Identification of a New Natural Vasorelaxatant Compound, (+)-Osbeckic Acid, from Rutin-free Tartary Buckwheat Extract

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 20; pp. 10876 - 10879
• Main Authors: Matsui, Toshiro, Kudo, Akihiro, Tokuda, Shinji, Matsumoto, Kiyoshi, Hosoyama, Hirokazu
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 27.10.2010
• Subjects: Animals; Aorta, Thoracic - drug effects; Aorta, Thoracic - physiology; Bioactive Constituents; Biological and medical sciences; Cereal and baking product industries; Fagopyrum - chemistry; Food industries; Fundamental and applied biological sciences. Psychology; Furans - chemistry; Furans - isolation & purification; Furans - pharmacology; In Vitro Techniques; Isomerism; Male; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Rats, Sprague-Dawley; Rutin - analysis; Seeds - chemistry; Vasodilation - drug effects; Vasodilator Agents - chemistry; Vasodilator Agents - isolation & purification; Vasodilator Agents - pharmacology; aorta; (+)-Osbeckic acid; vasorelaxation; tartary buckwheat; ( · )-Osbeckic acid; Buckwheat; Extract; Identification; Natural compound; Artery; Acids; Pseudocereals; Blood vessel; Aorta; Circulatory system
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf1028416

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.