Antineoplastic Agents 582. Isolation and Structure of a Cyclobutane-type Sesquiterpene Cancer Cell Growth Inhibitor from Coprinus cinereus (Coprinaceae)

• Published in: Bioorganic & medicinal chemistry Vol. 18; no. 14; pp. 4879 - 4883
• Main Authors: Pettit, George R., Meng, Yanhui, Pettit, Robin K., Herald, Delbert L., Hogan, Fiona, Cichacz, Zbigniew A.
• Format: Journal Article
• Language: English
• Published: 12-06-2010
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2010.06.023

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-2
S
,3
S
,9
R
-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.