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Myrtillin

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?]

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
  • 6906-38-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31463 N
ChemSpider
  • 391783 N
KEGG
  • C12138 Y
  • 165558
UNII
  • 474A9U89JS Y
  • 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).
N verify (what is YN ?)

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 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.[5]

References edit

  1. ^ Bilberry Leaf on florahealth.com 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. ^
  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.

myrtillin, anthocyanin, glucoside, delphinidin, found, green, plants, most, abundantly, black, beans, blackcurrant, blueberry, huckleberry, bilberry, leaves, various, myrtles, roselle, plants, centella, asiatica, plant, citation, needed, also, present, yeast, . 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 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 MirtillinMyrtillin chlorideDelphinidin 3 glucosideDelphinidol 3 glucosideDelphinidin 3 O glucosideDelphinidin 3 monoglucosideDelphinidine 3 monoglucosideDelphinidin 3 glucoside chlorideDelphinidin 3 O b D glucoside Identifiers CAS Number 6906 38 3 Y 3D model JSmol Interactive image ChEBI CHEBI 31463 N ChemSpider 391783 N KEGG C12138 Y PubChem CID 165558 UNII 474A9U89JS Y InChI 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 NKey XENHPQQLDPAYIJ PEVLUNPASA O N 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 Chemical formula C21H21ClO12C21H21O12 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 is Y N Infobox references 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 editThe 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 edit Bilberry Leaf on florahealth com Archived February 5 2009 at the Wayback Machine 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 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 Retrieved from https en wikipedia org w index php title Myrtillin amp oldid 1170582439, wikipedia, wiki, book, books, library,

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