Issue 48, 2012

Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

Abstract

A convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD calculations. (−)-Medicarpin and (−)-9-demethoxymedicarpin are both 6aR,11aR-configured, and consequently the corresponding enantiomers, (+)-medicarpin and (+)-9-demethoxymedicarpin, possess the 6aS,11aS-configuration. A comparative mechanism study for osteogenic (bone forming) activity of medicarpin (racemic versus enantiomerically pure material) revealed that (+)-(6aS,11aS)-medicarpin (6a) significantly increased the bone morphogenetic protein-2 (BMP2) expression and the level of the bone-specific transcription factor Runx-2 mRNA, while the effect was opposite for the other enantiomer, (−)-(6aR,11aR)-medicarpin (6a), and for the racemate, (±)-medicarpin, the combined effect of both the enantiomers on transcription levels was observed.

Graphical abstract: Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

Supplementary files

Article information

Article type
Paper
Submitted
04 Jun 2012
Accepted
16 Aug 2012
First published
17 Aug 2012

Org. Biomol. Chem., 2012,10, 9583-9592

Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

A. Goel, A. Kumar, Y. Hemberger, A. Raghuvanshi, R. Jeet, G. Tiwari, M. Knauer, J. Kureel, A. K. Singh, A. Gautam, R. Trivedi, D. Singh and G. Bringmann, Org. Biomol. Chem., 2012, 10, 9583 DOI: 10.1039/C2OB25722J

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