Six novel acyclic sulfides, named garlicnins L-1-L-4 (1-4), E (5), and F (6), were isolated from the acetone extracts, with the ability to suppress M2 macrophage activation, of the bulbs of garlic (Allium sativum L.), and their chemical structures were characterized.
Key words Allium sativum; acyclic sulfide; garlicnin L-1; garlicnin E; garlicnin F; macrophage activationGarlic, Allium sativum L. (Liliaceae) is at the top of the National Cancer Institute's list of designer foods that prevent cancer.1) Various biological activities of garlic are generally classified into two categories: (i) cardiovascular disease prevention and (ii) cancer prevention.2-5) The activities of the former include the inhibition of cholesterol synthesis, platelet aggregation, and arterial smooth muscle cell proliferation as well as anti-inflammatory, antioxidant, and hydrogen sulfidemediated vasodilatory effects. The activities of the latter include the effects on carcinogen metabolism (enhanced cellular glutathione synthesis induced cell cycle arrest and apoptosis) and the prevention of Helicobacter pylori infection, gastric cancer, and colorectal cancer are effects of the latter category.
2-5)The chemistry of garlic sulfides is summarized in a text book edited by Block.4) In a previous work, we isolated a novel, stable sulfide, named as onionin A,
6)5-(1-propenyl)-3,4-dimethyltetrahydrothiophene-2-sulfoxide-S-oxide, from the acetone extract of Allium cepa L. and found that it inhibits macrophage activation. Similarly, the sulfur-containing substances, garlicnins A, from the acetone-soluble extract of A. sativum L. were isolated along with E-azoene 10) and characterized to help in the development of natural, healthy foods that may prevent and combat disease, particularly tumors. Successively, the related acyclic sulfides garlicnins L-1-L-4, E, and F, were isolated and characterized. This paper discusses the characterization of the chemical structure of these compounds.Chinese garlic (1061 g) was roughly chopped and blended in a mixer along with acetone. Subsequently, the mixture was soaked in additional acetone for 3 d at room temperature. The filtrate was evaporated at 40°C in vacuo to obtain a residue (26.1 g), which was then subjected to polystyrene gel column chromatography . It was first eluted with water, then with methanol (the residue after evaporation: 5.90 g), and finally with acetone (the residue after evaporation: 0.32 g). A part of the methanolic eluate (3.0 g) was partitioned between ethyl acetate (EtOAc) and water. The respective residues (Fr.