Nat Prod Sci.  2017 Dec;23(4):306-309. 10.20307/nps.2017.23.4.306.

Microbial Transformation of Two Prenylated Naringenins

• Han F
• Lee IS

• KMID: 2401585
• DOI: http://doi.org/10.20307/nps.2017.23.4.306

Abstract

Microbial transformation of (±)-6-(1,1-dimethylallyl)naringenin (6-DMAN, 1) and (±)-5-(O-prenyl) naringenin-4"²,7-diacetate (5-O-PN, 2) was performed by using fungi. Scale-up fermentation studies with Mucor hiemalis, Cunninghamella elegans var. elegans, and Penicillium chrysogenum led to the isolation of five microbial metabolites. Chemical structures of the metabolites were determined by spectral analyses as (±)-8-prenylnaringenin (3), (2S)-5,4"²-dihydroxy-7,8-[(R)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofurano]flavanone (4), (±)-5-(O-prenyl)naringenin-4"²-acetate (5), (±)-naringenin-4"²-acetate (6), and (±)-naringenin (7), of which 5 was identified as a new compound.

Keyword

Microbial transformation; 6-(1,1-dimethylallyl)naringenin; 5-(O-prenyl)naringenin-4′; 7-diacetate; Mucor hiemalis; Cunninghamella elegans var. elegans; Penicillium chrysogenum

MeSH Terms

Cunninghamella
Fermentation
Fungi
Mucor
Penicillium chrysogenum

Figure

• 

  Fig. 1 Chemical structures of the compounds 1–7.

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