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

食品生锈：类前列腺素结构物质形成的红色素

• 批准号: 01560226
• 负责人: NAKAMURA Takashi
• 金额: $ 1.22万
• 依托单位: Kyushu University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1989
• 资助国家: 日本
• 起止时间: 1989 至 1990
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-01560226/
• 关键词: Rusting 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

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.

前列腺素样共轭羰基与氨基酸的反应形成的红色颜料的特性和结构被研究。在40^c的黑暗中氧化多不饱和的脂质后，羰基，0.05-0.1％的0.05-0.1％的最大产生施加脂质的最大产生是通过凝胶色谱法在Sephadex LH-20上成功制成的，在硅凝胶60和高性能色谱（HPLC）上，在Sephadex LH-20，圆柱色谱上制备了。在制备实验中，一种新的甲基5- [2-甲基乙烯基）-3-羟基-5-氧气环戊烯基]五烷酸盐，并且在自氧化的γ-粘醇中发现了前体。使用纯化的3-（2-乙基-5-羟基-3-氧基 - 环戊烯基）-2-苯甲酸和GLY，研究了pH和反应温度对红色颜料形成的影响：在pH 7时，获得了最大产量；在酸性pH下，观察到最小反应速率。在酒精pH或高温下，颜料不稳定并变成荧光物质。使用与紫外线，VIS和荧光探测器的HPLC设备，分析了通过与各种氨基酸反应获得的每种色素混合物。一个或多个色素峰（A_ <515nm>在没有荧光的情况下观察到所施加的氨基酸的特殊性。结果表明，氨基酸的整个分子在没有Schiff碱基浓缩的情况下掺入了红色颜料中。质量光谱和NMR光谱仪，红色颜料的结构分析是在红色颜料的过程中。

项目成果

Yoichiro Hama(濱 洋一郎): "Conjugated Carbonyls with a Hydroxypentanone ring in Autoxidized γーLinolenate" 油化学.

Yoichiro Hama：“自氧化 γ-亚麻酸酯中具有羟基戊酮环的共轭羰基”石油化学。

濱 洋一郎: "Conjugated Carbonyls with a Hydroxypentanone Ring in Autoxidized γーLinolenate" 油化学.

Yoichiro Hama：“自氧化 γ-亚麻酸酯中具有羟基戊酮环的共轭羰基”石油化学。

Yoichiro Hama and Takashi Nakamura: "Conjugated Carbonyls with a Hydroxypentanone Ring in Autooxidized gamma-Linolenate," YUKAGAKU. (1991)

Yoichiro Hama 和 Takashi Nakamura：“自氧化γ-亚麻酸酯中带有羟基戊酮环的共轭羰基”，YUKAGAKU。

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)

Yoichiro Hama：“自氧化脂质中具有类前列腺素环结构的共轭羰基的测定”，日本水产科学学会杂志 56. 147-152 (1990)。

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)

Yoichiro Hama、Hiroyuki Maeda 和 Takashi Nakamura：“自氧化脂质中具有前列腺素样环结构的共轭羰基的测定”Nippon Suisan Gakkaishi。