Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159

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20 Scopus citations

Abstract

Microbial biotransformation of four amino- and hydroxyanthraquinones catalyzed by Beauveria bassiana ATCC 7159 has been studied. Incubation of 1,2-diaminoanthraquinone (1) with B. bassiana ATCC 7159 afforded 1-amino-2-(4′-O-methyl-2β-N-D-glucopyranosylamino)anthraquinone (5) in a hitherto unprecedented biotransformation involving N-glycosylation of an amine. Biotransformation of 1-aminoanthraquinone (2) yielded 1-amino-2-(4′-O-methyl-2β-O-D-glucopyranosyloxy)anthraquinone (6) as a result of microbial hydroxylation of C-2 followed by 4′-O-methyl- glucosylation of the newly introduced hydroxyl group. 1,8-Dihydroxyanthraquinone (3) and 1,2-dihydroxyanthraquinone (4) afforded 8-hydroxy-1-(4′-O-methyl- 1β-O-D-glucopyranosyloxy)anthraquinone (7) and 1-hydroxy-2-(4′-O- methyl-2β-O-D-glucopyranosyloxy)anthraquinone (8), respectively, resulting from 4′-O-methyl-glucosylation of the existing hydroxyl groups of the substrates. The efficiency of these conversions suggests that microbial biotransformation reactions offer an attractive alternative to chemical 4′-O-methyl-glucosylation of amino- and hydroxyanthraquinones.

Original languageEnglish (US)
Pages (from-to)1525-1527
Number of pages3
JournalJournal Of Natural Products
Volume69
Issue number10
DOIs
StatePublished - Oct 1 2006

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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