Fungal biotransformation products of dehydroabietic acid

Teris A. Van Beek, Frank W. Claassen, Jose Dorado, Markus Godejohann, Reyes Sierra-Alvarez, Joannes B.P.A. Wijnberg

Research output: Contribution to journalArticle

35 Scopus citations

Abstract

Dehydroabietic acid (DHA) (1) is one of the main compounds in Scots pine wood responsible for aquatic and microbial toxicity. The degradation of 1 by Trametes versicolor and Phlebiopsis gigantea in liquid stationary cultures was followed by HPLC-DAD-ELSD. Both fungi rapidly degraded DHA relative to a control. More breakdown products were observed for T. versicolor than for P. gigantea. After 13 days, four compounds were identified by means of spectroscopic methods in P. gigantea cultures: 1β-hydroxy-DHA (2), 1β,7α-dihydroxy-DHA (3), 1β,16-dihydroxy-DHA (5), and tentatively 1β-hydroxy-7-oxo-DHA (4). In T. versicolor cultures, 1β,16-dihydroxy-DHA (5), 7β,16-dihydroxy-DHA (6), 1β,7β,16- trihydroxy-DHA (7), 1β,16-dihydroxy-7-oxo-DHA (8), 1β,15-dihydroxy-DHA (9), and 1β,7α,16-trihydroxy-DHA (10) were identified after 9 days of incubation. Thus the biotransformation of 1 by the two fungi was different, with only 5 being produced by both strains. Compounds 3, 7, 8, and 10 are reported for the first time as natural products.

Original languageEnglish (US)
Pages (from-to)154-159
Number of pages6
JournalJournal Of Natural Products
Volume70
Issue number2
DOIs
StatePublished - Feb 1 2007

ASJC Scopus subject areas

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

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  • Cite this

    Van Beek, T. A., Claassen, F. W., Dorado, J., Godejohann, M., Sierra-Alvarez, R., & Wijnberg, J. B. P. A. (2007). Fungal biotransformation products of dehydroabietic acid. Journal Of Natural Products, 70(2), 154-159. https://doi.org/10.1021/np060325e