Malvidin

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Malvidin
Malvidin.svg
Names
IUPAC name
3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxy)-1λ4-benzopyran-1-ylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: KZMACGJDUUWFCH-UHFFFAOYSA-O Yes check.svgY
  • 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
  • Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(OC)c(O)c(OC)c3
Properties
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.

Contents

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 blueberries ( Vaccinium corymbosum ) 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 Armenia.

Glycosides

See also

Related Research Articles

<i>Curcuma alismatifolia</i> Species of plant

Curcuma alismatifolia, Siam tulip or summer tulip is a tropical plant native to Laos, northern Thailand, and Cambodia. Despite its name, it is not related to the tulip, but is a close relative of turmeric. It can grow as an indoor plant. It is a perennial herb growing up to 2 feet tall.

<span class="mw-page-title-main">Delphinidin</span> Chemical compound

Delphinidin is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">Malvin</span> Chemical compound

Malvin is a naturally occurring chemical of the anthocyanin family.

<span class="mw-page-title-main">Pelargonidin</span> Red anthocyanidin pigment found in certain flowers and fruits

Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.

<span class="mw-page-title-main">Anthocyanin</span> Class of plant-based pigments

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart named a chemical compound that gives flowers a blue color, Anthokyan, in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Petunidin</span> Chemical compound

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many red berries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

<span class="mw-page-title-main">Daidzin</span> Chemical compound

Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.

<span class="mw-page-title-main">Aromadendrin</span> Chemical compound

Aromadendrin is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.

<span class="mw-page-title-main">Caftaric acid</span> Chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

<span class="mw-page-title-main">Oenin</span> Chemical compound

Oenin is an anthocyanin. It is the 3-glucoside of malvidin. It is one of the red pigments found in the skin of purple grapes and in wine.

<span class="mw-page-title-main">Antirrhinin</span> Chemical compound

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

<span class="mw-page-title-main">Syringetin</span> Chemical compound

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

<span class="mw-page-title-main">Patuletin</span> Chemical compound

Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.

<span class="mw-page-title-main">Malvidin glucoside-ethyl-catechin</span> Chemical compound

Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.

<span class="mw-page-title-main">Violdelphin</span> Chemical compound

Violdelphin is an anthocyanin, a plant pigment, has been found in the purplish blue flower of Aconitum chinense, in the blue flowers in the genus Campanula and in the blue flowers of Delphinium hybridum. It is a flavenoid natural product, incorporating two p-hydroxy benzoic acid residues, one rutinoside and two glucosides associated with a delphinidin.

<i>Silene jenisseensis</i> Species of flowering plant

Silene jenisseensis, is a species of flowering plant in the family Caryophyllaceae, native to Siberia, Far East and Mongolia.

References

  1. "Phytochemicals: Malvidin". Top Cultures. Archived from the original on April 1, 2010. Retrieved 2009-05-20.{{cite web}}: CS1 maint: unfit URL (link)
  2. Mazza G (2005). "Compositional and functional properties of saskatoon berry and blueberry". International Journal of Fruit Science. 5 (3): 99–118. doi: 10.1300/J492v05n03_10 .
  3. 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.
  4. 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.
  5. 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.
  6. 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.