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 Analjournal_title
Journal of pharmaceutical and biomedical analysisauthors
Wu E,Jung SH,Chen J,Kim YH,Park KL,Lee W,Kang JSdoi
10.1016/j.jpba.2009.08.014subject
Has Abstractpub_date
2010-01-05 00:00:00pages
103-6issue
1eissn
0731-7085issn
1873-264Xpii
S0731-7085(09)00518-4journal_volume
51pub_type
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