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Isorhamnetin

Chemical compound From Wikipedia, the free encyclopedia

Isorhamnetin
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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]

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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

  • Isorhamnetin-3-O-rutinoside-7-O-glucoside
  • Isorhamnetin-3-O-rutinoside-4'-O-glucoside
  • Narcissin (Isorhamnetin-3-O-rutinoside)

See also

References

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