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Flavonols

Class of plant and fungus secondary metabolites

Backbone of a flavonol, substituent numbers are indicated.

Flavonols are a class of flavonoids that have the 3-hydroxyflavone backbone (IUPAC name: 3-hydroxy-2-phenylchromen-4-one). Their diversity stems from the different positions of the phenolic –OH groups. They are distinct from flavanols (with "a") such as catechin, another class of flavonoids, and an unrelated group of metabolically important molecules, the flavins (with "i"), derived from the yellow B vitamin riboflavin.

Flavonols are present in a wide variety of fruits and vegetables. In Western populations, estimated daily intake is in the range of 20–50 mg per day for flavonols. Individual intake varies depending on the type of diet consumed.

The phenomenon of dual fluorescence (due to excited state intramolecular proton transfer or ESIPT) is induced by tautomerism of flavonols (and glucosides) and could contribute to plant UV protection and flower colour.

Besides being a subclass of flavonoids, flavonols are suggested by a study of cranberry juice to play a role along with proanthocyanidins, in the juice's ability to block bacterial adhesion, demonstrated by the compressing the fimbria of E. coli bacteria in the urinary tract so as to greatly reduce the ability of those bacteria to stay put and initiate an infection. Flavonol aglycones in plants are potent antioxidants that serve to protect the plant from reactive oxygen species (ROS).

Flavonols

Name	IUPAC name	5	6	7	8	2′	3′	4′	5′	6′
3-Hydroxyflavone	3-hydroxy-2-phenylchromen-4-one	H	H	H	H	H	H	H	H	H
Azaleatin	2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-one	OCH3	H	OH	H	H	H	OH	OH	H
Fisetin	3,3′,4′,7-tetrahydroxy-2-phenylchromen-4-one	H	H	OH	H	H	OH	OH	H	H
Galangin	3,5,7-trihydroxy-2-phenylchromen-4-one	OH	H	OH	H	H	H	H	H	H
Gossypetin	2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one	OH	H	OH	OH	H	OH	OH	H	H
Kaempferide	3,5,7-trihydroxy-2-(4-methoxyphenyl)chromen-4-one	OH	H	OH	H	H	H	OCH3	H	H
Kaempferol	3,4′,5,7-tetrahydroxy-2-phenylchromen-4-one	OH	H	OH	H	H	H	OH	H	H
Isorhamnetin	3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one	OH	H	OH	H	H	OCH3	OH	H	H
Morin	2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one	OH	H	OH	H	OH	H	OH	H	H
Myricetin	3,3′,4′,5′,5,7-hexahydroxy-2-phenylchromen-4-one	OH	H	OH	H	H	OH	OH	OH	H
Natsudaidain	2-(3,4-dimethoxyphenyl)-3-hydroxy-5,6,7,8-tetramethoxychromen-4-one	OCH3	OCH3	OCH3	OCH3	H	H	OCH3	OCH3	H
Pachypodol	5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one	OH	H	OCH3	H	H	OCH3	OH	H	H
Quercetin	3,3′,4′,5,7-pentahydroxy-2-phenylchromen-4-one	OH	H	OH	H	H	OH	OH	H	H
Rhamnazin	3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one	OH	H	OCH3	H	H	OCH3	OH	H	H
Rhamnetin	2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one	OH	H	OCH3	H	H	OH	OH	H	H

Flavonol glycosides

Name	Aglycone	3	7	8	3′	4′
Astragalin	Kaempferol	Glc
Azalein	Azaleatin	Rha
Hyperoside	Quercetin	Gal
Isoquercitin	Quercetin	Glc
Kaempferitrin	Kaempferol	Rha	Rha
Myricitrin	Myricetin	Rha
Quercitrin	Quercetin	Rha
Robinin	Kaempferol	Robinose	Rha
Rutin	Quercetin	Rutinose
Spiraeoside	Quercetin					Glc
Xanthorhamnin	Rhamnetin	trisaccharide
Amurensin	Kaempferol		Glc	tert-amyl
Icariin	Kaempferide	Rha	Glc	tert-amyl
Troxerutin	Quercetin	Rutinose	hydroxyethyl		hydroxyethyl	hydroxyethyl

Drug interactions

Flavonoids have effects on CYP (P450) activity. Flavonols are inhibitor of CYP2C9 and CYP3A4, which are enzymes that metabolize most drugs in the body.

Technological uses

A 2013 study showed that it is possible by optical methods to quantify the flavonol accumulation in some fruit and thus to sort fruit according to fruit quality and storage durability.

Effects on health

A 2022 study indicated an association between consumption of flavonols (found in food) and a lower rate of decline of cognitive ability, including memory.

References

(October 2006). "The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms". Curr. Drug Metab..
(1998). "Tautomerism of flavonol glucosides: relevance to plant UV protection and flower colour". Journal of Photochemistry and Photobiology A: Chemistry.
"Juicy news about cranberries".
Nakabayashi R, Yonekura-Sakakibara K, Urano K, Suzuki M, Yamada Y, Nishizawa T, Matsuda F, Kojima M, Sakakibara H, Shinozaki K, Michael AJ, Tohge T, Yamazaki M, Saito K.. (2014). "Enhancement of oxidative and drought tolerance in ''Arabidopsis'' by overaccumulation of antioxidant flavonoids.". Plant J.
(March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metab. Dispos..
(2013). "Characterisation of the Polyphenol Content in the Kiwifruit (''Actinidia deliciosa'') Exocarp for the Calibration of a Fruit-sorting Optical Sensor". Phytochemical Analysis.
(22 November 2022). "Association of Dietary Intake of Flavonols With Changes in Global Cognition and Several Cognitive Abilities". Neurology.

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flavonols cyp2c9-inhibitors

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