O-methylated flavonoid

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

* 1 Enzymes
* 1.1 Plant enzymes
* 1.2 Animal enzyme
* 2 O-methylated anthocyanidins
* 3 O-methylated flavanols
* 4 O-methylated flavanones
* 5 O-methylated flavanonols
* 6 O-methylated flavonols
* 7 O-methylated flavones
* 8 O-methylated isoflavones
* 9 See also
* 10 References

## 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

* Apigenin 4'-O-methyltransferase
* 8-hydroxyquercetin 8-O-methyltransferase
* Isoflavone 4'-O-methyltransferase
* Isoflavone 7-O-methyltransferase
* Isoliquiritigenin 2'-O-methyltransferase
* Isoorientin 3'-O-methyltransferase
* Kaempferol 4'-O-methyltransferase
* Luteolin O-methyltransferase
* Methylquercetagetin 6-O-methyltransferase
* 3-methylquercetin 7-O-methyltransferase
* Myricetin O-methyltransferase
* Quercetin 3-O-methyltransferase
* Vitexin 2"-O-rhamnoside 7-O-methyltransferase

### Animal enzyme

* Catechol-O-methyl transferase

## O-methylated anthocyanidins

* 5-desoxy-malvidin
* Capensinidin
* Europinidin
* Hirsutidin
* Malvidin
* Peonidin
* Petunidin
* Pulchellidin
* Rosinidin
* [5]

## O-methylated flavanols

* Meciadanol (3-O'methyl catechin)

## O-methylated flavanones

* Hesperetin
* Homoeriodictyol
* Isosakuranetin
* Sakuranetin
* Sterubin

## O-methylated flavanonols

* Dihydrokaempferide

## O-methylated flavonols

of kaempferol

* Kaempferide

of myricetin

* Annulatin
* Combretol
* Europetin
* Laricitrin (3'-O-Dimethylmyricetin)
* 5-O-methylmyricetin
* Syringetin (3',5'-O-Dimethylmyricetin)

of quercetin

* Ayanin
* Azaleatin
* Isorhamnetin
* Ombuin
* Pachypodol
* Retusin (Quercetin-3,7,3',4'-tetramethyl ether)
* Rhamnazin
* Rhamnetin
* Tamarixetin

other

* Eupatolitin
* Natsudaidain

## O-methylated flavones

* Acacetin
* Chrysoeriol
* Diosmetin
* Nepetin
* Nobiletin
* Oroxylin-A
* Sinensetin
* Tangeritin
* Thevetiaflavone
* Wogonin

## O-methylated isoflavones

* Biochanin A
* Calycosin
* Formononetin
* Glycitein
* Irigenin
* 5-O-methylgenistein
* Pratensein
* Prunetin
* Psi-tectorigenin
* Retusin
* Tectorigenin

## See also

* C-methylated flavonoid

## References

1. ↑ Kim, Dae Hwan; Kim, Bong-Gyu; Lee, Youngshim; Ryu, Ji Young; Lim, Yoongho; Hur, Hor-Gil; Ahn, Joong-Hoon (2005). "Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli". Journal of Biotechnology 119 (2): 155–62. doi:10.1016/j.jbiotec.2005.04.004. PMID 15961179.
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.

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Types of flavonoids

Flavonoids|

| Anthoxanthins|

| Flavones|

* Apigenin, Chrysin, et.c.

|

Flavonols|

* Quercetin, Kaempferol, et.c.

Isoflavones|

* Daidzein, Genistein, Orobol et.c.

Neoflavonoids|

* Dalbergichromene

Flavans|

| Flavan|

* Luteoliflavan

|

Flavan-3-ols
(flavanols)|

* Catechin, Gallocatechol, et.c.

Flavan-4-ols
(flavanols)|

* Apiforol, Luteoforol, et.c.

Flavan-3,4-diols|

* Leucocyanidin, Leucodelphinidin, et.c.

Flavanones|

* Hesperidin
* Naringenin
* Eriodictyol

Flavanonols|

* Taxifolin
* Aromadendrin, et.c.

Anthocyanidins|

| 3-deoxyanthocyanidins|

* Cyanidin, Delphinidin, et.c.

|

3-hydroxyanthocyanidin|

* Apigeninidin, Guibourtinidin, et.c.

Aurones|

* Aureusidin
* Leptosidin

Chalcones|

| Chalcones|

* Butein, Isoliquiritigenin, et.c.

|

Dihydrochalcone|

* Phloretin

Miscellaneous|

* List of phytochemicals in food
* C-methylated flavonoids
* O-methylated flavonoids
* Furanoflavonoids
* Pyranoflavonoids
* Prenylflavonoids
* Methylenedioxy
* Castavinols

Flavonoid biosynthesis

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