The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.
The title compound, C(32)H(43)NO(4) x CH(4)O x H(2)O, has a nearly planar cyano-enone A ring in an otherwise normal oleanane triterpenoid. Rings A, B and C are non-chairs, but rings D and E adopt essentially cyclohexane chair conformations. The structure clearly establishes the C-D-E ring stereochemistry as trans-syn-cis, as predicted from a nuclear Overhauser effect (NOE) NMR measurement.
Bore
Lothar
L
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.
Honda
Tadashi
T
Gribble
Gordon W
GW
Lork
Enno
E
Jasinski
Jerry P
JP
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D014315:Triterpenes; C455529:methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate; D009828:Oleanolic Acid