Isolation and Identification of Three γ-Glutamyl Tripeptides and Their Putative Production Mechanism in Aged Garlic Extract

被引：25
作者：
Nakamoto, Masashi [1 ]
Fujii, Takuto [2 ]
Matsutomo, Toshiaki [2 ]
Kodera, Yukihiro [2 ]
机构：
[1] Wakunaga Pharmaceut Co Ltd, Healthcare Res & Dev Div, 1624 Shimokotachi,Koda Cho, Akitakata, Hiroshima 7391195, Japan
[2] Wakunaga Pharmaceut Co Ltd, Cent Res Inst, 1624 Shimokotachi,Koda Cho, Akitakata, Hiroshima 7391195, Japan
来源：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2018年 / 66卷 / 11期
关键词：
aged garlic extract; garlic; gamma-glutamyl transpeptidase; gamma-glutamyl tripeptide; METHYL-L-CYSTEINE; TRANSFERASE PEPTIDES; ALLIUM; TRANS-S-1-PROPENYL-L-CYSTEINE; BIOSYNTHESIS; PRECURSORS; SULFUR; NK;
D O I：
10.1021/acs.jafc.7b05480
中图分类号：
S [农业科学];
学科分类号：
09 ;
摘要：
We analyzed aged garlic extract (AGE) to understand its complex sulfur chemistry using post-column high-performance liquid chromatography with an iodoplatinate reagent and liquid chromatography high resolution mass spectrometry (LC-MS). We observed unidentified peaks of putative sulfur compounds. Three compounds were isolated and identified as gamma-glutamyl-gamma-glutamyl-S-methylcysteine, gamma-glutamyl-gamma-glutamyl-S-allylcysteine (GGSAC) and gamma-glutamyl-gamma-glutamyl-S-1-propenyl-cysteine (GGS1PC) by nuclear magnetic resonance and LC-MS analysis based on comparisons with chemically synthesized reference compounds. GGSAC and GGS1PC were novel compounds. Trace amounts of these compounds were detected in raw garlic, but the contents of these compounds increased during the aging process. Production of these compounds was inhibited using a gamma-glutamyl transpeptidase (GGT) inhibitor in the model reaction mixtures. These findings suggest that gamma-glutamyl tripeptides in AGE are produced by GGT during the aging process.
引用
收藏
页码：2891 / 2899
页数：9
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