title: Cytotoxic Illudane Sesquiterpenes from the Fungus Granulobasidium vellereum (Ellis and Cragin) Jülich.
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.
authors.affiliation: Department of Chemistry and Biotechnology, Uppsala BioCenter, Swedish University of Agricultural Sciences , P.O. Box 7015, SE-75007, Uppsala, Sweden.
authors.forename: Christina
authors.initials: C
authors.lastname: Nord
authors.affiliation: Department of Forest Mycology and Plant Pathology, Uppsala BioCenter, Swedish University of Agricultural Sciences , P.O. Box 7026, SE-75007, Uppsala, Sweden.
authors.forename: Audrius
authors.initials: A
authors.lastname: Menkis
authors.affiliation: Department of Chemistry and Biotechnology, Uppsala BioCenter, Swedish University of Agricultural Sciences , P.O. Box 7015, SE-75007, Uppsala, Sweden.
authors.forename: Anders
authors.initials: A
authors.lastname: Broberg
mesh_terms: D001487:Basidiomycota / Q000737:chemistry*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D003603:Cytotoxins; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C052673:illudin M; C052674:dihydroilludin M; C008105:illudin S