Antineoplastic agents. 556. Isolation and structure of coprinastatin 1 from coprinus cinereus

George Pettit, Yanhui Meng, Robin Pettit, Delbert L. Herald, Zbigniew Cichacz, Dennis L. Doubek, Linda Richert

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Cancer cell line bioassay-guided separation of an ethyl acetate extract prepared from a plant-associated fungus, Coprinus cinereus, led to the isolation of three new sesquiterpenes, coprinastatin 1 (1), coprinol (2), and the epimer (4a), of the known sesquiterpene triol 4b. The previously described sesquiterpene 3 and oxazolinone 5 were also isolated. The structure and relative configuration of coprinastatin 1 (1) were determined by HRMS and by ID- and 2D-NMR spectroscopic analyses. The structure of terpene 2 was elucidated by single-crystal X-ray diffraction experiments. The remaining structures were similarly determined, structure 3 by spectroscopic analyses and both 4a and 5 by X-ray crystal structure determination. Coprinastatin 1 (1.) was found to inhibit growth of the murine P388 lymphocytic leukemia cell line and the pathogenic bacterium Neisseria gonorrhoeae.

Original languageEnglish (US)
Pages (from-to)388-392
Number of pages5
JournalJournal of Natural Products
Volume73
Issue number3
DOIs
StatePublished - Mar 26 2010

Fingerprint

Coprinus
Sesquiterpenes
Antineoplastic Agents
Cells
Lymphoid Leukemia
Cell Line
Neisseria gonorrhoeae
Bioassay
Terpenes
Fungi
X-Ray Diffraction
Biological Assay
Bacteria
Crystal structure
Nuclear magnetic resonance
X-Rays
Single crystals
X ray diffraction
X rays
Growth

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Antineoplastic agents. 556. Isolation and structure of coprinastatin 1 from coprinus cinereus. / Pettit, George; Meng, Yanhui; Pettit, Robin; Herald, Delbert L.; Cichacz, Zbigniew; Doubek, Dennis L.; Richert, Linda.

In: Journal of Natural Products, Vol. 73, No. 3, 26.03.2010, p. 388-392.

Research output: Contribution to journalArticle

Pettit, George ; Meng, Yanhui ; Pettit, Robin ; Herald, Delbert L. ; Cichacz, Zbigniew ; Doubek, Dennis L. ; Richert, Linda. / Antineoplastic agents. 556. Isolation and structure of coprinastatin 1 from coprinus cinereus. In: Journal of Natural Products. 2010 ; Vol. 73, No. 3. pp. 388-392.
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