Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products.

Abstract:

:Biotransformation of 20(S)-protopanaxatriol (1) by the fungus Mucor spinosus AS 3.3450 gave 10 metabolites (2-10), of which 2-5 were previously known. On the basis of NMR and MS analyses, structures 6-10 were established as 12-oxo-23beta-hydroxyl-20(S)-protopanaxatriol (6), 20S,24R-epoxy-dammaran-3beta,6alpha,25-triol-12-one (7), 29-hydroxyl-20(S)-protopanaxatriol (8a), 12-oxo-11beta-hydroxyl-20(S)-protopanaxatriol (8b), 28-hydroxyl-20(S)-protopanaxatriol (9) and 12-oxo-20(S)-protopanaxatriol (10). The biotransformation kinetics of 1 has been investigated and a possible biotransformation pathway proposed. The in vitro cytotoxic activities of metabolites against three human cancer cell lines were determined by the MTT method; compounds 8a, 9 and 10 had more potent inhibitory effects against HL-60 cell line than the substrate.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Zhang J,Guo H,Tian Y,Liu P,Li N,Zhou J,Guo D

doi

10.1016/j.phytochem.2007.05.028

subject

Has Abstract

pub_date

2007-10-01 00:00:00

pages

2523-30

issue

20

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(07)00342-1

journal_volume

68

pub_type

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