Benzanthrins A and B, a new class of quinone antibiotics. II. Isolation, elucidation of structure and potential antitumor activity.
The benzanthrins, which were produced by Nocardia lurida, were extracted from the fermentation broth with CH2Cl2. Subsequent purification on Sephadex LH-20 and diolbonded silica gel, followed by countercurrent chromatography, afforded analytically pure benzanthrins A and B. FAB-MS revealed that benzanthrins A and B were isomeric. It was demonstrated through degradative and spectroscopic studies that the benzanthrins were di-glycosides of a trihydroxy benz[a]anthraquinone chromophore where one of the sugars was linked through carbon and the other through oxygen. Benzanthrins A and B differed in the stereochemistry of the O-glycosidic sugar. Both compounds inhibited the growth of Gram-positive bacteria and 9KB, 9PS and 9ASK tumor cells in tissue culture.
D000818:Animals; D000880:Anthraquinones / Q000302:isolation & purification / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000302:isolation & purification* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009374:Neoplasms, Experimental / Q000188:drug therapy; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; C051052:benzanthrin A; C051053:benzanthrin B