Racemization of 6-methoxydihydrosanguinarine in methanol investigated by enantioselective dynamic HPLC.

Abstract:

:A biologically active benzophenanthridine alkaloid, 6-methoxydihydrosanguinarine (MS), was isolated from Hylomecon plants. Although enantiomers of MS can be separated by chiral HPLC, its isomers rapidly form a racemic mixture in methanol. The rate constants for the racemization of MS enantiomers were 9.20x10(-4)s(-1) and 9.95x10(-4)s(-1) for (+)-MS and (-)-MS, respectively, as determined by dynamic HPLC and chiral chromatography. This unusually rapid racemization may originate from the formation of a stable iminium ion intermediate, sanguinarine. Therefore, the variety of biological activities exhibited by MS may be attributable to a combination of (+)-MS, (-)-MS, and sanguinarine.

journal_name

J Pharm Biomed Anal

authors

Wu E,Jung SH,Chen J,Kim YH,Park KL,Lee W,Kang JS

doi

10.1016/j.jpba.2009.08.014

subject

Has Abstract

pub_date

2010-01-05 00:00:00

pages

103-6

issue

1

eissn

0731-7085

issn

1873-264X

pii

S0731-7085(09)00518-4

journal_volume

51

pub_type

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