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Stable isotope labeling and 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucopyranoside biosynthetic pathway characterization in Fallopia multiflora

Main conclusion The THSG biosynthetic pathway in F. multiflora was characterized, and enzymatic activities responsible for the resveratrol synthesis, hydroxylation, and glycosylation reactions involved in THSG biosynthesis were confirmed in vitro. The biosynthetic origin of 2,3,5,4′-tetrahydroxystil... Full description

Journal Title: Planta 2017-11-14, Vol.247 (3), p.613-623
Main Author: Xia, Wanxia
Other Authors: Rui, Wen , Zhao, Wei , Sheng, Shujing , Lei, Lei , Feng, Yifan , Zhao, Shujin
Format: Electronic Article Electronic Article
Language: English
Subjects:
Publisher: Berlin/Heidelberg: Springer Berlin Heidelberg
ID: ISSN: 0032-0935
Link: https://www.ncbi.nlm.nih.gov/pubmed/29138972
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recordid: cdi_crossref_primary_10_1007_s00425_017_2797_2
title: Stable isotope labeling and 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucopyranoside biosynthetic pathway characterization in Fallopia multiflora
format: Article
creator:
  • Xia, Wanxia
  • Rui, Wen
  • Zhao, Wei
  • Sheng, Shujing
  • Lei, Lei
  • Feng, Yifan
  • Zhao, Shujin
subjects:
  • Agriculture
  • Bicarbonate
  • Biomedical and Life Sciences
  • Biosynthesis
  • Callus
  • Carbonates
  • Chemical synthesis
  • Ecology
  • Enzymatic activity
  • Enzyme activity
  • Enzymes
  • Experiments
  • Fallopia multiflora - enzymology
  • Fallopia multiflora - metabolism
  • Feeding
  • Forestry
  • Glucosides - biosynthesis
  • Glycosylation
  • Glycosyltransferase
  • Hydroxylase
  • Hydroxylation
  • Intermediates
  • Isotope Labeling
  • Labeling
  • Labelling
  • Life Sciences
  • Metabolic Networks and Pathways
  • Original Article
  • Phenylalanine
  • Plant Sciences
  • Pyruvic acid
  • Resveratrol
  • Sodium
  • Sodium bicarbonate
  • Sodium pyruvate
  • Stilbenes - metabolism
ispartof: Planta, 2017-11-14, Vol.247 (3), p.613-623
description: Main conclusion The THSG biosynthetic pathway in F. multiflora was characterized, and enzymatic activities responsible for the resveratrol synthesis, hydroxylation, and glycosylation reactions involved in THSG biosynthesis were confirmed in vitro. The biosynthetic origin of 2,3,5,4′-tetrahydroxystilbene-2- O -β- d -glucopyranoside (THSG) and the enzymes involved in THSG biosynthesis in Fallopia multiflora were studied using stable isotope labeling and biocatalytic methods. UPLC-MS-based analyses were used to unravel the isotopologue composition of the biosynthetic intermediates and products, as well as to detect the products of the enzyme assay experiments. In this study, 13 C-labeled l -phenylalanine ( l -PHE), sodium pyruvate (SP), and sodium bicarbonate (SB) were used as putative precursors in the feeding experiment. Labeling of polydatin (PD) and THSG using [ 13 C 9 ]L-PHE and [ 13 C 1 ] l -PHE confirmed that the p -coumaric moiety of PD and THSG was derived from PHE. The results of the feeding experiments with [ 13 C] SB and [2, 3- 13 C 2 ] SP suggested that PD and THSG were derivatives of resveratrol that were synthesized by glycosylation and hydroxylation. We developed methods using total crude protein extracts (soluble and microsomal) for comprehensive and simultaneous analysis of resveratrol synthase, glycosyltransferase, and hydroxylase activities in various tissue types of wild F. multiflora and callus cultures. The activity of each tested enzyme was confirmed in one or more tissue types or cell cultures in vitro. The results of the enzyme activity experiments and the distributions of PD and THSG were used to determine the main site and pathway of THSG biosynthesis in F. multiflora .
language: eng
source:
identifier: ISSN: 0032-0935
fulltext: no_fulltext
issn:
  • 0032-0935
  • 1432-2048
url: Link


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titleStable isotope labeling and 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucopyranoside biosynthetic pathway characterization in Fallopia multiflora
creatorXia, Wanxia ; Rui, Wen ; Zhao, Wei ; Sheng, Shujing ; Lei, Lei ; Feng, Yifan ; Zhao, Shujin
creatorcontribXia, Wanxia ; Rui, Wen ; Zhao, Wei ; Sheng, Shujing ; Lei, Lei ; Feng, Yifan ; Zhao, Shujin
descriptionMain conclusion The THSG biosynthetic pathway in F. multiflora was characterized, and enzymatic activities responsible for the resveratrol synthesis, hydroxylation, and glycosylation reactions involved in THSG biosynthesis were confirmed in vitro. The biosynthetic origin of 2,3,5,4′-tetrahydroxystilbene-2- O -β- d -glucopyranoside (THSG) and the enzymes involved in THSG biosynthesis in Fallopia multiflora were studied using stable isotope labeling and biocatalytic methods. UPLC-MS-based analyses were used to unravel the isotopologue composition of the biosynthetic intermediates and products, as well as to detect the products of the enzyme assay experiments. In this study, 13 C-labeled l -phenylalanine ( l -PHE), sodium pyruvate (SP), and sodium bicarbonate (SB) were used as putative precursors in the feeding experiment. Labeling of polydatin (PD) and THSG using [ 13 C 9 ]L-PHE and [ 13 C 1 ] l -PHE confirmed that the p -coumaric moiety of PD and THSG was derived from PHE. The results of the feeding experiments with [ 13 C] SB and [2, 3- 13 C 2 ] SP suggested that PD and THSG were derivatives of resveratrol that were synthesized by glycosylation and hydroxylation. We developed methods using total crude protein extracts (soluble and microsomal) for comprehensive and simultaneous analysis of resveratrol synthase, glycosyltransferase, and hydroxylase activities in various tissue types of wild F. multiflora and callus cultures. The activity of each tested enzyme was confirmed in one or more tissue types or cell cultures in vitro. The results of the enzyme activity experiments and the distributions of PD and THSG were used to determine the main site and pathway of THSG biosynthesis in F. multiflora .
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subjectAgriculture ; Bicarbonate ; Biomedical and Life Sciences ; Biosynthesis ; Callus ; Carbonates ; Chemical synthesis ; Ecology ; Enzymatic activity ; Enzyme activity ; Enzymes ; Experiments ; Fallopia multiflora - enzymology ; Fallopia multiflora - metabolism ; Feeding ; Forestry ; Glucosides - biosynthesis ; Glycosylation ; Glycosyltransferase ; Hydroxylase ; Hydroxylation ; Intermediates ; Isotope Labeling ; Labeling ; Labelling ; Life Sciences ; Metabolic Networks and Pathways ; Original Article ; Phenylalanine ; Plant Sciences ; Pyruvic acid ; Resveratrol ; Sodium ; Sodium bicarbonate ; Sodium pyruvate ; Stilbenes - metabolism
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descriptionMain conclusion The THSG biosynthetic pathway in F. multiflora was characterized, and enzymatic activities responsible for the resveratrol synthesis, hydroxylation, and glycosylation reactions involved in THSG biosynthesis were confirmed in vitro. The biosynthetic origin of 2,3,5,4′-tetrahydroxystilbene-2- O -β- d -glucopyranoside (THSG) and the enzymes involved in THSG biosynthesis in Fallopia multiflora were studied using stable isotope labeling and biocatalytic methods. UPLC-MS-based analyses were used to unravel the isotopologue composition of the biosynthetic intermediates and products, as well as to detect the products of the enzyme assay experiments. In this study, 13 C-labeled l -phenylalanine ( l -PHE), sodium pyruvate (SP), and sodium bicarbonate (SB) were used as putative precursors in the feeding experiment. Labeling of polydatin (PD) and THSG using [ 13 C 9 ]L-PHE and [ 13 C 1 ] l -PHE confirmed that the p -coumaric moiety of PD and THSG was derived from PHE. The results of the feeding experiments with [ 13 C] SB and [2, 3- 13 C 2 ] SP suggested that PD and THSG were derivatives of resveratrol that were synthesized by glycosylation and hydroxylation. We developed methods using total crude protein extracts (soluble and microsomal) for comprehensive and simultaneous analysis of resveratrol synthase, glycosyltransferase, and hydroxylase activities in various tissue types of wild F. multiflora and callus cultures. The activity of each tested enzyme was confirmed in one or more tissue types or cell cultures in vitro. The results of the enzyme activity experiments and the distributions of PD and THSG were used to determine the main site and pathway of THSG biosynthesis in F. multiflora .
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2Biomedical and Life Sciences
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4Callus
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6Chemical synthesis
7Ecology
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10Enzymes
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28Phenylalanine
29Plant Sciences
30Pyruvic acid
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34Sodium pyruvate
35Stilbenes - metabolism
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titleStable isotope labeling and 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucopyranoside biosynthetic pathway characterization in Fallopia multiflora
authorXia, Wanxia ; Rui, Wen ; Zhao, Wei ; Sheng, Shujing ; Lei, Lei ; Feng, Yifan ; Zhao, Shujin
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abstractMain conclusion The THSG biosynthetic pathway in F. multiflora was characterized, and enzymatic activities responsible for the resveratrol synthesis, hydroxylation, and glycosylation reactions involved in THSG biosynthesis were confirmed in vitro. The biosynthetic origin of 2,3,5,4′-tetrahydroxystilbene-2- O -β- d -glucopyranoside (THSG) and the enzymes involved in THSG biosynthesis in Fallopia multiflora were studied using stable isotope labeling and biocatalytic methods. UPLC-MS-based analyses were used to unravel the isotopologue composition of the biosynthetic intermediates and products, as well as to detect the products of the enzyme assay experiments. In this study, 13 C-labeled l -phenylalanine ( l -PHE), sodium pyruvate (SP), and sodium bicarbonate (SB) were used as putative precursors in the feeding experiment. Labeling of polydatin (PD) and THSG using [ 13 C 9 ]L-PHE and [ 13 C 1 ] l -PHE confirmed that the p -coumaric moiety of PD and THSG was derived from PHE. The results of the feeding experiments with [ 13 C] SB and [2, 3- 13 C 2 ] SP suggested that PD and THSG were derivatives of resveratrol that were synthesized by glycosylation and hydroxylation. We developed methods using total crude protein extracts (soluble and microsomal) for comprehensive and simultaneous analysis of resveratrol synthase, glycosyltransferase, and hydroxylase activities in various tissue types of wild F. multiflora and callus cultures. The activity of each tested enzyme was confirmed in one or more tissue types or cell cultures in vitro. The results of the enzyme activity experiments and the distributions of PD and THSG were used to determine the main site and pathway of THSG biosynthesis in F. multiflora .
copBerlin/Heidelberg
pubSpringer Berlin Heidelberg
pmid29138972
doi10.1007/s00425-017-2797-2