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Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var. pubescens
Authors:Wang Jian-Rong  Shen Qiang  Fang Li  Peng Shu-Ying  Yang Yi-Ming  Li Jia  Liu Hai-Li  Guo Yue-Wei
Institution:State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhang Jiang High-Tech Park, Shanghai 201203, PR China
Abstract:Five new pregnane steroids, toonasterones A (1), B (2), (Z)-aglawone (3), (Z)-toonasterone C (4), and (E)-toonasterone C (5), were isolated from the stem bark of Toona ciliata var. pubescens. Their structures were elucidated by means of detailed spectroscopic (IR, MS, and 2D NMR) analysis, and the stereochemistry of 1 was secured by X-ray diffraction analysis. (Z)-aglawone (3) exhibited moderate inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), a potential drug target for treatment of type-II diabetes and obesity, with an IC50 value of 1.12 μg/mL.
Keywords:Toona ciliata var  pubescens  Meliaceae  Pregnane steroid  PTP1B inhibitory activity
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