Myrtillin

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Myrtillin

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
CAS number	6906-38-3^Y, 26770-35-4
PubChem	165558
	Jmol-3D images	{{#if: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-]\|Image 1
SMILES 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
Molecular formula	C₂₁H₂₁ClO₁₂ C₂₁H₂₁O₁₂⁺, Cl⁻
Molar mass	500.83 g/mol (chloride) 465.38 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

Metabolism

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

↑ "G-KOLA formulation on". Island.lk. Retrieved 2013-04-09.
↑ Bilberry Leaf on florahealth.com
↑ 3.0 3.1 "Pancreas panacea, Dr. John R. Christopher". Healingtools.tripod.com. 1927-11-05. Retrieved 2013-04-09.
↑ Sumac on spicesworld.net
↑ 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.
↑ "Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp". Kegg.jp. Retrieved 2013-04-09.

v t e Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins	5-Desoxy-peonidin Aurantinidin Cyanidin 6-Hydroxycyanidin Delphinidin Fisetinidin Guibourtinidin Pelargonidin Robinetinidin

3-deoxyanthocyanidins	Apigeninidin Columnidin Diosmetinidin Gesneridin Luteolinidin Tricetinidin

O-methylated anthocyanidins	5-Desoxy-malvidin Capensinidin Europinidin Hirsutidin Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

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-)	Cyanidin-3-O-(6-p-coumaroyl)glucoside Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) Petunidin-3-O-(6-p-coumaroyl)glucoside Peonidin-3-O-(6-p-coumaroyl)glucoside

Caffeoylated anthocyanins	Malvidin-3-O-(6-p-caffeoyl)glucoside Peonidin-3-O-(6-p-caffeoyl)glucoside Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

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