Delphinidin coumaroyl 3O glucoside
Delphinidin-3-O -(6-p -coumaroyl)glucoside
Names
IUPAC name
3′,4′,5,5′,7-Pentahydroxy-3-{6-O -[3-(4-hydroxyphenyl)prop-2-enoyl]-β-D -galactopyranosyloxy}flavylium
Systematic IUPAC name
(42 S ,43 R ,44 S ,45 S ,46 R ,8E )-13 ,14 ,15 ,25 ,27 ,43 ,44 ,45 ,104 -Nonahydroxy-7-oxo-3,6-dioxa-21 λ4 -2(2,3)-[1]benzopyrana-4(2,6)-oxana-1,10(1)-dibenzenadecaphan-8-en-21 -ylium
Other names
Delphinidin-3-O -p -coumaroyl glucoside
Identifiers
ChEBI
ChemSpider
KEGG
InChI=1S/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1
Key: DHTPVCYNNWQRMN-LHRGPQAGSA-O
InChI=1/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1
Key: DHTPVCYNNWQRMN-LEURJHHLBH
c1cc(ccc1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3cc4c(cc(cc4[o+]c3c5cc(c(c(c5)O)O)O)O)O)O)O)O)O
Properties
C30 H27 O+ 14
Molar mass
611.52 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Delphinidin 3-O -(6-p -coumaroyl)glucoside is a p -coumaroylated anthocyanin . It can be found in some red Vitis vinifera grape cultivars (like Graciano [2] ) and in red wine .[3]
It is formed by the enzyme anthocyanin 3-O -glucoside 6″-O -hydroxycinnamoyltransferase from delphinidin 3-O -glucoside and p -coumaroyl-CoA in the anthocyanin biosynthesis pathway.[4]
See also
References
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins (anthocyaninidin glycosides)Glucosides:
Diglucosides:
Cyanin (Cyanidin 3,5-O -diglucoside )
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O -diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)
Others glycosides:
Antirrhinin (Cyanidin 3-O -rutinoside)
Ideain (Cyanidin 3-O -galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O -galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O -rutinoside)Acylated anthocyanins
Acetylated anthocyanins
Cyanidin 3-O-(6-acetyl)glucoside
Delphinidin 3-O-(6-acetyl)glucoside
Malvidin 3-O-(6-acetyl)glucoside
Petunidin 3-O-(6-acetyl)galactoside
Petunidin 3-O-(6-acetyl)glucoside
Peonidin 3-O-(6-acetyl)glucoside
Coumaroylated anthocyanins (cis - and trans -) Caffeoylated anthocyanins
Malvidin 3-O-(6-p-caffeoyl)glucoside
Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins
Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides
Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
Petanin (petunidin 3-[6-O -(4-O -(E )-p -coumaroyl-O -α-l-rhamnopyranosyl)-β-D -glucopyranoside]-5-O -β-D -glucopyranoside)
Violdelphin (Delphinidin 3-rutinoside-7-O -(6-O -(4-(6-O -(4-hydroxybenzoyl)-β-D -glucosyl)oxybenzoyl)-β-D -glucoside)
Flavanol-anthocyanin adducts
Malvidin glucoside-ethyl-catechin
Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Miscellaneous
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