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 language | English (US) |
|---|---|
| Pages (from-to) | 4879-4883 |
| Number of pages | 5 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 18 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 15 2010 |
Fingerprint
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 journal › Article
}
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
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
UR - http://www.scopus.com/inward/record.url?scp=77955334834&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77955334834&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2010.06.023
DO - 10.1016/j.bmc.2010.06.023
M3 - Article
VL - 18
SP - 4879
EP - 4883
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 14
ER -