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.

研究了类前列腺素共轭羰基与氨基酸反应形成的红色素的性质和结构。在 40°C 的黑暗条件下氧化多不饱和脂质后，羰基的最大产量为 0.05-0.1%。通过Sephadex LH-20凝胶色谱、硅胶60柱色谱和高效色谱法成功制备了在制备实验中，在自氧化的γ-亚麻酸酯中发现了5-[2-(2-甲酰基乙烯基)-3-羟基-5-氧代环戊基]戊酸甲酯及其前体的新羰基。纯化的 3-(2-乙基-5-羟基-3-氧代-环戊基)-2-丙烯醛和甘氨酸，pH 和反应温度对研究了红色颜料的形成：在pH 7 时获得最大产量；在酸性pH 下观察到最小反应速率；在碱性pH 或高温下，颜料不稳定并转变为荧光物质。紫外、可见光和荧光检测器，对与各种氨基酸反应得到的每种色素混合物进行了分析，观察到所应用的氨基酸特有的一个或多个色素峰（A_<515nm>，没有荧光。结果表明：整个氨基酸分子在没有席夫碱缩合的情况下被纳入红色颜料中。红色颜料的结构分析正在通过质谱和核磁共振光谱法进行。

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。