Formation and conformation of baicalin-berberine and wogonoside-berberine complexes.

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.

authors

Wang JR,Tanaka T,Zhang H,Kouno I,Jiang ZH

doi

10.1248/cpb.60.706

subject

Has Abstract

pub_date

2012-01-01 00:00:00

pages

706-11

issue

6

eissn

0009-2363

issn

1347-5223

pii

DN/JST.JSTAGE/cpb/60.706

journal_volume

60

pub_type

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