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Structures of three antioxidant isoflavonoids isolated from the cultured broth of Streptomyces sp. OH-1049 were shown to be 4',7,8-trihydroxyisoflavone (1), 3',4',7-trihydroxyisoflavone (2) and 8-chloro-3',4',5,7-tetrahydroxyisoflavone (3), respectively. Among them, 3 is a novel isoflavonoid possessing a chlorine atom in the molecule. Compound 1 was synthesized and its antitumor activities were tested against IMC carcinoma, S180, P388 leukemia and P388/ADM leukemia in vivo. As a result, 1 showed 139% increase in life span (ILS) against S180 bearing mice whereas it showed slight or no ILS against IMC carcinoma, P388 leukemia and P388/ADM leukemia bearing mice.

Structural study of isoflavonoids possessing antioxidant activity isolated from the fermentation broth of Streptomyces sp.