Antineoplastic agents 582. Part 1: Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae)

George Pettit, Yanhui Meng, Robin Pettit, Delbert L. Herald, Fiona Hogan, Zbigniew Cichacz

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Bioassay-guided (murine P388 lymphocytic leukemia and human cancer cell lines) separation of an ethyl acetate extract prepared from the inky cap fungus Coprinus cinereus led to the isolation of three new sesquiterpenes, 7,7a-diepicoprinastatin 1 (1), 14-hydroxy-5-desoxy-2S,3S,9R-illudosin (2), and 4,5-dehydro-5-deoxyarmillol (3), together with the known armillol (4). The structure and relative configuration of 1 was determined by single-crystal X-ray diffraction experiments. The structures of compounds 2, 3, and 4 were each deduced by a combination of HRMS and 1D and 2D NMR techniques. Cyclobutane 2 led to modest inhibition of the murine P388 leukemia cell line.

Original languageEnglish (US)
Pages (from-to)4879-4883
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number14
DOIs
StatePublished - Jul 15 2010

Keywords

  • 14-Hydroxy-5-desoxy-2S,3S,9R- illudosin
  • 4,5-Dehydro-5-deoxyarmillol
  • 7,7a-Diepicoprinastatin 1
  • Coprinus cinereus

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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