Identification of a new natural vasorelaxatant compound, (+)-osbeckic acid, from rutin-free tartary buckwheat extract

Toshiro Matsui, Akihiro Kudo, Shinji Tokuda, Kiyoshi Matsumoto, Hirokazu Hosoyama

Research output: Contribution to journalArticle

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Abstract

The candidates responsible for vasorelaxation action of rutin-free tartary buckwheat extract (TBSP) were examined in this study. As a result of reversed-phase high-performance liquid chromatography (HPLC) separations, five prominent peaks in the acidic fraction of TBSP were obtained at 260 nm. Among the five collected peaks, we successfully identified four compounds by nuclear magnetic resonance (NMR) and mass spectrometry (MS) measurements: (+)-osbeckic acid as a dimer ([M - H]- m/z: 371.2 > 184.9 > 140.9), 5-hydroxymethyl-2-furoic acid, protocatechuic acid, and p-hydroxybenzoic acid. A vascular contractive measurement in 1.0 μM phenylephrine-contracted Sprague-Dawley rat thoracic aorta rings revealed that (+)-osbeckic acid dimer evoked a potent vasorelaxant effect with an EC50 value of 887 μM compared to other isolates (EC50: 5-hydroxymethyl-2-furoic acid, 3610 μM; protocatechuic acid, 2160 μM; p-hydroxybenzoic acid, no inhibition). Dimeric (+)-osbeckic acid was stable in solutions and at high temperatures, while its degraded peak on the HPLC chromatogram was observed when it was dissolved in dimethyl sulfoxide.

Original languageEnglish
Pages (from-to)10876-10879
Number of pages4
JournalJournal of Agricultural and Food Chemistry
Volume58
Issue number20
DOIs
Publication statusPublished - Oct 27 2010

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Fagopyrum
Rutin
buckwheat
rutin
Hydroxybenzoates
High performance liquid chromatography
Dimers
acids
extracts
protocatechuic acid
High Pressure Liquid Chromatography
4-hydroxybenzoic acid
vasodilation
Phenylephrine
Reverse-Phase Chromatography
Dimethyl Sulfoxide
Thoracic Aorta
Vasodilator Agents
Vasodilation
Mass spectrometry

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

Identification of a new natural vasorelaxatant compound, (+)-osbeckic acid, from rutin-free tartary buckwheat extract. / Matsui, Toshiro; Kudo, Akihiro; Tokuda, Shinji; Matsumoto, Kiyoshi; Hosoyama, Hirokazu.

In: Journal of Agricultural and Food Chemistry, Vol. 58, No. 20, 27.10.2010, p. 10876-10879.

Research output: Contribution to journalArticle

Matsui, Toshiro ; Kudo, Akihiro ; Tokuda, Shinji ; Matsumoto, Kiyoshi ; Hosoyama, Hirokazu. / Identification of a new natural vasorelaxatant compound, (+)-osbeckic acid, from rutin-free tartary buckwheat extract. In: Journal of Agricultural and Food Chemistry. 2010 ; Vol. 58, No. 20. pp. 10876-10879.
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