O-methylated flavonoid

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The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups (methoxy bonds). O-methylation has an effect on the solubility of flavonoids.

Contents

Enzymes

O-methylated flavonoids formation implies the presence of specific O-methyltransferase (OMT) enzymes which accept a variety of substrates. [1] Those enzymes mediate the O-methylation on a specific hydroxyl group, like on 4' (example in Catharanthus roseus [2] ) or 3' (example in rice [3] ) positions. Those positions can be ortho, meta, para and there can be a special 3-O-methyltransferase for the 3-OH position. Calamondin orange ( Citrus mitis ) exhibits all of those activities. [4]

Plant enzymes

Animal enzyme

O-methylated anthocyanidins

O-methylated flavanols

O-methylated flavanones

O-methylated flavanonols

O-methylated flavonols

of kaempferol

of myricetin

of quercetin

other

O-methylated flavones

O-methylated isoflavones

See also

Related Research Articles

Quercetin Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<i>Parietaria officinalis</i> Species of flowering plant

Parietaria officinalis, the eastern pellitory-of-the-wall, also known as upright pellitory and lichwort, is a plant of the nettle family. Its leaves, however, are non-stinging. The plant grows on rubbish and on walls, hence the name.

Malvidin Chemical compound

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.

In enzymology, an isoflavone 7-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a myricetin O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a secologanin synthase (EC 1.14.19.62, was wrongly classified as EC 1.3.3.9 in the past) is an enzyme that catalyzes the chemical reaction

Phenolic content in wine Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which 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.

Rosinidin Chemical compound

Rosinidin is an O-methylated anthocyanidin derived from Cyanidin. It is a pigment found in the flowers of Catharanthus roseus and, in lower concentration, in Primula rosea.

Caftaric acid Chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

Irigenin Chemical compound

Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily, and Iris kemaonensis.

Prenylflavonoid

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

Ayanin Chemical compound

Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylated derivative of quercetin.

Ombuin Chemical compound

Ombuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.

An O-methyltransferase (OMT) is a type of methyltransferase enzyme transferring a methyl group on a molecule.

Syringetin 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.

Calycosin Chemical compound

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L..

Mearnsetin Chemical compound

Mearnsetin is an O-methylated flavonol. It can be found in Eucalyptus globulus and in Elaeocarpus lanceofolius. The compound has antioxidative properties.

Flavonoid 4'-O-methyltransferase is an enzyme with systematic name S-adenosyl-L-methionine:flavonoid 4'-O-methyltransferase. This enzyme catalyses the following chemical reaction

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine Chemical compound

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine is a terpene indole alkaloid produced by Catharanthus roseus. The metabolite is a substrate for 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT) which transfers a methyl group to the nitrogen of the indole ring forming desacetoxyvindoline. The enzyme catalyzing the formation of 3-hydroxy-16-methoxy-2,3-dihydrotabersonine from 16-methoxytabersonine is currently unknown, but is a result of hydration of the double bond connecting the 6 and 13 position carbons.

Pisatin Chemical compound

Pisatin (3-hydroxy-7-methoxy-4′,5′-methylenedioxy-chromanocoumarane) is the major phytoalexin made by the pea plant Pisum sativum. It was the first phytoalexin to be purified and chemically identified. The molecular formula is C17H14O6.

References

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  2. Schroder, G; Wehinger, E; Lukacin, R; Wellmann, F; Seefelder, W; Schwab, W; Schröder, J (2004). "Flavonoid methylation: a novel 4′-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases". Phytochemistry. 65 (8): 1085–94. doi:10.1016/j.phytochem.2004.02.010. PMID   15110688.
  3. Kim, Bong-Gyu; Lee, Youngshim; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon (2006). "Flavonoid 3′-O-methyltransferase from rice: CDNA cloning, characterization and functional expression". Phytochemistry. 67 (4): 387–94. doi:10.1016/j.phytochem.2005.11.022. PMID   16412485.
  4. Brunet, Gunter; Ibrahim, Ragai K. (1980). "O-methylation of flavonoids by cell-free extracts of calamondin orange". Phytochemistry. 19 (5): 741–6. doi:10.1016/0031-9422(80)85102-8.
  5. Harborne, J.B. (1967). "Comparative biochemistry of the flavonoids-IV.: Correlations between chemistry, pollen morphology and systematics in the family plumbaginaceae". Phytochemistry. 6 (10): 1415–28. doi:10.1016/S0031-9422(00)82884-8.