Pyranoanthocyanin
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The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes[1] or during controlled oxygenation processes[2] during the aging of wine.[3] 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.[4]
Contents
Examples
- Carboxypyranoanthocyanidins, can be considered markers of microoxygenation techniques[5]
- Hydroxyphenyl-pyranoanthocyanins[6]
- Vitisin A and B[6]
- Pinotins
- Portosins (vinylpyranoanthocyanins)[7]
Vitisin A type
- Cyanidin-3-O-glucoside-pyruvic acid (m/z of [M+H]+ 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[8]
- Pyranone-malvidin-3-glucoside (Oxovitisin A)
- Pyranone-malvidin-3-coumaroylglucoside[9]
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)[10]
References
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- ↑ 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
- ↑ 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
- ↑ 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
