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Delphinidin-3-O-(6-p-coumaroyl)glucoside

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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
(42S,43R,44S,45S,46R,8E)-13,14,15,25,27,43,44,45,104-Nonahydroxy-7-oxo-3,6-dioxa-21λ4-2(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
3D model (JSmol)
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
C
30H
27O+
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).

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]

Biosynthesis

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The glucoside is formed by the enzyme anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase, first characterised from Perilla frutescens, which combines myrtillin and coumaroyl-CoA as part of the anthocyanin biosynthesis pathway.[4][5]

See also

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References

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  1. ↑ "Showing Compound Delphinidin 3-(6-p-coumaroylglucoside) (FDB017204) - FooDB". foodb.ca.
  2. ↑ Núñez, V.; Monagas, M.; Gomez Cordovés, M. C.; Bartolomé, B. (2004). "Vitis vinifera L. cv. Graciano grapes characterized by its anthocyanin profile". Postharvest Biology and Technology. 31: 69–79. doi:10.1016/S0925-5214(03)00140-6.
  3. ↑ "Delphinidin 3-(6-p-coumaroyl)glucoside on www.phenol-explorer.eu". Archived from the original on 2011-12-30. Retrieved 2012-02-21.
  4. ↑ Yonekura-Sakakibara K, Tanaka Y, Fukuchi-Mizutani M, Fujiwara H, Fukui Y, Ashikari T, Murakami Y, Yamaguchi M, Kusumi T (April 2000). "Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA: anthocyanin 3-O-glucoside-6"-O-acyltransferase from Perilla frutescens". Plant & Cell Physiology. 41 (4): 495–502. doi:10.1093/pcp/41.4.495. PMID 10845463.
  5. ↑ Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M, Kusumi T (1998). "Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens". Plant Science. 137 (1): 87–94. Bibcode:1998PlnSc.137...87F. doi:10.1016/S0168-9452(98)00119-8. INIST 2414423.
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