title: Benzanthrins A and B, a new class of quinone antibiotics. II. Isolation, elucidation of structure and potential antitumor activity.
abstract: 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.
mesh_terms: 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
chemical_list: D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; C051052:benzanthrin A; C051053:benzanthrin B