Myrtillin
Names
IUPAC name
(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
Other names
  • Mirtillin
  • Myrtillin chloride
  • Delphinidin 3-glucoside
  • Delphinidol 3-glucoside
  • Delphinidin 3-O-glucoside
  • Delphinidin 3-monoglucoside
  • Delphinidine 3-monoglucoside
  • Delphinidin-3-glucoside chloride
  • Delphinidin 3-O-β-D-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1 ☒N
    Key: XENHPQQLDPAYIJ-PEVLUNPASA-O ☒N
  • C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O.[Cl-]
Properties
C21H21ClO12
C21H21O12+, Cl−
Molar mass 500.83 g/mol (chloride)
465.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in black beans, blackcurrant, blueberry, huckleberry, bilberry leaves[1][2] and in various myrtles, roselle plants, and Centella asiatica plant.[citation needed] It is also present in yeast and oatmeal.[citation needed] The sumac fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.[3][unreliable source?]

The various colors, such as red, mauve, purple, violet, and blue in Hydrangea macrophylla are developed from myrtillin complexes with metal ions called metalloanthocyanins.[4]

Metabolism

The enzyme anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase produces delphinidin 3-(6-p-coumaroyl)glucoside from myrtillin and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway.[5]

References

  1. ^ Bilberry Leaf on florahealth.com Archived February 5, 2009, at the Wayback Machine
  2. ^ Yang W, Kortesniemi M, Ma X, Zheng J, Yang B. Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives. Food Chem. 2019 May 30;281:189-196. doi:10.1016/j.foodchem.2018.12.111 PMID 30658747
  3. ^ Sumac on spicesworld.net
  4. ^ Yoshida K, Mori M, Kondo T (2009). "Blue flower color development by anthocyanins: from chemical structure to cell physiology". Nat. Prod. Rep. 26 (7): 884–915. doi:10.1039/b800165k. PMID 19554240.
  5. ^ "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.
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