{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,28]],"date-time":"2026-04-28T17:23:14Z","timestamp":1777396994444,"version":"3.51.4"},"reference-count":30,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2019,7,4]],"date-time":"2019-07-04T00:00:00Z","timestamp":1562198400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2032,4\u2032-dihydroxyphenyl)-3-(2\u2033,4\u2033,6\u2033-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.<\/jats:p>","DOI":"10.3390\/molecules24132466","type":"journal-article","created":{"date-parts":[[2019,7,4]],"date-time":"2019-07-04T11:13:18Z","timestamp":1562238798000},"page":"2466","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Isolation of 1-(3\u2032,4\u2032-Dihydroxyphenyl)-3-(2\u2033,4\u2033,6\u2033-trihydroxyphenyl)-propan-2-ol from Grape Seed Extract and Evaluation of its Antioxidant and Antispasmodic Potential"],"prefix":"10.3390","volume":"24","author":[{"given":"Micha\u0142","family":"Gle\u0144sk","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, 50-556 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"William J.","family":"Hurst","sequence":"additional","affiliation":[{"name":"Gretna Scientific LLC, Mount Gretna, PA 17064, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vitold B.","family":"Glinski","sequence":"additional","affiliation":[{"name":"Planta Analytica LLC, New Milford, CT 06776, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4639-9913","authenticated-orcid":false,"given":"Marek","family":"Bednarski","sequence":"additional","affiliation":[{"name":"Department of Pharmacological Screening, Chair of Pharmacodynamics, Jagiellonian University Medical College, 30-688 Krak\u00f3w, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jan A.","family":"Gli\u0144ski","sequence":"additional","affiliation":[{"name":"Planta Analytica LLC, New Milford, CT 06776, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,7,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1093\/jn\/134.3.613","article-title":"Concentrations of proanthocyanidins in common foods and estimations of normal consumption","volume":"134","author":"Gu","year":"2004","journal-title":"J. Nutr."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2264","DOI":"10.1016\/j.phytochem.2005.03.025","article-title":"Occurrence and biological significance of proanthocyanidins in the American diet","volume":"66","author":"Prior","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1084","DOI":"10.1021\/jf803059z","article-title":"Procyanidin dimers are metabolized by human microbiota with 2-(3,4-Dihydroxyphenyl)acetic acid and 5-(3,4-Dihydroxyphenyl)-\u03b3-valerolactone as the major metabolites","volume":"57","author":"Appeldoorn","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_4","first-page":"1","article-title":"Grape seed proanthocyanidins (GSPs) inhibit the growth of cervical cancer by inducing apoptosis mediated by the mitochondrial pathway","volume":"9","author":"Chen","year":"2014","journal-title":"PLoS ONE"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1457","DOI":"10.1016\/j.foodchem.2007.05.026","article-title":"Evidence for galloylated type-A procyanidins in grape seeds","volume":"105","author":"Passos","year":"2007","journal-title":"Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1806","DOI":"10.3945\/jn.109.106864","article-title":"Grapes and Health, anticancer and cancer chemopreventive potential of grape seed extract and other grape-based products","volume":"139","author":"Kaur","year":"2009","journal-title":"J. Nutr."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/j.foodchem.2014.08.084","article-title":"Chemical Investigation of commercial grape seed derived products to assess quality and detect adulteration","volume":"170","author":"Villani","year":"2015","journal-title":"Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1371\/journal.pone.0021539","article-title":"Grape seed proanthocyanidins inhibit melanoma cell invasiveness by reduction of PGE2 synthesis and reversal of epithelial-to-mesenchymal transition","volume":"6","author":"Vaid","year":"2011","journal-title":"PLoS ONE"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"7142","DOI":"10.1021\/jf3006867","article-title":"Capability of Lactobacillus plantarum IFPL935 to catabolize flavan-3-ol compounds and complex phenolic extracts","volume":"60","author":"Tabasco","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1002\/mnfr.200900123","article-title":"A comparison of the in vitro biotransformation of (\u2013)-epicatechin and procyanidin B2 by human faecal microbiota","volume":"54","author":"Stoupi","year":"2010","journal-title":"Mol. Nutr. Food Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"711","DOI":"10.3109\/00498258409151469","article-title":"The microbial metabolism of (+)-catechin to two novel diarylpropan-2-ol metabolites in vitro","volume":"14","author":"Groenewould","year":"1984","journal-title":"Xenobiotica"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2733","DOI":"10.1093\/jn\/130.11.2733","article-title":"Polymeric proanthocyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids","volume":"130","author":"Deprez","year":"2000","journal-title":"J. Nutr."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"837","DOI":"10.1016\/S0891-5849(03)00394-0","article-title":"Metabolism of dietary procyanidins in rats","volume":"35","author":"Gonthier","year":"2003","journal-title":"Free Radic. Biol. Med."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1111\/j.1365-2672.2011.05025.x","article-title":"Isolation of catechin-converting human intestinal bacteria","volume":"111","author":"Kutschera","year":"2011","journal-title":"J. Appl. Microbiol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1415","DOI":"10.1016\/j.jnutbio.2013.05.001","article-title":"Benefits of polyphenols on gut microbiota and implications in human health","volume":"24","author":"Cardonaa","year":"2013","journal-title":"J. Nutr. Biochem."},{"key":"ref_16","first-page":"97","article-title":"Diarilpropanos y derivado indolico en madera de virola sebifera y virola calophylloidea","volume":"19","author":"Cuca","year":"1990","journal-title":"Rev. Colomb. Quim."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1080\/1028602031000111969","article-title":"Rotundifolinol, a new 1,3-diarylpropan-2-ol from bark of Litsea rotundifolia var. oblongifolia","volume":"5","author":"Ya","year":"2003","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1055\/s-2006-962610","article-title":"Isolation of smooth muscle relaxing 1,3-diarylpropan-2-ol derivatives from Acacia tortilis","volume":"53","author":"Mekonen","year":"1987","journal-title":"Planta Med."},{"key":"ref_19","first-page":"576","article-title":"Propterol\u2014An antibacterial agent from Pterocarpus marsupium","volume":"53","author":"Mathew","year":"1984","journal-title":"Curr. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1385","DOI":"10.1016\/0031-9422(81)80045-3","article-title":"Chemistry of Brazilian Myristicaceae. Part XV. 1,3-Diarylpropanes and propan-2-ols from Virola species","volume":"20","author":"Kijjoa","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1286","DOI":"10.1016\/j.fitote.2012.05.010","article-title":"Antispasmodic effect of 4\u2032-methylepigallocatechin on guinea pig ileum","volume":"83","author":"Souza","year":"2012","journal-title":"Fitoterapia"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1248\/cpb.45.888","article-title":"Biotransformation of (\u2013)-epicatechin 3-O-gallate by human intestinal bacteria","volume":"45","author":"Meselhy","year":"1997","journal-title":"Chem. Pharm. Bull."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1248\/cpb.49.1640","article-title":"The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. Strain SDG-2, a human intestinal bacterium","volume":"49","author":"Wang","year":"2001","journal-title":"Chem. Pharm. Bull."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4927","DOI":"10.1021\/jf304431v","article-title":"Catabolism of (+)-Catechin and (\u2212)-Epicatechin by Rat Intestinal Microbiota","volume":"61","author":"Takagaki","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"478","DOI":"10.1016\/j.jff.2014.12.007","article-title":"Plasma kinetics and microbial biotransformation of grape seed flavanols in rats","volume":"12","author":"Margalef","year":"2015","journal-title":"J. Funct. Foods"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1007\/s11418-014-0816-1","article-title":"Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea","volume":"68","author":"Shii","year":"2014","journal-title":"J. Nat. Med."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1016\/S0891-5849(98)00315-3","article-title":"Antioxidant activity applying an improved ABTS radical cation decolorization assay","volume":"26","author":"Re","year":"1999","journal-title":"Free Radic. Biol. Med."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/S0023-6438(95)80008-5","article-title":"Use of a free radical method to evaluate antioxidant activity","volume":"28","author":"Cuvelier","year":"1995","journal-title":"Lebensm Wiss Technol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1006\/abio.1996.0292","article-title":"The ferric reducing ability of plasma (FRAP) as a measure of \u201cAntioxidant power\u201d: The FRAP Assay","volume":"239","author":"Benzie","year":"1996","journal-title":"Anal. Biochem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.pbb.2015.03.019","article-title":"Antinociceptive, anti-inflammatory and smooth muscle relaxant activities of the pyrrolo[3,4-d]pyridazinone derivatives: Possible mechanisms of action","volume":"133","author":"Mogilski","year":"2015","journal-title":"Pharmacol. Biochem. Behav."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/13\/2466\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:02:41Z","timestamp":1760187761000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/13\/2466"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,7,4]]},"references-count":30,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2019,7]]}},"alternative-id":["molecules24132466"],"URL":"https:\/\/doi.org\/10.3390\/molecules24132466","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,7,4]]}}}