Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var. pubescens

Jian-Rong Wang; Qiang Shen; Li Fang; Shu-Ying Peng; Yi-Ming Yang; Jia Li; Hai-Li Liu; Yue-Wei Guo

doi:10.1016/j.steroids.2011.02.007

Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var. pubescens

Steroids. 2011 May;76(6):571-6. doi: 10.1016/j.steroids.2011.02.007. Epub 2011 Feb 22.

Authors

Jian-Rong Wang¹, Qiang Shen, Li Fang, Shu-Ying Peng, Yi-Ming Yang, Jia Li, Hai-Li Liu, Yue-Wei Guo

Affiliation

¹ 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.

PMID: 21349279
DOI: 10.1016/j.steroids.2011.02.007

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 IC(50) value of 1.12 μg/mL.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding, Competitive
Crystallography, X-Ray
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / isolation & purification
Molecular Conformation
Plant Bark / chemistry*
Plant Extracts / chemistry*
Plant Extracts / isolation & purification
Pregnanes / chemistry*
Pregnanes / isolation & purification
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
Sapindaceae*
Stereoisomerism

Substances

Enzyme Inhibitors
Plant Extracts
Pregnanes
PTPN1 protein, human
Protein Tyrosine Phosphatase, Non-Receptor Type 1