Allium Chemistry: Synthesis, Natural Occurrence, Biological Activity, and Chemistry of Se-Alk(en)ylselenocysteines and Their 
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- 作者：Eric Block ; Marc Birringer ; Weiqin Jiang ; Tsukasa Nakahodo ; Henry J. Thompson ; Paul J. Toscano ; Horst Uzar ; Xing Zhang ; and Zongjian Zhu
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2001
- 出版时间：January 2001
- 年：2001
- 卷：49
- 期：1
- 页码：458 - 470
- 全文大小：163K
- 年卷期：v.49,no.1(January 2001)
- ISSN：1520-5118
文摘
Syntheses are reported for 
-glutamyl Se-methylselenocysteine (8a), selenolanthionine (16), Se-1-propenylselenocysteine (6d), Se-2-methyl-2-propenyl-L-selenocysteine (6e), and Se-2-propynyl-L-selenocysteine (6f). Oxidation of 8a and Se-methylselenocysteine (6a) gives methaneseleninic acid(24), characterized by X-ray crystallography, and dimethyl diselenide (25). Oxidation of Se-2-propenyl-L-selenocysteine (6c) gives allyl alcohol and 3-seleninoalanine (22). Compound 22 is alsoformed on oxidation of 16 and selenocystine (4). Oxidation of 6d gives 2-[(E,Z)-1-propenylseleno]propanal (36). These oxidations occur by way of selenoxides, detected by chromatographic andspectroscopic methods. The natural occurrence of many of the Se-alk(en)ylselenocysteines and their-glutamyl derivatives and oxidation products is discussed. Three homologues of the potent cancerchemoprevention agents 6a and 6c, namely 6d-f, were evaluated for effects on cell growth, inductionof apoptosis, and DNA-damaging activity using two murine mammary epithelial cell lines. Althougheach compound displays a unique profile of activity, none of these compounds (6d-f) is likely toexceed the chemopreventive efficacy of selenocysteine Se-conjugates 6a and 6c.Keywords: -Glutamyl Se-methylselenocysteine; selenoxides; Allium species; selenocysteines
-glutamyl Se-methylselenocysteine (8a), selenolanthionine (16), Se-1-propenylselenocysteine (6d), Se-2-methyl-2-propenyl-L-selenocysteine (6e), and Se-2-propynyl-L-selenocysteine (6f). Oxidation of 8a and Se-methylselenocysteine (6a) gives methaneseleninic acid(24), characterized by X-ray crystallography, and dimethyl diselenide (25). Oxidation of Se-2-propenyl-L-selenocysteine (6c) gives allyl alcohol and 3-seleninoalanine (22). Compound 22 is alsoformed on oxidation of 16 and selenocystine (4). Oxidation of 6d gives 2-[(E,Z)-1-propenylseleno]propanal (36). These oxidations occur by way of selenoxides, detected by chromatographic andspectroscopic methods. The natural occurrence of many of the Se-alk(en)ylselenocysteines and their-glutamyl derivatives and oxidation products is discussed. Three homologues of the potent cancerchemoprevention agents 6a and 6c, namely 6d-f, were evaluated for effects on cell growth, inductionof apoptosis, and DNA-damaging activity using two murine mammary epithelial cell lines. Althougheach compound displays a unique profile of activity, none of these compounds (6d-f) is likely toexceed the chemopreventive efficacy of selenocysteine Se-conjugates 6a and 6c.Keywords: -Glutamyl Se-methylselenocysteine; selenoxides; Allium species; selenocysteines