Biotransformation of Licochalcone A by transgenic crown galls of Panax quinquefolium

Journal of Molecular Catalysis B: Enzymatic
2014.0

Abstract

Licochalcone A, as main constituent of Chinese Gancao (Glycyrrhiza inflate Bat), is responsible for thechemopreventive effect of the herbal. In order to get the bioactive modified molecules of Licochalcone A,it was biotransformed using transgenic crown galls of Panax quinquefolium to afford 9 products includinga new alkaloid together with 8 known compounds. Their structures were elucidated by physicochemicaland spectral methods as: methyl(12S)-1-[(5-formylfuran-2-yl)methyl]-5-oxopyrrolidine-2-carboxylate(1), methyl(12S)-1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate (2), 5-hydroxymethyl-2-furfural (3), (S)-methylpyroglutamate (4), 4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl) benz-aldehyde (5), 4-hydroxybenzoicacid (6), dibutyl phthalate (7), 3β,6α,12β,25-tetrahydroxy-(20S,24R)-epoxy-dammarane (8), β-sitosterol (9).Among them, compounds 5 and 6 were transformed from Licochalcone A, while 14 and 8 were derivedfrom the culture medium stimulated by the substrate. Furthermore, their cancer chemopreventive effectwere tested by the assay of NQO1 (NAD(P)H: quinine oxidoreductase 1) inducing activities in Hepa 1c1ccells. © 2014 Elsevier B.V. All rights reserved.

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