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1993 Fiscal Year Final Research Report Summary

Enantiomer resolution of glycerolipid components of fish oils by chromatography

Research Project

Project/Area Number 04660217
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Fisheries chemistry
Research InstitutionHokkaido University

Principal Investigator

ITABASHI Yutaka  Hokkaido Univ., Fac. of Fish., Assoc.Prof., 水産学部, 助教授 (60142709)

Co-Investigator(Kenkyū-buntansha) MIYASHITA Kazuo  Hokkaido Univ., Fac. of Fish., Instructor, 水産学部, 助手 (10182015)
OTA Toru  Hokkaido Univ., FAc. of Fish., Professor, 水産学部, 教授 (20001612)
Project Period (FY) 1992 – 1993
KeywordsPolyunsaturated fatty acids / Diacylglycerols / Phosphatidylcholines / HPLC / Grignard degradation / enantiomer resolution / GLC / Triacylglycerols
Research Abstract

A rapid ans sensitive high-performance liquid chloromatographic method for the enantiomer resolution of polyunsaturated sn-1,2- and sn-2,3- diacylglycerols as their 3,5-dinitrophenylurethanes was developed with a chiral column (25 cm long) containing (R)-(+)-1-(1-naphthyl)ethylamine. By an isocratic elution with n-hexane-1,2-dichloroethane-ethanol (40 : 30 : 1 by volume), complete enantiomer resolution was obtained within 15 min for monoacid sn-1,2- and sn-2,3-diacylglycerols of linoleic, linolenic, arachidonic, eicosapentaenoic and docosahexaenoic acids.
The methos was applied to the enantiomer resolution of the sn-1,2(2,3)-diacylglycerol moieties of triacylglycerols and phosphatidylcholines from some marine organisms. The sn-1,2(2,3)-diacylglycerols generated by Grignard degradation from the triacylglycerols of tuna fish orbital, pacific pomfret flesh, sardine flesh, mackerel flesh, salmon egg and scallop hepatopancreas were clearly resolved into two groups, which represented sn-1,2- and sn-2,3-diacylglycerol enantiomers. This clear resolution permits the preparative separation of the enatimeric diacylglycerols on the chiral column and the polar capillary GLC of the collected fractions, which would give the detailed enantiomer composition. Satisfactory enantiomer resolution was obtained for the sn-1,2(2,3)-diacylglycerols generated from the triacylglycerols of saury flesh and sea urchin gonard, although some peak overlapings between sn-1,2-enantiomers containing polyunsaturated acids and sn-2,3-enantiomers containing long-chain monounsaturated acids were observed. The diacylglycerols derived from phosphatidylcholines of saury, pacific pomfret and sea urchin by venom phospholipase C were only the sn-1,2-enantiomers. The method presented was also applied to the determination of the stereospecificity of lipases from porcine pancreas, scallop hepatopancreas and some microorganisms.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Yutaka Itabashi: "Chiral phase LC/MS of the 3,5-dinitrophenylurethanes of natural diacylglycerols" Proceedings of the Kyoto'92 international conference on biological mass spectrometry. 340-341 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 板橋 豊: "キラルHPLC/極性キャピラリーGCによるジアシルグリセロールエナンチオマーの分子種分析" 生体成分の分析化学シンポジウム. 10. 77-80 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 板橋 豊: "キラル相HPLCによる高度不飽和酸含有ジアシルグリセロールの光学分割" クロマトグラフィー. 14. 172-173 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 板橋 豊: "キラル相HPLCによるリパーゼの位置特異性の決定" クロマトグラフィー. 14. 170-171 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 板橋 豊: "豚すい臓リパーゼの立体特異性発現について" 脂質生化学研究. 35. 427-430 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yutaka Itabashi: "Lipase activity of scallop hepatopancreas" Fisheries Science. (in press). (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Itabashi: "Chiral phase LC/MS of the 3,5-dinitrophenylurethanes of natural diacylglycerols." Proc.Kyoto'92 Int.Conf.Biol.Mass Spec.340-341 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Itabashi: "Molecular species analysis of diacylglycerol enantiomers by chiral phase HPLC and polar capillary GLC." Tenth Symp.Anal.Chem.Biol.Subs.Kyoto. 77-80 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Itabashi: "Enantiomer resolution of diacylglycerols containing polyunsaturated fatty acids by chiral phase HPLC." Chromatography. 14. 172-173 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Itabashi: "Determination of lipase regiospecificity by chiral phase HPLC." Chromatography. 14. 170-171 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.itabashi: "Stereospecificity of porcine pancreatic lipase." Proc.Japan.Conf.Biochem.Lipids. 35. 427-430 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Itabashi: "Lipase activity of scallop hepatopancreas." Fisheries Science. (in press). (1994)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1995-03-27  

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