Malvidin

Not to be confused with Malvidine.

Malvidin
Names

IUPAC name 3,5,7-trihydroxy-2-(4-hydroxy- 3,5-dimethoxyphenyl)chromenium
Identifiers
CAS Number	643-84-5^N
ChEBI	CHEBI:6674^N
ChEMBL	ChEMBL255753^Y ChEMBL592005^Y
ChemSpider	140095^Y
Jmol interactive 3D	Image
PubChem	159287
InChI InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1^Y Key: KZMACGJDUUWFCH-UHFFFAOYSA-O^Y InChI=1/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1 Key: KZMACGJDUUWFCH-IKLDFBCSAG
SMILES O(c1cc(cc(OC)c1O)c3[o+]c2cc(O)cc(O)c2cc3O)C
Properties
Chemical formula	C₁₇H₁₅O₇+
Molar mass	331.2968 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 ?)
Infobox references

Malvidin (Mv) is an O-methylated anthocyanidin. As a primary plant pigment, its glycosides are highly abundant in nature.

Natural occurrences

Malvidin is responsible for the blue color found in petals of the Primula plants of the polyanthus group. Blue flowers of the blue pimpernel (Anagallis monelli) have also a higher concentration of malvidin.

It is responsible primarily for the color of red wine, Vitis vinifera being one of its sources.^[1] It is also present in other berries, such as the chokeberries (Aronia sp.) or the saskatoon berries (Amelanchier alnifolia).^[2]^[3]

Chemistry

Slightly acidic and neutral solutions of malvidin are characteristically of a red color, while basic solutions of malvidin yield a blue color.

The breakdown of malvidin releases syringic acid.

Use as a marker in archaeology

The breakdown of malvidin releases syringic acid as revealed in the examination of jars containing shedeh, a drink of Ancient Egypt. Malvidin is also present in the site of the Areni-1 winery, a 6,100-year-old winery discovered in 2007 in the Areni-1 cave complex in the village of Areni in the Vayots Dzor province of the Republic of Armenia.

Glycosides

Malvin is a malvidin diglucoside.
Oenin is the malvidin-3-glucoside.
Primulin is the 3-O-galactoside of malvidin.
Malvidin 3-rutinoside is a pigment responsible for bract color in Curcuma alismatifolia (the Siam tulip).^[4] Acylated malvidin 3-rutinosides are responsible for the violet color of Petunia integrifolia subsp. inflata.^[5]
Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) is a pigment responsible for the blue color in 'Johnson's Blue' and other 'blue' geraniums^[6]

References

↑ "Phytochemicals: Malvidin". Top Cultures. Retrieved 2009-05-20.
↑ Mazza G (2005). "Compositional and functional properties of saskatoon berry and blueberry". Int. J. Fruit Sci. 5 (3): 99–118. doi:10.1300/J492v05n03_10.
↑ Bakowska-barczak; Marianchuk, M; Kolodziejczyk, P (2007). "Survey of bioactive components in Western Canadian berries". Canadian Journal of Physiology and Pharmacology 85 (11): 1139–52. doi:10.1139/y07-102. PMID 18066116.
↑ Nakayama, M; Roh, MS; Uchida, K; Yamaguchi, Y; Takano, K; Koshioka, M (2000). "Malvidin 3-rutinoside as the pigment responsible for bract color in Curcuma alismatifolia". Bioscience, Biotechnology, and Biochemistry 64 (5): 1093–5. doi:10.1271/bbb.64.1093. PMID 10879491.
↑ Tatsuzawa, F (1999). "Acylated malvidin 3-rutinosides in dusky violet flowers of Petunia integrifolia subsp. Inflata". Phytochemistry 52 (2): 351–355. doi:10.1016/S0031-9422(99)00095-3.
↑ Markham, Kenneth R.; Mitchell, Kevin A.; Boase, Murray R. (1997). "Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) and its colour manifestation in 'Johnson's Blue' and other 'Blue' geraniums". Phytochemistry 45 (2): 417–423. doi:10.1016/S0031-9422(96)00831-X.

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

3-deoxyanthocyanidins

O-methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Callistephin (Pelargonidin 3-O-glucoside)
Chrysanthemin (Cyanidin-3-O-glucoside)
Myrtillin (Delphinidin-3-O-glucoside)
Oenin (Malvidin-3-O-glucoside)
Peonidin-3-O-glucoside
Petunidin-3-O-glucoside
Pulchellidin 3-glucoside

Diglucosides:

Cyanin (Cyanidin-3,5-O-diglucoside)
Delphin (Delphinidin-3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin-3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

Antirrhinin (Cyanidin-3-O-rutinoside)
Ideain (Cyanidin 3-O-galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin-3-O-rutinoside
Primulin (Malvidin-3-O-galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O-rutinoside)

Acylated anthocyanins

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 Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside 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

Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)

Acylated anthocyanin diglycosides	Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside)) Nasunin (Delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-beta-D-glucosyl)oxybenzoyl)-beta-D-glucoside)

Flavanol-anthocyanin adducts

Malvidin glucoside-ethyl-catechin
Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside

Misc.

Metalloanthocyanins (Commelinin
Cyanosalvianin
Protocyanin
Protodelphin)
Pyranoanthocyanins
Copigmentation
Anthocyanone A (degradation product of oenin)
Malvone (oxidation product of malvin)

This article is issued from Wikipedia - version of the Saturday, January 30, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.