19903-66-3Relevant academic research and scientific papers
Cytotoxic Illudane Sesquiterpenes from the Fungus Granulobasidium vellereum (Ellis and Cragin) Jülich
Nord, Christina,Menkis, Audrius,Broberg, Anders
, p. 2559 - 2564 (2015)
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.
Total synthesis of (±)-illudin M
Kinder,Bair
, p. 6965 - 6967 (2007/10/02)
(+)-Illudin M (1) was synthesized in six steps starting from 1-acetyl-1-(diazoacetyl)cyclopropane (4) and 4-bromo-5,5-dimethyl-2-cyclopentenone (5). The key step of the synthesis featured a carbonyl ylide 1,3-dipolar cycloaddition reaction that was mediat
