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The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring (formed between the OH group at C-5 and the C-4 of the anthocyanin pyranic ring) that may have different substituents linked directly at C-10.

Examples

• Carboxypyranoanthocyanidins, can be considered markers of microoxygenation techniques
• Hydroxyphenyl-pyranoanthocyanins
• Vitisin A and B
• Pinotins
• Portosins (vinylpyranoanthocyanins)

Vitisin A type

• Cyanidin-3-O-glucoside-pyruvic acid (m/z of + ion:517, λmax 506 nm)
• Cyanidin-3-O-acetylglucoside-pyruvic acid (559 - 507)
• Cyanidin-coumaroylglucoside-pyruvic acid (661 - 507 nm)
• Delphinidin-3-O-glucoside-pyruvic acid (533 - 507 nm)
• Delphinidin-3-O-acetylglucoside-pyruvic acid (575 - 509 nm)
• Delphinidin-3-O-coumaroylglucoside-pyruvic acid (679 - 511 nm)
• Peonidin-3-O-glucoside-pyruvic acid (531 - 509 nm)
• Peonidin-3-O-acetylglucoside-pyruvic acid (573 - 510 nm)
• Peonidin-3-O-coumaroylglucoside-pyruvic acid (677 - 511 nm)
• Petunidin-3-O-glucoside-pyruvic acid (547 - 508 nm)
• Petunidin-3-O-acetylglucoside-pyruvic acid (589 - 509 nm)
• Petunidin-3-O-coumaroylglucoside-pyruvic acid (693 - 510 nm)
• Malvidin-3-O-glucoside-pyruvic acid (561 - 513 nm)
• Malvidin-3-O-acetylglucoside-pyruvic acid (603 - 516 nm)
• Malvidin-3-O-coumaroylglucoside-pyruvic acid (707 - 513 nm)

Vitisin B type

• Malvidin-3-O-glucoside-acetaldehyde (517 - 490 nm)
• Malvidin-3-O-acetylglucoside-acetaldehyde (559 - 494 nm)
• Malvidin-3-O-coumaroylglucoside-acetaldehyde (663 - 497 nm)

Oxovitisins

Oxovitisins are pyranone-anthocyanin derivatives

• Pyranone-malvidin-3-glucoside (Oxovitisin A)
• Pyranone-malvidin-3-coumaroylglucoside

Pinotin type

• Delphinidin-3-O-glucoside-4-vinylcatechol (597 - 510 nm)
• Delphinidin-3-O-acetylglucoside-4-vinylcatechol (639 - 512 nm)
• Delphinidin-3-O-coumaroylglucoside-4-vinylcatechol (743 - 514 nm)
• Peonidin-3-O-glucoside-4-vinylcatechol (595 - 504 nm)
• Peonidin-3-O-acetylglucoside-4-vinylcatechol (637 - 506 nm)
• Peonidin-3-O-coumaroylglucoside-4-vinylcatechol (741 - 508 nm)
• Petunidin-3-O-glucoside-4-vinylcatechol (611 - 510 nm)
• Petunidin-3-O-acetylglucoside-4-vinylcatechol (653 - 512 nm)
• Petunidin-3-O-coumaroylglucoside-4-vinylcatechol (757 - 516 nm)
• Malvidin-3-O-glucoside-4-vinylcatechol (625 - 512 nm)
• Malvidin-3-O-acetylglucoside-4-vinylcatechol (667 - 514 nm)
• Malvidin-3-O-coumaroylglucoside-4-vinylcatechol (771 - 514 nm)
• Delphinidin-3-O-glucoside-4-vinylphenol (581 - 504 nm)
• Delphinidin-3-O-acetylglucoside-4-vinylphenol (623 - 506 nm)
• Delphinidin-3-O-coumaroylglucoside-4-vinylphenol (727 - 506 nm)
• Peonidin-3-O-glucoside-4-vinylphenol (579 - 499 nm)
• Peonidin-3-O-acetylglucoside-4-vinylphenol (621 - 504 nm)
• Peonidin-3-O-coumaroylglucoside-4-vinylphenol (725 - 505 nm)
• Petunidin-3-O-glucoside-4-vinylphenol (595 - 504 nm)
• Petunidin-3-O-acetylglucoside-4-vinylphenol (636 - 506 nm)
• Petunidin-3-O-coumaroylglucoside-4-vinylphenol (741 - 507 nm)
• Malvidin-3-O-glucoside-4-vinylphenol (609 - 504 nm)
• Malvidin-3-O-acetylglucoside-4-vinylphenol (651 - 507 nm)
• Malvidin-3-O-coumaroylglucoside-4-vinylphenol (755 - 509 nm)
• Malvidin-3-O-caffeoylglucoside-4-vinylphenol (771 - 532 nm)
• Delphinidin-3-O-glucoside-4-vinylguaiacol (611 - 502 nm)
• Peonidin-3-O-glucoside-4-vinylguaiacol (609 - 499 nm)
• Petunidin-3-O-glucoside-4-vinylguaiacol (625 - 502 nm)
• Malvidin-3-O-glucoside-4-vinylguaiacol (639 - 504 nm)
• Malvidin-3-O-acetylglucoside-4-vinylguaiacol (681 - 506 nm)
• Malvidin-3-O-coumaroylglucoside-vinylguaiacol (755 477 508 nm)

Flavanyl-pyranoanthocyanin type

• Delphinidin-3-O-glucoside-4-vinyl(epi)catechin (777 - 501 nm)
• Delphinidin-3-O-acetylglucoside-4-vinyl(epi)catechin (819 - 503 nm)
• Peonidin-3-O-glucoside-4-vinyl(epi)catechin (775 - 199 nm)
• Peonidin-3-O-acetylglucoside-4-vinyl(epi)catechin (817 - 501 nm)
• Petunidin-3-O-glucoside-4-vinyl(epi)catechin (791 - 502 nm)
• Petunidin-3-O-acetylglucoside-4-vinyl(epi)catechin (833 - 504 nm)
• Malvidin-3-O-glucoside-4-vinyl(epi)catechin (805 - 503 nm)
• Malvidin-3-O-acetylglucoside-4-vinyl(epi)catechin (847 - 508 nm)
• Malvidin-3-O-coumaroylglucoside-4-vinyl(epi)catechin (951 - 503 nm)

References

1. He, Jingren; Santos-Buelga, Celestino; Mateus, Nuno; De Freitas, Victor (2006). "Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques". Journal of Chromatography A. 1134 (1–2): 215–25. doi:10.1016/j.chroma.2006.09.011. PMID 16997314.
2. Atanasova, Vessela; Fulcrand, Hélène; Cheynier, Véronique; Moutounet, Michel (2002). "Effect of oxygenation on polyphenol changes occurring in the course of wine-making". Analytica Chimica Acta. 458: 15–27. doi:10.1016/S0003-2670(01)01617-8.
3. Brouillard, R; Chassaing, S; Fougerousse, A (2003). "Why are grape/fresh wine anthocyanins so simple and why is it that red wine color lasts so long?". Phytochemistry. 64 (7): 1179–86. doi:10.1016/S0031-9422(03)00518-1. PMID 14599515.
4. De Freitas, V; Mateus, N (2011). "Formation of pyranoanthocyanins in red wines: A new and diverse class of anthocyanin derivatives". Analytical and Bioanalytical Chemistry. 401 (5): 1463–73. doi:10.1007/s00216-010-4479-9. PMID 21181135. S2CID 22932267.
5. Wirth, J.; Morel-Salmi, C.; Souquet, J.M.; Dieval, J.B.; Aagaard, O.; Vidal, S.; Fulcrand, H.; Cheynier, V. (2010). "The impact of oxygen exposure before and after bottling on the polyphenolic composition of red wines". Food Chemistry. 123: 107–116. doi:10.1016/j.foodchem.2010.04.008.
6. ^ Nixdorf, Suzana Lucy; Hermosín-Gutiérrez, Isidro (2010). "Brazilian red wines made from the hybrid grape cultivar Isabel: Phenolic composition and antioxidant capacity". Analytica Chimica Acta. 659 (1–2): 208–15. doi:10.1016/j.aca.2009.11.058. PMID 20103126.
7. Mateus, N; Oliveira, J; Haettich-Motta, M; De Freitas, V (2004). "New Family of Bluish Pyranoanthocyanins". Journal of Biomedicine & Biotechnology. 2004 (5): 299–305. doi:10.1155/S1110724304404033. PMC 1082895. PMID 15577193.
8. Oxovitisins: A New Class of Neutral Pyranone-anthocyanin Derivatives in Red Wines. Jingren He, Joana Oliveira, Artur M. S. Silva, Nuno Mateus and Victor De Freitas, J. Agric. Food Chem., 2010, 58 (15), pages 8814–8819, doi:10.1021/jf101408q
9. Oxidative formation and structural characterisation of new α-pyranone (lactone) compounds of non-oxonium nature originated from fruit anthocyanins. Jingren He, Artur M.S. Silva, Nuno Mateus and Victor de Freitas, Food Chemistry, Volume 127, Issue 3, 1 August 2011, pages 984–992, doi:10.1016/j.foodchem.2011.01.069
10. Anthocyanins and Their Variation in Red Wines II. Anthocyanin Derived Pigments and Their Color Evolution. Fei He, Na-Na Liang, Lin Mu, Qiu-Hong Pan, Jun Wang, Malcolm J. Reeves and Chang-Qing Duan, Molecules, 2012, 17, pages 1483-1519, doi:10.3390/molecules17021483

See also

• Phenolic compounds in wine

• Pyranoanthocyanins