Enzymatic transformation of vina-ginsenoside R7 to rare notoginsenoside ST-4 using a new recombinant glycoside hydrolase from Herpetosiphon aurantiacus

Wang, Rufeng; Zheng, Ming-Min; Cao, Yue-De; Li, Hao; Li, Chun-Xiu; Xu, Jian‐He; Wang, Zhengtao

doi:10.1007/s00253-015-6446-z

Cited by 14 publications

(17 citation statements)

References 37 publications

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“…These data demonstrated that ginsenosides in root exudates could enrich host-pathogens in soil microbiota, which might be not beneficial for the health of P. notoginseng. Other previous reports also demonstrated that ginsenosides could be hydrolyzed by microbial glycosyl hydrolases, one type of carbohydrate-active enzymes, to release glycosyl as nutrient for microbes (Wang et al 2015;Yang et al 2018b). The present study also showed that soil fungi and bacteria enriched by ginsenosides had better growth in the medium with ginsenosides as the sole carbon source (Fig.…”

Section: Discussionsupporting

confidence: 81%

Ginsenosides in root exudates of Panax notoginseng drive the change of soil microbiota through carbon source different utilization

et al. 2020

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Background and aims Ginsenosides are the main bioactive components of Panax plants which could be secreted by root and show autotoxicity to root cells or promote the growth of soil-borne pathogens. However, comprehensive understanding of the effect of ginsenosides on soil microbiota is still lacking. Methods The ginsenosides in root exudates of P. notoginseng were quantified and exogenous ginsenosides on soil microbiota were tested using 16S rRNA and ITS gene tag sequencing. Then its underlying mechanism was deciphered through studying effects of ginsenosides on growth of the ginsenoside-modified culturable fungi and bacteria as well as the relationships between these fungi and bacteria. Results Exogenous root exudates and mixtures of Rg 1 + Rb 1 + Rd had similar ability to drive the change of soil microbiota. Further studies demonstrated that Rg 1 + Rb 1 + Rd mixture could enrich or suppress special fungi and bacteria to modify soil community through differential utilization of carbon source during the early stage (30 days), followed by antagonism between ginsenoside-modified fungi and bacteria to determine soil microbial community modification at later stage (60 and 90 days). Conclusions Ginsenosides were the main substances in exogenous root exudates of P. notoginseng that drove the change in soil microbiota, mediating the special interaction between the plant and the microbiota.

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Section: Discussionsupporting

confidence: 81%

Ginsenosides in root exudates of Panax notoginseng drive the change of soil microbiota through carbon source different utilization

et al. 2020

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“…2 ). Ginsenosides can be hydrolyzed by microbial CAZY enzymes 44 . Based on genomic analysis, we predicted 901 genes that putatively encode CAZY enzymes in P. cactorum .…”

Section: Resultsmentioning

confidence: 99%

“…3 ; Supplementary Tables 18 and 19 ). Previous study demonstrated that ginsenosides could be hydrolyzed by microbial glycosyl hydrolases to release glycosyl as nutrient for microbes 44 . Although the function of ginsenosides induced detoxification-related genes in P. cactorum should be proven by further genetic studies, these genes were frequently reported in chemoresistance 45 – 47 .…”

Section: Resultsmentioning

confidence: 99%

The Phytophthora cactorum genome provides insights into the adaptation to host defense compounds and fungicides

Yang

Duan

Mei

et al. 2018

Sci Rep

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Phytophthora cactorum is a homothallic oomycete pathogen, which has a wide host range and high capability to adapt to host defense compounds and fungicides. Here we report the 121.5 Mb genome assembly of the P. cactorum using the third-generation single-molecule real-time (SMRT) sequencing technology. It is the second largest genome sequenced so far in the Phytophthora genera, which contains 27,981 protein-coding genes. Comparison with other Phytophthora genomes showed that P. cactorum had a closer relationship with P. parasitica, P. infestans and P. capsici. P. cactorum has similar gene families in the secondary metabolism and pathogenicity-related effector proteins compared with other oomycete species, but specific gene families associated with detoxification enzymes and carbohydrate-active enzymes (CAZymes) underwent expansion in P. cactorum. P. cactorum had a higher utilization and detoxification ability against ginsenosides–a group of defense compounds from Panax notoginseng–compared with the narrow host pathogen P. sojae. The elevated expression levels of detoxification enzymes and hydrolase activity-associated genes after exposure to ginsenosides further supported that the high detoxification and utilization ability of P. cactorum play a crucial role in the rapid adaptability of the pathogen to host plant defense compounds and fungicides.

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“…At present, most studies on UGTs are concentrated on the catalyzing capability using purified recombinant proteins with the much more expensive active UDP-glucose as substrate in vitro [23], [28]. By taking advantage of the host E. coli cells to synthesize the active UDP-glucose with its own UDP and supplemented glucose, PPD or PPT could be converted into the corresponding glycosylated products with UGT-modified E. coli in vivo , which provides a much more convenient and economical method to explore the activity of UGTs.…”

Section: Resultsmentioning

confidence: 99%

“…Ginsenosides Rb1, Rb2, and Rc were also selected for use as substrates to prepare CK through biotransformation with microorganisms such as intestinal bacteria [20], fungus [21], and food microorganisms [22]. In our recent studies, the rare notoginsenoside ST-4 [20 ( S ) type] and Ft1 [20 ( R ) type] through enzymatic transformation and acid hydrolyzing strategy, respectively [23], [24]. Ginsenoside CK has also been produced using PPD as substrate through microbial metabolic engineering by heterologous expressing uridine diphosphate glycosyltransferase (UGT) in yeast [25].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of rare 20(R)-protopanaxadiol/protopanaxatriol type ginsenosides through Escherichia coli engineered with uridine diphosphate glycosyltransferase genes

Chen

Shi

et al. 2019

Journal of Ginseng Research

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BackgroundGinsenosides are known as the principal pharmacological active constituents in Panax medicinal plants such as Asian ginseng, American ginseng, and Notoginseng. Some ginsenosides, especially the 20(R) isomers, are found in trace amounts in natural sources and are difficult to chemically synthesize. The present study provides an approach to produce such trace ginsenosides applying biotransformation through Escherichia coli modified with relevant genes.MethodsSeven uridine diphosphate glycosyltransferase (UGT) genes originating from Panax notoginseng, Medicago sativa, and Bacillus subtilis were synthesized or cloned and constructed into pETM6, an ePathBrick vector, which were then introduced into E. coli BL21star (DE3) separately. 20(R)-Protopanaxadiol (PPD), 20(R)-protopanaxatriol (PPT), and 20(R)-type ginsenosides were used as substrates for biotransformation with recombinant E. coli modified with those UGT genes.ResultsE. coli engineered with GT95syn selectively transfers a glucose moiety to the C20 hydroxyl of 20(R)-PPD and 20(R)-PPT to produce 20(R)-CK and 20(R)-F1, respectively. GTK1- and GTC1-modified E. coli glycosylated the C3—OH of 20(R)-PPD to form 20(R)-Rh2. Moreover, E. coli containing p2GT95synK1, a recreated two-step glycosylation pathway via the ePathBrich, implemented the successive glycosylation at C20—OH and C3—OH of 20(R)-PPD and yielded 20(R)-F2 in the biotransformation broth.ConclusionThis study demonstrates that rare 20(R)-ginsenosides can be produced through E. coli engineered with UTG genes.

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Enzymatic transformation of vina-ginsenoside R7 to rare notoginsenoside ST-4 using a new recombinant glycoside hydrolase from Herpetosiphon aurantiacus

Cited by 14 publications

References 37 publications

Ginsenosides in root exudates of Panax notoginseng drive the change of soil microbiota through carbon source different utilization

Ginsenosides in root exudates of Panax notoginseng drive the change of soil microbiota through carbon source different utilization

The Phytophthora cactorum genome provides insights into the adaptation to host defense compounds and fungicides

Biosynthesis of rare 20(R)-protopanaxadiol/protopanaxatriol type ginsenosides through Escherichia coli engineered with uridine diphosphate glycosyltransferase genes

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