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Formation and Conformation of Baicalin–Berberine and Wogonoside–Berberine Complexes


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Title: Formation and Conformation of Baicalin–Berberine and Wogonoside–Berberine Complexes
Authors: Rong Wang, Jing / Tanaka, Takashi / Zhang, Hong / Kouno, Isao / Hong Jiang, Zhi
Issue Date: 1-Jun-2012
Publisher: 日本薬学会 / The Pharmaceutical Society of Japan
Citation: Chemical and Pharmaceutical Bulletin, 60(6), pp.706-711; 2012
Abstract: It is well-known that baicalin–berberine complex (1) precipitates in the water decoction of numerous Chinese Medicinal formulae containing Radix Scutellariae and Rhizoma Coptidis or Cortex Phellodendri. In the current study, ionic interaction between the carboxylate ion of baicalin and the quaternary ammonium ion of berberine was revealed to be responsible for the formation of 1 and wogonoside–berberine (2) by using FAB-MS and NMR titration experiments. In addition, nuclear Overhauser effect spectroscopy (NOESY) correlations observed in 1 and 2 suggested quite different conformation of the two complexes, which was further supported by the fact that the [α]D of the canadine obtained by reduction of 1 is of an opposite sign to that obtained from 2. Partition coefficients (n-octanol/water) determination demonstrated 12–20 times larger partition coefficient of each complex (1, 2) than that of each single compound (baicalin, wogonoside, and berberine), indicating the significant role of the formation of the complex in the bioavailability enhancement of these pharmacologically active constituents.
Keywords: Baicalin / Baicalin-berberine complex / Berberine / Ionic interaction / Wogonoside
URI: http://hdl.handle.net/10069/29407
ISSN: 00092363
Rights: © 2012 The Pharmaceutical Society of Japan.
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/29407

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