Cyclic Sulfoxides Garlicnins B2, B3, B4, C2, and C3 from Allium sativum

Toshihiro Nohara; Yukio Fujiwara; Tsuyoshi Ikeda; Kohtaro Murakami; Masateru Ono; Daisuke Nakano; Junei Kinjo

doi:10.1248/cpb.c13-00082

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Cyclic Sulfoxides Garlicnins B₂, B₃, B₄, C₂, and C₃ from Allium sativum

Toshihiro Nohara , Yukio Fujiwara, Tsuyoshi Ikeda, Kohtaro Murakami, Masateru Ono, Daisuke Nakano, Junei Kinjo

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Keywords: Allium sativum, cyclic sulfoxide, tetrahydrothiophene-S-oxide, garlicnin B, garlicnin C, macrophage activation

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2013 Volume 61 Issue 7 Pages 695-699

DOI https://doi.org/10.1248/cpb.c13-00082

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Abstract

Several novel sulfides, called garlicnins B₂ (1), B₃ (2), B₄ (3), C₂ (4), and C₃ (5), were isolated from acetone extracts of garlic, Allium sativum L. and characterized. These garlicnins are capable of suppressing M2 macrophage activation and they have a novel skeleton of cyclic sulfoxide. The structures of the former 3 and latter of 2 were deduced to be 2-(sulfenic acid)-5-(allyl)-3,4-dimethyltetrahydrothiophene-S-oxides and 2-(allyldithiine)-5-(propenylsulfoxide)-3,4-dimethyltetrahydrothiophene-S-oxides, respectively. The mechanism of the proposed production of these compounds is discussed. The identification of these novel sulfoxides from garlic accumulates a great deal of new chemistry in the Allium sulfide field, and future pharmacological investigations of these compounds will aid the development of natural, healthy foods and anti-cancer agents that may prevent or combat disease.

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