Anti-riboflavin activity of 8-O-alkyl derivatives of riboflavin in some gram-positive bacteria.

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  • KASAI Sabu
    Division of Biology, Research Institute for Atomic Energy, Osaka City University
  • YAMANAKA Shigeko
    Division of Biology, Research Institute for Atomic Energy, Osaka City University
  • WANG Shiu-Chuan
    Division of Biology, Research Institute for Atomic Energy, Osaka City University
  • MATSUI Kunio
    Division of Biology, Research Institute for Atomic Energy, Osaka City University

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  • Anti Riboflavin Activity of 8 O Alkyl D

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Abstract

Two new 8-O-alkyl derivatives of riboflavin (RF), i.e., 8-methoxy- (MOF), and 8-ethoxy-8-demethyl-D-riboflavin (EOF), their tetraacetate, and the tetraacetate of 8-hydroxy-8-demethyl-D-riboflavin (HOF) were synthesized. The anti-RF activity of MOF, EOF and HOF was estimated from the ratio CR/CI, where CI is the concentration of test flavin added to the culture medium and CR is the minimum concentration of RF needed to restore the growth inhibition. Their activity was also compared with that of roseoflavin (RoF). The decreasing order of anti-RF activity was as follows: MOF>RoF>EOF in Sarcina lutea; RoF>MOF>EOF in Bacillus cereus and Staphylococcus aureus. HOF showed no activity in any of the bacteria tested. The redox potential of these compounds decreases as follows: RF>RoF>EOF>MOF>HOF, and the anti-RF activity of MOF and EOF could be explained by the redox potential difference between these compounds and RF.

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