Subscribe to RSS
DOI: 10.1055/s-0035-1558260
The Evidence for the Production Mechanism of cis-S-1-Propenylcysteine in Aged Garlic Extract Based on a Model Reaction Approach Using Its Isomers and Deuterated Solvents
Publication History
received 29 June 2015
revised 14 September 2015
accepted 21 October 2015
Publication Date:
21 December 2015 (online)
Abstract
cis-S-1-Propenylcysteine has been identified in aged garlic extract, however, its production mechanism is still unclear. The content of cis-S-1-propenylcysteine in aged garlic extract at 22 months of aging was more than twice the molarity of γ-glutamyl-cis-S-1-propenylcysteine in raw garlic, a plausible precursor of cis-S-1-propenylcysteine. We found that cis-S-1-propenylcysteine was generated through the isomerization of trans-S-1-propenylcysteine in the model reactions. These results suggested that the isomerization was induced by the electron-releasing conjugative effect of the sulfur atom in S-1-propenylcysteine.
-
References
- 1 Koch HP, Lawson LD. Garlic. The science and therapeutic application of Allium sativum L. and related species. 2nd. edition. Baltimore: Williams & Wilkins; 1996: 37-107
- 2 Amagase H. Clarifying the real bioactive constituents of garlic. J Nutr 2006; 136: 716S-725S
- 3 Matsutomo T, Kodera Y. Development of an analytical method for sulfur compounds in aged garlic extract using a post-column high performance liquid chromatography method with sulfur-specific detection. J Nutr 2015; , in press
- 4 Lawson LD, Wang ZJ, Hughes BG. γ-Glutamyl-S-alkylcysteine in garlic and other Allium spp.: Precursor of age-dependent trans-1-propenyl thiosulfinates. J Nat Prod 1991; 54: 436-444
- 5 Oae S, Tamagaki S, Kunieda N. Organic sulfur chemistry. Kyoto: Kagakudojin; 1982: 41-81
- 6 Oae S, Ohno A, Tagaki W. Acid-catalyzed hydrogen-deuterium exchange reaction of deuterated anisole, thioanisole and benzene. Bull Chem Soc Jpn 1962; 35: 681-683
- 7 King FE, Kidd DAA. A new synthesis of glutamine and of γ-dipeptides of glutamic acid from phthalylated intermediates. J Chem Soc 1949; 3315-3319
- 8 Carson JF, Wong FF. Synthesis of cis-S-prop-1-enyl-L-cysteine. Chem Ind 1963; 2: 764-776
- 9 Moriguchi T, Matsuura H, Kodera Y, Itakura Y, Katsuki H, Saito H, Nishiyama N. Neurotrophic activity of organosulfur compounds having a thioallyl group on cultured rat hippocampal neurons. Neurochem Res 1997; 22: 1449-1452
- 10 Namyslo JC, Stanitzek C. A palladium-catalyzed synthesis of isoalliin, the main cysteine sulfoxide in onions (Allium cepa). Synthesis 2006; 20: 3367-3369
- 11 Ryu K, Ide N, Matsuura H, Itakura Y. Nα-(1-Deoxy-D-fructos-1-yl)-L-arginine, an antioxidant compound identified in aged garlic extract. J Nutr 2001; 131: 972S-976S