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

• Published in: Molecules (Basel, Switzerland) Vol. 24; no. 13; p. 2466
• Main Authors: Gleńsk, Michał, Hurst, William J, Glinski, Vitold B, Bednarski, Marek, Gliński, Jan A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 04-07-2019; MDPI
• Subjects: 1-(3′,4′-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol; 2-Propanol - isolation & purification; 2-Propanol - pharmacology; 3,4-diHPP-2-ol; Acids; Anaerobic bacteria; Anaerobic processes; Animals; antioxidant activity; Antioxidants; Antioxidants - pharmacology; antispasmodic effect; Bacteria; Catechin; Communication; Contraction; Dimerization; Epicatechin; Free Radical Scavengers - pharmacology; Fruits; Gallic acid; grape seed extract; Grape Seed Extract - chemistry; Grapes; Guinea Pigs; High-performance liquid chromatography; Histamine; Ileum; Intestine; Isopropyl alcohol; Liquid chromatography; Male; marker for grape seed extract; Metabolites; Microbiota; Muscle relaxants; Parasympathetic nervous system; Parasympatholytics - pharmacology; Phenols; Phenols - chemistry; Plant extracts; Polyphenols; procyanidins; Seeds; Small intestine; Smooth muscle; Tea; France; United States > US; phenols; 1-(3′,4′-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol; grape seed extract; procyanidins; marker for grape seed extract; antispasmodic effect; antioxidant activity; 3,4-diHPP-2-ol
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24132466

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
as 1-(3',4'-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol.
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
. Because compound
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
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
significantly reduced guinea pig ileum contraction induced by histamine.