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Large-scale separation of antipsychotic alkaloids from Rauwolfia tetraphylla L. by pH-zone-refining fast centrifugal partition chromatography

Authors

  • Anupam Maurya,

    1. Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic Plants, Council of Scientific and Industrial Research (CSIR), Lucknow, India
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  • Shikha Gupta,

    1. Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic Plants, Council of Scientific and Industrial Research (CSIR), Lucknow, India
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  • Santosh K. Srivastava

    Corresponding author
    • Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic Plants, Council of Scientific and Industrial Research (CSIR), Lucknow, India
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  • Part of this paper was presented at the 4th National Interactive Meet (NIM-08), CIMAP, Lucknow (UP), India, November 29–30, 2008.

Correspondence: Dr. Santosh K. Srivastava, Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic Plants, Council of Scientific and Industrial Research (CSIR), Lucknow 226015, India

E-mail: santoshkumar_1955@yahoo.com

Fax: +91-522-2342666

Abstract

pH-zone-refining centrifugal partition chromatography was successively applied in the large-scale separation of close Rf antipsychotic indole alkaloids directly from CHCl3 fraction of Rauwolfia tetraphylla leaves. Two experiments with increasing mass from 500 mg to 3 g of crude alkaloid extracts (1C) of R. tetraphylla were carried out in normal-displacement mode using a two-phase solvent system composed of methyl tert-butyl ether/ACN/water (4:1:5, v/v/v) where HCl (12 mM) was added to the lower aqueous stationary phase as a retainer and triethylamine (5 mM) to the organic mobile phase as an eluter. The two centrifugal partition chromatography separations afforded a total of 162.6 mg of 10-methoxytetrahydroalstonine (1) and 296.5 mg of isoreserpiline (2) in 97% and 95.5% purity, respectively, along with a 400.9 mg mixture of α-yohimbine and reserpiline (3 and 4). Further, this mixture was resolved over medium pressure LC using TLC grade silica gel H (average particle size 10 μm), which afforded 160.4 mg of α-yohimbine (3) and 150.2 mg of reserpiline (4) in >95% purities. The purity of the isolated antipsychotic alkaloids was analyzed by high-performance LC and their structures were characterized on the basis of their 1D, 2D NMR and electrospray ionization-mass spectroscopic data.

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