Pyranoanthocyanin

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]

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]