{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T20:47:44Z","timestamp":1777668464766,"version":"3.51.4"},"reference-count":25,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2017,4,4]],"date-time":"2017-04-04T00:00:00Z","timestamp":1491264000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BPD\/112465\/2015"],"award-info":[{"award-number":["SFRH\/BPD\/112465\/2015"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["IF\/00225\/2015"],"award-info":[{"award-number":["IF\/00225\/2015"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/AGR-TEC\/2789\/2014"],"award-info":[{"award-number":["PTDC\/AGR-TEC\/2789\/2014"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["REDE\/1517\/RMN\/2005"],"award-info":[{"award-number":["REDE\/1517\/RMN\/2005"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FCT\/MEC\/FEDER","award":["UID\/QUI\/50006\/2013 - POCI\/01\/0145\/FEDER\/007265"],"award-info":[{"award-number":["UID\/QUI\/50006\/2013 - POCI\/01\/0145\/FEDER\/007265"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. This is due to the revealed high reactivity of OAA with anthocyanins compared with the already known precursor (pyruvic acid, PA). In model solutions at wine pH (3.5), when malvidin-3-O-glucoside (mv-3-glc) is in contact with OAA and PA a decrease in the OAA concentration is observed along with the formation of A-type vitisin. Moreover, part of the OAA is also chemically converted into PA in model solutions. The reaction yields were also determined for OAA and PA using different mv-3-glc:organic acid molar ratios (1:0.5, 1:1, 1:5, 1:10; 1:50, and 1:100) and these values were always higher for OAA when compared to PA, even at the lowest molar ratio (1:0.5). The reaction yields were higher at pH 2.6 in comparison to pH 1.5 and 3.5, being less affected at pH 3.5 for OAA. These results support the idea that OAA can be at the origin of A-type vitisins in the first stages of wine production and PA in the subsequent ageing process.<\/jats:p>","DOI":"10.3390\/ijms18040762","type":"journal-article","created":{"date-parts":[[2017,4,4]],"date-time":"2017-04-04T10:15:12Z","timestamp":1491300912000},"page":"762","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["A New Chemical Pathway Yielding A-Type Vitisins in Red Wines"],"prefix":"10.3390","volume":"18","author":[{"given":"Paula","family":"Ara\u00fajo","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio Associado para a Qu\u00edmica Verde, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3914-6117","authenticated-orcid":false,"given":"Ana","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio Associado para a Qu\u00edmica Verde, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]},{"given":"Victor","family":"De Freitas","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio Associado para a Qu\u00edmica Verde, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9996-1463","authenticated-orcid":false,"given":"Joana","family":"Oliveira","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio Associado para a Qu\u00edmica Verde, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,4,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1111\/j.1755-0238.1996.tb00104.x","article-title":"Anthocyanin composition and anthocyanin pathway gene expression in grapevine sports differing in berry skin colour","volume":"2","author":"Boss","year":"1996","journal-title":"Aust. J. Grape Wine Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"7402","DOI":"10.1021\/jf0304167","article-title":"Pyruvic acid and acetaldehyde production by different strains of Saccharomyces cerevisiae: Relationship with vitisin A and B formation in red wines","volume":"51","author":"Morata","year":"2003","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1021\/jf960252c","article-title":"Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines","volume":"45","author":"Bakker","year":"1997","journal-title":"J. Agric. Food Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"12210","DOI":"10.1021\/jf303854u","article-title":"Synthesis, isolation, structure elucidation, and color properties of 10-acetyl-pyranoanthocyanins","volume":"60","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"9598","DOI":"10.1021\/jf062325q","article-title":"Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines","volume":"54","author":"He","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4836","DOI":"10.1021\/jf001505b","article-title":"Occurrence of anthocyanin-derived pigments in red wines","volume":"49","author":"Mateus","year":"2001","journal-title":"J. Agric. Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1002\/1097-0061(20000615)16:8<675::AID-YEA585>3.0.CO;2-B","article-title":"Tailoring wine yeast for the new millennium: Novel approaches to the ancient art of winemaking","volume":"16","author":"Pretorius","year":"2000","journal-title":"Yeast"},{"key":"ref_8","unstructured":"Fleet, G.H. (1992). Yeasts\u2014Metabolism of organic acids. Wine Microbiology and Biotechnology, Harwood Academic Publisher."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1046\/j.1365-2621.2000.00372.x","article-title":"Effect of acetaldehyde and several acids on the formation of vitisin A in model wine anthocyanin and colour evolution","volume":"35","author":"Romero","year":"2000","journal-title":"Int. J. Food Sci. Technol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.1016\/j.foodchem.2005.11.024","article-title":"Formation of the highly stable pyranoanthocyanins (vitisins A and B) in red wines by the addition of pyruvic acid and acetaldehyde","volume":"100","author":"Morata","year":"2007","journal-title":"Food Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"370","DOI":"10.5344\/ajev.2013.13001","article-title":"Impact of malolactic fermentation on the color and color stability of pinot noir and merlot wine","volume":"64","author":"Burns","year":"2013","journal-title":"Am. J. Enol. Vitic."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"5106","DOI":"10.1016\/j.tetlet.2013.07.046","article-title":"Network of carboxypyranomalvidin-3-O-glucoside (vitisin A) equilibrium forms in aqueous solution","volume":"54","author":"Oliveira","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6894","DOI":"10.1021\/jf061085b","article-title":"Color properties of four cyanidin-pyruvic acid adducts","volume":"54","author":"Oliveira","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3455","DOI":"10.1016\/j.tetlet.2004.03.007","article-title":"NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin)","volume":"45","author":"Mateus","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"6349","DOI":"10.1021\/jf070968f","article-title":"Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins","volume":"55","author":"Oliveira","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5154","DOI":"10.1021\/jf9044414","article-title":"Pyranoanthocyanin dimers: A new family of turquoise blue anthocyanin-derived pigments found in Port wine","volume":"58","author":"Oliveira","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"8814","DOI":"10.1021\/jf101408q","article-title":"Oxovitisins: A new class of neutral pyranone-anthocyanin derivatives in red wines","volume":"58","author":"He","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Ribereau-Gayon, P., Glories, Y., Maujean, A., and Dubourdieu, D. (2006). Organic acids in wines. Handbook of Enology: The Chemistry of Wine and Stabilization and Treatments, John Wiley & Sons, Ltd.","DOI":"10.1002\/0470010398"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Rib\u00e9reau-Gayon, P., Dubourdieu, D., Don\u00e8che, B., and Lonvaud, A. (2006). The grape and its maturation. Handbook of Enology, John Wiley & Sons, Ltd.","DOI":"10.1002\/0470010398"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"608","DOI":"10.1016\/j.foodchem.2011.04.074","article-title":"Rapid and accurate determination of malate, citrate, pyruvate and oxaloacetate by enzymatic reactions coupled to formation of a fluorochromophore: Application in colorful juices and fermentable food (yogurt, wine) analysis","volume":"129","author":"Shapiro","year":"2011","journal-title":"Food Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"117","DOI":"10.15583\/jpchrom.2014.017","article-title":"Development of a new LC-MS\/MS method for the quantification of keto acids","volume":"35","author":"Noguchi","year":"2014","journal-title":"Chromatography"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1007\/s00216-010-4479-9","article-title":"Formation of pyranoanthocyanins in red wines: A new and diverse class of anthocyanin derivatives","volume":"401","author":"Mateus","year":"2011","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1111\/j.1755-0238.2003.tb00230.x","article-title":"Formation of vitisin A during red wine fermentation and maturation","volume":"9","author":"Asenstorfer","year":"2003","journal-title":"Aust. J. Grape Wine Res."},{"key":"ref_24","unstructured":"Ara\u00fajo, P., Fernandes, A., de Freitas, V., and Oliveira, J. (2017). Detection of A-Type Vitisins in Red Grape Must at the Beggining of Fermentation, Instituto de Ci\u00eancias, Tecnologias e Agroambiente da Universidade do Porto\/Rede de Qu\u00edmica e Tecnologia."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1987","DOI":"10.1016\/j.foodchem.2013.04.091","article-title":"Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine","volume":"141","author":"Oliveira","year":"2013","journal-title":"Food Chem."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/18\/4\/762\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:31:57Z","timestamp":1760207517000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/18\/4\/762"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,4,4]]},"references-count":25,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2017,4]]}},"alternative-id":["ijms18040762"],"URL":"https:\/\/doi.org\/10.3390\/ijms18040762","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,4,4]]}}}