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 language | English (US) |
---|---|
Pages (from-to) | 1525-1527 |
Number of pages | 3 |
Journal | Journal Of Natural Products |
Volume | 69 |
Issue number | 10 |
DOIs | |
State | Published - Oct 2006 |
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry