Fungal Biotransormation Products of Dehydroabietic Acid

T.A. van Beek, F.W. Claassen, J. Dorado, M. Godejohann, R. Sierra-Alvarez, J.B.P.A. Wijnberg

Research output: Contribution to journalArticleAcademicpeer-review

36 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: 1 beta-hydroxy-DHA (2), 1 beta,7 alpha-dihydroxy-DHA (3), 1 beta,16-dihydroxy-DHA (5), and tentatively 1 beta-hydroxy-7-oxo-DHA (4). In T. versicolor cultures, 1 beta,16-dihydroxy-DHA (5), 7 beta,16-dihydroxy-DHA (6), 1 beta,7 beta,16-trihydroxy-DHA (7), 1 beta,16-dihydroxy-7-oxo-DHA (8), 1 beta,15-dihydroxy-DHA (9), and 1 beta,7 alpha,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
Pages (from-to)154-159
JournalJournal of Natural Products
Volume70
Issue number2
DOIs
Publication statusPublished - 2007

Keywords

  • pseudomonas-abietaniphila bkme-9
  • mill effluent
  • kraft pulp
  • mortierella-isabellina
  • bacterial degradation
  • resin acids
  • paper-mill
  • hydroxylation
  • diterpenoids
  • constituents

Fingerprint Dive into the research topics of 'Fungal Biotransormation Products of Dehydroabietic Acid'. Together they form a unique fingerprint.

  • Cite this

    van Beek, T. A., Claassen, F. W., Dorado, J., Godejohann, M., Sierra-Alvarez, R., & Wijnberg, J. B. P. A. (2007). Fungal Biotransormation Products of Dehydroabietic Acid. Journal of Natural Products, 70(2), 154-159. https://doi.org/10.1021/np060325e