O-methylated flavonoid
Encyclopedia
The O-methylated flavonoids or methoxyflavonoids are flavonoid
s with methylation
s on hydroxyl
groups (methoxy
bonds). O-methylation has an effect on the solubility of flavonoids.
(OMT) enzymes which accept a variety of substrates. Those enzymes mediate the O-methylation on a specific hydroxyl group, like on 4' (example in Catharanthus roseus
) or 3' (example in rice) 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.
.
of myricetin
of quercetin
other
Flavonoid
Flavonoids , are a class of plant secondary metabolites....
s with methylation
Methylation
In the chemical sciences, methylation denotes the addition of a methyl group to a substrate or the substitution of an atom or group by a methyl group. Methylation is a form of alkylation with, to be specific, a methyl group, rather than a larger carbon chain, replacing a hydrogen atom...
s on hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
groups (methoxy
Methoxy
In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
bonds). O-methylation has an effect on the solubility of flavonoids.
Enzymes
O-methylated flavonoids formation implies the presence of specific O-methyltransferaseO-methyltransferase
An O-methylated flavonoid is a type of methyltransferase enzyme transferring a methyl group on a molecule.Examples are :* Acetylserotonin O-methyltransferase* Apigenin 4'-O-methyltransferase* Caffeate O-methyltransferase...
(OMT) enzymes which accept a variety of substrates. Those enzymes mediate the O-methylation on a specific hydroxyl group, like on 4' (example in Catharanthus roseus
Catharanthus roseus
Catharanthus roseus is a species of Catharanthus native and endemic to Madagascar. Synonyms include Vinca rosea , Ammocallis rosea, and Lochnera rosea; other English names occasionally used include Cape Periwinkle, Rose Periwinkle, Rosy Periwinkle, and "Old-maid".In the wild, it is an endangered...
) or 3' (example in rice) positions. Those positions can be ortho, meta, para
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...
and there can be a special 3-O-methyltransferase for the 3-OH position. Calamondin orange (Citrus mitis) exhibits all of those activities.
Plant enzymes
- Apigenin 4'-O-methyltransferaseApigenin 4'-O-methyltransferaseIn enzymology, an apigenin 4'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 5,7,4'-trihydroxyflavone , whereas its two products are S-adenosylhomocysteine and 4'-methoxy-5,7-dihydroxyflavone .This enzyme...
- 8-hydroxyquercetin 8-O-methyltransferase8-hydroxyquercetin 8-O-methyltransferaseIn enzymology, a 8-hydroxyquercetin 8-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 3,5,7,8,3',4'-hexahydroxyflavone , whereas its two products are S-adenosylhomocysteine and...
- Isoflavone 4'-O-methyltransferaseIsoflavone 4'-O-methyltransferaseIn enzymology, an isoflavone 4'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and isoflavone, whereas its two products are S-adenosylhomocysteine and 4'-O-methylisoflavone.This enzyme belongs to the family of...
- Isoflavone 7-O-methyltransferaseIsoflavone 7-O-methyltransferaseIn enzymology, an isoflavone 7-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 7-hydroxyisoflavone, whereas its two products are S-adenosylhomocysteine and 7-methoxyisoflavone.This enzyme belongs to the...
- Isoliquiritigenin 2'-O-methyltransferaseIsoliquiritigenin 2'-O-methyltransferaseIn enzymology, an isoliquiritigenin 2'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and isoliquiritigenin, whereas its two products are S-adenosylhomocysteine and 2'-O-methylisoliquiritigenin.This enzyme...
- Isoorientin 3'-O-methyltransferaseIsoorientin 3'-O-methyltransferaseIn enzymology, an isoorientin 3'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and isoorientin, whereas its two products are S-adenosylhomocysteine and isoscoparin....
- Kaempferol 4'-O-methyltransferaseKaempferol 4'-O-methyltransferaseIn enzymology, a kaempferol 4'-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and kaempferol, whereas its two products are S-adenosylhomocysteine and kaempferide....
- Luteolin O-methyltransferaseLuteolin O-methyltransferaseIn enzymology, a luteolin O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 5,7,3',4'-tetrahydroxyflavone , whereas its two products are S-adenosylhomocysteine and 5,7,4'-trihydroxy-3'-methoxyflavone.This...
- Methylquercetagetin 6-O-methyltransferaseMethylquercetagetin 6-O-methyltransferaseIn enzymology, a methylquercetagetin 6-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 5,6,3',4'-tetrahydroxy-3,7-dimethoxyflavone, whereas its two products are S-adenosylhomocysteine and...
- 3-methylquercetin 7-O-methyltransferase3-methylquercetin 7-O-methyltransferaseIn enzymology, a 3-methylquercetin 7-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 5,7,3',4'-tetrahydroxy-3-methoxyflavone , whereas its two products are S-adenosylhomocysteine and...
- Myricetin O-methyltransferaseMyricetin O-methyltransferaseIn enzymology, a myricetin O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and myricetin, whereas its two products are S-adenosylhomocysteine and syringetin....
- Quercetin 3-O-methyltransferaseQuercetin 3-O-methyltransferaseIn enzymology, a quercetin 3-O-methyltransferase is an enzyme that catalyzes the chemical reactionThus, the two substrates of this enzyme are S-adenosyl methionine and 3,5,7,3',4'-pentahydroxyflavone, whereas its two products are S-adenosylhomocysteine and...
- Vitexin 2"-O-rhamnoside 7-O-methyltransferase
O-methylted anthocyanidins
- 5-desoxy-malvidin
- capensinidinCapensinidinCapensinidin is an O-methylated anthocyanidin. It is a water soluble, blue-red plant dye. It is a 5-methoxy analog of malvidin, has been obtained from Plumbago capensis ....
- europinidinEuropinidinEuropinidin is an O-methylated anthocyanidin. It is a water soluble, bluish red plant dye. It is a rare O-methylated flavonoid, a derivative of delphinidin. It can be found in species of Plumbago and Ceratostigma.-External links:* *...
- hirsutidinHirsutidinHirsutidin is an O-methylated anthocyanidin, a chemical compound belonging to the anthocyanins. It can be found in Catharanthus roseus where it is the prominent compound in petals and can also be found in callus cultures....
- malvidinMalvidinMalvidin is an O-methylated anthocyanidin. As a primary plant pigment, its glycosides are highly abundant in nature. It is responsible primarily for the color of red wine, Vitis vinifera being one of its sources...
- PeonidinPeonidinPeonidin is an O-methylated anthocyanidin, and a primary plant pigment. Peonidin gives purplish-red hues to flowers such as the peony, from which it takes its name, and roses. It is also present in some blue flowers, such as the morning glory....
- PetunidinPetunidinPetunidin is an O-methylated anthocyanidin. It is a natural organic compound and a particular type of anthocyanidin. It is a dark-red or purple water-soluble pigment found in many redberries including chokeberries , Saskatoon berries or different species of grape , and...
- pulchellidinPulchellidinPulchellidin is an O-methylated anthocyanidin. It is a blue-red plant pigment. It can be found in Plumbago pulchella.-Glycosides:* Pulchellidin 3-rhamnoside is reported in Plumbago coerulea whereas pulchellidin 3-glucoside is reported in Plumbago pulchella...
- RosinidinRosinidinRosinidin is an O-methylated anthocyanidin. It is a pigment found in the flowers of Catharanthus roseus and, in lower concentration, in Primula rosea....
.
O-methylated flavanones
- HesperetinHesperetinHesperetin is a bioflavonoid and, to be more specific, a flavanone. Hesperidin is water-soluble due to the presence of the sugar part in its structure, so on ingestion it releases its aglycone, i.e, hesperetin....
- HomoeriodictyolHomoeriodictyolHomoeriodictyol is a bitter-masking flavanone extracted from Herba Santa a plant growing in America.Homoeriodictyol is one of the 4 flavanones identified by Symrise in this plant eliciting taste-modifying property: homoeriodictyol sodium salt, eriodictyol and sterubin...
- IsosakuranetinIsosakuranetinIsosakuranetin is a flavanone, a type of flavonoid. It can be found in the fruit of Citrus sinensis , in the fruit of Citrus x paradisi and in Monarda didyma ....
- SakuranetinSakuranetinSakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.-Metabolism:...
- SterubinSterubinSterubin is a bitter-masking flavanone extracted from Herba Santa a plant growing in America....
O-methylated flavonols
of kaempferol- KaempferideKaempferideKaempferide is an O-methylated flavonol, a type of chemical compound. It can be found in Kaempferia galanga .-Metabolism:...
of myricetin
- AnnulatinAnnulatinAnnulatin is an O-methylated flavonol found in the roots of Pteroxygonum giraldii....
- CombretolCombretolCombretol is an O-methylated flavonol, a type of flavonoid. It is the 3,7,3',4',5'-O-methylation of myricetin and can be extracted from Rhodomyrtus tomentosa....
- EuropetinEuropetinEuropetin is an O-methylated flavonol. It can be found in Plumbago europaea....
- LaricitrinLaricitrinLaricitrin is a O-methylated flavonol, a type of flavonoid. It is found in red grape and in Vaccinium uliginosum . It is one of the phenolic compounds present in wine.-Metabolism:...
(3'-O-Dimethylmyricetin) - 5-O-methylmyricetin5-O-Methylmyricetin5-O-Methylmyricetin is a O-methylated flavonol, a type of flavonoid. It is the 5-O-methyl derivative of myricetin.It occurs naturally and can also be synthetized....
- SyringetinSyringetinSyringetin is a O-methylated flavonol, a type of flavonoid. It is found in red grape , in Lysimachia congestiflora and in Vaccinium uliginosum...
(3',5'-O-Dimethylmyricetin)
of quercetin
- AyaninAyaninAyanin is a O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylation of quercetin.It can be found in Croton schiedeanus...
- AzaleatinAzaleatinAzaleatin is a chemical compound. It is an O-methylated flavonol, a type of flavonoid. It was first isolated from the flowers of Rhododendron mucronatum in 1956 and has since been recorded in forty-four other Rhododendron species, in Plumbago capensis, in Ceratostigma willmottiana and in Carya...
- IsorhamnetinIsorhamnetinIsorhamnetin is an O-methylated flavonol, a type of chemical compound. It can be found in Tagetes lucida, a psychedelic plant from Mexico and Central America.-Metabolism:...
- OmbuinOmbuinOmbuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.Ombuin can be found in species of the genus Erythroxylum. It can also be synthetized. Ombuin 3-sulfate can be isolated from Flaveria chloraefolia.-Glycosides :Ombuin-3-rutinoside can be isolated...
- PachypodolPachypodolPachypodol is an O-methylated flavonol, a type of chemical compound. It can be isolated from Pachypodanthium confine, from Chinese herb Agastache folium and from leaves of Agastache rugosa ....
- RetusinRetusin (flavonol)Retusin is a O-methylated flavonol, a type of flavonoid. It can be found in Origanum vulgare and in Ariocarpus retusus....
(Quercetin-3,7,3',4'-tetramethyl ether) - RhamnazinRhamnazinRhamnazin is an O-methylated flavonol, a type of chemical compound. It can be found in Rhamnus petiolaris, a buckthorn plant endemic to Sri Lanka.-Metabolism:...
- RhamnetinRhamnetinRhamnetin is an O-methylated flavonol, a type of chemical compound. It can be isolated from cloves.The structure of the molecule has been discovered by Austrian chemist Josef Herzig ....
- Tamarixetin
other
- EupatolitinEupatolitinEupatolitin is a chemical compound. It is an O-methylated flavonol, a type of flavonoid. Eupatolitin can be found in Brickellia veronicaefolia and in Ipomopsis aggregata.-Glycoside:...
- NatsudaidainNatsudaidainNatsudaidain is an O-methylated flavonol, a type of chemical compound. It can be isolated from Citrus plants ....
O-methylated flavones
- AcacetinAcacetinAcacetin is an O-methylated flavone found in Robinia pseudoacacia and Turnera diffusa .The enzyme apigenin 4'-O-methyltransferase uses S-adenosyl methionine and 5,7,4'-trihydroxyflavone to produce S-adenosylhomocysteine and 4'-methoxy-5,7-dihydroxyflavone ....
- NepetinNepetinNepetin is an O-methylated flavone. It can be found in Eupatorium ballotaefolium....
- NobiletinNobiletinNobiletin is a chemical compound. It is an O-methylated flavone, a flavonoid isolated from citrus peels like in tangerine.-External links:* , phytochemicals.info...
- Oroxylin-A
- SinensetinSinensetinSinensetin is a methylated flavone. It can be found in Orthosiphon stamineus....
- TangeritinTangeritinTangeritin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeritin strengthens the cell wall and protects it from invasion ....
- WogoninWogoninWogonin is an O-methylated flavone, a flavonoid-like chemical compound which was found in Scutellaria baicalensisThe glycosides of wogonin are known as wogonosides. For example, oroxindin is a wogonin glucuronide isolated from Oroxylum indicum...
O-methylated isoflavones
- Biochanin ABiochanin ABiochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea and in other legumes.Biochanin A is classified as a phytoestrogen and has...
- CalycosinCalycosinCalycosin is a O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense .-Biosynthesis:...
- FormononetinFormononetinFormononetin is an O-methylated isoflavone. It is found in a number of plants and herbs like the red clover. Along with other phytoestrogens, it predominantly occurs in leguminous plants and Fabaceae, particularly in beans, such as green beans, lima beans, soy and many others, as the free aglycone...
- GlyciteinGlyciteinGlycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones....
- IrigeninIrigeninIrigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily ....
- 5-O-methylgenistein5-O-Methylgenistein5-O-Methylgenistein is an O-methylated isoflavone. It can be found in Ormosia excelsa....
- PratenseinPratenseinPratensein is an O-methylated isoflavone, a type of flavonoid. It can be found in Trifolium pratense and can have effects for the prevention of atherosclerosis....
- PrunetinPrunetinPrunetin is a O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata . Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores...
- Psi-tectorigeninPsi-tectorigeninPsi-tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from Nocardiopsis sp, Belamcanda chinensis, Dalbergia sissoo and Stemphilium sp. No. 644....
- RetusinRetusin (isoflavone)Retusin is a O-methylated isoflavone, a type of flavonoid. It can be found in Dipteryx odorata, in Dalbergia retusa and in Millettia nitita....
- TectorigeninTectorigeninTectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from leopard lily or Pueraria thunbergiana....