Fungal biotransformation products of dehydroabietic acid

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

Research output: Contribution to journalArticle

35 Citations (Scopus)

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 2007

Fingerprint

Biotransformation
biotransformation
acids
Phlebia gigantea
Coriolus versicolor
Keto Acids
Fungi
dehydroabietic acid
Trametes
Hydroxy Acids
fungi
Biological Products
Pinus sylvestris
Toxicity
Wood
High Pressure Liquid Chromatography
toxicity
Degradation

ASJC Scopus subject areas

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

Cite this

Van Beek, T. A., Claassen, F. W., Dorado, J., Godejohann, M., Sierra Alvarez, M. 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

Fungal biotransformation products of dehydroabietic acid. / Van Beek, Teris A.; Claassen, Frank W.; Dorado, Jose; Godejohann, Markus; Sierra Alvarez, Maria Reye; Wijnberg, Joannes B P A.

In: Journal of Natural Products, Vol. 70, No. 2, 02.2007, p. 154-159.

Research output: Contribution to journalArticle

Van Beek, TA, Claassen, FW, Dorado, J, Godejohann, M, Sierra Alvarez, MR & Wijnberg, JBPA 2007, 'Fungal biotransformation products of dehydroabietic acid', Journal of Natural Products, vol. 70, no. 2, pp. 154-159. https://doi.org/10.1021/np060325e
Van Beek TA, Claassen FW, Dorado J, Godejohann M, Sierra Alvarez MR, Wijnberg JBPA. Fungal biotransformation products of dehydroabietic acid. Journal of Natural Products. 2007 Feb;70(2):154-159. https://doi.org/10.1021/np060325e
Van Beek, Teris A. ; Claassen, Frank W. ; Dorado, Jose ; Godejohann, Markus ; Sierra Alvarez, Maria Reye ; Wijnberg, Joannes B P A. / Fungal biotransformation products of dehydroabietic acid. In: Journal of Natural Products. 2007 ; Vol. 70, No. 2. pp. 154-159.
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