Manipulation of heterogeneity product in 4'-demethylepipodophyllotoxin biotransformation process by using yeast extract as nitrogen source.

Abstract:

:Manipulation of product heterogeneity was attempted by using yeast extract as nitrogen source in Alternaria alternata S-f6 transformation process of 4'-demethylepipodophyllotoxin. When the nitrogen source of NaNO(3) was replaced by yeast extract, the heterogeneity of biotransformation products was significantly varied from a single product (i.e., 4'-demethylpodophyllotoxone) to four podophyllum derivates. According to the kinetics of 4'-demethylepipodophyllotoxin biotransformation process by A. alternata S-f6, the starting substrate of 4'-demethylepipodophyllotoxin was preferentially transformed to produce 4'-demethylpodophyllotoxone (1) with an oxidation reaction. By the further comparison of products configuration, 4β-caprinoyl-4'-demethylepipodophyllotoxin (3) was produced from 4'-demethylpodophyllotoxone (1) instead of 4'-demethylisopicropodophyllone (2), which might be produced from 4'-demethylpodophyllotoxone (1) with the isomerization of lactone. Finally, 4'-demethylisopicropodophyllone (2) was hydrolyzed to produce 3α-hydroxymethyl-(6, 7)-dioxol-4-one-naphthalene (4). This work shows new information on the 4'-demethylepipodophyllotoxin biotransformation process by A. alternata S-f6 and provides a foundation for further studies on the structural diversification of a bioactive natural lead compound.

authors

Zhao W,Li HM,Wan DJ,Tang YJ

doi

10.1007/s00253-011-3424-y

subject

Has Abstract

pub_date

2012-01-01 00:00:00

pages

107-15

issue

1

eissn

0175-7598

issn

1432-0614

journal_volume

93

pub_type

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