Isorhamnetin

Last updated
Isorhamnetin
3-methylquercetin.svg
Isorhamnetin.png
Names
IUPAC name
3,4′,5,7-Tetrahydroxy-3′-methoxyflavone
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
Other names
3-methylquercetin
3-Methylquercetin
Isorhamnetol
isorhamentin
isorhamnetine
iso-rhamnetin
3'-Methoxyquercetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.860 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3 X mark.svgN
    Key: IZQSVPBOUDKVDZ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
    Key: IZQSVPBOUDKVDZ-UHFFFAOYAD
  • COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
C16H12O7
Molar mass 316.26 g/mol
Melting point 307 °C (585 °F; 580 K)
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 ?)

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments. [1] Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. [2] Almond skin is a rich source of isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-glucoside, in some cultivars they comprise 75% of the polyphenol content, the total of which can exceed 10 mg/100 gram almond. [3] Others sources include the spice, herbal medicinal [4] and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate. [5] Nopal (Opuntia ficus-indica (L.)) is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes. [6]

Contents

Metabolism

The enzyme quercetin 3-O-methyltransferase uses S-adenosyl methionine and quercetin to produce S-adenosylhomocysteine and isorhamnetin.

The enzyme 3-methylquercetin 7-O-methyltransferase uses S-adenosyl methionine and 5,7,3',4'-tetrahydroxy-3-methoxyflavone (isorhamnetin) to produce S-adenosylhomocysteine and 5,3',4'-trihydroxy-3,7-dimethoxyflavone (rhamnazin).

Glycosides

See also

Related Research Articles

<span class="mw-page-title-main">Quercetin</span> 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>Opuntia ficus-indica</i> Species of cactus

Opuntia ficus-indica, the Indian fig opuntia, fig opuntia, or prickly pear, is a species of cactus that has long been a domesticated crop plant grown in agricultural economies throughout arid and semiarid parts of the world. O. ficus-indica is the most widespread and most commercially important cactus. It is grown primarily as a fruit crop, and also for the vegetable nopales and other uses. Cacti are good crops for dry areas because they efficiently convert water into biomass. O. ficus-indica, as the most widespread of the long-domesticated cactuses, is as economically important as maize and blue agave in Mexico. Opuntia species hybridize easily, but the wild origin of O. ficus-indica is likely to have been in central Mexico, where its closest genetic relatives are found.

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

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<i>Tagetes lucida</i> Species of flowering plant

Tagetes lucida is a perennial plant native to Mexico and Central America. It is used as a medicinal plant and as a culinary herb. The leaves have a tarragon-like scent, with hints of anise, and it has entered the nursery trade in North America as a tarragon substitute. Common names include sweetscented marigold, Mexican marigold, Mexican mint marigold, Mexican tarragon, sweet mace, Texas tarragon, pericón, yerbaniz, and hierbanís.

In enzymology, a 3,7-dimethylquercetin 4'-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a 3-methylquercetin 7-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an apigenin 4'-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a hexaprenyldihydroxybenzoate methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an inositol 3-methyltransferase is an enzyme that catalyzes the chemical reaction

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

In enzymology, an isoorientin 3'-O-methyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a kaempferol 4'-O-methyltransferase is an enzyme that catalyzes the chemical reaction

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

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

In enzymology, a quercetin 3-O-methyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

<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 redberries 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.

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

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

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

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

Acacetin is a 4′-O-methylated flavone of the parent compound apigenin, found in Robinia pseudoacacia, Turnera diffusa (damiana), shows moderate aromatase inhibition, Betula pendula, and in the fern Asplenium normale.

References

  1. Slimestad, R; Fossen, T; Vågen, IM (December 2007). "Onions: a source of unique dietary flavonoids". J. Agric. Food Chem. 55 (25): 10067–80. doi:10.1021/jf0712503. PMID   17997520.
  2. Holland, Thomas M.; Agarwal, Puja; Wang, Yamin; Leurgans, Sue E.; Bennett, David A.; Booth, Sarah L.; Morris, Martha Clare (2020-01-29). "Dietary flavonols and risk of Alzheimer dementia". Neurology. 94 (16): e1749–e1756. doi:10.1212/WNL.0000000000008981. ISSN   0028-3878. PMC   7282875 . PMID   31996451.
  3. PMID 25544797 PMC4276397
  4. Céspedes, Carlos L. (2006). "Antifungal and Antibacterial Activities of Mexican Tarragon (Tagetes lucida)". Journal of Agricultural and Food Chemistry. 54 (10): 3521–3527. doi:10.1021/jf053071w. PMID   19127719.
  5. Abdala, 1999
  6. Antunes-Ricardo M, Garcia-Cayuela T, Mendiola JA, Ibañez E, Gutierrez-Uribe JA, Cano MP, Guajardo-Flores D (November 2018). "Supercritical CO2 enzyme hydrolysis as a pretreatment for the release of isorhamnetin conjugates from Opuntia ficus-indica (L.) Mill". The Journal of Supercritical Fluids. 141: 21–28. doi:10.1016/j.supflu.2017.11.030. S2CID   103893093.