Flavonol 3-O-beta-D-glucoside
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Flavonols are a class of
flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...
s that have the 3-hydroxyflavone backbone (IUPAC name : 3-hydroxy-2-phenylchromen-4-one). Their diversity stems from the different positions of the
phenolic Phenolic is an adjective and a substantive (noun) that may apply to : * Phenol (or carbolic acid), a colorless crystalline solid and aromatic compound * Phenols, a class of chemical compounds that include phenol * Phenolic content in wine * Phenol ...
-OH In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
groups. They are distinct from flavanols (with "a") such as catechin, another class of flavonoids. 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 Excited state intramolecular proton transfer (ESIPT) is a process in which photoexcited molecules relax their energy through tautomerization by transfer of protons. Some kinds of molecules could have different minimum-energy tautomers in different ...
or ESIPT) is induced by tautomerism of flavonols (and glucosides) and could contribute to plant
UV protection Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30  PHz) to 400 nm (750  THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
and
flower colour Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective Absorption (electromagnetic radiation), color absorption. Biological pigments include plant ...
. 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


Flavonol glycosides


Drug interactions

Flavonoids have effects on CYP ( P450) activity. Flavonols are
inhibitor Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
of CYP2C9 and
CYP3A4 Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine. It oxidizes small foreign organic molecules (xenobiotics), such as toxins or drugs, so that they can be removed from t ...
, 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.


See also

* Phenolic compounds in wine * Algar-Flynn-Oyamada reaction


References


External links

* {{flavonol