Microbial transformation of ginsenoside Rb1 by Acremonium strictum

Abstract

Preparative-scale fermentation of ginsenoside Rb(1) (1) with Acremonium strictum AS 3.2058 gave three new compounds, 12beta-hydroxydammar-3-one-20 (S)-O-beta-D -glucopyranoside (7), 12beta, 25-dihydroxydammar-(E)-20(22)-ene-3-O-beta-D -glucopyranosyl-(1-->2)-beta-D -glucopyranoside (8), and 12beta, 20 (R), 25-trihydroxydammar-3-O-beta-D -glucopyranosyl-(1-->2)-beta-D -glucopyranoside (9), along with five known compounds, ginsenoside Rd (2), gypenoside XVII (3), ginsenoside Rg(3) (4), ginsenoside F(2) (5), and compound K (6). The structural elucidation of these metabolites was based primarily on one- and two-dimensional nuclear magnetic resonance and high-resolution electron spray ionization mass spectra analyses. Among these compounds, 2-6 are also the metabolites of ginsenoside Rb(1) in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, A. strictum might be a useful tool for generating mammalian metabolites of related analogs of ginsenosides for complete structural identification and for further use in pharmaceutical research in this series of compounds. In addition, the biotransformation kinetics was also investigated.

Comparative analysis on microbial and rat metabolism of ginsenoside Rb1 by high‐performance liquid chromatography coupled with tandem mass spectrometry

“…1). The n-BuOH extract was separated by silica gel column chromatography, and eight metabolites were obtained (Chen et al, 2007). On the basis of the spectral data, their structures were identified as ginsenoside Rd, gypenoside XVII, 20(S)-ginsenoside Rg 3 , 20(R)-ginsenoside Rg 3 , ginsenoside F 2 , compound K, 12β-hydroxydammar-3-one-20(S)-O-β -Dglucopyranoside and 25-hydroxyl-(E)-20(22)-ene-ginsenoside Rg 3 , respectively (Chen et al, 2007).…”

Co-transformation of Panax major ginsenosides Rb1 and Rg1 to minor ginsenosides C–K and F1 by Cladosporium cladosporioides

“…Ginsenoside F 1 is an enzymatic metabolite generated from ginsenoside Rg 1 , which shows anti-proliferation, anti-migration, and keratinocytes protective effects [13,21]. Therefore, many studies have aimed to convert major ginsenosides to the more active minor ginsenosides [1,4,9]. Although the production of minor ginsenoside has been performed using ginsenoside Rb 1 or Rg 1 in microorganisms, Rb 1 and Rg 1 cotransformation has not yet been reported [2,5,7,11].…”

“…Ginsenosides are regarded as the principal components responsible for numerous pharmacological properties. Up to now, more than 40 ginsenosides have been isolated and characterized from ginseng roots, which including with the major ginsenosides Rb 1 , Rb 2 , Rc, Rg 1 and Re that constituting more than 90% of the total ginsenosides [18]. Ginsenosides Rb 1 and Rg 1 have a higher ginseng content.…”

Identification and Characterization of the Rhizobium sp. Strain GIN611 Glycoside Oxidoreductase Resulting in the Deglycosylation of Ginsenosides

“…There have been several attempts to produce such biologically active deglycosylated ginsenosides (2,15,16,29), using microbial transformation (7,8), enzymatic deglycosylation (23,33), and mild acid hydrolysis (12). Among them, enzymatic deglycosylation is the most preferred method, since it is substrate specific, produces fewer by-products, requires simple separation, results in high yields, and is environmentally friendly.…”