Myrtillin

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Myrtillin
Mirtillin.svg
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 (Jmol)
ChEBI
ChemSpider
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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Infobox references

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in blackcurrant, blueberry, huckleberry, bilberry leaves[1][unreliable source?] and in various myrtles, roselle plants, and Centella asiatica plant.[citation needed] It is also present in yeast and oatmeal.[citation needed] The sumac fruits pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.[2][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.[3]

Metabolism[edit]

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.[4]

References[edit]

  1. ^ Bilberry Leaf on florahealth.com Archived February 5, 2009, at the Wayback Machine.
  2. ^ Sumac on spicesworld.net
  3. ^ 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. 
  4. ^ "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.