Molecular structure of the flavone backbone (2-phenyl-1,4-benzopyrone)
Flavonoids (or bioflavonoids) (from the Latin word flavus meaning yellow, their colour in nature) are a class of plantsecondary metabolites. Flavonoids were referred to as Vitamin P (probably because of the effect they had on the permeability of vascular capillaries) from the mid-1930s to early 50s, but the term has since fallen out of use.
According to the IUPAC nomenclature, they can be classified into:
The three flavonoid classes above are all ketone-containing compounds, and as such, are anthoxanthins (flavones and flavonols). This class was the first to be termed "bioflavonoids." The terms flavonoid and bioflavonoid have also been more loosely used to describe non-ketone polyhydroxy polyphenol compounds which are more specifically termed flavanoids. The three cycle or heterocycles in the flavonoid backbone are generally called ring A, B and C. Ring A usually shows a phloroglucinol substitution pattern.
Flavonoids are widely distributed in plants, fulfilling many functions. Flavonoids are the most important plant pigments for flower coloration, producing yellow or red/blue pigmentation in petals designed to attract pollinator animals. In higher plants, flavonoids are involved in UV filtration, symbiotic nitrogen fixation and floral pigmentation. They may also act as chemical messengers, physiological regulators, and cell cycle inhibitors. Flavonoids secreted by the root of their host plant help Rhizobia in the infection stage of their symbiotic relationship with legumes like peas, beans, clover, and soy. Rhizobia living in soil are able to sense the flavonoids and this triggers the secretion of Nod factors, which in turn are recognized by the host plant and can lead to root hair deformation and several cellular responses such as ion fluxes and the formation of a root nodule. In addition, some flavonoids have inhibitory activity against organisms that cause plant disease e.g. Fusarium oxysporum.
Flavonoid-rich grape-seed extract has been shown to have antioxidant activity in in vivo studies with rats, protecting their gastrointestinal mucosa against the reactive oxygen species generated by acute and chronic stress. In the absence of any additional in vivo data, it is impossible to say if these findings are generalizable to all flavonoids. Also, without any clinical studies, it is impossible to say if the antioxidant activity of grape-seed flavonoids offers any protection against oxidative stress in the human gastrointestinal tract.
Systemic antioxidant activity
Research at the Linus Pauling Institute and the European Food Safety Authority shows that flavonoids are poorly absorbed in the human body (less than 5%), with most of what is absorbed being quickly metabolized and excreted. These findings suggest that flavonoids have negligible systemic antioxidant activity, and that the increase in antioxidant capacity of blood seen after consumption of flavonoid-rich foods is not caused directly by flavonoids, but due to increased production of uric acid resulting from excretion of flavonoids from the body.
Potential anti-cancer or carcinogenic activities
In 2012, researchers from the European Prospective Investigation into Cancer and Nutrition (EPIC) reported the findings of one such prospective study. After comparing dietary flavonoid and lignan intake with the incidence of gastric carcinoma in ~475,000 people from 10 European countries, they concluded that dietary flavonoid intake is associated with reduced gastric carcinoma risk in women but not men. Further research is needed to understand the nature of this association, and determine whether or not the association exists in women from non-European countries.
Flavonoids exist naturally in cacao, but because they can be bitter, they are often removed from chocolate, even dark chocolate. Although flavonoids are present in milk chocolate, milk may interfere with their absorption.
Over 5000 naturally occurring flavonoids have been characterized from various plants. They have been classified according to their chemical structure, and are usually subdivided into the following subgroups (for further reading see ):
Several recent research articles have demonstrated the efficient production of flavonoid molecules from genetically engineered microorganisms.
Tests for detection
Four pieces of magnesium fillings (ribbon) are added to the ethanolic extract followed by few drops of concentrated hydrochloric acid. A pink or red colour indicates the presence of flavonoid. Colours varying from orange to red indicated flavones, red to crimson indicated flavonoids, crimson to magenta indicated flavonones.
Sodium hydroxide test
About 5 mg of the compound is dissolved in water, warmed and filtered. 10% aqueous sodium hydroxide is added to 2 ml of this solution. This produces a yellow coloration. A change in color from yellow to colorless on addition of dilute hydrochloric acid is an indication for the presence of flavonoids.
A colorimetric assay based upon the reaction of A-rings with the chromogen p-dimethylaminocinnamaldehyde (DMACA) has been developed for flavanoids in beer that can be compared with the vanillin procedure.
Lamaison and Carnet have designed a test for the determination of the total flavonoid content of a sample (AlCI3 method). After proper mixing of the sample and the reagent, the mixture is incubated for 10 minutes at ambient temperature and the absorbance of the solution is read at 440 nm. Flavonoid content is expressed in mg/g of quercetin.
^flavonoids (isoflavonoids and neoflavonoids) IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006–) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. Last update: 2012-08-19; version: 2.3.2. DOI of this term: doi:10.1351/goldbook.F02424. (Original PDF version: http://www.iupac.org/goldbook/F02424.pdf. The PDF version is out of date and is provided for reference purposes only.) Retrieved 16 September 2012.
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Andersen, Ø.M. / Markham, K.R. (2006). Flavonoids: Chemistry, Biochemistry and Applications. CRC Press. ISBN 978-0-8493-2021-7
FlavonoidViewer.jp (Japanese, English), a database on flavonoids by Arita Group (Univ of Tokyo, RIKEN Plant Science Center, and Keio Univ), Nishioka Group (Kyoto and Keio Univ) and Kanaya Group (NAIST)