Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of

polyphenol 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 ...

secondary metabolite Secondary metabolites, also called ''specialised metabolites'', ''secondary products'', or ''natural products'', are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved ...

s found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

rings (A and B) and a heterocyclic ring (C, the ring containing the embedded

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

). This carbon structure can be abbreviated C6-C3-C6. According to the

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

nomenclature, they can be classified into: *flavonoids or bioflavonoids *

isoflavonoid Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estr ...

s, derived from 3-phenyl chromen-4-one (3-phenyl-1,4-

benzopyrone Benzopyrone may refer to either of two ketone derivatives of benzopyran 4H-1-Benzopyran is an organic compound with the formula . It is one of two isomers of benzopyran, the other being 2H-1-Benzopyran, 2H-1-benzopyran, which is more prevalent ...

) structure *

neoflavonoids Neoflavonoids are a class of polyphenolic compounds. While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, neoflavonoids have the 4-phenylchromen backbone with no hydroxyl group substitution at position 2. Types Neoflavo ...

, derived from 4-phenyl

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , forming a second six-me ...

(4-phenyl-1,2-

) structure The three flavonoid classes above are all

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

-containing compounds and as such, anthoxanthins (

flavone Flavone is an organic compound with the formula . A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but substituted derivatives, ...

s 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 cycles or heterocycles in the flavonoid backbone are generally called ring A, B, and C. Ring A usually shows a

phloroglucinol Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the organic synthesis, synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isom ...

substitution pattern.

History

In the 1930s,

Albert Szent-Györgyi Albert Imre Szent-Györgyi de Rapoltu Mare, Nagyrápolt (; September 16, 1893 – October 22, 1986) was a Hungarian biochemist who won the Nobel Prize in Physiology or Medicine in 1937. He is credited with first isolating vitamin C and disc ...

and other scientists discovered that

Vitamin C Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription di ...

alone was not as effective at preventing

scurvy Scurvy is a deficiency disease (state of malnutrition) resulting from a lack of vitamin C (ascorbic acid). Early symptoms of deficiency include weakness, fatigue, and sore arms and legs. Without treatment, anemia, decreased red blood cells, gum d ...

as the crude yellow extract from oranges, lemons or paprika. They attributed the increased activity of this extract to the other substances in this mixture, which they referred to as "citrin" (referring to citrus) or "Vitamin P" (a reference to its effect on reducing the permeability of

capillaries A capillary is a small blood vessel, from 5 to 10 micrometres in diameter, and is part of the microcirculation system. Capillaries are microvessels and the smallest blood vessels in the body. They are composed of only the tunica intima (the in ...

). The substances in question ( hesperidin, eriodictyol, hesperidin methyl chalcone and neohesperidin) were however later shown not to fulfil the criteria of a vitamin, so that this term is now obsolete.

Biosynthesis

Flavonoids are secondary metabolites synthesized mainly by plants. The general structure of flavonoids is a fifteen-carbon skeleton, containing two benzene rings connected by a three-carbon linking chain. Therefore, they are depicted as C6-C3-C6 compounds. Depending on the chemical structure, degree of oxidation, and unsaturation of the linking chain (C3), flavonoids can be classified into different groups, such as anthocyanidins, flavonols, flavanones, flavan-3-ols, flavanonols, flavones, and isoflavones. Chalcones, also called chalconoids, although lacking the heterocyclic ring, are also classified as flavonoids. Furthermore, flavonoids can be found in plants in glycoside-bound and free aglycone forms. The glycoside-bound form is the most common flavone and flavonol form consumed in the diet. Flavonoids Biochemistry

Functions of flavonoids in plants

Flavonoids are widely distributed in plants, fulfilling many functions. They are the most important plant pigments for flower coloration, producing yellow or red/blue pigmentation in petals evolved to attract

pollinator A pollinator is an animal that moves pollen from the male anther of a flower to the female carpel, stigma of a flower. This helps to bring about fertilization of the ovules in the flower by the male gametes from the pollen grains. Insects are ...

animals. In higher plants, they 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 Rhizobia are diazotrophic bacteria that fix nitrogen after becoming established inside the root nodules of legumes (Fabaceae). To express genes for nitrogen fixation, rhizobia require a plant host; they cannot independently fix nitrogen. I ...

'' in the infection stage of their

symbiotic Symbiosis (Ancient Greek : living with, companionship < : together; and ''bíōsis'': living) is any type of a close and long-term biolo ...

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 Root nodules are found on the roots of plants, primarily legumes, that form a symbiosis with nitrogen-fixing bacteria. Under nitrogen-limiting conditions, capable plants form a symbiotic relationship with a host-specific strain of bacteria known ...

. In addition, some flavonoids have inhibitory activity against organisms that cause plant diseases, e.g. ''Fusarium oxysporum''.

Subgroups

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):

Anthocyanidins

Anthocyanidin Anthocyanidins are common plant pigments, the aglycones of anthocyanins. They are based on the flavylium cation, an oxonium ion, with various groups substituent, substituted for its hydrogen atoms. They generally change color from red through p ...

s are the

aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...

s of

anthocyanin Anthocyanins (), also called anthocyans, are solubility, water-soluble vacuole, 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 compou ...

s; they use the flavylium (2-phenylchromenylium) ion skeleton. :Examples:

cyanidin Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (glycoside version called anthocyanin#Structure, anthocyanins). It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherr ...

delphinidin Delphinidin (also delphinidine) is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera ''Viola'' and ''Delphinium''. It also gives the blue-red color of the grape variety Cab ...

malvidin Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature. Natural occurrences Malvidin is responsible for the blue color found in petals ...

, pelargonidin, peonidin,

petunidin Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many red berries includi ...

Anthoxanthins

Anthoxanthins are divided into two groups: :

Flavanones

Flavanone The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides. List of flavanones * Blumeatin * Butin * Dichamanetin * Eriodictyol * Hesperetin * Hesperidin * Hom ...

Flavanonols

Flavans

Include

flavan-3-ol Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compo ...

s (flavanols),

flavan-4-ol The flavan-4-ols (3-deoxyflavonoids) are flavone-derived Alcohol (chemistry), alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments. They can be found in the sorghum. Gl ...

s, and flavan-3,4-diols. * Flavan-3-ols (flavanols) ** Flavan-''3-ols'' use the 2-phenyl-3,4-dihydro-2''H''-chromen-''3-ol'' skeleton *:Examples:

catechin 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. The name of the catechin chemical family derives from ''catechu'', which is the tannic ...

(C),

gallocatechin Gallocatechol or gallocatechin (GC) is a flavan-3-ol, a type of chemical compound including catechin, with the gallate residue being in an Cis-trans isomerism, isomeric ''trans'' position. This compound possesses two epimers. The most common, (+) ...

(GC), catechin 3-gallate (Cg), gallocatechin 3-gallate (GCg),

epicatechin 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. The name of the catechin chemical family derives from '' catechu'', which is the tann ...

s (EC), epigallocatechin (EGC), epicatechin 3-gallate (ECg), epigallocatechin 3-gallate (EGCg) **

Theaflavin Theaflavin (TF) and its derivatives, known collectively as ''theaflavins'', are antioxidant polyphenols in tea, polyphenols that are formed from the condensation of flavan-3-ols in tea leaves during the enzymatic oxidation (sometimes erroneously re ...

*:Examples: theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3,3'-digallate ** Thearubigin ** Proanthocyanidins are dimers, trimers, oligomers, or polymers of the flavanols

Isoflavonoids

Isoflavonoid Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estr ...

s **

Isoflavone Isoflavones are a type of naturally-occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans. Although isoflavones and closely-related phytoestrogens ar ...

s use the 3-phenylchromen-''4-one'' skeleton (with no hydroxyl group substitution on carbon at position 2) *:Examples:

Genistein Genistein (C15H10O5) is a plant-derived, aglycone isoflavone. Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein has estrogenic activity in vitro; consequ ...

Daidzein Daidzein (7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one) is a naturally occurring compound found exclusively in soybeans and other legumes, and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones a ...

Glycitein Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones. Glycitin (glycitein 7-' ...

** Isoflavanes ** Isoflavandiols ** Isoflavenes **

Coumestan Coumestan is a heterocyclic organic compound. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of pterocarpan that are similar to coumarin. Coumestans, inclu ...

s ** Pterocarpans

Dietary sources

Flavonoids (specifically flavanoids such as the catechins) are "the most common group of

ic compounds in the human diet and are found ubiquitously in plants". Flavonols, the original bioflavonoids such as

quercetin 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 ...

, are also found ubiquitously, but in lesser quantities. The widespread distribution of flavonoids, their variety and their relatively low

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...

compared to other active plant compounds (for instance

alkaloids Alkaloids are a broad class of naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large variety of organisms i ...

) mean that many animals, including

humans Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are Hominidae, great apes characterized by their Prehistory of nakedness and clothing ...

, ingest significant quantities in their diet. Foods with a high flavonoid content include

parsley Parsley, or garden parsley (''Petroselinum crispum''), is a species of flowering plant in the family Apiaceae that is native to Greece, Morocco and the former Yugoslavia. It has been introduced and naturalisation (biology), naturalized in Eur ...

onion An onion (''Allium cepa'' , from Latin ), also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus '' Allium''. The shallot is a botanical variety of the onion which was classifie ...

blueberries Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' with the genus ''Vaccinium''. Commercial blueberries—both wild (lowbush) ...

and

strawberries The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit is appreciated f ...

black tea Black tea (also literally translated as red tea from various East Asian languages) is a type of tea that is more tea processing, oxidized than oolong, yellow tea, yellow, white tea, white, and green tea, green teas. Black tea is generally st ...

banana A banana is an elongated, edible fruit – botanically a berry – produced by several kinds of large treelike herbaceous flowering plants in the genus '' Musa''. In some countries, cooking bananas are called plantains, distinguishing the ...

s, and

citrus ''Citrus'' is a genus of flowering trees and shrubs in the family Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, mandarins, lemons, grapefruits, pomelos, and limes. ''Citrus'' is nativ ...

fruits. One study found high flavonoid content in

buckwheat Buckwheat (''Fagopyrum esculentum'') or common buckwheat is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. Buckwheat originated around the 6th millennium BCE in the region of what ...

. Citrus flavonoids include hesperidin (a glycoside of the flavanone hesperetin), quercitrin,

rutin Rutin (rutoside, quercetin-3-O-rutinoside or sophorin) is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a flavonoid glycoside found in a wide variety of pla ...

(two

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

s of quercetin, and the flavone tangeritin. The flavonoids are less concentrated in the pulp than in the peels (for example, 165 versus 1156 mg/100 g in pulp versus peel of satsuma mandarin, and 164 vis-à-vis 804 mg/100 g in pulp versus peel of

clementine A clementine (''Citrus × clementina'') is a tangor, a citrus fruit hybrid between a willowleaf mandarin orange ( ''C.'' × ''deliciosa'') and a sweet orange (''C. × sinensis''), named in honor of Clément Rodier, a French missionary who f ...

Peanut The peanut (''Arachis hypogaea''), also known as the groundnut, goober (US), goober pea, pindar (US) or monkey nut (UK), is a legume crop grown mainly for its edible seeds. It is widely grown in the tropics and subtropics by small and large ...

(red) skin contains significant polyphenol content, including flavonoids. :

Dietary intake

Food composition data Food composition data (FCD) are detailed sets of information on the nutritionally important components of foods and provide values for energy and nutrients including protein, carbohydrates, fat, vitamins and minerals and for other important food c ...

for flavonoids were provided by the

USDA The United States Department of Agriculture (USDA) is an United States federal executive departments, executive department of the Federal government of the United States, United States federal government that aims to meet the needs of commerc ...

database on flavonoids. In the United States NHANES survey, mean flavonoid intake was 190 mg per day in adults, with

s as the main contributor. In the

European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

, based on data from EFSA, mean flavonoid intake was 140 mg/d, although there were considerable differences among individual countries. The main type of flavonoids consumed in the EU and USA were flavan-3-ols (80% for USA adults), mainly from tea or cocoa in chocolate, while intake of other flavonoids was considerably lower.

Research

Neither the United States

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...

(FDA) nor the

European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002 ...

(EFSA) has approved any flavonoids as

prescription drug A prescription drug (also prescription medication, prescription medicine or prescription-only medication) is a pharmaceutical drug that is permitted to be dispensed only to those with a medical prescription. In contrast, over-the-counter drugs c ...

s. The U.S. FDA has warned numerous dietary supplement and food manufacturers, including

Unilever Unilever PLC () is a British multinational consumer packaged goods company headquartered in London, England. It was founded on 2 September 1929 following the merger of Dutch margarine producer Margarine Unie with British soap maker Lever B ...

, producer of

Lipton tea Lipton is a brand named after its founder, Sir Tom Lipton, who started an eponymous grocery retail business in the United Kingdom in 1871. The brand was used for various consumer goods sold in Lipton stores, including tea from 1890 for which ...

in the U.S., about illegal advertising and misleading health claims regarding flavonoids, such as that they lower cholesterol or relieve pain.

Metabolism and excretion

Flavonoids are poorly absorbed in the human body (less than 5%), then are quickly metabolized into smaller fragments with unknown properties, and rapidly excreted. Flavonoids have negligible antioxidant activity in the body, and the increase in antioxidant capacity of blood seen after consumption of flavonoid-rich foods is not caused directly by flavonoids, but by production of

uric acid Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the Chemical formula, formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the meta ...

resulting from flavonoid

depolymerization Depolymerization (or depolymerisation) is the process of converting a polymer into a monomer or a mixture of monomers. This process is driven by an increase in entropy. Ceiling temperature The tendency of polymers to depolymerize is indicated by ...

and

excretion Excretion is elimination of metabolic waste, which is an essential process in all organisms. In vertebrates, this is primarily carried out by the lungs, Kidney (vertebrates), kidneys, and skin. This is in contrast with secretion, where the substa ...

. Microbial metabolism is a major contributor to the overall metabolism of dietary flavonoids.

Inflammation

Inflammation Inflammation (from ) is part of the biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. The five cardinal signs are heat, pain, redness, swelling, and loss of function (Latin ''calor'', '' ...

has been implicated as a possible origin of numerous local and systemic diseases, such as

cancer Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...

, cardiovascular disorders,

diabetes mellitus Diabetes mellitus, commonly known as diabetes, is a group of common endocrine diseases characterized by sustained hyperglycemia, high blood sugar levels. Diabetes is due to either the pancreas not producing enough of the hormone insulin, or th ...

, and

celiac disease Coeliac disease (British English) or celiac disease (American English) is a long-term autoimmune disorder, primarily affecting the small intestine. Patients develop intolerance to gluten, which is present in foods such as wheat, rye, spel ...

. There is no clinical evidence that dietary flavonoids affect any of these diseases.

Cancer

Clinical studies Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, dietar ...

investigating the relationship between flavonoid consumption and cancer prevention or development are conflicting for most types of cancer, probably because most human studies have weak designs, such as a small

sample size Sample size determination or estimation is the act of choosing the number of observations or replicates to include in a statistical sample. The sample size is an important feature of any empirical study in which the goal is to make inferences abo ...

. There is little evidence to indicate that dietary flavonoids affect human cancer risk in general.

Cardiovascular diseases

Although no significant association has been found between flavan-3-ol intake and cardiovascular disease mortality, clinical trials have shown improved endothelial function and reduced

blood pressure Blood pressure (BP) is the pressure of Circulatory system, circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term ...

(with a few studies showing inconsistent results). Reviews of

cohort studies A cohort study is a particular form of longitudinal study that samples a cohort (a group of people who share a defining characteristic, typically those who experienced a common event in a selected period, such as birth or graduation), performing ...

in 2013 found that the studies had too many limitations to determine a possible relationship between increased flavonoid intake and decreased risk of cardiovascular disease, although a trend for an inverse relationship existed. In 2013, the EFSA decided to permit health claims that 200 mg/day of cocoa flavanols "help maintain the elasticity of blood vessels." The FDA followed suit in 2023, stating that there is "supportive, but not conclusive" evidence that 200 mg per day of cocoa flavanols can reduce the risk of cardiovascular disease. This is greater than the levels found in typical chocolate bars, which can also contribute to weight gain, potentially harming cardiovascular health.

Synthesis, detection, quantification, and semi-synthetic alterations

Color spectrum

Flavonoid synthesis in plants is induced by light color spectrums at both high and low energy radiations. Low energy radiations are accepted by

phytochrome Phytochromes are a class of photoreceptor proteins found in plants, bacteria and fungi. They respond to light in the red and far-red regions of the visible spectrum and can be classed as either Type I, which are activated by far-red light, or ...

, while high energy radiations are accepted by

carotenoid Carotenoids () are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, cana ...

s, flavins,

cryptochrome Cryptochromes (from the Greek κρυπτός χρώμα, "hidden colour") are a class of flavoproteins found in plants and animals that are sensitive to blue light. They are involved in the circadian rhythms and the sensing of magnetic fiel ...

s in addition to phytochromes. The photomorphogenic process of phytochrome-mediated flavonoid biosynthesis has been observed in ''Amaranthus'',

barley Barley (), a member of the grass family, is a major cereal grain grown in temperate climates globally. It was one of the first cultivated grains; it was domesticated in the Fertile Crescent around 9000 BC, giving it nonshattering spikele ...

maize Maize (; ''Zea mays''), also known as corn in North American English, is a tall stout grass that produces cereal grain. It was domesticated by indigenous peoples in southern Mexico about 9,000 years ago from wild teosinte. Native American ...

, ''

Sorghum ''Sorghum bicolor'', commonly called sorghum () and also known as great millet, broomcorn, guinea corn, durra, imphee, jowar, or milo, is a species in the Poaceae, grass genus ''Sorghum (genus), Sorghum'' cultivated for its grain. The grain i ...

'' and

turnip The turnip or white turnip ('' Brassica rapa'' subsp. ''rapa'') is a root vegetable commonly grown in temperate climates worldwide for its white, fleshy taproot. Small, tender varieties are grown for human consumption, while larger varieties a ...

. Red light promotes flavonoid synthesis.

Availability through microorganisms

Research has shown production of flavonoid molecules from genetically engineered microorganisms.

Tests for detection

Shinoda test

Four pieces of magnesium filings are added to the ethanolic extract followed by few drops of concentrated

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

. A pink or red colour indicates the presence of flavonoid. Colours varying from orange to red indicated

s, 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 Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

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.

p-Dimethylaminocinnamaldehyde test

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 Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the ethanolic extract of the vanilla bean. Synthetic vanillin ...

procedure.

Quantification

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 ten minutes at ambient temperature and the absorbance of the solution is read at 440 nm. Flavonoid content is expressed in mg/g of

Semi-synthetic alterations

Immobilized '' Candida antarctica'' lipase can be used to catalyze the

regioselective In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a str ...

acylation of flavonoids.