Myrtillin

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Myrtillin
Mirtillin.svg
Names
IUPAC name
(2''S'',3''R'',4''S'',5''S'',6''R'')-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-beta-D-glucoside
Identifiers
6906-38-3 YesY
26770-35-4 N
ChEBI CHEBI:31463 N
ChemSpider 391783 N
Jmol-3D images Image
PubChem 165558
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).
 N verify (what isYesY/N?)
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, in blueberry or huckleberry leaves and various myrtles, in the roselle plant, in the Centella asiatica plant (Hydrocotyle asiatica)[1] and in the bilberry leaf.[2] It is also present in yeast and oatmeal.[3] The sumac fruits pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.[4]

The various colors, such as red, mauve, purple, violet and blue in, Hydrangea macrophylla are developed from delphinidin 3-glucoside foming complexes with metal ions called metalloanthocyanins.[5]

Health effects[edit]

Myrtillin tends to stabilize the blood sugar, which otherwise fluctuates widely, and that it spares insulin.[3]

Metabolism[edit]

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

References[edit]

  1. ^ "G-KOLA formulation on". Island.lk. Retrieved 2013-04-09. 
  2. ^ Bilberry Leaf on florahealth.com[dead link]
  3. ^ a b "Pancreas panacea, Dr. John R. Christopher". Healingtools.tripod.com. 1927-11-05. Retrieved 2013-04-09. 
  4. ^ Sumac on spicesworld.net
  5. ^ 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. [dead link]
  6. ^ "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.