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Issue 48, 2012
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Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

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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

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Publication details

The article was received on 04 Jun 2012, accepted on 16 Aug 2012 and first published on 17 Aug 2012


Article type: Paper
DOI: 10.1039/C2OB25722J
Citation: Org. Biomol. Chem., 2012,10, 9583-9592
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    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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