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 apotiruca...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-09, Vol.69 (9), p.1315-1318
Main Authors: Grosvenor, Sumieya N. J, Mascoll, Keisha, McLean, Stewart, Reynolds, William F, Tinto, Winston F
Format: Article
Language:English
Subjects:
apotirucallane
Barbados
Biological and medical sciences
chemical structure
General pharmacology
Medical sciences
medicinal plants
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
octanorapotirucallane
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plants, Medicinal - chemistry
secondary metabolites
Simarouba - chemistry
Simarouba amara
Simaroubaceae
simaroubin
tirucallane
Triterpenes - chemistry
Triterpenes - isolation & purification
triterpenoids
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Summary: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 ε-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 C8 side chain. The structures of all compounds were determined by interpretation of physical data.
ISSN:0163-3864
1520-6025
DOI:10.1021/np060214f