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

Jixun Zhan, Leslie Gunatilaka

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 2006

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Beauveria
Anthraquinones
anthraquinones
Beauveria bassiana
Biotransformation
biotransformation
Hydroxyl Radical
Glycosylation
Hydroxylation
hydroxylation
glycosylation
amines
Amines
Substrates

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159. / Zhan, Jixun; Gunatilaka, Leslie.

In: Journal of Natural Products, Vol. 69, No. 10, 10.2006, p. 1525-1527.

Research output: Contribution to journalArticle

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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.",
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