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

9 Citations (Scopus)

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

Fingerprint

Coprinus
Cyclobutanes
Growth Inhibitors
Sesquiterpenes
Antineoplastic Agents
Cells
Leukemia P388
Lymphoid Leukemia
Cell Line
Cell Separation
Bioassay
Fungi
X-Ray Diffraction
Biological Assay
Neoplasms
Nuclear magnetic resonance
Single crystals
X ray diffraction
Experiments

Keywords

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

ASJC Scopus subject areas

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

Cite this

Antineoplastic agents 582. Part 1 : Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae). / Pettit, George; Meng, Yanhui; Pettit, Robin; Herald, Delbert L.; Hogan, Fiona; Cichacz, Zbigniew.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 14, 15.07.2010, p. 4879-4883.

Research output: Contribution to journalArticle

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