Flavonols

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Backbone of a flavonol, substituent numbers are indicated. Flavonol num.svg
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.

Contents

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. [1]

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. [2]

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. [3] Flavonol aglycones in plants are potent antioxidants that serve to protect the plant from reactive oxygen species (ROS). [4]

Flavonols

Flavonols
NameIUPAC name56782′3′4′5′6′
3-Hydroxyflavone 3-hydroxy-2-phenylchromen-4-oneHHHHHHHHH
Azaleatin 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-oneOCH3HOHHHHOHOHH
Fisetin 3,3′,4′,7-tetrahydroxy-2-phenylchromen-4-oneHHOHHHOHOHHH
Galangin 3,5,7-trihydroxy-2-phenylchromen-4-oneOHHOHHHHHHH
Gossypetin 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-oneOHHOHOHHOHOHHH
Kaempferide 3,5,7-trihydroxy-2-(4-methoxyphenyl)chromen-4-oneOHHOHHHHOCH3HH
Kaempferol 3,4′,5,7-tetrahydroxy-2-phenylchromen-4-oneOHHOHHHHOHHH
Isorhamnetin 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-oneOHHOHHHOCH3OHHH
Morin 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-oneOHHOHHOHHOHHH
Myricetin 3,3′,4′,5′,5,7-hexahydroxy-2-phenylchromen-4-oneOHHOHHHOHOHOHH
Natsudaidain 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,6,7,8-tetramethoxychromen-4-oneOCH3OCH3OCH3OCH3HHOCH3OCH3H
Pachypodol 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-oneOHHOCH3HHOCH3OHHH
Quercetin 3,3′,4′,5,7-pentahydroxy-2-phenylchromen-4-oneOHHOHHHOHOHHH
Rhamnazin 3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-oneOHHOCH3HHOCH3OHHH
Rhamnetin 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-oneOHHOCH3HHOHOHHH

Flavonol glycosides

Flavonols glycosides and acetylated glycosides
NameAglycone356782′3′4′5′6′
Astragalin Kaempferol Glc
Azalein Azaleatin Rha
Hyperoside Quercetin Gal
Isoquercitin Quercetin Glc
Kaempferitrin Kaempferol RhaRha
Myricitrin Myricetin Rha
Quercitrin Quercetin Rha
Robinin Kaempferol RobinoseRha
Rutin Quercetin Rutinose
Spiraeoside Quercetin Glc
Xanthorhamnin Rhamnetin trisaccharide
Amurensin Kaempferol Glctert-amyl
Icariin Kaempferide RhaGlctert-amyl
Troxerutin Quercetin Rutinosehydroxyethylhydroxyethylhydroxyethyl

Drug interactions

Flavonoids have effects on CYP (P450) activity. Flavonols are inhibitor of CYP2C9 [5] and CYP3A4, [1] 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. [6]

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. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.

<i>Citrus depressa</i> Species of fruit and plant

Citrus depressa (Citrus × depressa, formerly C. pectinifera, Okinawan: シークヮーサー/シークァーサー, romanized: shiikwaasa, Japanese: ヒラミレモン, romanized: hirami remon or シークヮーサー, shiikwāsā, in English sometimes called shiikuwasha, shequasar, Taiwan tangerine, Okinawa lime, flat lemon, hirami lemon, or thin-skinned flat lemon, is a small citrus fruit often harvested and used when green, rich in flavonoids and native to East Asia.

<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.

<span class="mw-page-title-main">Cranberry juice</span> Liquid juice of the cranberry

Cranberry juice is the liquid juice of the cranberry – a fruit recognized for its bright red color, tart taste, and versatility for product manufacturing. Major cranberry products include cranberry juice, dried cranberry, cranberry sauce, frozen cranberry, cranberry powder, and dietary supplements containing cranberry extracts.

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

Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.

<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.

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

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.

<span class="mw-page-title-main">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetized type of antioxidant, in which each instance would contain a polyphenolic substructure; such instances which have been studied in vitro. Numbering over 4,000 distinct chemical structures, such polyphenols may have antioxidant activity {{{1}}} in vitro (although they are unlikely to be antioxidants in vivo). Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

<span class="mw-page-title-main">Flavones</span> Class of flavonoid chemical compounds

Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

<span class="mw-page-title-main">Anthocyanin</span> Class of plant-based pigments

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart named a chemical compound that gives flowers a blue color, Anthokyan, in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

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

Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.

<span class="mw-page-title-main">3-Hydroxyflavone</span> Chemical compound

3-Hydroxyflavone is a chemical compound. It is the backbone of all flavonols, a type of flavonoid. It is a synthetic compound, which is not found naturally in plants. It serves as a model molecule as it possesses an excited-state intramolecular proton transfer (ESIPT) effect to serve as a fluorescent probe to study membranes for example or intermembrane proteins. The green tautomer emission and blue-violet normal emission originate from two different ground state populations of 3HF molecules. The phenomenon also exists in natural flavonols. Although 3-hydroxyflavone is almost insoluble in water, its aqueous solubility can be increased by encapsulation in cyclodextrin cavities.

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

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

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

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

<span class="mw-page-title-main">Sanguiin H-6</span> Chemical compound

Sanguiin H-6 is an ellagitannin.

References

  1. 1 2 Cermak R, Wolffram S (October 2006). "The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms". Curr. Drug Metab. 7 (7): 729–44. doi:10.2174/138920006778520570. PMID   17073577. Archived from the original on 2012-07-20.{{cite journal}}: CS1 maint: unfit URL (link)
  2. Smith, Gerald J.; Markham, Kenneth R. (1998). "Tautomerism of flavonol glucosides: relevance to plant UV protection and flower colour". Journal of Photochemistry and Photobiology A: Chemistry. 118 (2): 99–105. doi:10.1016/s1010-6030(98)00354-2.
  3. "Juicy news about cranberries". medicalxpress.com. Retrieved 13 April 2018.
  4. 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. 77 (3): 367–79. doi:10.1111/tpj.12388. PMC   4282528 . PMID   24274116.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Si D, Wang Y, Zhou YH, et al. (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metab. Dispos. 37 (3): 629–34. doi:10.1124/dmd.108.023416. PMID   19074529. S2CID   285706.
  6. Pinelli, Patrizia; Romani, Annalisa; Fierini, Elisa; Remorini, Damiano; Agati, Giovanni (2013). "Characterisation of the Polyphenol Content in the Kiwifruit (Actinidia deliciosa) Exocarp for the Calibration of a Fruit-sorting Optical Sensor". Phytochemical Analysis. 24 (5): 460–466. doi:10.1002/pca.2443. hdl: 2158/1013486 . PMID   23716352. S2CID   33903704.
  7. Holland, Thomas Monroe; Agarwal, Puja; Wang, Yamin; Dhana, Klodian; Leurgans, Sue E.; Shea, Kyla; Booth, Sarah L; Rajan, Kumar; Schneider, Julie A.; Barnes, Lisa L. (22 November 2022). "Association of Dietary Intake of Flavonols With Changes in Global Cognition and Several Cognitive Abilities". Neurology. 100 (7): e694–e702. doi:10.1212/WNL.0000000000201541. PMC   9969915 . S2CID   253800625.