TY - JOUR
T1 - Antineoplastic agents 582. Part 1
T2 - Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae)
AU - Pettit, George
AU - Meng, Yanhui
AU - Pettit, Robin
AU - Herald, Delbert L.
AU - Hogan, Fiona
AU - Cichacz, Zbigniew
N1 - Funding Information:
Very necessary financial assistance was received with appreciation from Grants RO1 CA 90441-03-05 , 2R56-CA 090441-06A1 , and 5RO1 CA 090441-07 with the Division of Cancer Treatment and Diagnosis, NCI, DHHS ; the Arizona Biomedical Research Commission ; the Fannie E. Rippel Foundation ; and the Robert B. Dalton Endowment Fund. Also very helpful technical assistance was provided by Drs. John C. Knight, Dennis L. Doubek, and Jean-Charles Chapuis, as well as by Christine Weber and Lee Williams.
PY - 2010/7/15
Y1 - 2010/7/15
N2 - 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.
AB - 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.
KW - 14-Hydroxy-5-desoxy-2S,3S,9R- illudosin
KW - 4,5-Dehydro-5-deoxyarmillol
KW - 7,7a-Diepicoprinastatin 1
KW - Coprinus cinereus
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U2 - 10.1016/j.bmc.2010.06.023
DO - 10.1016/j.bmc.2010.06.023
M3 - Article
C2 - 20598551
AN - SCOPUS:77955334834
VL - 18
SP - 4879
EP - 4883
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 14
ER -