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

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.