2013•MoleculesOpen access

Uncarilic Acid and Secouncarilic Acid, Two New Triterpenoids from Uucaria sessilifructus

Mao-Juan Zhang, Bing Liu, Shang‐Gao Liao, You‐Kai Xu, Deqiang Feng, Kai‐Long Ji, Yan Li

Abstract

Two new compounds, the 6-oxo oleanane-type triterpenoid uncarilic acid, and its 5,6-secotriterpenoid derivative, secouncarilic acid, were isolated from the hooks and stems of Uucaria sessilifructus together with seven known ursane-type triterpenoids. Uncarilic acid is the second 6-oxo oleanane-type triterpenoid ever reported, while secouncarilic acid is the first oleanane-type 5,6-secotriterpenoid. A plausible biosynthetic pathway from uncarilic acid to secouncarilic acid was also postulated. The inhibitory activities of all the nine compounds against LPS-induced nitric oxide production in RAW264.7 macrophages were evaluated.

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Key concepts: Oleanane, Triterpenoid, Chemistry, Nitric acid, Stereochemistry, Biochemistry, Organic chemistry, Triterpene