Isolation of 1-(3′,4′-Dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol from Grape Seed Extract and Evaluation of its Antioxidant and Antispasmodic Potential

Molecules

Michał Gleńsk¹  Marek Bednarski²  WilliamJ. Hurst³  JanA. Gliński⁴  VitoldB. Glinski⁴ 

[1] Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, 50-556 Wrocław, Poland;Department of Pharmacological Screening, Chair of Pharmacodynamics, Jagiellonian University Medical College, 30-688 Kraków, Poland;Gretna Scientific LLC, Mount Gretna, PA 17064, USA;Planta Analytica LLC, New Milford, CT 06776, USA;

关键词: 1-(3′,4′-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol;    3,4-diHPP-2-ol;    procyanidins;    grape seed extract;    phenols;    antioxidant activity;    antispasmodic effect;    marker for grape seed extract;   

DOI  :  10.3390/molecules24132466

来源: DOAJ

【 摘 要 】

HPLC profiling of phenolics in grape seed extracts revealed a prominent peak of an unknown substance with concentrations up to 5.3%. Spectroscopic data allowed the identification of the compound 1 as 1-(3′,4′-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol. 1 is known to be produced from catechin and epicatechin through anaerobic bacteria from human, as well as the rat, intestines. It was hypothesized that the marc remaining after expression of juice from grapes became infested during storage, resulting in the production of 1. Because compound 1 is infrequently found in nature and has never been found in grape seeds, its presence may be considered a marker of an unwanted anaerobic bacterial process occurring during production. The antioxidant potential of 1 was determined by DPPH, ABTS, and FRAP (ferric reducing antioxidant power) assays and compared to the potential of the following compounds: phloroglucine, pyrogallol, gallic acid, catechin, and epicatechin. Furthermore, it was established that 1 significantly reduced guinea pig ileum contraction induced by histamine.

【 授权许可】

Unknown