The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
BENZANTHRINS A AND B, A NEW CLASS OF QUINONE ANTIBIOTICS
II. ISOLATION, ELUCIDATION OF STRUCTURE AND POTENTIAL ANTITUMOR ACTIVITY
RONALD R. RASMUSSENMERRILL E. NUSSMICHAEL H. SCHERRSANDRA L. MUELLERJAMES B. MCALPINELESTER A. MITSCHER
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1986 Volume 39 Issue 11 Pages 1515-1526

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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 diglycosides 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.

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