Chemistry: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]

Biosynthesis and metabolism

The enzyme luteolin O-methyltransferase uses S-adenosyl methionine to methylate the flavanol, quercetin, giving isorhamnetin.[7][8]

The enzyme 3-methylquercetin 7-O-methyltransferase further methylates isorhamnetin to produce rhamnazin.[9]

Isorhamnetin is an inhibitor of CYP1B1.[10]

Glycosides

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

See also

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. Bibcode: 2007JAFC...5510067S. 
  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" (in en). Neurology 94 (16): e1749–e1756. doi:10.1212/WNL.0000000000008981. ISSN 0028-3878. 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. Bibcode: 2006JAFC...54.3521C. 
  5. ↑ Abdala, 1999
  6. ↑ "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. November 2018. doi:10.1016/j.supflu.2017.11.030. 
  7. ↑ Muzac, Ingrid; Wang, Jing; Anzellotti, Dominique; Zhang, Hong; Ibrahim, Ragai K. (2000). "Functional Expression of an Arabidopsis cDNA Clone Encoding a Flavonol 3′-O-Methyltransferase and Characterization of the Gene Product". Archives of Biochemistry and Biophysics 375 (2): 385–388. doi:10.1006/abbi.1999.1681. PMID 10700397. 
  8. ↑ Liu, Weixin; Feng, Yi; Yu, Suhang; Fan, Zhengqi; Li, Xinlei; Li, Jiyuan; Yin, Hengfu (2021). "The Flavonoid Biosynthesis Network in Plants". International Journal of Molecular Sciences 22 (23). doi:10.3390/ijms222312824. PMID 34884627. 
  9. ↑ "Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of S-adenosyl-L-methionine:flavonol 3-, 6-, 7-, and 4'-O-methyltransferases". Arch. Biochem. Biophys. 238 (2): 596–605. 1985. doi:10.1016/0003-9861(85)90205-X. PMID 3994393. 
  10. ↑ Li, Fei; Zhu, Weifeng; Gonzalez, Frank J (October 2017). "Potential role of CYP1B1 in the development and treatment of metabolic diseases". Pharmacology & Therapeutics 178: 18-30. doi:10.1016/j.pharmthera.2017.03.007. PMID 28322972. 



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