Abstract
Ginsenoside Rg3 is a bioactive compound from Panax ginseng and exhibits diverse notable biological properties. Glycosylation catalyzed by uridine diphosphate-dependent glycosyltransferase (UGT) is the final biosynthetic step of ginsenoside Rg3 and determines its diverse pharmacological activities. In the present study, promiscuous UGT Bs-YjiC from Bacillus subtilis 168 was expressed in Escherichia coli and purified via one-step nickel chelate affinity chromatography. The in vitro glycosylation reaction demonstrated Bs-Yjic could selectively glycosylate the C12 hydroxyl group of ginsenoside Rg3 to synthesize an unnatural ginsenoside Rd12. Ginsenoside Rd12 was about 40-fold more water-soluble than that of ginsenoside Rg3 (90 μM). Furthermore, in vitro cytotoxicity of ginsenoside Rd12 against diverse cancer cells was much stronger than that of ginsenoside Rg3. Our studies report the UGT-catalyzed synthesis of unnatural ginsenoside Rd12 for the first time. Ginsenoside Rd12 with antiproliferative activity might be further exploited as a potential anticancer drug.
Highlights
Ginseng (Panax ginseng) is the most famous medicinal-edible plant recorded in the ChinesePharmacopoeia [1,2]
Glycosylation catalyzed by uridine diphosphate-dependent glycosyltransferase (UGT) is the last biosynthetic step of ginsenosides and determines their tremendous structural and functional diversity [12]
Glycosyltransferase activity of Bs-YjiC toward ginsenoside Rg3 was determined with uridine diphosphate diphosphate glucose glucose (UDPG) as the Glycosyltransferase activity of Bs-YjiC toward ginsenoside Rg3 was determined with UDPG as glucosyl donor
Summary
Ginseng (Panax ginseng) is the most famous medicinal-edible plant recorded in the Chinese. Ginsenosides are the principal effective ingredients of ginseng [5] These natural compounds are a group of glycosylated triterpene saponins and exhibit diverse intriguing pharmacological activities, including anti-inflammatory, antiaging, anticancer, antitumor, neuroprotective, skin-whitening, and immunoregulatory effects [6,7,8,9]. Over 140 ginsenosides have been isolated from diverse Panax species [10] These naturally occurring products are mainly grouped into protopanaxadiol-type (PPD) and protopanaxatriol-type (PPT) according to the structure of the aglycone skeleton [11]. For PPD-type ginsenosides, the sugar moieties are attached to the C3 and/or C20 hydroxyl groups. For PPT-type ginsenosides, the sugar moieties are attached to the C6 and/or C20 hydroxyl groups. Bs-YjiC groups two-step glucosylation of the C3 and C12 hydroxyl groups of PPD to synthesize ginsenoside Rh2 and.
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