59 放線菌Streptomyces chromofuscus SM-173株が生産する新規抗生物質SM-173Bおよびその構造について

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A soil isolate, Streptomyces chromofuscus SM-173, produced two pigment antibiotics, SM-173A and SM-173B. SM173A was easily converted into SM-173B in the culture, particularly under limited aeration. In this report are described production, isolation and structure determination of a new antibiotic SM-173B. Streptomyces chromofuscus SM-173 was aerobically cultivated in a medium containing glucose and natural nitrogen sources as main components. SM-173A and SM-173B were produced after 3-4 days of cultivation, when aeration and agitation were stopped and the culture was kept standing. Under this condition, SM-173A was quantitatively converted into SM-173B. SM-173B in the culture was extracted into ethylacetate and obtained as orange crystals after silica gel column chromatographies. SM-173B is an indicator, whose UV spectrum shows a partial structure of 1,8-dihydroxyanthraquinone. Analyses of NMR spectra of SM-173B as well as its derivatives indicated that SM-173B belongs to anthracyclines. SM-173A, on the other hand, was a glycoside having the same chromophore as that of SM-173B and was identified to be aranciamycin. The structure was determined to be a glycoside with 2-O-methyl-L-rhamnose attached to C7 position of SM-173B through oxygen atom. Both SM-173A and SM-173B exhibited antibacterial activity against Gram-positive bacteria including Mycobacterium and Staphylococcus.
1979-09-20