Structural study of isoflavonoids possessing antioxidant activity isolated from the fermentation broth of Streptomyces sp.
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.
Funayama
S
S
Kitasato Institute, Tokyo, Japan.
Anraku
Y
Y
Mita
A
A
Komiyama
K
K
Omura
S
S
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000302:isolation & purification* / Q000627:therapeutic use; D000975:Antioxidants / Q000302:isolation & purification* / Q000627:therapeutic use; D055598:Chemical Phenomena; D002621:Chemistry; D004353:Drug Evaluation, Preclinical; D005260:Female; D005285:Fermentation; D005419:Flavonoids / Q000302:isolation & purification*; D007529:Isoflavones / Q000302:isolation & purification* / Q000627:therapeutic use; D007942:Leukemia, Experimental / Q000188:drug therapy; D051379:Mice; D013302:Streptomyces; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D000975:Antioxidants; D005419:Flavonoids; D007529:Isoflavones; C061216:8-chloro-3',4',5,7-tetrahydroxyisoflavone; C061214:4',7,8-trihydroxyisoflavone; C061213:3',4',7-trihydroxyisoflavone