Planta Medica Letters 2015; 2(01): e69-e72
DOI: 10.1055/s-0035-1558260
Letter
Georg Thieme Verlag KG Stuttgart · New York

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

Yukihiro Kodera
Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Akitakata-shi, Japan
,
Toshiaki Matsutomo
Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Akitakata-shi, Japan
,
Kenji Itoh
Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Akitakata-shi, Japan
› Author Affiliations
Further Information

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.