Myrtillin
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| 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
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CompTox Dashboard (EPA) |
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| 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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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.[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 been identified.[3][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.[4]
Biosynthesis and metabolism
[edit]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]
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]
glucoside.svg)
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 (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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.