Tirucallane, apotirucallane, and octanorapotirucallane triterpenes of Simarouba amara.
A chemical investigation of the bark of Simarouba amara, collected in Barbados, resulted in the isolation of six new triterpenes (3-8), in addition to two known compounds, 3-oxatirucalla-7, 24-dien-23-ol (1) and niloticin (2). Compound 3 is a tirucallane triterpene, while compounds 4-7 are apotirucallane derivatives containing an epsilon-lactone in ring A. Compounds 6 and 7 were obtained as a mixture that could not be separated, while compound 8 is an octanorapotirucallane derivative that lacks the C(8) side chain. The structures of all compounds were determined by interpretation of physical data.
Grosvenor
Sumieya N J
SN
Laboratory of Bioorganic Chemistry, Department of Biological & Chemical Sciences, The University of the West Indies, Cave Hill Campus, Bridgetown, P.O. Box 64, Barbados, BB11000.
Mascoll
Keisha
K
McLean
Stewart
S
Reynolds
William F
WF
Tinto
Winston F
WF
D001460:Barbados; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D032272:Simarouba / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification*
D014315:Triterpenes; C514394:apotirucallane; C514395:octanorapotirucallane; C514393:tirucallane