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Last Updated :2024/08/28

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Master

Affiliation (Master)

  • Faculty of Fisheries Sciences　Marine Life Science　Marine Bioresources Chemistry

Affiliation (Master)

  • Faculty of Fisheries Sciences　Marine Life Science　Marine Bioresources Chemistry

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Profile and Settings

Affiliation

  • Hokkaido University, Faculty of Fisheries Sciences, Division of Marine Life Science, Laboratory of Marine Bioresources Chemistry, Associate Professor

Profile and Settings

  • Name (Japanese)

    Ando

  • Name (Kana)

    Yasuhiro

  • Name

    200901043118301080

Affiliation

  • Hokkaido University, Faculty of Fisheries Sciences, Division of Marine Life Science, Laboratory of Marine Bioresources Chemistry, Associate Professor

Achievement

Research Interests

  • HPLC   Gas chromatography   Lipid analysis   水産脂質   Chemistry and Biochemistry on Marine Lipids (6301   

Research Areas

  • Life sciences / Marine/Aquatic life sciences

Research Experience

  • 2005 - 2007 大学院水産科学研究院海洋生命科学部門生物資源化学分野 助教授
  • 2005 - 2007 Associate Professor
  • 2007 - 大学院水産科学研究院海洋生命科学部門生物資源化学分野 准教授
  • 2000 - 2005 大学院水産科学研究科生命資源科学専攻生物資源化学講座 助教授
  • 2000 - 2005 Associate Professor
  • 1999 - 2000 水産学部海洋生物資源化学科生物機能化学講座 助教授
  • 1999 - 2000 Associate Professor
  • 1995 - 1999 水産学部海洋生物資源化学科生物機能化学講座 助手
  • 1995 - 1999 Research Associate
  • 1994 - 1995 Hokkaido University School of Fisheries Sciences
  • 1994 - 1995 Research Associate
  • 1993 - 1994 日本学術振興会特別研究員 日本学術振興会特別研究員
  • 1993 - 1994 Postdoctoral Fellowships of Japan Society for the Promotion of Science

Education

  •        - 1993  Hokkaido University
  •        - 1993  Hokkaido University  Graduate School, Division of Fisheries
  •        - 1990  Hokkaido University
  •        - 1990  Hokkaido University  Graduate School, Division of Fisheries
  •        - 1988  Hokkaido University  School of Fisheries Sciences
  •        - 1988  Hokkaido University  Faculty of Fisheries

Published Papers

  • Rika Kudo, Ryota Yamano, Juanwen Yu, Shuya Hatakeyama, Chunqi Jiang, Sayaka Mino, Shogo Yamaki, Yasuhiro Ando, Yuichi Sakai, Tomoo Sawabe
    Current microbiology 81 (8) 246 - 246 2024/06/28 [Refereed]
     
    Three novel bacterial strains, FE4T, FE10T, and LA51T, which are phylogenetically affiliated to the genera Pseudoalteromonas, Vibrio, or Marinobacter, respectively, isolated from fertilized eggs and juveniles of sea cucumber Apostichopus japonicus were characterized by a genome-based taxonomical approach including multilocus sequence analysis (MLSA) combined with classical phenotypic and chemotaxonomic characterizations. A molecular network reconstructed on the basis of nucleotide sequences of four phylogenetic maker protein genes revealed that the strains FE4T, FE10T, and LA51T were closely related to Pseudoalteromonas shioyasakiensis, Vibrio lentus, and Marinobacter similis, respectively. Average nucleotide identity (ANI) comparisons against phylogenetically related species to FE4T, FE10T, and LA51T demonstrated that each newly described strain could not be identified as any previously described species within each genus showing < 95% ANI: 91.3% of FE4T against P. shioyasakiensis JCM 18891 T, 92.6% of FE10T against "V. bathopelagicus" Sal10, and 92.6% of LA51T against M. similis A3d10T, in maximum, respectively. Here, we show molecular phylogenetic, genomic, phenotypic, and chemotaxonomic features of the newly described species FE4T, FE10T, and LA51T. We also propose Pseudoalteromonas apostichopi sp. nov. with FE4T (JCM 36173 T = LMG 33143 T) as the type strain, Vibrio apostichopi sp. nov. with FE10T (JCM 36174 T = LMG 33144 T) as the type strain, and Marinobacter apostichopi sp. nov. with LA51T (JCM 36175 T = LMG 33145 T) as the type strain.
  • Seiji Ohshimo, Yuko Hiraoka, Yasuhiro Ando
    Aquaculture and Fisheries 2468-550X 2023/11 [Refereed]
  • Sayaka Mino, So Fukazawa, Jiro Tsuchiya, Jesse C McNichol, Stefan M Sievert, Shogo Yamaki, Yasuhiro Ando, Tomoo Sawabe
    International journal of systematic and evolutionary microbiology 73 (11) 2023/11 [Refereed]
     
    A novel mesophilic, hydrogen- and thiosulfate-oxidizing bacterium, strain ISO32T, was isolated from diffuse-flow hydrothermal fluids from the Crab Spa vent on the East Pacific Rise. Cells of ISO32T were rods, being motile by means of a single polar flagellum. The isolate grew at a temperature range between 30 and 55 °C (optimum, 43 °C), at a pH range between 5.3 and 7.6 (optimum, pH 5.8) and in the presence of 2.0-4.0 % NaCl (optimum, 2.5 %). The isolate was able to grow chemolithoautotrophically with molecular hydrogen, thiosulfate or elemental sulfur as the sole electron donor. Thiosulfate, elemental sulfur, nitrate and molecular oxygen were each used as a sole electron acceptor. Phylogenetic analysis of 16S rRNA gene sequences placed ISO32T in the genus Hydrogenimonas of the class Epsilonproteobacteria, with Hydrogenimonas thermophila EP1-55-1 %T as its closest relative (95.95 % similarity). On the basis of the phylogenetic, physiological and genomic characteristics, it is proposed that the organism represents a novel species within the genus Hydrogenimonas, Hydrogenimonas cancrithermarum sp. nov. The type strain is ISO32T (=JCM 39185T =KCTC 25252T). Furthermore, the genomic properties of members of the genus Hydrogenimonas are distinguished from those of members of other thermophilic genera in the orders Campylobacterales (Nitratiruptor and Nitrosophilus) and Nautiliales (Caminibacter, Nautilia and Lebetimonas), with larger genome sizes and lower 16S rRNA G+C content values. Comprehensive metabolic comparisons based on genomes revealed that genes responsible for the Pta-AckA pathway were observed exclusively in members of mesophilic genera in the order Campylobacterales and of the genus Hydrogenimonas. Our results indicate that the genus Hydrogenimonas contributes to elucidating the evolutionary history of Epsilonproteobacteria in terms of metabolism and transition from a thermophilic to a mesophilic lifestyle.
  • Minami Ishihara, Kohei Matsuno, Koki Tokuhiro, Yasuhiro Ando, Kazutoshi Sato, Atsushi Yamaguchi
    Frontiers in Marine Science 10 2023/09/20 [Refereed]
     
    Calanus glacialis/marshallae is a dominant zooplankton species in the Pacific Arctic Ocean that is widely distributed in shelf areas, and it plays a vital role in connecting primary production to higher trophic levels. Its phenology is well adapted to hydrography, but there is little available information about regional and diel changes in population structure and grazing features. In this study, we investigated C. glacialis/marshallae during autumn 2019 in the Eastern and Northeastern Chukchi and Canadian basins to reveal geographic and diel variations in population structure, body size, grazing activity, and fatty acid composition. The abundance of C. glacialis/marshallae was found to be high on the slopes and low on the shelves. Body size (prosome length) was well described by the Bělehrádek equation combined with in-situ temperature throughout the sampling region. Cluster analyses based on hydrographic parameters were divided into four regions: southern shelf, northern shelf, slope, and basin. The southern shelf was dominated by copepodite stage five (C5) transported from the Bering Sea by Pacific waters. C4 and C5 were dominant on the northern shelf, suggesting that they grew slower than those on the southern shelf, and the populations also exhibited higher concentrations of fatty acids originating from dinoflagellates than those originating from the pan-Arctic Ocean, indicating low productivity in the region. The population on the slope had the highest abundance, C4 was dominant, and large amounts of diatom-derived eicosapentaenoic acid (EPA). These features are attributed to the upwelling of populations and nutrients that support diatom growth. In the basin, the early copepodite stages of composition were distinctly higher than those recorded in previous studies, because larger amounts of organisms flow into the region, resulting in more extended reproduction periods. In the basin, small and large forms of C5 were simultaneously found, and the small form exhibited a diel grazing activity pattern, but the large forms did not. These findings suggest their well adaptation in changing of the Pacific Arctic Ocean.
  • Seiji Ohshimo, Yuko Hiraoka, Satoshi Suyama, Toshihiro Tsuji, Ryuji Yukami, Tohya Yasuda, Yasuhiro Ando
    Bulletin of Marine Science 98 (3) 247 - 270 0007-4977 2022/07/01 [Refereed]
     
    We analyzed stable isotope ratios, fatty acid, and lipid components of chub mackerel, Scomber japonicus, to evaluate their applicability as chemical biomarkers. Chub mackerel were collected in the East China Sea, the Sea of Japan, and the Pacific Ocean, with body sizes ranging from 51 to 388 mm. The total fatty acid and lipid contents (mg g–1) increased with growth, and the percent composition of fatty acids and lipids changed drastically. The percentages of docosahexaenoic acid (%DHA), stearic acid (%Ste), and arachidonic acid (%ARA) decreased and the percentage of oleic acid (%Ole) increased when the body length (fork length, FL) was about 250 mm. The amounts of triacylglycerols (TAG) in fish in the East China Sea were lower than in the Sea of Japan and Pacific Ocean. The percentage of TAG drastically increased at around 250 mm FL, however, the phosphatidylcholines (PC) drastically decreased. The ontogenetic differences in the fatty acid and lipid composition might be influenced by metabolic events such as growth and reproduction. The geographical differences in chub mackerel can be distinguished by using stable isotope ratios, the ω3:ω6 fatty acid and DHA:EPA (eicosapentaenoic acid) ratios, and six main fatty acids. These chemical biomarkers could be available for understanding habitat and migration of chub mackerel.
  • Y Hiraoka, T Ishihara, A Tawa, Y Tanaka, S Ohshimo, Y Ando
    Marine Ecology Progress Series 689 127 - 136 0171-8630 2022/05/12 [Refereed]
     
    Fatty acid composition and total fatty acids of field-caught Pacific bluefin tuna (PBF) Thunnus orientalis larvae were investigated to identify relationships between spawning ground, physiological condition, and growth rate. Multivariate statistical analyses revealed that both growth rate and environmental conditions at spawning grounds were substantially associated with variations in fatty acid compositions. Fast-growing larvae typically contained more α-linolenic acid and 22:5n-3, which are important as metabolic precursors of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Larval PBF fatty acid compositions differed by spawning ground; larvae caught around the Nansei Islands contained more 15:0, 17:0, 19:0, and 22:5n-6, and less EPA and arachidonic acid (ARA) than those from the Sea of Japan. Differences in larval odd-numbered fatty acid compositions might indicate different degrees of dependence on microbial loop energy supply between spawning grounds. Environments subject to sudden changes, such as those in water temperature and prey density in the Sea of Japan, might cause variability in fatty acid profiles, including extremely low %DHA. We suggest that continuous food intake and subsequent fatty acid catabolism for energy generation would be needed to facilitate fast growth.
  • Hiraoka Y, Okochi Y, Ohshimo S, Shimose T, Ashida H, Sato T, Ando Y
    PloS one 14 (9) e0222824  2019 [Refereed][Not invited]
  • A simplified gas chromatographic fatty acid analysis by the direct saponification/methylation procedure and its application of Pacific bluefin tuna, yellowfin tuna and skipjack tuna larvae.
    Matsumoto Y, Ando, Y, Hiraoka, Y, Tawa, A, Ohshimo, S
    Lipids 2018/12 [Refereed][Not invited]
  • Matsumoto Y, Ando Y, Hiraoka Y, Tawa A, Ohshimo S
    Lipids 53 (9) 919 - 929 0024-4201 2018/09 [Refereed][Not invited]
  • ANDO Yasuhiro, MATSUMOTO Nobuto, YONETA Yukino, TADA Naoto
    Bulletin of Fisheries Sciences, Hokkaido University 68 (2) 33 - 41 1346-1842 2018/08/02 [Not refereed][Not invited]
  • 中塚 美紀子, 安藤 靖浩
    北海道大学水産科学研究彙報 北海道大学大学院水産科学研究院 66 (2) 69 - 76 1346-1842 2016/08 [Not refereed][Not invited]
     
    Lipid content, lipid class composition, and fatty acid composition were determined for 28 minor marine fish species caught from the waters around Hokkaido, Japan. The samples include some rare fish such as dusky rockfish Sebastes variabilis "nagamenuke" and prowfish Zaprora silenus "bouzuginpo." Most samples had low lipid contents, and therefore, can be used in low-fat fish foods. In contrast, the fish of four species and the liver of eight species were rich in lipid as they contained triacylgycerols or diacylglycerylethers as major lipid classes. Such fatty fish can be used as a source of marine lipids. The liver of brown hakeling Physiculus maximowiczi "donko" and ocean sunfish Mola mola "manbou" was found to be useful for including EPA and DHA. Prowfish and other two species were shown to contain tetracosahexaenoic acid in their fatty flesh and/or liver. These findings are useful fundamental information on the minor marine fish.
  • Naoto Tada, Honami Fujita, Yasuhiro Ando
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 91 (7) 1131 - 1137 0003-021X 2014/07 [Refereed][Not invited]
     
    This paper presents a convenient method for the preparation of reference standards for high-performance liquid chromatography (HPLC) used in stereospecific analysis of triacyl-sn-glycerols via monoacylglycerol or diacylglycerol intermediates. In the analysis, these partial acylglycerols are separated into their respective positional and enantiomeric isomer classes by chiral HPLC as their 3,5-dinitrophenylurethane derivatives or by silicic acid HPLC as their (S)- or (R)-1-(1-naphthyl)ethyl urethane derivatives. In this study, these urethane derivative standards were synthesized by the following novel procedure: first, partial urethane derivatives of glycerol were prepared by carbamoylation of glycerol with isocyanates; secondly, the products were separated into positional isomer classes by silicic acid HPLC, and; finally, a fatty acid was added to the partial urethanes using N,N'-dicyclohexylcarbodiimide. The identities of the resulting urethane derivatives of glycerol were verified by mass spectrometry and HPLC. This new procedure is advantageous in that standard urethane derivatives of partial acylglycerols can be synthesized from no more than 50 mu g of fatty acids. This benefit is especially important in the case of rare and expensive fatty acids, such as very long chain polyunsaturated fatty acids, tetracosahexaenoic acid, and hexacosaheptaenoic acid, found in marine lipids.
  • Yuko Hiraoka, Tetsuya Takatsu, Yasuhiro Ando
    MARINE BIOLOGY 161 (7) 1615 - 1625 0025-3162 2014/07 [Refereed][Not invited]
     
    We investigated the fatty acid compositions and concentrations of wild marine fish larvae with a highly accurate method because our knowledge of them has been seriously limited compared with cultured larvae. This study presents estimates of the fatty-acid-based nutritional condition of individual larvae in the field. Because the pointhead flounder Cleisthenes pinetorum displays relatively high stock size fluctuations, we investigated the developmental change in the fatty acid compositions of the body trunk, head, and eye and the annual fluctuations in the fatty acid concentrations in the trunk. We show that the process of fatty acid accumulation is not uniform across body parts and that the trunk is a better indicator of larval nutritional status than other parts because there is less time lag. Starved larvae with simultaneously high docosahexaenomic acid ratios and low total fatty acid concentrations, as observed in laboratory experiments, are rare in the wild. Thus, starved larvae must be removed rapidly by predators before they can experience a relatively long period of starvation in the wild. Fatty acid accumulation was greater in the larvae of the 2005 year class than in those of the 2006 year class in their first feeding stage, according to the optimal model derived with generalized linear model. A previous study indicated that the 2005 year class showed stronger recruitment than the 2006 year class. We conclude that the fatty acid analysis of wild larvae is a useful index of their nutritional status and mortality, especially in the first feeding stage.
  • Yutarou Nakamura, Yuuki Fukuda, Kana Shimizu, Yasuhiro Ando
    FISHERIES SCIENCE 80 (3) 613 - 620 0919-9268 2014/05 [Refereed][Not invited]
     
    This article reports the concentration and composition of the isomers of cis-icosenoic acid (20:1) in the fatty acids of various species of Japanese marine animals. The main purpose of this study is to reveal the distribution of a positional isomer, cis-7-20:1 (c7-20:1), in marine animals. Because this isomer overlaps with the c9-20:1 isomer in gas chromatography (GC) on the commonly used polar capillary columns, less information is available on its occurrence and distribution. In this study, the monounsaturated fatty acids isolated by argentation thin-layer chromatography were analyzed by GC using a highly polar capillary column, SLB-IL111 (100 m long), with the highest polarity among the commercially available GC columns. A clear separation between the c7-20:1 and c9-20:1 isomers enabled the analysis of all the isomers of 20:1 present in marine animals. The results confirmed that the c7 isomer was a minor component in the 20:1 in the pelagic fish, which is rich in the c9 and/or c11 isomers as reported previously. In contrast, the c7 isomer was one of the major isomers in flatfish, shellfish, crabs, and brittle stars. In these samples, the c13 isomer also occurred at higher concentrations rather than the c9 isomer. Because such a specific pattern of the 20:1 positional isomers was generally observed in both benthic fish and its dietary animals, the c7 isomer in the benthic fish probably originated from its diet. These marine animals are used as food in Japan, and therefore the c7-20:1 isomer is consumed by humans.
  • NAKAMUA Yutarou, SHIMIZU Kana, ANDO Yasuhiro
    Bulletin of Fisheries Sciences, Hokkaido University 北海道大学大学院水産科学研究科編集出版委員会 64 (1) 9 - 16 1346-1842 2014/03/14 [Not refereed][Not invited]
     
    This paper reports the retention data of fatty acid methyl esters on a novel ionic liquid column, SLB-IL111, which hashigher polarity than commercially available columns for gas chromatography (GC). The fatty acids analyzed using GC includebranched-chain saturated fatty acids, C16-C22 monounsaturated fatty acid cis/trans and positional isomers, and polyunsaturatedfatty acids commonly found in natural products. Fatty acids of sardine oil were also analyzed using GC. GC was carried outon a 100-m column under isothermal conditions within the range 120-170°C, using helium as a carrier gas. The retention dataof fatty acid methyl esters were represented by equivalent chain length (ECL) values calculated from the retention times of eachfatty acid related to those of saturated fatty acids with an even carbon number. This is novel information, obtained on an SLBIL111column being operated at various temperatures with a single GC system. The results show that the column temperaturegreatly affected the ECL values of unsaturated fatty acids. Thus, when using this column for the analysis of fish oil fattya cids, itis necessary to precisely control the column temperature.
  • Kana Shimizu, Yasuhiro Ando
    JOURNAL OF OLEO SCIENCE 61 (8) 421 - 426 1345-8957 2012/08 [Refereed][Not invited]
     
    Gas chromatography (GC) of docosenoic acid (22:1) has been performed for the separation of positional isomers on the novel SLB-IL100 column with a highly polar ionic liquid stationary phase. A test mixture of 22:1 methyl esters prepared from total lipids of flounder was subjected to GC on a 60 m x 0.32 mm i.d. column at an isothermal temperature of 150 degrees C-180 degrees C. On this column, all five positional isomers separated in the elution order of 22:1n-15, 22:1n-13, 22:1n-11, 22:1n-9, and 22:1n-7. The positional isomers, 22:1n-15, 22:1n-13, and 22:1n-11, unresolvable on conventional polar polymer phase columns, were almost completely separated from each other within 24 min at 170 degrees C. The equivalent chain length values of 22:1n-11 to 22:1n-7 were parallel to those on polyethylene glycol and cyanopropyl polysiloxane columns, whereas 22:1n-15 and 22:1n-13 were relatively lower and closer to saturated 22:0 acid. Similar findings were also obtained for co-injected 20:1n-15 to 20:1n-11 isomers. Analysis of fish 22:1 revealed that 22:1n-13 is not always a minor isomer, as previously reported for several samples. The results of this study confirm the view that SLB-IL100 is a powerful tool for GC analysis of monounsaturated fatty acids.
  • Yuuki Fukuda, Yasuhiro Ando
    FISHERIES SCIENCE 77 (5) 875 - 882 0919-9268 2011/09 [Refereed][Not invited]
     
    Fatty acid analysis of roughscale sole Clidoderma asperrimum flesh lipids was carried out by gas chromatography. An unidentified peak appeared in the chromatogram in the elution region of a parts per thousand yenC24 fatty acids. After enrichment by solvent partitioning, reversed-phase thin-layer chromatography (TLC), and argentation TLC, the peak component was subjected to structural analyses. The partially hydrogenated products after reaction with hydrazine hydrate gave seven isomers of cis-hexacosenoic acid (26:1). Gas chromatography-mass spectrometry (GC-MS) analyses of their dimethyl disulfide adducts identified the monounsaturates as 5-, 8-, 11-, 14-, 17-, 20-, and 23-26:1. The peak component was assigned to all-cis-5,8,11,14,17,20,23-hexacosaheptaenoic acid (26:7n-3). GC-MS analyses of the 4,4-dimethyloxazoline derivative and methyl ester confirmed this structure. This fatty acid is a rare, very long-chain polyunsaturated fatty acid (VLCPUFA). The concentrations of the acid found in roughscale sole were 0.69 +/- A 0.34% (N = 5) of total fatty acids in flesh lipids. Roughscale sole appears to be characterized by the occurrence of 26:7n-3, which is lacking in popular sources of methylene-interrupted VLCPUFA, such as vertebrate retina, spermatozoa, and herring.
  • Yasuhiro Ando, Tsubasa Sasaki
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 88 (6) 743 - 748 0003-021X 2011/06 [Refereed][Not invited]
     
    Gas chromatography (GC) of cis-eicosenoic acid (20:1) positional isomers has been investigated on a capillary column of ionic liquid 1,9-di(3-vinyl-imidazolium)nonane bis(trifluoromethyl)sulfonylimidate stationary phase (SLB-IL100). A test mixture of isomeric 20:1 methyl esters was prepared from flathead flounder flesh lipids. On a 60-m column operated at 150-180 A degrees C, six peaks appeared in the elution order of 20:ln-15 -> 20:ln-13 -> 20:ln-11 -> 20:ln-9 -> 20:ln-7 -> 20:ln-5. These peaks were baseline resolved within 20 min at 180 A degrees C. The 20:ln-13 and 20:ln-11 isomers, poorly resolved on conventional polar polysiloxane stationary phases, were completely separated from each other with separation factor alpha = 1.02 and peak resolution (Rs) a parts per thousand yen 1.57. When equivalent chain length (ECL) values were compared between the SLB-IL100 and CP-Sil 88 (biscyanopropyl polysiloxane), those of 20:ln-15 and 20:ln-13 exceptionally tended to be lower on the SLB-IL100. The excellent separation of 20:1 isomers seems due to less retention of 20:ln-15 and 20:ln-13 on SLB-IL100 rather than simply due to its high polarity. Analysis of herring oil 20:1 revealed the occurrence of 20:ln-13 in the Pacific herring but not in the Atlantic herring. The ionic liquid stationary phase, SLB-IL100, is effective for analyzing 20:1 isomers occurring in fish and other natural oils.
  • HABA YUSUKE, ANDO YASUHIRO
    北海道大学水産科学研究い報 北海道大学大学院水産科学研究院 = Research Faculty of Fisheries Sciences, Hokkaido University 59 (3) 67 - 72 1346-1842 2009/12/08 [Not refereed][Not invited]
     
    A fluorescent-labeling reagent 9-anthracenemethanol was purified by recrystallization for use in microanalysis of natural oil fatty acids. A commercial reagent was dissolved in ethyl acetate at the boiling point, and allowed to stand at room temperature until the crystals precipitated in yellow needles. The product given in the yield of 74% was analyzed by reversed-phase high-performance liquid chromatography. Many contaminant peaks found in the crude material disappeared in the chromatogram, indicating successful purification of the reagent. The purified reagent could be used for fatty acid analysis of 1-5μg of natural triacylglycerols including those of cod liver/mackerel oil and bonito head oil. 2-Butanone was also effective solvent for the purification. With these solvents, commercially available 9-anthracenemethanol can be purified by the simple recrystallization.
  • Yuki Tomita, Yasuhiro Ando
    FISHERIES SCIENCE 75 (2) 445 - 451 0919-9268 2009/04 [Refereed][Not invited]
     
    Positional distribution of fatty acids in triacyl-sn-glycerols (TAG) of the flathead flounder Hippoglossoides dubius has been reinvestigated in order to accurately determine the contents of tetracosahexaenoic acid (24:6n-3) in the sn-1, sn-2, and sn-3 positions. Flesh TAG obtained from three flounders were subjected to stereospecific analysis using a suitable procedure for fish TAG analysis. The 24:6n-3 acid was found in the three positions at the concentrations of 0.3-5.5 mole% (the sn-1 position), 1.6-23.3 mole% (the sn-2 position), and 0.6-8.9 mole% (the sn-3 position). In contrast to a previous analysis, the present analysis revealed that 24:6n-3 is preferentially esterified in the sn-2 position followed by the sn-3 and sn-1 positions. Other polyunsaturated fatty acids, docosahexaenoic acid (22:6n-3; DHA) and docosapentaenoic acid (22:5n-3; DPA), showed a similar distribution pattern. These results indicate that the general tendency observed for long-chain polyunsaturated fatty acids in marine fish TAG can be extended to the distribution of 24:6n-3 in flathead flounder TAG. Because the use of flathead flounders is entirely for human food, we thus intake 24:6n-3 concentrated in the sn-2 position of their TAG.
  • Ryuichi Matsukura, Tohru Mukai, Yasuhiro Ando, Kohji Iida
    NIPPON SUISAN GAKKAISHI 公益社団法人日本水産学会 75 (1) 38 - 44 0021-5392 2009/01 [Refereed][Not invited]
     
    The density and sound speed contrasts between Euphausia pacifica and sea water change with the season. In this study, we examined the effect on target strength (TS) and lipid content which is a cause of these changes. Density contrasts increased from spring to summer, but sound speed contrasts decreased. There was a negative correlation between density contrasts and wax esters, which are one of the lipid contents, and a positive correlation between sound speed contrasts and total lipid. The range of variation estimated by the DWBA model using both ratios was narrow. The mean TS of E. pacifica (TL 15 mm) ranged from -105.9 to -105.2 dB at 38 kHz, from -91.3 to -90.5 dB at 120 kHz and from -86.3 to -85.4 dB at 200 kHz.
  • Yasuhiro Ando, Yuki Tomita, Yusuke Haba
    JOURNAL OF OLEO SCIENCE 57 (8) 459 - 462 1345-8957 2008/08 [Refereed][Not invited]
     
    This paper presents a procedure for preparation of a Grignard reagent, ethyl magnesium bromide, used for partial deacylation of triacylglycerols (TAG) in their regiospecific analysis. Magnesium turnings were reacted with ethereal solution of bromoethane in a screw-capped test tube to synthesize 2 mL of 1 M ethyl magnesium bromide. Continuously stirred with a vortex mixer, the reaction smoothly proceeded at room temperature. Regiospecific analysis of 1,3-distearoyl-2-oleoylglycerol using this product showed that fatty acid compositions of the sn-1(3) and sn-2 positions were contaminated by less than 2 mol% of fatty acids migrated from isomeric positions. The analyses of lard and cod liver/mackerel oil TAG showed typical distribution patterns of 16:0, 22:5n-3 and 22:6n-3 in pig and fish depot TAG. These results confirmed the view that the freshly prepared reagent is usable for regiospecific analysis of TAG.
  • ANDO YASUHIRO, HABA YUSUKE, TAKASE KIWAMU, SAKAI SHINYA
    北海道大学水産科学研究い報 北海道大学大学院水産科学研究院 = RESEARCH FACULTY OF FISHERIES SCIENCES, HOKKAIDO UNIVERSITY 57 (3) 37 - 41 1346-1842 2007/12/13 [Not refereed][Not invited]
     
    This paper presents a smaller-sized procedure for regiospecific analysis of triacylglycerols (TAG) using boric acid high-performance thin-layer chromatography (HPTLC). Cod liver/mackerel, bonito head, and seal oils TAG (2mg) were partially hydrolyzed by ethyl magnesium bromide, and resulting 1(3)-and 2-monoacylglycerols (MAG) were isolated by the HPTLC. Fatty acids of the 1(3)-and 2-MAG were analyzed by gas-liquid chromatography (GLC). Positional distributions of fatty acids in TAG observed for the three marine oils were similar to those previously determined by the procedure requiring 100mg of starting TAG. The new procedure appeared to be usable for regiospecific analysis of a few milligrams of marine oils TAG.
  • Yasuhiro Ando, Yusuke Haba, Kazutaka Soma, Yuko Hiraoka, Tetsuya Takatsu
    LIPIDS 42 (10) 955 - 960 0024-4201 2007/10 [Refereed][Not invited]
     
    This paper proposes a one-step method for preparation of fluorescent 9-anthrylmethyl esters from triacylglycerols (TAG) ranging in amount from 0.1 to 5 mu g. It involves base-catalyzed transesterification using potassium 9-anthracenemethoxide, prepared by proton exchange between 9-anthracenemethanol and potassium tert-butoxide. Transesterification for 10 min at room temperature gave the fatty acid 9-anthrylmethyl esters in nearly maximal yields (82-85%). The products could be analyzed by reversed-phase HPLC without purification. Excellent linear relationships were observed for standard curves of 10-250 pmol of TAG standards (16:0, 19:0, 18:2 and 22:6), and differences in the slopes were less than 5% among the standards. Almost consistent compositions of the esters were observed for the products formed from 0.5 to 5 mu g or less of fish oils TAG, and they were similar to those obtained by HPLC of ordinary multi-step synthesis products and by GLC of methyl esters. The present method is a great improvement of derivatization time, and is powerful for fatty acid analysis of small amounts of natural TAG.
  • ANDO YASUHIRO, NOZAKI MANTARO
    J Oleo Sci Japan Oil Chemists' Society 56 (9) 471-478 (J-STAGE) - 478 1345-8957 2007 [Refereed][Not invited]
     
    There has been no information on lipids of brackish water mysid Neomysis intermedia, which is the most important mysid for human food in Japan. The present study revealed their lipid content, lipid class composition, and fatty acid compositions of total lipids (TL) and major lipid classes. Lipid content of the mysid was 1.0% on wet-weight base. Major lipid classes were phosphatidylcholines (PC, 26%), phosphatidylethanolamines (PE, 24%), and phosphatidylinositols (PI, 14%), whereas the content of triacylglycerols (TAG) was relatively low (7%). Major fatty acids of the TL were 16:0 (21%), 18:1n-9 (12%), 20:5n-3 (EPA; 19%) and 22:6n-3 (DHA; 14%), and the latter two polyunsaturated fatty acids were concentrated in PI (totally 47%) and PE (43%) fractions rather than in PC (20%) and TAG (18%). Arachidonic acid (4%) was also higher in the PI (7%) and PE (5%). When the mysid was fed tri-, di- and monoacylglycerols prepared from DHA-rich fish oil, DHA mainly increased in the TAG fraction of the mysid. The mysid appeared to primarily incorporate exogenous DHA into TAG fraction.
  • Ando Yasuhiro, Abe Tomomi, Ookubo Yuka, Namikawa Saori
    Bulletin of Fisheries Sciences, Hokkaido University 北海道大学 56 (3) 61 - 65 1346-1842 2005/12/22 [Not refereed][Not invited]
  • SHIOZAKI Rieko, ANDO Yasuhiro
    Journal of Oleo Science 公益社団法人 日本油化学会 54 (3) 161 - 166 1345-8957 2005 [Refereed][Not invited]
     
    Positional distribution of fatty acids in triacyl-sn-glycerols (TAG) has been investigated for Artemia franciscana nauplii used in marine fish larviculture as an important live food. For enhancement of essential highly unsaturated fatty acids, the nauplii were enriched for 4 to 24 h with two emulsions containing fish roe polar lipids (PL), (i) a mixture of bonito head oil TAG and salmon roe PL concentrate (88:12, wt/wt) and (ii) an unmixed salmon roe PL concentrate. In TAG isolated from all enriched Artemia nauplii, docosahexaenoic acid (DHA) was preferentially esterified in the sn-3 position (0.7-22.9 mol%) followed in sequence by the sn-2 (0.1-7.5 mol%) and sn-1 (0.0-4.6 mol%) positions. This distribution pattern was the same as previously observed for enrichment with bonito head oil TAG free from salmon roe PL. Addition of fish roe PL to DHA-rich fish oil enricher does not seem to practically affect the distribution pattern of DHA characteristic of Artemia nauplii.
  • Y Ando, S Kobayashi
    AQUACULTURE RESEARCH 35 (14) 1391 - 1394 1355-557X 2004/11 [Refereed][Not invited]
  • Y Ando, H Samoto, Y Murayama
    AQUACULTURE 233 (1-4) 321 - 335 0044-8486 2004/04 [Refereed][Not invited]
     
    This paper reports the positional distribution of fatty acids in triacyl-sn-glycerols (TAG) of Artemia franciscana nauplii. The nauplii were enriched for 4 to 24 h with fatty acid ethyl esters (EE) and TAG prepared from two fish oils, bonito head oil and cod liver/mackerel oil. TAG isolated from the enriched Artemia nauplii were subjected to stereospecific analysis in order to determine the content of each fatty acid in the sn-1, sn-2 and sn-3 positions. In TAG of the enriched Artemia nauplii (24 h), docosahexaenoic acid (DHA) was esterified in the sn-3 position (5.0-35.0 mol%) in preference to the sn-1 position (0.7-7.3 mol%) and sn-2 position (1.0-10.4 mol%). Eicosapentaenoic acid (EPA) was preferentially esterified in the sn-2 position (10.2-12.8 mol%) followed in sequence by the sn-3 position (6.4-8.8 mol%) and sn-1 position (2.5-5.8 mol%). The Artemia nauplii tended to attract 18:1 and 18:0 fatty acids to the sn-1 position, EPA and 16:0 to the sn-2 position, and DHA, 22: 1, and 20:1 to the sn-3 position of their TAG. The positional distribution of fatty acids in the dietary fish oils TAG was not held in the Artemia nauplii. Once fatty acids are released from dietary fish oils EE and TAG, these fatty acids seem to be incorporated into Artemia TAG in a consistent manner independent of their origin, fish oils EE or TAG. (C) 2004 Elsevier B.V. All rights reserved.
  • Nami Kusumoto, Yasuhiro Ando, Ryuichi Matsukura, Tohru Mukai
    Journal of Oleo Science 53 (1) 45 - 51 1347-3352 2004 [Refereed][Not invited]
     
    This paper reports the total lipid content, lipid class composition, and fatty acid composition of the krill Euphausia pacifica collected in the northwestern Pacific Ocean near Funka Bay, Hokkaido, Japan. The krill were caught in spring, summer, and winter in three consecutive years, 2000-2002. Lipid content of the E. pacifica samples was ranged from 5.1 to 11.6% on the basis of dry weight. Major lipid classes determined for the samples of 2002 were triacylglycerols (TAG) (3.4-27.3%), free fatty acids (FFA) (6.9-22.2%), sterols (5.4-12.9%), phosphatidylethanolamines (PE) (3.4-17.5%), and phosphatidylcholines (PC) (36.2-53.8%). All of the samples subjected to fatty acid analysis were high in 16:0 (19.0-24.5% of total fatty acids), 18:1n-9 (7.5-10.0%), 18:1n-7 (6.3-8.1%), 20:5n-3 (IPA) (15.3-24.7%), and 22:6n-3 (DHA) (8.420.7%). The lipids of E. pacifica were found to be generally rich in PC and in IPA and DHA. Lipid content and proportion of TAG were higher in the spring samples than in the summer samples. The summer samples were higher in the concentration of DHA in total fatty acids. © 2004, Japan Oil Chemists' Society. All rights reserved.
  • Y Ando, S Kobayashi, T Sugimoto, N Takamaru
    AQUACULTURE 229 (1-4) 275 - 288 0044-8486 2004/01 [Refereed][Not invited]
     
    This paper reports the positional distribution of fatty acids in triacyl-sn-glycerols (TAG) of rotifers Brachionus plicatilis enriched with marine oils TAG. The rotifers were enriched with fish and seal oils TAG for 4-24 h, and TAG isolated from the enriched rotifers were subjected to stereospecific analysis in order to determine the content of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) in the sn-1, sn-2 and sn-3 positions of the TAG. In rotifers enriched with fish oil TAG, DHA was esterified in the three positions of TAG with the distribution patterns of sn-2 (highest)>sn-3>sn-1 (lowest) positions (4- and 8-h enrichments), sn-2 approximate to sn-3>sn-1 positions (12- and 18-h enrichments) and sn-3>sn-2>sn-1 positions (24-h enrichment). In rotifers enriched with seal oil TAG, DHA showed a consistent pattern of sn-3>sn-1>sn-2 positions (4-24 h). EPA in the 24-h enriched rotifers showed the patterns of sn-3>sn-2 approximate to sn-1 positions (fish oil TAG enrichment) and sn-3>sn-1>sn-2 positions (seal oil TAG enrichment). In the seal oil TAG enrichment, distribution patterns of DHA and EPA were similar between the dietary TAG and rotifers TAG. In contrast, distribution patterns of these fatty acids in the fish oil TAG (sn-2>sn-3>sn-1 positions) were not entirely held in the enriched rotifers. (C) 2004 Elsevier Science B.V. All rights reserved.
  • Kusumoto Nami, Ando Yasuhiro, Matsukura Ryuichi, Mukai Tohru
    Bulletin of Fisheries Sciences, Hokkaido University 北海道大学 54 (3) 73 - 77 1346-1842 2003 [Not refereed][Not invited]
  • Yasuhiro Ando, Hiromi Samoto, Shigefumi Sasaki
    Journal of Oleo Science 52 (8) 443 - 447 1347-3352 2003 [Refereed][Not invited]
     
    Polar lipids (PL) concentrate was prepared from total lipids (TL) of salmon roe in order to use for highly unsaturated fatty acids (HUFA) enricher of Artemia nauplii, an important live food for marine fish larvae. The PL were concentrated by a solvent partition procedure using a solvent system of equilibrated hexane, ethanol and water. Starting with 120 g of TL, the solvent partition procedure resulted in 29.3 g (27.2 %) of the salmon roe PL concentrate. Major components of the concentrate were phosphatidylcholines (PC 80.0 %), phosphatidylethanolamines (PE 7.0 %), and phosphatidylinositols (PI 5.5 %). Lesser amounts of free fatty acids, sterols and monoacylglycerols were also found in the PL concentrate. Fatty acid analysis revealed the contents of docosahexaenoic acid (DHA 26.9 %), icosapentaenoic acid (IPA 14.2 %), and arachidonic acid (AA 2.4 %). PC and PE isolated from the concentrate were rich in DHA and IPA, whereas PI were rich in AA. The salmon roe PL concentrate appeared to have a potential as an effective HUFA enricher of Artemia nauplii. The solvent partition procedure seems to be useful for convenient preparation of such fish roe PL concentrate. © 2003, Japan Oil Chemists' Society. All rights reserved.
  • Y Ando, Y Oomi, K Narukawa
    COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY 133 (2) 191 - 199 1096-4959 2002/10 [Refereed][Not invited]
     
    This paper reports the positional distribution of fatty acids in triacylglycerols (TAG) of Artemia franciscana nauplii enriched with each of palmitic (16:0), oleic (18:1n-9), linoleic (18:2n-6), linolenic (18:3n-3), eicosapentaenoic (20:5n-3), and docosahexaenoic (22:6n-3) acid ethyl esters. TAG extracted from the enriched and unenriched nauplii were subjected to regiospecific analysis to determine the fatty acid compositions of the sn-1(3) and sn-2 positions of TAG. In the unenriched nauplii, 16:0, 18:1n-9, and 18:2n-6 were preferentially located in the sn-1(3) position followed by the sn-2 position [i.e. sn-1(3)>sn-2], whereas 18:3n-3 was concentrated in the sn-2 position [i.e. sn-2>sn-1(3)]. Contents of 20:5n-3 and 22:6n-3 were low. After the nauplii were enriched with each of the ethyl esters for 18 h, fatty acid fed to the nauplii showed higher content in the sn-1(3) position than in the sn-2 position [i.e. sn-1(3)>sn-2]. Distribution pattern of 18:3n-3 changed from sn-2>sn-1(3) to sn-1(3)>sn-2 during the enrichment with 18:3n-3 ethyl ester. Increases in all of the fatty acids in TAG were attributed to that in the sn-1(3) position much more than that in the sn-2 position. Artemia nauplii appear to be characterized by preferential incorporation of exogenous fatty acids into the sn-1(3) position of TAG, even though endogenous fatty acids are esterified in the opposite position. (C) 2002 Elsevier Science Inc. All rights reserved.
  • NU Sata, M Kaneniwa, Y Masuda, Y Ando, H IIda
    FISHERIES SCIENCE 68 (1) 236 - 238 0919-9268 2002/02 [Refereed][Not invited]
  • Yasuhiro Ando, Keiichi Narukawa
    Journal of Oleo Science 51 (9) 615 - 620 1347-3352 2002 [Refereed][Not invited]
     
    Brine shrimp Artemia nauplii, an important live food used in aquaculture, were enriched with five marine oil triacylglycerols (TAG) in order to enhance n-3 highly unsaturated fatty acids (HUFA) essential for fish larvae. Positional distribution of fatty acids in TAG was determined for both of the enriched Artemia nauplii and dietary marine oils. In all of the enriched Artemia nauplii, docosahexaenoic acid was preferentially located in the sn-1,3 position followed by the sn-2 position. Icosapentaenoic acid was preferentially located in the sn-2 position. Distribution patterns of these fatty acids were not similar to those in dietary TAG of fish oil origin. Positional distribution of HUFA characteristic of marine fish TAG does not appear to hold for Artemia TAG during the HUFA enrichment. © 2002, Japan Oil Chemists' Society. All rights reserved.
  • Daisuke Sato, Yasuhiro Ando
    Journal of Oleo Science 51 (8) 563 - 567 1347-3352 2002 [Refereed][Not invited]
     
    Fatty acid compositions of neutral lipids (NL) and polar lipids (PL) have been analyzed for a unique sample of Ophiuroidea (brittle star) Ophiura sarsi containing novel nonmethylene-interruped (NMI) fatty acids, 7E, 13E-icosadienoic (20:2), 7E,13E,17Z-icosatrienoic (20:3), 9E, 15, E, 19Z-docosatrienoic (22:3), and 4Z, 9E, 15E, 19Z-docosatetraenoic (22:4) acids. All of the NMI fatty acids were concentrated in NL (mainly triacylglycerols) rather than in PL (mainly phosphatidylcholines and phosphatidylethanolamines). On the other hand, 6, 9, 12, 15, 18, 21-tetracosahexaenoic acid (24:6n-3) usually observed in Ophiuroidea lipids was found in PL at higher concentration than in NL. Biological property and origin of the novel NMI fatty acids appear to be different from those of 24:6n-3. © 2002, Japan Oil Chemists' Society. All rights reserved.
  • D Sato, Y Ando, R Tsujimoto, K Kawasaki
    LIPIDS 36 (12) 1371 - 1375 0024-4201 2001/12 [Refereed][Not invited]
     
    Fatty acids of Ophiuroidea (brittle star) Ophiura sarsi have been investigated by gas-liquid chromatography (GLC). About 2-13% of four unidentified fatty acids were found in total fatty acids from a sample caught at a depth of 1,100 m. Structural analyses were undertaken after partial hydrogenation of their concentrates with hydrazine hydrate and subsequent isolation of the monoenoate products by argentation thin-layer chromatography. The structures of the unidentified fatty acids were determined as 7E, 13E-eicosadienoic (20:2), 7E,13E,17Z-eicosatrienoic (20:3), 9E,15E,19Z-docosatrienoic (22:3), and 4Z,9E,15E,19Z-docosatetraenoic (22:4) acids by gas chromatography-mass spectrometry of dimethyl disulfide adducts and GLC of the monoenoates on a polar column. These fatty acids belong to a family of nonmethylene-interrupted (NMI) polyunsaturated fatty acids frequently observed in marine invertebrates and conifer seeds. As far as the authors know, however, these NMI fatty acid types with mixed geometry of ethylenic bonds have not been reported previously.
  • Y Ando, Y Oomi
    LIPIDS 36 (7) 733 - 740 0024-4201 2001/07 [Refereed][Not invited]
     
    This paper presents the positional distribution of fatty acids in triacyl-sn-glycerols (TAG) of Artemia nauplii used in aquaculture as a live food for marine fish larvae. The nauplii were enriched with docosahexaenoic acid (DHA) ethyl ester (EE) in the form of gelatin-acacia microcapsules for 4, 18, and 24 h. TAG of the initial, enriched, and unenriched Artemia nauplii were subjected to stereospecific analysis. A remarkable increase of DHA content in the enriched Artemia TAG confirmed the view that DHA-EE is effectively assimilated and incorporated into the TAG fraction of Artemia nauplii. TAG of the nauplii enriched with 25 mg/L of DHA-EE contained DHA at concentrations of 5.9-6.8, 4.3-6.0, and 14.3-22.3 mol% in the sn-1, sn-2, and sn-3 positions, respectively. When the nauplii were enriched with 100 mg/L of DHA-EE, proportions of DHA in the sn-1, sn-2, and sn-3 positions were 5.2-8.6, 3.9-6.0, and 12.2-25.4 mol%, respectively. In all of the enriched Artemia, DHA was preferentially located in the sn-3 position followed in sequence by the sn-1 and sn-2 positions. The lower content of DHA in the sn-1 and sn-2 positions was consistent with low content of this acid in 1,2-diacyl-sn-glycerophospholipids. When fish larvae are reared on Artemia nauplii enriched with EE-type DHA oil, the larvae feed on DHA esterified in TAG with a positional distribution pattern similar to that of marine mammals (sn-3 > > sn-1 > > sn-2) rather than that of fish or marine invertebrates (sn-2 > > sn-3 > > sn-1).
  • Y Ando, M Satake, Y Takahashi
    LIPIDS 35 (5) 579 - 582 0024-4201 2000/05 [Refereed][Not invited]
     
    Positional distribution of fatty acids in triacyl-sn-glycerols of docosahexaenoic acid (DHA)-rich tuna orbital and bonito head oils has been reanalyzed by a method based on chromatographic separation of isomeric and enantiomeric monoacyl-sn-glycerol (MAG) derivatives. When boric acid thin-layer chromatography (TLC) was used for separation of 1(3)- and 2-MAG analytical intermediates, the stereospecific analysis showed the preferential association of DHA to the sn-2 position followed by the sn-3 position. This distribution pattern differed from that obtained by silicic acid TLC of their bis-3,5-dinitro-phenylurethane (DNPU) derivatives. Reversed-phase high-performance liquid chromatography elution profiles of 1(3)- and 2-MAG intermediates revealed that 1(3)- and 2-MAG made up of both short- and long-chain lengths cannot be clearly resolved by TLC after preparation of the DNPU derivatives. The 1 (3)- and 2-MAG must be resolved by boric acid TLC prior to derivatization.
  • Y Ando, S Morita, N Tadokoro, T Ota, T Sugimoto, N Takamaru
    FISHERIES SCIENCE 65 (5) 808 - 809 0919-9268 1999/10 [Refereed][Not invited]
  • LEE Hong - Wu, BAN Syuhei, ANDO Yasuhiro, OTA Toru, IKEDA Tsutomu
    Plankton Biology and Ecology Plankton Society of Japan 46 (2) 104 - 112 1343-0874 1999/08/01 [Refereed][Not invited]
  • ANDO Yasuhiro
    Journal of Japan Oil Chemists' Society 日本油化学会 47 (10) 953 - 962 1341-8327 1998/10/20 [Refereed][Not invited]
     
    High-performance liquid chromatography (HPLC) for stereospecific analysis of triacyl-<I>sn</I>-glycerols (TG) does not have the drawbacks attending enzymatic methods and involves the separation of isomeric and enantiomeric partial acylglycerols, <I>i.e.</I>, monoacylglycerols (MG) and diacylglycerols (DG), farmed from TG. In this method, the Grignard hydrolysis of TG to partial acylglycerols and their isolation are carried out followed by the preparation of enantiomeric or diastereomeric urethane derivatives, their resolution by chiral- or achiral-phase HPLC and fatty acid analysis as methyl esters. The accuracy of this method depends on acyl group migration during analysis, differential loss in conversion, resolution of enantiomers and calculation for acyl compositions in <I>sn</I>-1, <I>sn</I>-2, and <I>sn</I>-3 positions. Soybean, pine seed, yew seed, and saucy oil TG have been analyzed.
  • Y Ando, Y Kawabata, K Narukawa, T Ota
    FISHERIES SCIENCE 64 (1) 136 - 139 0919-9268 1998/02 [Refereed][Not invited]
     
    Gas-liquid chromatography (GLC) analysis revealed a high content of very long chain fatty acids in the marine sponge Halichondria panicea from the coast of south Hokkaido, Japan. Three major components of the fatty acids were concentrated by argentation thin-layer chromatography (TLC) and reversed phase TLC. They were identified as demospongic acids, 5,9-hexacosadienoic (26:2), 5,9,19-hexacosatrienoic (26:3), and 5,9,20-heptacosatrienoic acids (27:3) by gas chromatographic-mass spectrometry analysis of their picolinyl esters and GLC analysis of the oxidative ozonolysis products. The proportion of 5,9,20-27:3 (25.4%) in total fatty acids was much higher than that had been observed for other sponges. The contents of 5,9-26:2 (10.0%) and 5,9,19-26:3 (7.2%) were comparable to those reported. All three demospongic acids were abunduntly found in the lipid classes of phosphatidylserines and phosphatidylethanolamines.
  • Y Ando, J Nakamura, T Ota
    FISHERIES SCIENCE 63 (6) 1048 - 1049 0919-9268 1997/12 [Refereed][Not invited]
  • Y Ando, M Kotake, T Ota
    FISHERIES SCIENCE 63 (4) 605 - 609 0919-9268 1997/08 [Refereed][Not invited]
     
    Lipid profiles were compared between Artemia nauplii enriched with fish oh triacylglycerols (TG) containing docosahexaenoic acid (DHA, 22:6n-3) in different positional distribution patterns. Four fish oils were selected on the basis of the positional distribution determined by a nonenzymatic analytical method, and directly given to Artemia nauplii in the form of oil emulsions. Time-courses of the lipid contents, lipid compositions, and fatty acid compositions were not so different between the nauplii enriched with tuna orbital and bonito head oil TG, in which 22:6n-3 (22.9-24.0%) was esterified in the sn-3>sn-1 much greater than sn-2 positions and the sn-3 much greater than sn-2=sn-1 positions, respectively. In both of the enrichments, the level of 22:6n-3 initially not detected reached a plateau (3.4-3.6% of total fatty acids) after 12 h and then decreased to 1.7% (48 h). Slight differences were also observed between the lipids of nauplii fed on sardine (22:6n-3, 11.5%; sn-2 much greater than sn-3 > sn-1) and seal (22:6n-3, 7.6%; sn-3 > sn-1 > sn-2) oil TG. The levels of 22:6n-3 after 24 h enrichment were 0.4% of total fatty acids. Such similarities of the lipid profiles in Artemia nauplii indicate that the positional distribution of 22:6n-3 in dietary TG has practically no influence to enrichment of Artemia nauplii with this fatty acid. It is probable that any TG with different positional distribution patterns of 22:6n-3 can be used for enrichment of Artemia, when 22:6n-3 is concentrated in the TG at an adequate level.
  • Y Ando, T Ota, Y Matsuhira, K Yazawa
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 73 (4) 483 - 487 0003-021X 1996/04 [Refereed][Not invited]
     
    This paper presents the positional distribution of fatty acids in docosahexaenoic acid (22:6n-3)-rich fish oil triacyl-sn-glycerols (TG). Stereospecific analysis of TC was carried out by a nonenzymatic method. The TG of bonito head oil, obtained after a winterization process, contained 22:6n-3 at concentrations of 28, 7, and 49 mole % in the sn-1, sn-2, and sn-3 positions, respectively. In the TG of oil before the winterization process, 22:6n-3 was concentrated in the sn-3 position, followed evenly by the sn-1 and sn-2 positions. Tuna orbital oil, obtained after winterization, showed the preferential association of 22:6n-3 to the sn-3 position, followed by the sn-1 position. This distribution pattern was similar to that observed for seal oil TG rather than sardine oil TG. The bonito head and tuna orbital oils are useful as fish oils with characteristics different from those of common fish oils, such as menhaden, sardine, and herring oils.
  • Y Ando, A Shimoyama, T Ota
    COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY 113 (1) 89 - 93 0305-0491 1996/01 [Refereed][Not invited]
     
    Positional distributions of fatty acids in dorsal muscle triacyl-sn-glycerols (TGs) were compared between the chum salmon, Oncorhynchus keta, caught on the coast and upstream at spawning season. The upstream salmon TGs contained 22:6 in the sn-1 and sn-3 positions at the concentrations higher than the coast salmon TGs. The level of it in the sn-2 position was not so different between them. The proportions of 16:0 in the sn-1 and sn-3 positions were much lower in the upstream salmon. TGs than in the coast salmon TGs. The upstream salmon TGs also contained lower proportions of 20:5 in the sn-2 and sn-3 positions and of 16:1 in the sn-2 position. Such differences in positional distribution confirmed the view that the depletion of TGs occurred unevenly during the migration from coast to upstream. The uneven depletion of TGs was found to depend on the position in which the fatty acids are esterified.
  • TAKAGI Toru, ANDO Yasuhiro, ICHIKAWA Kazuaki
    Journal of Japan Oil Chemists' Society 日本油化学会 44 (11) 971 - 976 0513-398X 1995/11/20 [Refereed][Not invited]
     
    The steric structures of the triacylglycerols (TGs) in the seed oil of <I>carrot Daucus carota</I> L. var. <I>sativa</I> DC. were studied by the stereospecific analysis of the acyl distributions using the chiral-phase high-performance liquid chromatography of the monoacylglycerol derivatives. Total fatty acids of the seed oil TGs contained 71 mol % petroselinic acid (6-18 : 1), 12 mol % oleic acid (9-18 : 1), 11 mol %linoleic acid (18 : 2 <I>n</I>-6), and 4 mol % palmitic acid (16 : 0). Fatty acid percents in each <I>sn</I>-1, <I>sn</I>-2 and <I>sn</I>-3 position of the TGs were 6-18 : 1 (38, 23 and 40 %), 9-18 : 1 (21, 66 and 13 %), and 18 : 2 <I>n</I>-6 (20, 65and 15 %). Structures and estimated contents of the major TG components in the carrot seed oil wasfound to be (6-18 : 1) (6-18 : 1) (6-18 : 1) 3248 %, (6-18 : 1) (9-18 : 1) (6-18 : 1) 1725 %, (6-18 : 1) (18 : 2 <I>n</I>-6) (6-18 : 1) 1522 %. Petroselinic acid distributes preferentially at the <I>sn</I>-1 and <I>sn</I>-3 positionsin the carrot seed oil TGs in analogy with 16 : 0 and 18 : 0 in the ordinary seed oil TGs.
  • 安藤 靖浩, 板橋 豊
    化学と生物 学会出版センタ- 33 (8) 545 - 552 0453-073X 1995/08/25 [Refereed][Not invited]
  • T OTA, Y KAWABATA, Y ANDO
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 71 (5) 475 - 478 0003-021X 1994/05 [Refereed][Not invited]
     
    This paper presents the positional distribution of very long chain fatty acids, 24:6(n-3), in triacyl-sn-glycerols (TG) of flathead flounder (Hippoglossoides dubius). Each of the liver and flesh TGs was subjected to the stereospecific analysis. The liver TGs contained 24:6(n-3) at concentrations of 1.5, 1.2 and 1.7 mole % in the sn-1, sn-2 and sn-3 positions, respectively, and the flesh TGs had 9.0, 7.8 and 7.1 mole % in the sn-1, sn-2 and sn-3 positions, respectively. This fatty acid was distributed almost evenly among the three positions of the TGs. No preference for the sn-2 position was observed in contrast to the general tendency for the distribution of longer-chain polyunsaturated fatty acids, such as 22:6(n-3), 22:5(n-3) and 20:5(n-3). There was essentially no difference in the positional distributions of the liver and flesh TGs. The results obtained in this study give new fundamental information to the investigation of very long-chain fatty acids.
  • TAKAGI Toru, ANDO Yasuhiro
    Journal of Japan Oil Chemists' Society 日本油化学会 40 (4) 288 - 292 1884-2003 1991 [Refereed][Not invited]
     
    A modified method for the stereospecific analysis of triacylglycerols (TGs) is presented. Partially hydrolyzed products of TG with ethyl magnesium bromide were converted to 3, 5-dinitrophenylurethane (3, 5-DNPU) derivatives, and recemic 1-and 2-monoacylglycerol (MG) derivatives were separated by thin layer chromatography (TLC) on silicic acid plates. The 1-MG fraction was separated into <I>sn</I>-1 and <I>sn</I>-3 enantiomers by high performance liquid chromatography (HPLC) on a chiral stationary phase; <I>N</I>- (<I>R</I>) -1- (α-naphthyl) ethylaminocarbonyl- (<I>S</I>) -valine which was chemically bound to γ-aminopropyl silanized silica. Total TG, <I>sn</I>-1, <I>sn</I>-2 and sn-3 MG fractions were converted to the methyl esters, and each of which was analyzed by gas chromatography (GC) with an opentubular column. Acyl distribution at <I>sn</I>-1, <I>sn</I>-2 and <I>sn</I>-3 positions was determined based on the results of GC analysis. A cacao fat sample was analyzed by this method. Direct derivation prior to fractionation was found effective for reducing isomerization of MGs.
  • TAKAGI Toru, ANDO Yasuhiro
    Journal of Japan Oil Chemists' Society 日本油化学会 39 (9) 622 - 628 1884-2003 1990 [Refereed][Not invited]
     
    High-performance liquid chromatography (HPLC) using a chiral stationary phase <I>N</I>- (S) -2- (4-chlorophenyl) -D-isovaleroyl-D-phenylglycine chemically bound to γ-aminopropyl silanized silica (Sumipax OA 2100) was improved for the separation of homologous mixtures of saturated and unsaturated 1-monoacylglycerol (MG) enantiomers as 3, 5-dinitrophenylurethane (3, 5-DNPU) derivatives. By this HPLC method, it was possible to separate three saturated 1-MGs having consecutive even-carbon numbers, and 1-MG mixtures of 18 : 0, 18 : 1, 18 : 2, and 18 : 3 to <I>sn</I>-1 and <I>sn</I>-3 enantiomers of each component. It was used for the stereospecific analysis of acyl group distributions in triacylglycerols from linseed oil.<BR>A 1-MG sample from the degradation of TGs with Grignard reagent was fractionated to saturated and unsaturated fractions by thin layer chromatography on silver nitrate and boric acid-impregnated silicic acid plates. The total, saturated and unsaturated 1-MG samples were then analyzed as 3, 5-DNPU derivatives by HPLC on the chiral stationary phase. Acyl group distributions at the <I>sn</I>-1, <I>sn</I>-2 and <I>sn</I>-3 positions were determined based on the data obtained.
  • Y ANDO, T OTA, T TAKAGI
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 66 (9) 1323 - 1325 0003-021X 1989/09 [Refereed][Not invited]

MISC

  • T Mukai, K Iida, Y Ando, H Mikami, Y Maki, R Matsukura  OCEANS '04 MTS/IEEE TECHNO-OCEAN '04, VOLS 1- 2, CONFERENCE PROCEEDINGS, VOLS. 1-4  1-  383  -388  2004  [Not refereed][Not invited]
     
    In recent years, acoustic technology has been used extensively to estimate krill abundance. Acoustic assessment is required to obtain precise estimates of krill target strength (TS). However, predictions of target strength from theoretical scattering models are often influenced by the swimming angle, density, and sound speed contrasts between krill and seawater. Density and sound speed contrasts are known to show annual cycles. In this study, swimming angles and seasonal variations of the specific density and sound speed contrasts of Euphausia Pacifica are presented. Biological sampling was carried out during twilight, when the sound-scattering layer migrates up to the surface. Sound speed measurements were performed on a vessel 2 hours after net sampling, using a T-shaped velocimeter with two transducers mounted at the ends of a horizontal tube. The swimming angles and specific densities of E. Pacifica were measured at a laboratory within 48 hours of net sampling. The specific densities of the krill were measured using a series of glycerol solutions of variable densities. Moreover, the total lipid content, lipid composition, and fatty acid composition of the krill were analyzed. The swimming angles of the krill varied from 30 to 50 degrees in low illumination condition (0.1 Ix). The density and sound speed contrasts changed with the season. These variations depended on the lipid content in the krill body. In particular, the density of the krill changed with the wax ester content. The variations of TS estimated by the distorted-wave Born approximation (DWBA) method will be discussed.

Books etc

Presentations

Association Memberships

  • 日本水産学会   アメリカ油化学会   日本油化学会   The American Oil Chemists' Society   Japan Oil Chemists' Society   The Japanese Society of Fisheries Science   

Works

Research Projects

  • 日本学術振興会：科学研究費助成事業 基盤研究(C)
    Date (from‐to) : 2020/04 -2025/03 
    Author : 安藤 靖浩
     
    海産魚の食性解明に資するエイコセン酸異性体組成のデータベース構築を目的として、表層および中層の中間捕食者に焦点を当てて日本近海で採集されたマサバ、サンマ、イカ3種、ハダカイワシ9種の合計105検体のエイコセン酸の6種の異性体（20:1n-15, n-13, n-11, n-9, n-7, n-5）の組成を決定した。 マサバとサンマの筋肉では20:1n-11と20:1n-9が主要異性体であった。これら2つの異性体の組成値は海域による差異が顕著であった。北西太平洋、三陸沖、福島沖では20:1n-11が全20:1の60％以上を占め最も割合が高かったのに対し、東シナ海では20:1n-9が60-80％と首位が逆転した。イカは外套膜では20:1n-9が90％以上であり海域間の差異は認められなかった。肝臓においても外套膜と同様に20:1n-9が最も高い割合であったが、それに次ぐ20:1n-11は三陸沖と石川沖で20-30％であったのに対し東シナ海は10％に満たず、海域間の違いが認められた。ハダカイワシの筋肉は、福島沖と東シナ海の4種で20:1n-9が60％以上で最も多かった。一方、三陸沖の5種は20:1n-9が多い2種と20:1n-11が多い3種に分かれ種間の違いが認められた。三陸沖のハダカイワシは種ごとに鉛直移動を行う水深が異なることが知られており、本研究の結果は深い生息域をもつ種で20:1n-11が優先することを示した。 以上、表層魚と中層魚は同一種あるいは近縁種であっても海域や水深によってエイコセン酸異性体組成が異なることを明らかにすることができた。異性体組成の海域差は太平洋と大西洋といった大洋間だけでなく、日本周辺でも認められることが初めて明らかとなった。
  • 日本学術振興会：科学研究費助成事業 基盤研究(C)
    Date (from‐to) : 2021/04 -2024/03 
    Author : 平岡 優子, 安藤 靖浩, 橋本 博
  • 日本学術振興会：科学研究費助成事業 基盤研究(C)
    Date (from‐to) : 2020/04 -2023/03 
    Author : 芦田 拡士, 安藤 靖浩
     
    クロマグロは1産卵期に1個体が複数回産卵する多回性産卵魚である。多回性産卵魚では1回あたりの産卵数は個体の内的・外的要因によって変動することが知られている。本課題では、産卵数と卵1個当たりの脂質・脂肪酸量を用いて、1回の産卵で卵に投資する脂質・脂肪酸量 (繁殖投資量)を推定することを目的とする。 今年度のクロマグロの卵巣サンプリングを通じ、50個体の吸水卵を持つ卵巣を収集することができた。また、脂質・脂肪酸分析の実施予定のある38個体において1回あたりの産卵数を推定した。南西諸島では1回あたりの産卵数は尾叉長、漁期開始からの経過日数が有意な影響を与えることが明らかになった。 昨年度に開発した脂質・脂肪酸用分析用の吸水卵のサンプリング方法に不備が発見され、一部の個体の脂質・脂肪酸分析値にバイアスが含まれる可能性が明らかになった。そのため、サンプリング方法を改善し、吸水卵の脂質・脂肪酸の再分析を行った。吸水卵の1個当たりの総脂肪酸量は卵1個当たりの乾燥重量と正の相関がある事が改めて確認した。一方で、卵1個当たりの総脂肪酸量は1回あたりの産卵数、表面水温、尾叉長、肥満度とは有意な相関は認められなかった。 1個の吸水卵に含まれる脂質量を推定するために、13個体から卵1個当たりの脂質および脂肪酸量をそれぞれ測定し、卵1個における総脂肪酸量-総脂質量の回帰式を作成した。作成した回帰式、個体の卵1個当たりの総脂肪酸量および1回あたりの産卵数を用いて、1回あたりの産卵で吸水卵に投資される総脂質量(繁殖投資量)を32個体から推定した。推定された繁殖投資量は個体の体サイズと正の相関が認められた。
  • Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
    Date (from‐to) : 2003 -2004 
    Author : ANDO Yasuhiro, TAKATSU Tetsuya
     
    A sensitive and convenient procedure for fatty acid analysis of marine fish larvae has been developed in order to determine docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) contents as an indicator of their nutritional condition. Fatty acid content and composition in each individual of the wild marine fish larvae have been analyzed by the new procedure.1.High-performance liquid chromatography (HPLC) of fatty acid 9-anthrylmethyl esters was introduced to the new procedure. Highly sensitive fluorescent detection of the esters enabled the analysis of one eye and somatic part from one individual.2.Some processes of the analysis were modified to reduce time-consuming complicated operations. All processes after lipid extraction could be carried out in a single disposable glass vial. The analysis was completed within 3.5 hours, and about ten samples could be analyzed in one day.3.Somatic part of the 326 individuals of wild fish larvae (18 species) caught in the Funka and Mutsu Bays, Japan, were subjected to the fatty acid analysis. In all individuals, remarkable fatty acids were only five components, DHA (18-32 %), palmitic acid (18-27 %), EPA (4-19 %), octadecenoic acid (7-12 %) and stearic acid (4-23 %).4.DHA contents of the somatic part (μg/individual) were summarized for every nine individuals classified by body lengths. Coefficient of variance (CV) was high in the 2.4-3.1 and 4.4-5.2 mm brown sole (CV 0.6-1.0) and 4.8-6.0 mm Japanese anchovy (CV 0.7-0.9). Pacific sandlance showed generally lower CV (0.2-0.5 with one exception 0.9). The contents of DHA essential for marine fish larvae widely vary at specific stages during development of wild marine fish larvae.
  • Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
    Date (from‐to) : 2001 -2003 
    Author : ITABASHI Yutaka, ANDO Yasuhiro, SAWABE Tomoo
     
    The aim of this study was to clarify the distribution and physiological function of unusual glycerophospho- and glycolipids in marine organisms. For this purpose, chiral phase HPLC, reversed-phase HPLC and reversed-phase HPLC in conjunction with electrospray ionization mass spectrometry(ESI-MS) were applied to the separation and identification of stereoisomeric and regio-isomeric glycerolipids. Using these techniques, we found an unnatural phosphatidylglycerol (1,2-diacyl-sn-glycero-3-phospho-3'-sn-glycerol, R, R configurations at the two chiral centers) from various kinds of microorganisms including marine bacteria. The R, R isomer content increased with increasing culture temperature. The results strongly suggest that the bacteria adapt to temperature by alternating not only the degree of unsaturation but also the stereoisomer composition of phosphatidylglycerols. In the present study, we also investigated the separation and identification of the reverse isomers of glycerophospholipids (PtdCho,PtdEtn,PtdIno) and glycoglycerolipids (MGDG,DGDG,SQDG) by reversed-phase HPLC/ESI-MS. These glycerolipids were chromatographed as intact forms or 3,5-dinitrophenylurethanes of the 1,2-diacyl-sn-glycerols derived from the parent molecules. Excellent resolution was achieved for reverse isomers of very different pairs of acyl groups, such as 20:5-16:0 and 22:6-16:0, on highly efficient C18 columns. Using the method, we analyzed the glycerolipids from some fish and marine algae, and found that only MGDG from marine red algae, such as Porphyra yezoensis and Gracilaria verrucosa, gave two clearly resolved peaks, representing the reverse isomers of 20:5(sn-1)/16:0(sn-2) and 16:0(sn-1)/20:5(sn-2), and 20:4(sn-1)/16:0(sn-2) and 16:0(sn-1)/20:5(sn-2), respectively. The present method provides the first direct demonstration of the occurrence of reverse isomers in natural glycoglycerolipids and should be helpful in promoting work on the biosynthetic pathway and physiological importance of the reverse isomers in the red algae.
  • 日本学術振興会：科学研究費助成事業 奨励研究(A)
    Date (from‐to) : 1995 -1995 
    Author : 安藤 靖浩
     
    1.魚介類の種苗生産で利用される餌料用植物プランクトンについて、脂溶性摂餌刺激物質であるホスファチジルコリン、ジガラクトシルジアシルグリセロール、スルホキノボシルジアシルグリセロールを含む脂質成分の分析を行った。(1)脂肪酸組成を決定した。使用した5種の植物プランクトンでは構成脂肪酸が大きく異なり、飽和酸およびモノエン酸が主要成分であるもの、ジエンないしテトラエン酸を多く含むもの、ペンタエン以上の不飽和酸を著量含むものが存在することを明らかにした。(2)P.lutheriの脂質から摂餌刺激物質を単離し、含有率と構成脂肪酸を決定した。上記の摂餌刺激物質は脂肪酸含有脂質の約3分の1を占めた。ホスファチジルコリンとジガラクトシルジアシルグリセロールには高度不飽和酸が40〜60%含まれ、これらの摂餌刺激物質では不飽和度の高い分子種が多量に存在する可能性を明らかにした。2.天然の脂溶性摂餌刺激物質を構成し得る分子種を使用して、水産生物に対する摂餌刺激活性試験を実施した。(1)藻食性巻貝に対する活性試験として結晶セルロース板(アビセル板)法の適用を検討した。試験板の解析方法をわずかに改変することによって、摂餌刺激物質の分子種の場合でも本法が活性の検出・判定に有効であることを確認した。(2)植物脂質含有性で構造既知のホスファチジルコリン分子種を選定し、エゾアワビに対する摂餌刺激活性を比較した。分子種の活性は一様ではなく、特定の分子種間の活性には大きな有意差が存在した。活性と分子種の構造(不飽和度・炭素鎖長・異性体など)との関連性を検討し、供試試料(13分子種)の範囲内では分子種の不飽和度の違いがホスファチジルコリンの摂餌刺激活性に関与することを明らかにした。
  • 水産脂質成分の組成および構造分析
    Date (from‐to) : 1987
  • Analysis of marine lipids
    Date (from‐to) : 1987

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