title: Chemical and Biological Properties of S-1-Propenyl-l-Cysteine in Aged Garlic Extract.
abstract: S-1-Propenyl-l-cysteine (S1PC) is a stereoisomer of S-1-Propenyl-l-cysteine (SAC), an important sulfur-containing amino acid that plays a role for the beneficial pharmacological effects of aged garlic extract (AGE). The existence of S1PC in garlic preparations has been known since the 1960's. However, there was no report regarding the biological and/or pharmacological activity of S1PC until 2016. Recently, we performed a series of studies to examine the chemical, biological, pharmacological and pharmacokinetic properties of S1PC, and obtained some interesting results. S1PC existed only in trace amounts in raw garlic, but its concentration increased almost up to the level similar of SAC through aging process of AGE. S1PC showed immunomodulatory effects in vitro and in vivo, and reduced blood pressure in a hypertensive animal model. A pharmacokinetic study revealed that S1PC was readily absorbed after oral administration in rats and dogs with bioavailability of 88-100%. Additionally, S1PC had little inhibitory influence on human cytochrome P450 activities, even at a concentration of 1 mM. Based on these findings, S1PC was suggested to be another important, pharmacologically active and safe component of AGE similar to SAC. In this review, we highlight some results from recent studies on S1PC and discuss the potential medicinal value of S1PC.
authors.affiliation: Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Hiroshima 739-1195, Japan. kodera_y@wakunaga.co.jp.
authors.forename: Yukihioro
authors.initials: Y
authors.lastname: Kodera
authors.affiliation: Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Hiroshima 739-1195, Japan. ushijima_m@wakunaga.co.jp.
authors.forename: Mitsuyasu
authors.initials: M
authors.lastname: Ushijima
authors.affiliation: Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Hiroshima 739-1195, Japan. amano_h@wakunaga.co.jp.
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Amano
authors.affiliation: Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Hiroshima 739-1195, Japan. suzuki_j@wakunaga.co.jp.
authors.forename: Jun-Ichiro
authors.initials: JI
authors.lastname: Suzuki
authors.affiliation: Drug Discovery Laboratory, Wakunaga Pharmaceutical Co., Ltd., Hiroshima 739-1195, Japan. matsutomo_t@wakunaga.co.jp.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Matsutomo
mesh_terms: D053898:Biosynthetic Pathways; D003545:Cysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D005737:Garlic / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D013455:Sulfur / Q000737:chemistry; D013997:Time Factors
chemical_list: D010936:Plant Extracts; C000619278:S-1-propenyl-l-cysteine; D013455:Sulfur; D003545:Cysteine
keywords: S-1-propenyl-L-cysteine; aged garlic extract; antihypertension; drug-drug interactions; garlic (Allium sativum L.); immunomodulatory effect; isomerization; organic synthesis; pharmacokinetics; processing