Enhancing the inhibition of cell proliferation and induction of apoptosis in H22 hepatoma cells through biotransformation of notoginsenoside R1 by Lactiplantibacillus plantarum S165 into 20(S/R)-notoginsenoside R2

Wang, Penghui; Gao, Yansong; Yang, Ge; Zhao, Yujuan; Zhao, Zijian; Gao, Ge; Zhao, Lei; Li, Shengyu

doi:10.1039/d3ra06029b

RSC Adv.

2023

DOI: 10.1039/d3ra06029b

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Enhancing the inhibition of cell proliferation and induction of apoptosis in H22 hepatoma cells through biotransformation of notoginsenoside R1 by Lactiplantibacillus plantarum S165 into 20(S/R)-notoginsenoside R2

Penghui Wang,

Yansong Gao,

Ge Yang

et al.

Abstract: The biotransformation method employed yielded 20(S)-notoginsenoside R2 and 20(R)-notoginsenoside R2 from notoginsenoside R1, and the anti-tumor activity of the transformed compound markly improved.

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2024

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Cited by 3 publications

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Notoginsenoside R1 treatment facilitated Nrf2 nuclear translocation to suppress ferroptosis via Keap1/Nrf2 signaling pathway to alleviated high-altitude myocardial injury

Wang,

Yin,

Liu

et al. 2024

Biomedicine & Pharmacotherapy

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Notoginsenoside R1 treatment facilitated Nrf2 nuclear translocation to suppress ferroptosis via Keap1/Nrf2 signaling pathway to alleviated high-altitude myocardial injury

Wang,

Yin,

Liu

et al. 2024

Biomedicine & Pharmacotherapy

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Characterization of a Xylosyltransferase from Panax notoginseng Catalyzing Ginsenoside 2′-O Glycosylation in the Biosynthesis of Notoginsenosides

Liu,

Wu,

Jiang

et al. 2024

J. Nat. Prod.

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Notoginsenosides are important bioactive compounds from Panax notoginseng (Burk.) F. H. Chen, most of which have xylose in their sugar chains. However, the xylosyltransferases involved in the generation of notoginsenosides remain poorly understood, posing a bottleneck for further study of the biosynthesis of notoginsenosides. In this work, a new xylosyltransferase gene, PnUGT57 (named UGT94BW1), was identified from P. notoginseng, which has a distinct sequence and could catalyze the 2′-O glycosylation of ginsenosides Rh1 and Rg1 to produce notoginsenosides R2 and R1, respectively. We first characterized the optimal conditions for the PnUGT57 activity and its enzymatic kinetic parameters, and then, molecular docking and site-directed mutagenesis were performed to elucidate the catalytic mechanism of PnUGT57. Combined with the results of site-directed mutagenesis, Glu26, Ser266, Glu267, Trp347, Ser348, and Glu352 in PnUGT57 were identified as the key residues involved in 2′-O glycosylation of C-6 O-Glc, and PnUGT57 R175A and PnUGT57 G237A could significantly improve the catalytic activity of PnUGT57. These findings not only provide a new xylosyltransferase gene for augmenting the plant xylosyltransferase database but also identify the pivotal sites and catalytic mechanism of the enzyme, which would provide reference for the modification and application of xylosyltransferases in the future.

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Conversion of notoginsenoside R1 to 3β,12β-dihydroxydammar-(E)-20(22),24-diene-6-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside by Lactiplantibacillus plantarum S165 enhanced protective effects of LPS-induced intestinal epithelial barrier injury in Caco-2 cells

Wang,

Gao,

Yang

et al. 2024

Journal of Applied Microbiology

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Aim Microbial transformation to modify saponins and enhance their biological activities has received increasing attention in recent years. This study aimed to screen the strain can biotransform notoginsenoside R1, identify the product and study its biological activity. Methods A Lactic acid bacteria strain S165 with glycosidase-producing activity was isolated from traditional Chinese fermented foods, which was identified and grouped according to API 50 CHL kit and 16S rDNA sequence analysis. Subsequently, notoginsenoside R1 underwent a 30-day fermentation period by the strain S165, and the resulting products were analyzed using HPLC, UPLC-MS/MS, and 13C-NMR techniques. Employing a model of LPS-induced damage to Caco-2 cells, the damage of caco-2 cells was detected by Hoechst 33 258 staining, the activity of notoginsenoside R1 biotransformation product was investigated by CCK-8 and western blotting assay. Results The strain S165 was identified as Lactiplantibacillus plantarum and was used to biotransform notoginsenoside R1. Through a 30-day biotransformation, Lactiplantibacillus plantarum S165 predominantly converts notoginsenoside R1 into 3β,12β-dihydroxydammar-(E)-20(22),24-diene-6-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside, temporarily named notoginsenoside T6 (NGT6) according to HPLC, UPLC-MS/MS and 13C-NMR analysis. Results from CCK-8 and Hoechst 33 258 staining indicated that the ability notoginsenoside T6 to alleviate the intestinal injury induced by LPS in the Caco-2 cell was stronger than that of notoginsenoside R1. In addition, Western blotting result showed that notoginsenoside could intestinal injury by protecting tight junction proteins (Claudin-1, Occludin, ZO-1). Conclusion Notoginsenoside R1 was biotransformed into the notoginsenoside T6 by Lactiplantibacillus plantarum S165, and the biotransformed product showed an enhanced intestinal protective effect in vitro.

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Enhancing the inhibition of cell proliferation and induction of apoptosis in H22 hepatoma cells through biotransformation of notoginsenoside R1 by Lactiplantibacillus plantarum S165 into 20(S/R)-notoginsenoside R2

Abstract: The biotransformation method employed yielded 20(S)-notoginsenoside R2 and 20(R)-notoginsenoside R2 from notoginsenoside R1, and the anti-tumor activity of the transformed compound markly improved.

Cited by 3 publications

References 44 publications

Notoginsenoside R1 treatment facilitated Nrf2 nuclear translocation to suppress ferroptosis via Keap1/Nrf2 signaling pathway to alleviated high-altitude myocardial injury

Notoginsenoside R1 treatment facilitated Nrf2 nuclear translocation to suppress ferroptosis via Keap1/Nrf2 signaling pathway to alleviated high-altitude myocardial injury

Characterization of a Xylosyltransferase from Panax notoginseng Catalyzing Ginsenoside 2′-O Glycosylation in the Biosynthesis of Notoginsenosides

Conversion of notoginsenoside R1 to 3β,12β-dihydroxydammar-(E)-20(22),24-diene-6-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside by Lactiplantibacillus plantarum S165 enhanced protective effects of LPS-induced intestinal epithelial barrier injury in Caco-2 cells

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