Combined application of chromatographic techniques for the separation of phenolic compounds from<i>Stenoloma chusanum</i>Ching

Ren, Dabing; Han, Binsong; Xin, Zhongquan; Ma, Shuanhong; Liu, Wenbin; Yi, Lunzhao

doi:10.1002/jssc.201600994

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…Ferns are the most highly evolved spore plants and sister groups of the seed plants. Stenoloma chusanum belongs to the family Lindsaeaceae (Ching, 1959) and is rich in flavonoids, including kaempferol, apigenin, luteolin, apigenin‐7‐ O ‐glucopyranoside, kaempferol‐3‐ O ‐glucopyranoside, quercetin‐3‐ O ‐rhamnoside, vitexin, and orientin (Ren et al, 2017). In this study, the transcriptome data of S. chusanum was mined and two 4CLs and one CHS genes were functionally characterized.…”

Section: Introductionmentioning

confidence: 99%

Molecular and structural characterization of a promiscuous chalcone synthase from the fern species Stenoloma chusanum

Niu

et al. 2022

JIPB

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The key enzymes involved in the flavonoid biosynthesis pathway have been extensively studied in seed plants, but relatively less in ferns. In this study, two 4‐Coumarate: coenzyme A ligases (Sc4CL1 and Sc4CL2) and one novel chalcone synthase (ScCHS1) were functionally characterized by mining the Stenoloma chusanum transcriptome database. Recombinant Sc4CLs were able to esterify various hydroxycinnamic acids to corresponding acyl‐coenzyme A (CoA). ScCHS1 could catalyze p‐coumaroyl‐CoA, cinnamoyl‐CoA, caffeoyl‐CoA, and feruloyl‐CoA to form naringenin, pinocembrin, eriodictyol, and homoeriodictyol, respectively. Moreover, enzymatic kinetics studies revealed that the optimal substrates of ScCHS1 were feruloyl‐CoA and caffeoyl‐CoA, rather than p‐coumaroyl‐CoA, which was substantially different from the common CHSs. Crystallographic and site‐directed mutagenesis experiments indicated that the amino acid residues, Leu87, Leu97, Met165, and Ile200, located in the substrate‐binding pocket near the B‐ring of products, could exert a significant impact on the unique catalytic activity of ScCHS1. Furthermore, overexpression of ScCHS1 in tt4 mutants could partially rescue the mutant phenotypes. Finally, ScCHS1 and Sc4CL1 were used to synthesize flavanones and flavones with multi‐substituted hydroxyl and methoxyl B‐ring in Escherichia coli, which can effectively eliminate the need for the cytochrome P450 hydroxylation/O‐methyltransferase from simple phenylpropanoid acids. In summary, the identification of these important Stenoloma enzymes provides a springboard for the future production of various flavonoids in E. coli.

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Section: Introductionmentioning

confidence: 99%

Molecular and structural characterization of a promiscuous chalcone synthase from the fern species Stenoloma chusanum

Niu

et al. 2022

JIPB

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“…Stenoloma chusanum is a traditional Chinese medicinal herb, which belongs to the family of Lindsaeaceae. Two bioactive C-glycosides orientin and vitexin have been isolated from S. chusanum [29]. However, the corresponding CGTs have not been studied.…”

Section: Introductionmentioning

confidence: 99%

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Zhang

et al. 2022

Microb Cell Fact

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Background Flavonoid C-glycosides have many beneficial effects and are widely used in food and medicine. However, plants contain a limited number of flavonoid C-glycosides, and it is challenging to create these substances chemically. Results To screen more robust C-glycosyltransferases (CGTs) for the biosynthesis of flavonoid C-glycosides, one CGT enzyme from Stenoloma chusanum (ScCGT1) was characterized. Biochemical analyses revealed that ScCGT1 showed the C-glycosylation activity for phloretin, 2-hydroxynaringenin, and 2-hydroxyeriodictyol. Structure modeling and mutagenesis experiments indicated that the glycosylation of ScCGT1 may be initiated by the synergistic action of conserved residue His26 and Asp14. The P164T mutation increased C-glycosylation activity by forming a hydrogen bond with the sugar donor. Furthermore, when using phloretin as a substrate, the extracellular nothofagin production obtained from the Escherichia coli strain ScCGT1-P164T reached 38 mg/L, which was 2.3-fold higher than that of the wild-type strain. Finally, it is proved that the coupling catalysis of CjFNS I/F2H and ScCGT1-P164T could convert naringenin into vitexin and isovitexin. Conclusion This is the first time that C-glycosyltransferase has been characterized from fern species and provides a candidate gene and strategy for the efficient production of bioactive C-glycosides using enzyme catalysis and metabolic engineering.

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“…For some complex mixtures, it is sometimes not easy to find a prefect solvent system to perform in high purity in a one‐step separation by HSCCC. Preparative HPLC has been commonly used for further purification for their complementary and orthogonal properties .…”

Section: Introductionmentioning

confidence: 99%

Combined chromatographic strategy based on macroporous resin, high‐speed counter‐current chromatography and preparative HPLC for systematic separation of seven antioxidants from the fruit of Terminalia billerica

Yang

Shen

et al. 2019

J of Separation Science

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In the present study, combined chromatographic strategy based on macroporous resin, high-speed counter-current chromatography and preparative high-performance liquid chromatography for systematic separation of antioxidants from crude samples guided by high-performance liquid chromatography with 1,1-diphenyl-2-picrylhydrazyl has been successfully established. Based on this strategy, seven antioxidants including isorugosin A, β -1,2,3,6-tetragalloyl-D-glucose, chebulinic acid, 1,2,3,4,6-penta-Ogalloylβ -D-glucose, chebulagic acid, ethyl gallate, and gallic acid were obtained from the fruit of Terminalia billerica. First, high-performance liquid chromatography with 1,1-diphenyl-2-picrylhydrazyl experiment showed the presence of seven main antioxidants in the crude extract of the fruit of Terminalia billerica. Then, a macroporous resin column chromatography method was developed for the enrichment of these seven antioxidants. Finally, an efficient method based on high-speed counter-current chromatography and preparative high-performance liquid chromatography was developed for the separation of these antioxidants. In the selection of solvent systems, it was found that acetic acid could be a good regulator for modifying the partition coefficient values of tannins. The present study provides a reference for systematic separation of antioxidants from crude samples. Considering the general existence of antioxidants in crude samples, this combined chromatographic strategy might lead to broader application prospects. K E Y W O R D Santioxidants, macroporous resin, systematic separation, Terminalia bellirica, traditional Chinese medicine

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Combined application of chromatographic techniques for the separation of phenolic compounds fromStenoloma chusanumChing

Cited by 6 publications

References 18 publications

Molecular and structural characterization of a promiscuous chalcone synthase from the fern species Stenoloma chusanum

Molecular and structural characterization of a promiscuous chalcone synthase from the fern species Stenoloma chusanum

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Combined chromatographic strategy based on macroporous resin, high‐speed counter‐current chromatography and preparative HPLC for systematic separation of seven antioxidants from the fruit of Terminalia billerica

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