Myrtillin

☆ Save On Wikipedia ↗
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 checkY
    Key: XENHPQQLDPAYIJ-PEVLUNPASA-O checkY
  • 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).

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

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]

Biosynthesis and metabolism

Anthocyanidin 3-O-glucosyltransferase converts delphinidin to myrtillin in plants including Silene dioica and Vitis vinifera. The glucose unit is transferred from UDP-glucose, giving uridine diphosphate (UDP) as a byproduct.[5][6][7]

2D representation of the chemical structure of delphinidin .
delphinidin
+ UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of myrtillin.
myrtillin

The enzyme anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase from Perilla frutescens produces delphinidin 3-(6-p-coumaroyl)glucoside from myrtillin and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway.[8][9]

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 (May 2019). "Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives". Food Chem. 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. Nakajima J, Tanaka Y, Yamazaki M, Saito K (2001). "Reaction mechanism from leucoanthocyanidin to anthocyanidin 3-glucoside, a key reaction for coloring in anthocyanin biosynthesis". J. Biol. Chem. 276 (28): 25797–803. doi:10.1074/jbc.M100744200. PMID 11316805.
  6. Kamsteeg J, van Brederode J, van Nigtevecht G (1978). "Identification and properties of UDP-glucose: cyanidin-3-O-glucosyltransferase isolated from petals of the red campion (Silene dioica)". Biochem. Genet. 16 (11–12): 1045–58. doi:10.1007/BF00484525. PMID 751640.
  7. Ford CM, Boss PK, Hoj PB (1998). "Cloning and characterization of Vitis vinifera UDP-glucose:flavonoid 3-O-glucosyltransferase, a homologue of the enzyme encoded by the maize Bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo". J. Biol. Chem. 273 (15): 9224–33. doi:10.1074/jbc.273.15.9224. PMID 9535914.
  8. Yonekura-Sakakibara K, Tanaka Y, Fukuchi-Mizutani M, Fujiwara H, Fukui Y, Ashikari T, Murakami Y, Yamaguchi M, Kusumi T (April 2000). "Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA: anthocyanin 3-O-glucoside-6"-O-acyltransferase from Perilla frutescens". Plant & Cell Physiology. 41 (4): 495–502. doi:10.1093/pcp/41.4.495. PMID 10845463.
  9. Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M, Kusumi T (1998). "Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens". Plant Science. 137 (1): 87–94. Bibcode:1998PlnSc.137...87F. doi:10.1016/S0168-9452(98)00119-8. INIST 2414423.