Abstract

Eight illudane sesquiterpenes were obtained from the wood-decomposing fungus Granulobasidium vellereum (Ellis and Cragin) Jülich; among them were the enantiomers of the known compounds illudin M (1) and dihydroilludin M (4) and the diastereomers of illudin M (2) and illudin S (3), as well as two previously undescribed illudanes (5, 6). The cytotoxicity of compounds 1-4 and 6 was evaluated against two tumor cell lines (Huh7 and MT4), which showed that compounds 1-3 had potent cytotoxic activity, whereas compounds 4 and 6 had no or only moderate effects at concentrations up to 400 μM. Surprisingly, both compounds 2 and 3 were about 10 times more potent than 1. When the chemical reactivity of 1 and 2 was tested, compound 2 was shown to have a substantially higher reaction rate when reacted both with 2 M HCl and with cysteine, indicating that the difference in cytotoxicity is probably due to chemical reactivity and not to enzymatic affinity.

Published in

Journal of Natural Products
2015, Volume: 78, number: 11, pages: 2559-2564
Publisher: American Chemical Society

SLU Authors

• Nord, Christina

  • The Department of Chemistry and Biotechnology, Swedish University of Agricultural Sciences
    

• Menkis, Audrius

  • Department of Forest Mycology and Plant Pathology, Swedish University of Agricultural Sciences
    

• Broberg, Anders

  • The Department of Chemistry and Biotechnology, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Organic Chemistry


Publication identifier

DOI: https://doi.org/10.1021/acs.jnatprod.5b00500

Permanent link to this page (URI)

https://res.slu.se/id/publ/68868