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2′-Epi-uscharin from the Latex of Calotropis gigantea with HIF-1 Inhibitory Activity

Parhira Supawadee,Zhu Guo-Yuan,Jiang Ren-Wang,Liu Liang,Bai Li-Ping,Jiang Zhi-Hong

Two stereoisomeric cardenolides, uscharin (1) and a new compound, 2′- epi -uscharin (2), were isolated from the latex of Calotropis gigantea (Asclepiadaceae). Their structures were fully elucidated based on their spectroscopic data, X-ray crystallographic data and chemical evidences. Both epimers (1 and 2) exhibited strong inhibitory effects on HIF-1 activity with different magnitudes. Compound 1 showed much more potent activity than 2 and digoxin, a well-known HIF-1 inhibitor. Discrepancy in potencies between 1 and 2 revealed the contribution of a β-configuration of 2′ hydroxyl moiety for HIF-1 inhibitory activity. This is a first report of the activity of HIF-1 inhibition of thiazoline ring-containing cardenolides.