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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

1
Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, 50-556 Wrocław, Poland
2
Gretna Scientific LLC, Mount Gretna, PA 17064, USA
3
Planta Analytica LLC, New Milford, CT 06776, USA
4
Department of Pharmacological Screening, Chair of Pharmacodynamics, Jagiellonian University Medical College, 30-688 Kraków, Poland
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(13), 2466; https://doi.org/10.3390/molecules24132466
Received: 24 June 2019 / Revised: 2 July 2019 / Accepted: 2 July 2019 / Published: 4 July 2019
(This article belongs to the Section Natural Products Chemistry)
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Abstract

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. View Full-Text
Keywords: 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 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
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Gleńsk, M.; Hurst, W.J.; Glinski, V.B.; Bednarski, M.; Gliński, J.A. 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 2019, 24, 2466.

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