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. 1983 Aug;46(2):468–474. doi: 10.1128/aem.46.2.468-474.1983

Novel Biotransformations of 7-Ethoxycoumarin by Streptomyces griseus

F Sima Sariaslani 1, John P Rosazza 1
PMCID: PMC239413  PMID: 16346369

Abstract

Biotransformation of 7-ethoxycoumarin by Streptomyces griseus resulted in the accumulation of two metabolites which were isolated and identified as 7-hydroxycoumarin and 7-hydroxy-6-methoxycoumarin. A novel series of biotransformation reactions is implicated in the conversion of the ethoxycoumarin substrate to these products, including O-deethylation, 6-hydroxylation to form a 6,7-dihydroxycoumarin catechol, and subsequent O-methylation. Either 7-hydroxycoumarin or 6,7-dihydroxycoumarin was biotransformed to 7-hydroxy-6-methoxycoumarin by S. griseus. Trace amounts of the isomeric 6-hydroxy-7-methoxycoumarin were detected when 6,7-dihydroxycoumarin was used as the substrate. Efforts to obtain a cell-free catechol-O-methyltransferase enzyme system from S. griseus were unsuccessful. However, [methyl-14C]methionine was used with cultures of S. griseus to form 7-hydroxy-6-[14C]methoxycoumarin.

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Selected References

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