Bioorganic & Medicinal Chemistry Letters 2008-04-15

Hypoxia-inducible factor-1 and nuclear factor-kappaB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia.

Cheng-Zhu Wu, Seong Su Hong, Xing Fu Cai, Nguyen Tien Dat, Ji-Xing Nan, Bang Yeon Hwang, Jung Joon Lee, Dongho Lee

Index: Bioorg. Med. Chem. Lett. 18(8) , 2619-23, (2008)

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Abstract

Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12'S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-kappaB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-kappaB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.