff Ahmed; Washio Kenji; Morikawa Masaaki; Okino Tatsufumi, Symposium on the Chemistry of Natural Products, symposium papers, 57, PosterP23, 2015
Cyanobacteria are prolific sources of novel bioactive compounds. The chemical profiles we obtained using LC-MS and checked with the MarinLit database showed that there are potential new compounds from Moorea producens samples obtained from the Red Sea. In this presentation the isolation and structure elucidation of a new cyclic dodecapeptide, wewakazole B (1), is reported.
The brownish-red filamentous sample was obtained by SCUBA near Jeddah, Saudi Arabia. A small portion of the sample was preserved in RNAlater and identified as M. producens by standard 16S rRNA gene sequencing using cyanobacteria-specific primers 106F and 1509R, and internal primers 359F and 781R (Martinez-Murcia et al., 1995; Nubel et al., 1997). The bulk of the sample was extracted with methanol followed by solvent partition using EtOAc and water, then, BuOH. These extracts were tested for antifouling activity against the barnacle larvae Amphibalanus amphitrite, cytotoxicity against MCF-7 breast cancer cells, and trypsin inhibition. LC-MS was carried out in parallel for dereplication in conjunction with the MarinLit database. The extracts were found to be inactive but a unique [M+H]+ m/z of 1127 was detected in the EtOAc extract and was pursued. A series of open column chromatography and HPLCs afforded 0.4 mg of 1.
The molecular formula, C58H70N12O12, determined by HRESIMS ([M+H]+ m/z1127.5310, ∆ = 0.39 ppm), suggested thirty unsaturations. Dereplication using mass and 1H NMR data showed wewakazole (Nogle et al., 2003) as the nearest candidate. HSQC, COSY, and TOCSY revealed nine common and three modified amino acid residues which were connected by HMBC and ROESY correlations acquiring five fragments. Connections to the oxazole and methyloxazole fragments proved to be a challenge due to the lack of correlations towards neighboring amino acids. All possible combinations were considered that lead to the most logical planar structure and cyclic sequence. Chiral LC-MS and HPLC analysis showed that all amino acid residues possess the L- configuration. The wewakazoles are the only cyclic peptides from marine cyanobacteria having both Oxz and MeOxz. Their function and bioactivity require further investigation., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 紅藻ウラソゾLaurencia nipponica由来バナジウム依存型ブロモペルオキシダーゼの性状解析
KANEKO KENSUKE; WASHIO KENJI; UMEZAWA DAIKI; MATSUDA FUYUHIKO; MORIKAWA MASAAKI; OKINO TATSUFUMI, 日本水産学会大会講演要旨集, 2014, 119, 27 Mar. 2014
Japanese - Bromoperoxidases from Laurencia species
Kaneko Kensuke; Washio Kenji; Umezawa Taiki; Kobayashi Daiki; Tang Xiaorong; Matsuda Fuyuhiko; Morikawa Masaaki; Okino Tatsufumi, Symposium on the Chemistry of Natural Products, symposium papers, 56, Poster53, 2014
The genus of red alga Laurencia is one of the richest producers of halogenated compounds (mostly brominated) 3). Murai et al 4) and Butler et al 9) showed enzymatic bromination of Laurencia C15acetogenins including laurencin (1) 1,2)and sesquiterpenoids snyderols using partially purified bromoperoxidase (BPO) from L. nipponica and vanadium-dependent BPO (VBPO) from a mixture of red algae including L. pacifica. However, since the lack of information of sequences, the structural information and biochemical aspects of BPO from L. nipponica and VBPO from L. pacifica remains unknown. Here, we report cDNA cloning of VBPOs from L. nipponicaand in vitro enzymatic bromination of putative biosynthetic precursors using recombinant enzymes.
Two VBPOs (LnVBPO1 and LnVBPO2) were cloned from L. nipponica and recombinant LnVBPOs were prepared. Recombinant LnVBPOs were subjected to enzyme activity assay. A general substrate, monochlorodimedone (MCD), was utilized for Km determination for H2O2 and , essential for bromination of organic substrate. Km for H2O2was 0.03 mM in both LnVBPOs, Km for were 0.53 mM for LnVBPO1 and 0.35 mM for LnVBPO2, respectively. A derivative of putative precursor of laurencin (1), TMS-capped (3E, 6R, 7R)-laurediol (4) was subjected to LnVBPOs enzymatic bromination and gave similar MS/MS spectrum of deacetylaurencin (3). Since the compound 3 is considered to be the final precursor of 1, it is suggested that VBPO catalyzes bromination in Laurenciametabolites.
We also cloned VBPOs from other Laurencia spp. which produce brominated sesquiterpenoids (L. okamurae) and triterpenoids (L. saitoi). We will discuss in vitro enzymatic bromination of these two LaurenciaVBPOs., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 紅藻ウラソゾLaurencia nipponica由来バナジウム依存型ブロモペルオキシダーゼの性状解析
KANEKO KENSUKE; WASHIO KENJI; UMEZAWA DAIKI; MATSUDA FUYUHIKO; MORIKAWA MASAAKI; OKINO TATSUFUMI, マリンバイオテクノロジー学会大会講演要旨集, 15th, 68, 01 Jun. 2013
Japanese - 紅藻ウラソゾと軟体動物クロヘリアメフラシから得られた付着阻害物質laurencin
沖野龍文; 金子賢介; 吉村えり奈; 古田岳志; 野方靖行, 日本水産学会大会講演要旨集, 2013, 107, 26 Mar. 2013
Japanese - Total Synthesis of Omaezallene and Determination of its Absolute Stereochemistries
Umezawa Taiki; Yamazaki Shohei; Oguri Yuko; Matsuura Hiroshi; Suzuki Masahiro; Okino Tatsufumi; Matsuda Fuyuhiko, Symposium on the Chemistry of Natural Products, symposium papers, 55, Oral24, 2013
Omaezallene (1) was isolated from Laurencia sp. and showed strong antifouling activity against the larvae of the barnacle amphitrite. Although organotin compounds, such as tributyltin (TBT), had been widely used as a fouling inhibitor, the use of TBT was prohibited by IMO in 2008 due to its toxicity. Therefore, the development of the potent nontoxic fouling inhibitor is desired strongly, and 1 is expected to be a lead compound as the fouling inhibitor. Although the relative and absolute structure of 1 was assumed using 1D- and 2D-NMR experiments, the relative configurations have not been determined completely, especially the configuration at C9 position. To determine the relative configurations as well as the absolute configuration, the synthetic study toward 1 was started.
The synthesis commenced with the known aldehyde 3, derived from D-glucose in 5 steps, which was transformed into the unsaturated ester 8 with E geometry. The ester 8 was next converted to the hemiacetal 10 in 3 steps. The treatment of ethynylmagnesium chloride to 10 afforded the desired propargy alcohol 4 as a major diastereomer. Cyclization of 4 with NBS furnished the construction of the two contiguous stereocenters to give bromoether 11 in a highly stereoselective manner, which was then derived to the aldehyde 6 in 4 steps. 6 was successfully converted to 1via cyanohydrin formation, HWE reaction, and Wittig reaction involving in-situ bromination of reagent. By the total synthesis, the absolute configuration of 1was unambiguously determined as shown in scheme 5., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 紅藻ウラソゾにおける種内構造の解明
木下大旗; 小亀一弘; 渡邉摩美; 沖野龍文; 阿部剛史, 藻類, 60, 2, 2012 - オマエザレンの全合成
UMEZAWA TAIKI; SUZUKI MASAHIRO; OGURI YUKO; MATSUURA HIROSHI; OKINO TATSUFUMI; MATSUDA FUYUHIKO, 天然有機化合物討論会講演要旨集, 53rd, 637, 642, 02 Sep. 2011
Japanese - 御前崎産ソゾ属紅藻から得られた付着阻害活性を有するジテルペノイドomaezol
渡邉摩美; 小栗祐子; 松浦裕志; 沖野龍文; 吉村えり奈; 野方靖行, 日本水産学会大会講演要旨集, 2011, 101, 27 Mar. 2011
Japanese - 北海道沿岸における紅藻ウラソゾのケミカルレースと遺伝的多様性
木下大旗; 小亀一弘; 渡邉摩美; 沖野龍文; 阿部剛史, 藻類, 59, 1, 2011 - 黄金色藻 Ochromonas danica の特異な脂質クロロスルホリピド : 発見から40年後に単離して立体化学を解明
河原 哲平; 沖野 龍文, 化学と生物, 48, 12, 814, 817, 01 Dec. 2010
Japan Society for Bioscience, Biotechnology, and Agrochemistry, Japanese - Isocyanocadinene及びその立体異性体の合成とそれらの着生阻害活性の評価
西川慶祐; 代蔵陽介; 野方靖行; 吉村えり奈; 梅澤大樹; 沖野龍文; 松田冬彦, 日本化学会講演予稿集, 90th, 4, 1043, 12 Mar. 2010
Japanese - 黄金色藻Ochromonas danicaのクロロスルフォリピッド類の単離と立体化学
河原哲平; 沖野龍文, 日本水産学会大会講演要旨集, 2009, 2009 - 御前崎産紅藻Laurencia sp.より得られたタテジマフジツボ幼生着生阻害物質(第2報)
小栗祐子; 松浦裕志; 鈴木稔; 沖野龍文; 古田岳志; 野方靖行, 日本化学会北海道支部研究発表会講演要旨集, 2008, 65, 18 Jan. 2008
Japanese - Holocene temperature change in the northern East China Sea
Nakanishi Takahiro; Yamamoto Masanobu; Okino Tatsufumi; Irino Tomohisa; Oda Hirokuni; Yokoyama Yusuke; Matsuzaki Hiroyuki; Tada Ryuji, Abstracts of Annual Meeting of the Geochemical Society of Japan, 55, 414, 414, 2008
KY07-04航海により採取されたピストンコアPC-1とマルチプルコアPL-1を使用して、東シナ海北部の過去5000年間の表層水温を、バイオマーカー指標であるアルケノンに基づくUK37’とGDGT指標であるTEX86を用いて、40年から80年間隔と時間的解像度を高めて水温変動を復元した。アルケノン水温は過去5000年間に渡って23.5℃から24℃とほぼ一定の値を示した。一方、TEX86水温はアルケノン水温とは異なり、20.4℃から24.8℃の間で激しく変動した。両者の水温変動に違いが見られる理由として、それぞれの物質をつくる生物の生息時期や深度の違いが挙げられるが、GDGTをつくるクレンアーキオータの生息深度は不明である。これを解決する手段として、本年５月に行われたKT08-10航海にてコアサイト付近の表層から中層の海水を採取し、ろ過後脂質を抽出し、GDGTを分析した。発表では、海水より求めたTEX86水温の結果も合わせて報告する。, GEOCHEMICAL SOCIETY OF JAPAN - Reconstruction of TEX86 paleotemperatures reconstruction in the Beppu Bay over the last 1500 years.
ichikawa norio; yamamoto masanobu; okino tatsufumi; kuwae mishinobu; sugimoto takashige; takeoka hidetaka, Abstracts of Annual Meeting of the Geochemical Society of Japan, 55, 413, 413, 2008
地球環境の将来予測において，歴史時代の気温，降水量の変化を復元することが急務である。本研究では，別府湾から採取した海底コアに含まれるテトラエーテル脂質（GDGT）を分析することにより，過去1500年間の別府湾の水温の変動を復元した。復元した結果、西暦500年頃から1040年頃にかけては14～16℃前後の低い値を推移し、1050年頃から1400年頃の間では17℃前後の高温になり、1300年頃から2005年までは13℃～17℃まで範囲で激しく変動した。, GEOCHEMICAL SOCIETY OF JAPAN - 黄金色藻Ochromonas danicaから得られるchlorosulfolipid類の構造解析
河原哲平; 沖野龍文, 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, 2008, 2008 - 御前崎産紅藻Laurencia sp.より得られたタテジマフジツボ幼生着生阻害物質
小栗祐子; 松浦裕志; 鈴木稔; 沖野龍文; 古田岳志; 野方靖行, 日本水産学会大会講演要旨集, 2007, 10, 25 Sep. 2007
Japanese - Kalkitoxin類縁体の合成と生物活性
韓雪容; 末田学; 河原哲平; 沖野龍文; 松田冬彦, 日本化学会北海道支部研究発表会講演要旨集, 2007, 2007 - ラン藻Microcystis aeruginosaから得られた酵素阻害ペプチド—第16回 天然薬物の開発と応用シンポジウム講演要旨集
来生 貴也; 沖野 龍文, 薬学雑誌 / 日本薬学会 編, 126, -, 250, 253, 2006
日本薬学会, Japanese - Synthesis and Biological Properties of Kalkitoxin
末田学; 韓雪容; 河原哲平; 沖野龍文; 松田冬彦, 日本化学会講演予稿集, 86th, 2, 2006 - Heterocycles from cyanobacteria
Okino, T, 1, 2006 - 自然科学実験
学術図書出版社, 2005 - ラン藻由来の微量神経活性成分の構造決定
沖野 龍文, 化学と生物, 41, 8, 517, 521, 25 Aug. 2003
Japan Society for Bioscience, Biotechnology, and Agrochemistry, Japanese - 「アレロパシー現象」
『２１世紀初頭の藻学の現況』, 63, 66, 2002 - 30 Kalkitoxin, a Potent Neurotoxin from the Marine Cyanobacterium Lyngbya majuscula
Okino Tatsufumi; Wu Min; Sitachitta Namthip; Nogle Lisa M.; Marquez Brian L.; Williamson R. Thomas; Gerwick William H.; Murray Thomas F.; Colson Kimberly; Asano Toshinobu; Yokokawa Fumiaki; Shioiri Takayuki, Symposium on the Chemistry of Natural Products, symposium papers, 42, 175, 180, 2000
Marine cyanobacteria are a rich source of a variety of structurally-unique and biologically-active natural products. Isolation and structure elucidation of kalkitoxin, a potent neurotoxin from the marine cyanobacterium Lyngbya majuscula, is presented. Isolation of this compound was aided by bioassay-guided fractionation using the brine shrimp and gold fish toxicity assays. The planar structure of this thiazoline-containing lipid was elucidated by standard 1D and 2D NMR data. The stereochemistry of C-3 was determined to be R by Marfey's method, while the relative stereochemistry within the aliphatic chain of kalkitoxin was suggested to be 7R^*, 8S^*, 10S^* by J-based configuration analysis using a new NMR pulse sequence, HSQMBC, and a cryoproba NMR technology. Five synthetic isomers of kalkitoxin were compared to the natural compound by ^1H and ^<13>C NMR and CD spectroscopy. ^<13>C NMR chemical shifts showed very small differences in the range of less than 0.2ppm to natural kalkitoxin. However, the 3R,7R,8S,10S,2'R isomer showed maximal ^<13>C NMR differences of 0.026ppm with an average difference of only 0.008ppm. In addition, its CD spectrum was identical with natural kalkitoxin. Natural kalkitoxin is strongly ichthyotoxic (LC_<50> 700nM) and potently brine shrimp toxic (LC_<50> 170nM). Synthesized kalkitoxin was similarly potent in the brine shrimp assay (LC_<50> 170nM). Interestingly the synthesized enantiomer of kalkitoxin was relatively inactive (LC_<50> 9300nM). Kalkitoxin also showed potent NMDA receptor-mediated neurotoxicity (LC_<50> 3.86±1.91nM)., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 116(P-48) Total Synthesis of Kalkitoxin, a Neurotoxin from the Marine Cyanobacterium Lyngbya majuscula
Asano Toshinobu; Yokokawa Fumiaki; Shioiri Takayuki; Okino Tatsufumi; Gerwick William H., Symposium on the Chemistry of Natural Products, symposium papers, 42, 691, 696, 2000
Kalkitoxin (1) is a potent ichthyotoxic metabolite of the marine cyanobacterium, Lyngbya majuscula collected in Curacao. It has also exhibited a neurotoxicity in rat cerebellar granule neurons. Kalkitoxin is a small molecule, which consists of 5 asymmetric carbons, N-methyl amide moiety and a thiazoline ring. Its NMR spectra are complicated due to a high degree of methylation and the presence of tertiary amide isomers. Furthermore, the amount of natural kalkitoxin is very minute, and firm assignment of structure by method other than synthesis might be difficult. According to our strategy, we initially started to synthesize (3R,7R,8S,10R,2'S)-kalkitoxin. Synthesis of the chiral alcohol 8 having 1,3-dimethyl moiety was prepared from 6 in 9 steps. The primary alcohol of 6 was converted to the corresponding azide 9 by our one-pot p-NO_2-DPPA-DBU method. Selective reduction of azide, coupling with (S)-2 using DEPC, and N-methylation afforded 10. Oxidation followed by a Horner-Emmons reaction simultaneously homologated and introduced the (R)-phenylglycine derived auxiliary. Introduction of C7 methyl group by Hruby's method proceeded smoothly to give methyl adduct 13 as a single isomer. Finally, removal of chiral auxiliary, coupling with (R)-2-amino-3-butenol and thiazoline formation by Wipf's oxazoline-thazoline interconversion provided (3R,7R,8S,10R,2'S)-kalkitoxin (16). We also prepared enimide 17 having (S)-phenylglycine derived oxazolidinone in the same manner, followed by 1,4-addition to give 7S adduct 18 selectively. As the above result, we found that the introduction of C7 methyl group using 1,4-addition could be completely controlled by the chiral auxiliary. During this investigation, the relative stereochemistry 7R^*,8S^*,10S^* was deduced and the absolute stereochemistry 3R was determined by our co-workers. Thus, we synthesized (3R,7R,8S,10S,2'S)-, (3S,7R,8S,10S,2'S)-, (3R,7S,8R,10R,2'S),- (3S,7S,8R,10R,2'S)-, and (3R,7R,8S,10S,2'R)-configurations. (3R,7R,8S,10S,2'R)-kalkitoxin was found to be identical in all respects to natural kalkitoxin (1)., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - Chemical languages in larval settlement of marine organisms - Settlement inhibiting substances against barnacles, and settlement inducing substances in ascidians
H Hirota; S Tsukamoto; T Okino; N Fusetani, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 55, 12, 1134, 1145, Dec. 1997
Japanese, Book review - Bioactive Products from Blue-Green Algae
OKINO Tatsufumi, 化学と生物, 35, 8, 556, 563, 25 Aug. 1997
学会出版センタ-, Japanese - Bioactive Products from Blue-Green Algae.
OKINO Tatsufumi, KAGAKU TO SEIBUTSU, 35, 8, 556, 563, 1997
Japan Society for Bioscience, Biotechnology, and Agrochemistry, Japanese - P-26 THROMBIN INHIBITORS FROM THE BLUE-GREEN ALGA MICROCYSTIS VIRIDIS (NIES-102)
MATSUDA Hisashi; OKINO Tatsufumi; OKITA Yuji; ISHIDA Keishi; MURAKAMI Masahiro; YAMAGUCHI Katsumi, Symposium on the Chemistry of Natural Products, symposium papers, 37, 421, 426, 1995
We have found that blue-green algae Microcystis spp. are a new and rich source of unique protease inhibitors, and in fact have reported the isolation and structure elucidation of several protease inhibitors from some strains of M. aeruginosa. Here we describe the isolation and structure elucidation of aeruginosins 102-A(1) and B(2) from M. viridis (NIES-102). Microcystis viridis (NIES-102) was obtained from the National Institute for Environmental Studies, Japan. The 80% methanol extract of lyophilized alga (207g) was subjected to solvent partition, ODS column chromatography followed by ODS HPLC to obtain 1 and 2. Aeruginosins 102-A(1) and B(2) separeted into three peaks each in the HPLC due to the tautomerization of Argal in the same manner as in leupeptin. Molecular formula of 1 was decided as C_<33>H_<44>N_6O_<11>S from HRFABMS (731.2704 [M-H]^- Δ-0.7mmu) and NMR data. Amino acid analysis of the acid hydrolyzate gave Tyr. ^1H-^1H COSY, HMQC and HMBC spectra showed the presence of Hpla sulfate (p-hydroxyphenyllactic acid sulfate), Tyr, Choi (2-carboxy-6-hydroxyoctahydroindole) and Argal (argininal). Interpretation of HMBC and NOESY spectra revealed the planar structure of 1 and 2. The absolute stereochemistries of Hpla sulfate, Tyr and Argal were determined to be D-, D- and L-form by the chiral GC or HPLC, respectively. The structure of 2 were identical to those of 1 except the absolute stereochemistry of Argal(D-form). The IC_<50> of 1 and 2 against thrombin were 0.04 and 0.1μg/mL, respectively., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - アオコに含まれるプロテア-ゼ阻害物質--タ-ゲットを毒素以外の成分にしてスクリ-ニング(今日の話題)
沖野 竜文; 村上 昌弘, 化学と生物, 32, 4, p213, 215, Apr. 1994
学会出版センタ-, Japanese - P-15 SERINE PROTEASE INHIBITORS FROM THE BLUE-GREEN ALGA MICROSYSTIS AERUGINOSA (NIES-98)
Murakami M.; Ishida K.; Okino T.; Okita Y.; Matsuda H.; Yamaguchi K., Symposium on the Chemistry of Natural Products, symposium papers, 36, 493, 500, 1994
Recently, Microcystis aeruginosa has been demonstrated to be a valuable source of unique biologically active peptides. In the course of our studies of protease inhibitors from microalgae, freshwater blue-green alga M aeruginosa (NIES-98) showed potent serine protease inhibitory activities. Here we report the isolation and structure elucidation of aeruginosin 98-A(1), B(2) and C(3) which inhibit trypsin, and aeruginoguanidine 98-A(4), B(5) and C(6) which shows weak cytotoxic activities. Microcystis aeruginosa (NIES-98) was obtained from the NIES-collection (Microbial Culture Collection, the National Institute for Environmental Studies, Japan). The 80% methanol extract of freeze-dried alga was partitioned between water and diethyl ether. The aqueous layer that showed potent trypsin inhibitory activity was further extracted with n-butanol and subjected to ODS column chromatography, followed by ODS HPLC to yield 1-6. Molecular formula of 1 was decided as C_<29>H_<45>N_6O_9ClS from HRFABMS and NMR data. Amino acid analysis of the acid hydrolyzate gave allo-Ile and an unknown imino acid. ^1H-^1H COSY, HMQC and HMBC data showed the presence of Chloro Hpla (3-chloro-4-hydroxyphenyllactic acid), allo-Ile, Choi sulfate (2-carboxy-6-hydroxyoctahydroindole sulfate) and agmatin. Interpretation of HMBC spectra revealed the structure of 1. The stereochemistry of allo-Ile was determined to be D-form by the chiral GC analysis. The relative stereochemistry of Choi sulfate was elucidated by NOESY spectra. The structures of 2 and 3 only differ from 1 in the substitution of the benzene ring of Chloro Hpla. The IC_<50> of 1, 2 and 3 against trypsin was 0.55, 0.6 and 3.93μg/mL, respectively. Molecular formula of 5 was decided as C_<34>H_<59>N_9O_<14>S_3 from HRFABMS and NMR data. ^1H-^1H COSY, HOHAHA, HMQC and HMBC data showed the presence of Hphpa trisulfate (1-(4-hydroxy-3-hydroxymethyl)phenyl-1 -hyciroxy-2-propylamine 4',3', 1-tri- O-sulfate), N-MeArg and NmgArg (Na^α-methyl-N^ω-geranylarginine). Interpretation of HMBC and NOESY spectra revealed the structure of 5. The structures of 4 and 6 were elucidated as analogs of 5, having the different side chains of N-MeArg. These compounds showed weak cytotoxity against P388 leukemia cells., Symposium on the Chemistry of Natural Products Steering Committee, Japanese - 84 STRUCTURES OF SERINE PROTEASE INHIBITORS FROM FRESHWATER BLUE-GREEN ALGAE
Matsuda H.; Okino T.; Haraguchi R.; Murakami M.; Yamaguchi K., Symposium on the Chemistry of Natural Products, symposium papers, 35, 654, 661, 1993
In the course of our studies of protease inhibitors from microalgae, freshwater blue-green algae showed potent serine protease inhibitory activities. Here, we describe the isolation and structure elucidation of nostopeptin A, a chymotrypsin and elastase inhibitor from Nostoc minutum and radiosumin, a trypsin inhibitor from Plectonema radiosum. Nostoc minutum (NIES-26) was obtained from the National Institute for Environmental Studies, Japan. The methanol extract of lyophilized alga was subjected to solvent partition, ODS column chromatography, followed by ODS HPLC to obtain nostopeptin A (1). Molecular formula of 1 was decided as C_<48>H_<74>N_8O_<12> from HRFABMS and NMR data. Amino acid analysis of the acid hydrolyzate gave Glu, Ile and Leu. ^1H-^1H COSY, HOHAHA, HMQC and HMBC data showed the presence of Leu, Gln, N-MeTyr, 3-amino-6-hydroxy-2-piperidone, butyric acid, 3-hydroxy-4-methylproline and two Ile. Interpretation of HMBC and ROESY spectra revealed the sequence of 1. The stereochemistries of the usual amino acids were assigned to be L by the chiral GC analysis of the derivatives of the hydrolyzate. The 80% methanol extract of lyophilized Plectonema radiosum (NIES-515) was subjected to solvent partition, ODS column chromatography, followed by ODS HPLC to yield radiosumin (2). Molecular formula of 2 was established to be C_<22>H_<32>N_4O_5 by the HRFABMS and NMR data. ^1H-^1H COSY, HMQC and HMBC spectra showed the presence of two amino acid residues, 2-amino-3-(4-amino-2-cyclohexen-1-ylidene)propionic acid and 2-amino-3-(4-amino-2-cyclohexylidene)propionic acid, and two acetyl groups. Further analyses of HMBC and NOESY spectra revealed the structure of 2. The stereochemistries were inspected by the chiral GC analyses of the derivatives of degradation products of 2. The IC_<50> of 1 against elastase and chymotrypsin was 1.3 and 1.4μg/mL, respectively. The IC_<50> of 2 against trypsin was 0.14μg/mL., Symposium on the Chemistry of Natural Products Steering Committee, Japanese
- Marine surfactants Preparations and applications
J. J. Mehjabin; T. Okino, 8 Marine algal and cyanobacterial surface-active compounds
CRC Press, 2023, 9781003307464, [Contributor] - 環境修復の科学と技術
北海道大学出版会, 2007 - 「海洋生物成分の利用 マリンバイオのフロンティア」<(伏谷伸宏 監修)>
エヌ・ティー・エス, 2005
- 再生可能エネルギー総論, 2024年, 修士課程, 環境科学
- 大学院共通授業科目（教育プログラム）：One program for Global Goals, 2024年, 修士課程, 大学院共通科目
- 生体物質科学特論Ⅱ, 2024年, 修士課程, 環境科学院
- 国際環境保全学総論, 2024年, 修士課程, 環境科学院
- 環境科学研究基礎論, 2024年, 修士課程, 環境科学院
- 環境起学特別講義Ⅱ, 2024年, 修士課程, 環境科学院
- 統合環境分析法実習, 2024年, 修士課程, 環境科学院
- 環境起学基礎演習, 2024年, 修士課程, 環境科学院
- 大学院共通授業科目（教育プログラム）：JICA開発大学院連携プログラム環境科学, 2024年, 修士課程, 大学院共通科目
- 大学院共通授業科目（一般科目）：自然科学・応用科学, 2024年, 修士課程, 大学院共通科目
- 大学院共通授業科目（教育プログラム）：JICA開発大学院連携プログラム環境科学, 2024年, 修士課程, 大学院共通科目
- 環境計量学特論, 2024年, 修士課程, 環境科学院
- 環境適応学総論, 2024年, 修士課程, 環境科学院
- 環境適応学特論, 2024年, 修士課程, 環境科学院
- 環境科学英語ﾗｲﾃｨﾝｸﾞ特論, 2024年, 修士課程, 環境科学院
- 化学Ⅱ, 2024年, 学士課程, 全学教育
- 環境と人間, 2024年, 学士課程, 全学教育
■ Research Themes
- Elucidation study of antifouling mechanism with natural product derivatives for development of green antifoulant
Grants-in-Aid for Scientific Research
01 Apr. 2018 - 31 Mar. 2022
Umezawa Taiki
Utilization of marine is essential for human activities. The utilizations through ship or cooling pipe for power plant result settlement by organisms to induce waste costs through excess use of oil or clogging pipes. To prevent the settlement, although compounds including heavy metals are used, they are pointed to be toxic against marine organism and environmental. In this study, it was envisioned that natural marine products as defense system of marine livings against the fouling organisms can be used for a green and potent antifouling material through revealing the mechanism of the antifouling system by these compounds.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 18H02271 - 分子ネットワーキングと共培養の統合アプローチによる藍藻からの抗藻ペプチドの探索
科学研究費助成事業
24 Jul. 2019 - 31 Mar. 2021
沖野 龍文; PHAN CHIN SOON
藍藻の生物活性物質の生合成能力を最大限活用するため、自然条件あるいは通常培養条件下では発現していない生合成酵素を誘導することを試みた。マレーシアの藍藻を検討することを当初計画していたが、海外出張ができない状況であったため、前年度同様国内で入手可能な淡水産藍藻に絞って検討した。共培養あるいは種々の培養条件を検討し、LC/MSで生成化合物のプロファイルを検討した結果、淡水産藍藻２種の生産する化合物をターゲットとして定めた。アオコ形成種のMicrocystis aeruginosaから得られた環状ペプチドの平面構造は前年度決定済みであり、今年度は立体配置を決定した。また、天然にはみられない修飾がみられたので、その修飾酵素について、ゲノム解析後クローニングして、組み換えタンパク質を調製して種々の性質を検討した。その修飾の有無によって抗菌活性に違いが生じることが見いだされた。残りの特別研究員の期間を使って、論文発表の予定である。また、別種の藍藻からは、トリプシンを阻害する直鎖ペプチドを発見した。構造決定の結果、spumigin類と類似の構造であるものの、アミノ酸残基が一つ少ないという点でこれまでにない化合物であった。本種についてもゲノム解析を行った結果、見いだされた生合成酵素クラスターにより生産されることが合理的に説明できることがわかった。今回の研究を通して、これまでよく研究されていたラン藻株においても新規化合物を生産するポテンシャルがあることが示された。
日本学術振興会, 特別研究員奨励費, 北海道大学, 19F19096 - Chemical Biology of Halogenated Antifouling Compounds
Grants-in-Aid for Scientific Research
01 Apr. 2016 - 31 Mar. 2020
Okino Tatsufumi
Reaction condition of vanadium-dependent bromoperoxidase from the red alga Laurencia saitoi was optimized to propose its products by MS. Chlorinated compounds were isolated from marine cyanobacteria.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 16H04975 - Synthetic Study on Chlorosulfolipids Fluorescent Probe Directed toward Elucidation of Action Mechanism
Grants-in-Aid for Scientific Research
01 Apr. 2016 - 31 Mar. 2019
Matsuda Fuyuhiko; UMEZAWA Taiki
Chlorosulfolipids (CSLs), first isolated from the freshwater alga, are a unusual family of natural products includes Danicalipin A and Mytilipin C. CSLs are unique in featuring straight chain hydrocarbon skeleton densely functionalized with chlorine atoms. They have drawn considerable attention as substances of toxicological concern, because some of them display cytotoxicity and are associated with seafood poisoning. Due to the unprecedented structure and interesting biological activity, CSLs recently garnered interest as targets of total synthesis. Several groups including our group have achieved total syntheses of CSLs. In this research, synthetic study on fluorescent probes of Mytilipin C and Danicalipin A directed toward elucidation of action mechanism was carried out. We developed synthetic process to stereoselectively construct polychlorinated skeleton of Mytilipin C. We also succeeded synthesis of fluorescent probe of Danicalipin A which exhibited toxicity against brine shrimp.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Hokkaido University, 16K01908 - Chemical factors for spawaning of Japanese eels
Grants-in-Aid for Scientific Research
01 Apr. 2014 - 31 Mar. 2017
Okino Tatsufumi; MARUYAMA Kanako; HAYASHI Shohei; FUKUI Yuri
Sea water of West Mariana Ridge which is a spawning area of Japanese eel was analyzed for amino acids and other small molecules. Amino acid compositions and concentrations were different in depth, sampling point and time. However its PCA results showed the amino acid composition of the spawning area was different from Japanese coastal water and river water. In addition, other small molecule compositions showed some charactersitics in the spawning area. In the laboratory, sea water was anayzed during spawning experiments.
Japan Society for the Promotion of Science, Grant-in-Aid for Challenging Exploratory Research, Hokkaido University, 26660165 - Biosynthetic enzymes of antifouling halogenated compounds
Grants-in-Aid for Scientific Research
01 Apr. 2012 - 31 Mar. 2016
Okino Tatsufumi; MATSUDA Fuyuhiko; UMEZAWA Taiki; NOGATA Yasuyuki; WASHIO Kenji
Vanadium dependent bromoperoxidase (VBPO) was cloned from the red alga Laurencia nipponica which produces a halogenated compound, laurencin. The enzyme catalyzed cyclization and bromination of a precursor of laurencin. Bromination activity of recombinant enzyme was investigated. A similar type of VBPO was cloned from L. okamurae which produces a halogenated sesquiterpenoid, laurinterol. The recombinant enzyme showed bromination activity. In addition, another type of VBPO was cloned from L. saitoi which produces a halogenated triterpenoid. Its properties were investigated by using its recombinant protein. The structure of bromoallene containing C15 compound, omaezallene was reported. Its totaly syntehsis was successfully achieved.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 24380112 - Reconstruction of changes in the atmospheric convection activity in the tropical Pacific Ocean during the last 150,000 years using hydrogen isotopes of biomarkers
Grants-in-Aid for Scientific Research
2007 - 2011
YAMAMOTO Masanobu; IRINO Tomohisa; SUGIMOTO Atsuko; OKINO Tatsufumi
We reconstructed the atmospheric convection activity in the tropical Pacific by analyzing biomarkers in marine cores retrieved from five locations in the tropical Pacific. Paleotemperature records demonstrated that the cold tongue shrunk, the western Pacific warm pool expanded, and zonal temperature gradient was relaxed during the last deglaciation. A deuterium record of fatty acids from the southern South China Sea disagrees with a published stalagmite record from northern Borneo. The latter is consistent with paleotemperature records, suggesting that zonal temperature gradient and the position of convection center has varied in response to precession.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (A), Hokkaido University, 19204051 - 海藻の含ハロゲン化合物の生合成
2008
Competitive research funding - TEX86指標を用いた過去600万年間の北半球水温緯度勾配変化の復元
科学研究費助成事業
2006 - 2007
山本 正伸; 沖野 龍文
本研究では,赤道,低緯度,中緯度,北極の4地点から掘削採取された海底コアに含まれるアーキア(古細菌)起源脂質の分析を行い過去600万年間の古水温の緯度勾配の変化を復元し,緯度方向熱輸送効率の変化と全球的寒冷化の関係を検討した.
平成18年度に確立した液体クロマトグラフ質量分析計を用いたTEX86指標のルーチン分析法を平成19年度は熱帯太平洋コアODP1209,亜熱帯太平洋コアODP1207,温帯太平洋コアODP1014,北極点コアIODP M0004に適用した.
熱帯・亜熱帯太平洋では,過去600年間にTEX86水温は約6℃低下したことを示した.温帯太平洋では10℃程度の温度低下であり,熱帯・温帯間の水温の緯度勾配は500万年前から300万年前は現在の7割程度であり,300万年前以降,徐々に水温勾配が大きくなり,現在のレベルに達したことが明らかにした.
他方,北極点コアではアーキア脂質の組成を詳細に検討した結果,それらの脂質の大部分は陸上土壌中アーキア起源であると推測し,TEX86値から過去の水温を推定することは困難であると判断した.
日本学術振興会, 萌芽研究, 北海道大学, 18654089 - Chemical signal for settlement of echinoderm larvae
Grants-in-Aid for Scientific Research
2005 - 2006
OKINO Tatsufumi; YAZAKI Ikuko
To understand chemical inducers of echinoderma larval metamorphosis and settlement, larvae of sea urchin and sea cucumber were investigated.
Sea urchin larval metamorphosis was induced by water soluble extract of the green alga Ulvella lens, which is used at aquaculture facilities. The active component of the extract was identified as phenylalanine. Phenylalanine showed metamorphosis inducing activity at 5 μM. However, the morphological change by the amino acid was different from the case induced by the alga itself. Combined effect of phenylalanine with other components was suggested.
Sea cucumber larval metamorphosis was investigated using a number of physiologically active compounds. As a result, dopamine, L-DOPA, L-adrenalin, and L-noradrenalin showed larval metamorphosis induction. Especially, dopamine showed strong activity. However, the effect of dopamine was slow-acting.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Hokkaido University, 17580176 - ゲルと海洋生物起源忌避物質のハイブリッド防汚剤・塗料の研究開発
2005
沖野 龍文
貝類や藻類の船底への付着を防ぐための船底塗料は、従来有害な重金属等が使用され深刻な環境問題を引き起こしてきた。本研究開発では、付着生物以外には影響を与えない安全性の高い海洋生物起源の忌避物質の高い付着阻害機能と既存の塗料にはない低摩擦抵抗機能をもつ高分子ゲルを融合させたハイブリッド防汚剤・塗料を開発・実用化する。本技術は海洋環境の保全に貢献するほか船舶の長寿命化にも貢献する。
科学技術振興機構, 産学が連携した研究開発成果の展開/研究成果展開事業/平成20年度までに募集を終了した事業/独創的シーズ展開事業/大学発ベンチャー創出推進, 08005312 - 海洋ラン藻の生産するポリケチド・ペプチド複合化合物
科学研究費助成事業
2001 - 2002
沖野 龍文
海洋ラン藻Lyngbya majusculaより得られたポリケチド・ペプチド複合化合物antillatoxinについて、天然およびその立体異性体3種の構造をもつ化合物が合成されたので、供与を受け、その生物活性と溶液中の構造を調べた。まず、天然物と一致するスペクトルを与えた合成品の構造が、推定構造と異なっていたので、天然物の構造を最新のNMRのテクニックを用いて、誤りの原因とスペクトル的にも合成品の構造と矛盾しないことを確認した。次に、生物活性を5種の方法、つまり魚毒性、ラット小脳顆粒ニューロンを用いたマイクロフィジオメトリー法およびLDH活性、細胞内カルシウム濃度、neuro2a細胞に対する細胞毒性を調べた。その結果、いずれの場合も非常に高い活性を天然物の構造の化合物のみが示した。次に、NOEおよびカップリング定数の情報をNMRにより得た上で、MM2法によるモデリングにより、4種の立体異性体の溶液中の高次構造を推定した。その結果、天然物は、L型の構造を有しており、極性官能基が分子の表面に位置していることが予想された。さらに、他の異性体との活性の差は、高次構造が顕著に異なるためであることが判った。この結果は現在投稿中である。
次に、北海道沿岸の海洋藻類を採集し、抽出物を調製のうえ、スクリーニングに供した。スクリーニング法としては、抗菌活性と今年度開発した簡便な付着珪藻着生阻害活性を用いた。その結果、得られた活性種のうち、4種について付着珪藻着生阻害活性を指標に活性成分の分離を試み、再現性のある活性画分を得ることができた。
日本学術振興会, 若手研究(B), 北海道大学, 13760153 - 天然物由来船底防汚剤の開発
2001
Competitive research funding - Natural antifouling compounds
2001
Competitive research funding - Studies on postharvest sciences of agricultural and marine products in Thailand
Grants-in-Aid for Scientific Research
1998 - 2000
YANAGISAWA Tadashi; YONEYAMA Kouichi; YOSHIDA Masao; KANNO Chouemon; YAMANE Kenji; OKINO Tatsufumi
Large quantity of agricultural and marine products were harvested in Thailand according to the hot climates. Some of the harvested products were, nevertheless, discarded owing to the deterioration. So, the postharvest studies, so-called high quality maintenance studies are necessary.
This study is composed of two projects. 1. In the field of horticulture (for example flowers), how to keep the flowers fresh? In this study, Prof.Yoshida, Prof.Yoneyama and Assoc.Prof.Yamane discussed with Prof.Saichol Ketsa in Kasetsart University. 2. In the field of marine products (for example shrimp), how to select the strong strains? In this study, Prof.Yanagisawa, Prof.Kanno and Assoc.Prof.Okino discussed with Doctor Somvong Tragoonrung in Kasetsart University.
In these three years, we visited Bangkok (3 times), Chiang Mai (once) and Phuket (once) Two foreign scientists visited Utsunomiya University 3 times. We were able to discussed many valuable postharvest sciences of agricultural and marine products in Thailand and get more friendly with each other.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B)., Utsunomiya University, 10045059 - 高温環境に生息するラン藻が産生する蛋白分解阻害剤の構造と阻害機構
科学研究費助成事業
1997 - 1998
沖野 龍文
温泉などの高温環境に生息するラン藻をターゲットに、他の環境からは得られない新規の化合物を得て、様々な生命現象に関与する蛋白分解の阻害剤の開発を目的に本研究を行った。
まず第1に、昨年度確立した高熱環境に生息するラン藻からのスクリーニングシステムにより、蛋白分解阻害活性のスクリーニングを継続した。栃木県内の温泉より採取したラン藻を、研究室で予備培養後、単一な藻種として単離し、数リットル規模の培養を行い、培養藻体からの抽出液および培養ろ液からスクリーニング用試料を調製した。これまでに培養の完了した約70種の株について、パパイン、トリプシン、キモトリプシン、トロンビン、エラスターゼ、ロイシンアミノペプチダーゼ、アミノペプチダーゼM、プロリルエンドペプチダーゼなどの酵素阻害活性を測定し、昨年度の結果に加え、多くの株に阻害活性を見いだした。
次に、トロンビンに対し阻害活性を示した未同定藻類とプロリルエンドペプチダーゼに阻害活性を示した未同定藻類について大量培養を行い、その活性本体の精製を試みた。脂溶性の低極性物質の複数成分により活性を発現すると考えられた。また、アミノペプチダーゼMに対し阻害活性を示した未同定ラン藻についても、大量培養後、活性物質の精製を試みた。その結果、水溶性のペプチド性化合物であることが示唆された。
今後、これら化合物から実用的な蛋白阻害剤が開発されることが期待される。
日本学術振興会, 奨励研究(A), 宇都宮大学, 09760189 - 土壌および温泉環境に生息する藍藻生産とその二次代謝産物
科学研究費助成事業
1996 - 1996
沖野 龍文
土壌および温泉環境に生息する藍藻の二次代謝産物に関し、研究を行い以下の成果をあげた。
まず、大学近郊の温泉、水田などより採集を行い、実験室に持ち帰り、予備培養後、単離を試みた。その際、培養温度を2段階に設定したところ、高温でのみ生息するものも見られた。これらにつき、中規模培養を行い、その藻体及び培養ろ液を抽出、粗分画し、各種プロテアーゼ阻害活性試験を行った。その結果、トロンビン、パパインに強い活性をもつものが多数認められた。これまで、藍藻類ではパパイン阻害活性がみられることは少なく、またトリプシンなどに阻害活性を示すことなくトロンビンに阻害活性が認められることもほとんどなかったので、新しいタイプの阻害物質が生産されていることが示唆された。このうち、Chroococcus属の1種は広範囲の酵素に阻害活性を示したが、特にトロンビンには非常に強い活性を示し、有望である。そこで、それらにつき大量培養を行い、活性物質の精製を試みているところである。
また、コレクションより入手した藍藻について酵素阻害物質の探索を行い、以下の物質を得ることが出来た。Microcystis viridisからトロンビン阻害活性を示す互換異性のあるペプチドaeruginosins102-A,Bを単離・構造決定した。Plectonema radiosumからはトリプシン阻害活性を示すジペプチドradiosuminを単離・構造決定した。Nostoc minutumからエラスターゼに阻害活性を示すAhpを含むデプシペプチドnostopeptins A,Bを単離・構造決定した。さらに、同じ藻体からやはりエラスターゼ阻害活性を示す3環性のペプチドmicroviridin類を単離・構造決定することができた。
日本学術振興会, 奨励研究(A), 宇都宮大学, 08760195 - Synthesis of cyclic peptides containing His and its possibility of brain activating
Grants-in-Aid for Scientific Research
1995 - 1996
YANAGISAWA Tadashi; OKINO Tatsufumi; SUGUTA Shoei
Pitutitary hormone-releasing hormones which are synthesized in the hypothalamus of the mammalian brain are now known as TRH,LHRH,CRH,GHRH,and so on. Among them, low molecular weight peptides, TRH and LHRH show the structural similarities. Both peptides have pyroGlu as N-terminal amino acid, His, and amino acid amide as C-terminal. We have already cleared that there is pyrogrutamyl peptidase in rat brain and the protease makes cyclic peptide ; histidyl-proline diketopiperazine. This cyclic peptide is supposed to behave as a brain activating substance. Biological activities of the releasing-hormones which show many functions including brain activating ability might be due to the cyclic peptides.
Under the circumstances we synthesized four peptides which contain His, then succeeded in making antibodies which have specificities against each cyclic peptide. Using the antibodies we wanted to develop the microdetermination and immunohistochemical methods which can clear the peptide distribution in the brain. Besides those, using pituitary cell culture and western blotting methods, we wanted to know the pituitary hormonereleasing abilities of cyclic peptides. Two years was not enough for this project. We now need more time, and the possibility of cyclic peptides as brain activating substances needs the experiments using animals in vivo.
This project was planned among 4 members at first, but two members were tranferred and were not able to join this project. Only 2 members started this project (afterwards another joined). So, we now making haste.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Utsunomiya University, 07556125 - 海洋生物の生物間相互作用に関する物質
Competitive research funding - Bioactive substancec in marine life
Competitive research funding
- Novel Prenylation Enzyme
Patent right, Wakimoto, Toshiyuki; Okino, Tatsufumi; Matsuda, Kenichi; Phan, Chin Soon
特願PCT/JP2022/004501, 02 May 2021 - 水棲生物が付着しない防汚被膜、防汚被膜を得るための手段およびその使用
Patent right, 沖野 龍文; 野方 靖行; 北野 克和; 岩井 薫; 平沢 洋治, 一般財団法人電力中央研究所, 国立大学法人奈良女子大学, 国立大学法人東京農工大学, 平沢 洋治
特願2009-554163, 20 Feb. 2008
特許第5569677号
04 Jul. 2014
201403013634649433 - 紅藻ソゾの有機溶媒抽出物およびそこから単離された化合物からなるフジツボ付着防止剤
Patent right, 沖野 龍文; 野方 靖行, 一般財団法人電力中央研究所
特願2009-531286, 05 Sep. 2008
特許第5374371号
27 Sep. 2013
201403083181774477 - イソニトリルの製造方法
Patent right, 沖野 龍文; 北野 克和, 国立大学法人北海道大学
特願2007-108567, 17 Apr. 2007
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