Coriariin M, a trimeric hydrolysable tannin with dehydrodigalloyl and valoneoyl groups as linking units, and accompanying dimeric hydrolysable tannins from Coriaria japonica

Yuuki Shimozu, Takayasu Hirai, Tsutomu Hatano

Research output: Contribution to journalArticle

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Abstract

Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules.

Original languageEnglish
Pages (from-to)110-118
Number of pages9
JournalPhytochemistry
Volume151
DOIs
Publication statusPublished - Jul 1 2018

Fingerprint

Coriaria
Hydrolyzable Tannins
tannins
Macromolecules
Native Polyacrylamide Gel Electrophoresis
bovine serum albumin
Bovine Serum Albumin
Electrophoresis
Complexation
linkage groups
Nuclear magnetic resonance spectroscopy
polyacrylamide gel electrophoresis
nuclear magnetic resonance spectroscopy
spectroscopy
Spectrum Analysis
Magnetic Resonance Spectroscopy
Monomers
Spectroscopy

Keywords

  • Coriaria japonica
  • Coriariaceae
  • Hydrolysable tannin
  • Polyphenol
  • Protein complexation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

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title = "Coriariin M, a trimeric hydrolysable tannin with dehydrodigalloyl and valoneoyl groups as linking units, and accompanying dimeric hydrolysable tannins from Coriaria japonica",
abstract = "Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules.",
keywords = "Coriaria japonica, Coriariaceae, Hydrolysable tannin, Polyphenol, Protein complexation",
author = "Yuuki Shimozu and Takayasu Hirai and Tsutomu Hatano",
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T1 - Coriariin M, a trimeric hydrolysable tannin with dehydrodigalloyl and valoneoyl groups as linking units, and accompanying dimeric hydrolysable tannins from Coriaria japonica

AU - Shimozu, Yuuki

AU - Hirai, Takayasu

AU - Hatano, Tsutomu

PY - 2018/7/1

Y1 - 2018/7/1

N2 - Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules.

AB - Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules.

KW - Coriaria japonica

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KW - Polyphenol

KW - Protein complexation

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