Garlicnins B1, C1, and D, from the Fraction Regulating Macrophage Activation of Allium sativum

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Several novel sulfides from acetone extracts of bulbs of garlic (Allium sativum L.), were identified and investigated. These were named garlicnins B1 (1), C1 (2), and D (3), and they were found to have the ability to control macrophage activation. Garlicnins B1 (1) and C1 (2) possess a new skeleton of cyclic sulfoxide and their structures of garlicnins B1 (1) and C1 (2) were characterized as 3,4-dimethyltetrahydrothiophene-S-oxide derivatives carrying the substitutions of a propenyl and a sulfenic acid, and an allyldithiine and a 1-propene-sulfenic acid (a), respectively. The mechanism of the proposed production of these compounds is discussed. Garlicnin D (3), dithiine-type, was estimated to be derived by addition of (a)+allyl thiosulfenic acid (b) derived from allicin. The identification of these novel sufoxides from onion and garlic accumulates a great deal of new chemistry to the Allium sulfide field, and future pharmacological investigations aid the development of natural, healthy foods and anti-cancer agents that could potentially prevent or combat disease.