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Rusting of Foods : Red Pigments Formed by Prostaglandin-Like Structure Substances

Research Project

Project/Area Number 01560226
Research Category

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

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

Principal Investigator

NAKAMURA Takashi  Kyushu Univ., Agric. Associate Prof., 農学部, 助教授 (10038292)

Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1990: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsRusting of foods / Peroxidized lipids / Red pigment / Prostaglandin / Amino acid / Conjugated aldehyde / Discoloration of foods / Formation mechanism / アシノ酸 / 赤変 / 油焼け
Research Abstract

Properties and structures of the red pigments formed by the reaction of prostaglandin-like conjugated carbonyls with amino acids were studied. After oxidation of polyunsaturated lipids in the dark at 40^゚C, the carbonyls, 0.05-0.1 % maximum production of applied lipids, were prepared successively by gel chromatography on Sephadex LH-20, column chromatography on Silica gel 60 and High Performance Chromatography (HPLC) on mu-Porasil. In the preparatory experiment, a new carbonyl of methyl 5-[2-(2-formylvinyl)-3-hydroxy-5-oxocyclopentyl] pentanoate and it's precursor were found in autooxidized gamma-linolenate. Using purified 3-(2-ethyl-5-hydroxy-3-oxo-cyclopentyl)-2-propenal and Gly, effects of pH and reaction temperature on the formation of red pigments were investigated : at pH 7 the maximum production was obtained ; at acidic pH the least reaction rate was observed ; at alkaline pH or in high temperature the pigments were unstable and changed into fluorescent substances. Using a HPLC-equipment with UV, VIS, and fluorescence detectors, each of the pigment mixtures obtained by the reaction with various amino acids was analyzed. One or more of pigment peaks (A_<515nm> peculiar to the applied amino acids were observed without fluorescence. The results suggested that the whole molecules of amino acids were incorporated without Schiff base condensation into red pigments. Structure analyses of red pigments are in progress by mass spectrometry and NMR-spectrometry.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (5 results)

All Other

All Publications (5 results)

  • [Publications] Yoichiro Hama(濱 洋一郎): "Determination of Conjugated Carbonyls with a Prostaglandinーlike Ring Structure in Autoxidized Lipids," 日本水産学会誌. 56. 147-152 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Yoichiro Hama(濱 洋一郎): "Conjugated Carbonyls with a Hydroxypentanone ring in Autoxidized γーLinolenate" 油化学.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Yoichiro Hama, Hiroyuki Maeda, and Takashi Nakamura: "Determination of Conjugated Carbonyls with a Prostaglandin- like Ring Structure in Autooxidized Lipids" Nippon Suisan Gakkaishi. 56(1). 147-152 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Yoichiro Hama and Takashi Nakamura: "Conjugated Carbonyls with a Hydroxypentanone Ring in Autooxidized gamma-Linolenate," YUKAGAKU. (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 濱 洋一郎: "Conjugated Carbonyls with a Hydroxypentanone Ring in Autoxidized γーLinolenate" 油化学.

    • Related Report
      1990 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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