| Revision as of 01:55, 19 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 22:59, 15 August 2023 edit undo173.88.246.138 (talk)No edit summary |
| (38 intermediate revisions by 25 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 414762680 |
|
|
|
| Watchedfields = changed |
|
| name = Myrtillin |
|
|
⚫ |
| verifiedrevid = 440231978 |
| ⚫ |
| ImageFile = Mirtillin.svg |
|
|
| ImageSize = 300px |
|
| Name = Myrtillin |
|
⚫ |
| ImageFile = Mirtillin.svg |
| ⚫ |
| IUPACName = <nowiki>(2''S'',3''R'',4''S'',5''S'',6''R'')-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride</nowiki> |
|
|
|
| ImageSize = 300px |
| ⚫ |
| OtherNames = Mirtillin<br>Myrtillin chloride<br>Delphinidin 3-glucoside<br>Delphinidol 3-glucoside<br>Delphinidin 3-O-glucoside<br>Delphinidin 3-monoglucoside<br>Delphinidine 3-monoglucoside<br>Delphinidin-3-glucoside chloride<br>Delphinidin 3-O-beta-D-glucoside |
|
|
⚫ |
| IUPACName = (2''S'',3''R'',4''S'',5''S'',6''R'')-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride |
| ⚫ |
| Section1={{Chembox Identifiers |
|
|
⚫ |
| OtherNames = {{bulletedlist|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-<small>D</small>-glucoside}} |
| ⚫ |
| CASNo = 6906-38-3 |
|
|
⚫ |
|Section1={{Chembox Identifiers |
|
| CASOther = 26770-35-4 |
|
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
| ⚫ |
| PubChem = 165558 |
|
|
⚫ |
| CASNo = 6906-38-3 |
| ⚫ |
| SMILES = C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=2)O)O)OC4C(C(C(C(O4)CO)O)O)O. |
|
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 474A9U89JS |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
| KEGG = C12138 |
|
⚫ |
| PubChem = 165558 |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEBI = 31463 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 391783 |
|
⚫ |
| SMILES = C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=2)O)O)OC4C(C(C(C(O4)CO)O)O)O. |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 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 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = XENHPQQLDPAYIJ-PEVLUNPASA-O |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>21</sub>H<sub>21</sub>ClO<sub>12</sub><br>C<sub>21</sub>H<sub>21</sub>O<sub>12</sub><sup>+</sup>, Cl<sup>-</sup> |
|
| Formula = C<sub>21</sub>H<sub>21</sub>ClO<sub>12</sub><br>C<sub>21</sub>H<sub>21</sub>O<sub>12</sub><sup>+</sup>, Cl<sup>−</sup> |
|
| MolarMass = 500.83 g/mol (chloride)<br>465.38 g/mol |
|
| MolarMass = 500.83 g/mol (chloride)<br>465.38 g/mol |
|
|
| Appearance = |
|
| ExactMass = 500.072154 (chloride)<br>465.10330107 |
|
|
| Appearance = |
|
| Density = |
|
| Density = |
|
| MeltingPt = |
|
| MeltingPt = |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = |
|
| Solubility = |
|
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards = |
|
| MainHazards = |
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = |
|
| AutoignitionPt = |
|
}} |
|
}} |
|
}} |
|
}} |
|
'''Myrtillin''' is an ]. It is the 3-] of ]. It can be found in all green plants, most abundantly in ], in ] or ] leaves and various ]s, in the ], in the '']'' plant (''Hydrocotyle asiatica'')<ref></ref> and in the ] leaf<ref></ref>. It is also present in ] and ]<ref name="Christopher"></ref>. The ] fruits pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified<ref></ref>. |
|
|
|
|
|
|
|
'''Myrtillin''' is an ]. It is the 3-] of ]. It can be found in all green plants, most abundantly in ], ], ], ], ] leaves<ref> {{webarchive |url=https://web.archive.org/web/20090205123323/http://www.florahealth.com/flora/home/USA/HealthInformation/Encyclopedias/BilberryLeaf.htm |date=February 5, 2009 }}</ref><ref>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}}</ref> and in various ]s, ]s, and '']'' plant.{{cn|date=October 2016}} It is also present in ] and ].{{cn|date=October 2016}} The ] fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.<ref> </ref>{{Unreliable source?|date=October 2016}} |
|
Myrtillin tends to stabilize the blood sugar, which otherwise fluctuates widely, and that it spares insulin<ref name="Christopher"/>. |
|
|
|
|
|
|
|
The various colors, such as red, mauve, purple, violet, and blue in '']'' are developed from myrtillin complexes with metal ions called ]s.<ref>{{cite journal |vauthors=Yoshida K, Mori M, Kondo T |title=Blue flower color development by anthocyanins: from chemical structure to cell physiology |journal=Nat. Prod. Rep. |volume=26 |issue=7 |pages=884–915 |year=2009 |pmid=19554240 |doi=10.1039/b800165k }}</ref> |
|
<!-- ==Metabolism== --> |
|
|
|
|
|
|
==References== |
|
== Metabolism == |
|
|
The enzyme ] produces ] from myrtillin and ''p''-] in the ] pathway.<ref>{{cite web|url=http://www.kegg.jp/dbget-bin/www_bget?rn:R07929 |title=Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp |publisher=Kegg.jp |date= |accessdate=2013-04-09}}</ref> |
|
|
|
|
|
== References == |
|
{{Reflist}} |
|
{{Reflist}} |
|
|
|
|
|
{{Anthocyanins}} |
|
{{Anthocyanins}} |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
|
|
] |
|
|
] |
|