Isorhamnetin
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Names | |
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IUPAC name
3,4′,5,7-Tetrahydroxy-3′-methoxyflavone
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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)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.860 |
KEGG | |
PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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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 theirstandard state(at 25 °C [77 °F], 100 kPa).
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Isorhamnetinis anO-methylatedflavon-olfrom the class offlavonoids.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]andpsychoactiveMexican 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 bysupercritical fluid extractionassisted by enzymes.[6]
Metabolism
[edit]The enzymequercetin 3-O-methyltransferaseusesS-adenosyl methionineandquercetinto produceS-adenosylhomocysteineand isorhamnetin.
The enzyme3-methylquercetin 7-O-methyltransferaseuses 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
[edit]- Isorhamnetin-3-O-rutinoside-7-O-glucoside
- Isorhamnetin-3-O-rutinoside-4'-O-glucoside
- Narcissin(Isorhamnetin-3-O-rutinoside)
See also
[edit]- List of antioxidants in food
- List of phytochemicals in food
- Tamarixetin,the 4'-methyl analog
References
[edit]- ^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.PMID17997520.
- ^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.ISSN0028-3878.PMC7282875.PMID31996451.
- ^PMID 25544797 PMC4276397
- ^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.PMID19127719.
- ^Abdala, 1999
- ^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.S2CID103893093.