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Flavonoids
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 have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and a heterocyclic ring (C, the ring containing the embedded oxygen). This carbon structure can be abbreviated C6-C3-C6. According to the IUPAC nomenclature, they can be classified into: *flavonoids or bioflavonoids *isoflavonoids, derived from 3-phenyl chromen-4-one (3-phenyl-1,4-benzopyrone) structure * neoflavonoids, derived from 4-phenylcoumarin (4-phenyl-1,2-benzopyrone) structure The three flavonoid classes above are all ketone-containing compounds and as such, 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 n ...
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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 dyes and for tanning (leather), tanning garments. Etymology The name derives from the Ancient Greek word (, meaning "many, much") and the word ‘phenol’ which refers to a chemical structure formed by attachment of an aromatic benzenoid (phenyl) ring to a hydroxyl (-OH) group (hence the ''-ol'' suffix). The term "polyphenol" has been in use at least since 1894. Definition Polyphenols are natural products with "one or several hydroxyl groups on aromatic rings", including four principal classes: phenolic acids, flavonoids, stilbenes, and lignans. Flavonoids can be grouped as flavones, flavonols, flavanols, flavanones, isoflavones, proanthocyanidins, and anthocyanins. Particularly abundant flavanoids in foods are catechin (tea, frui ...
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Anthoxanthin
Anthoxanthins (flavones and flavonols)Isolation of a UDP-glucose: Flavonoid 5-O-glucosyltransferase gene and expression analysis of anthocyanin biosynthetic genes in herbaceous peony (Paeonia lactiflora Pall.). Da Qiu Zhao, Chen Xia Han, Jin Tao Ge and Jun Tao, Electronic Journal of Biotechnology, 15 November 2012, Volume 15, Number 6, are a type of flavonoid pigments in plants. Anthoxanthins are water-soluble pigments which range in color from white or colorless to a creamy to yellow, often on petals of flowers. These pigments are generally whiter in an acid medium and yellowed in an alkaline medium. They are very susceptible to color changes with minerals and metal ions, similar to anthocyanins. Uses As with all flavonoids, anthoxanthins have antioxidant properties and are important for nutrition. They are sometimes used as food additives to add color or flavor to foods. One of the most well-known anthoxanthins is quercetin Quercetin is a plant flavonol from the flavono ...
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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 in the normal cell growth, growth, Biological development, development, or reproduction of the organism. Instead, they generally mediate ecological biological interaction, interactions, which may produce a Natural selection, selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs. The term secondary metabolite was first coined by Albrecht Kossel, the 1910 Nobel Prize laureate for medicine and physio ...
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Flavonol
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 ...
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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 Neoflavonoids include 4-arylcoumarins (neoflavones), 4-arylchromanes, dalbergiones and dalbergiquinols. * Neoflavones are derived from the 4-phenylcoumarin (or 4-aryl-coumarin) backbone (C15H12O2). The first neoflavone isolated from natural sources was calophyllolide from ''Calophyllum inophyllum'' seeds (1951). It is also found in the bark and timber of the plant '' Mesua thwaitesii'', endemic to Sri Lanka. * Neoflavenes possess the 4-phenylchromen backbone (C15H10O2). Dalbergichromene, extracted from the stem-bark and heartwood of ''Dalbergia sissoo'', is an example of such compounds Other examples * Coutareagenin (5-hydroxy-7-methoxy-4-(3,4-dihydroxyphenyl)-2H-benzo-1-pyran-2-on) found in ''Hintonia latiflora ''Hintonia latiflora'' is a pl ...
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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 estrogen receptor. Medically, isoflavonoids and related compounds have been used in many dietary supplements but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including biliatresone which may cause biliary atresia when infants are exposed to the plant product. The isoflavonoid group is broad, and includes many structurally similar groups, including: * isoflavones * isoflavanones * isoflavans * pterocarpans * rotenoids Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin. Chemical makeup While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3- ...
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Hesperidin
Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees. Hesperidin was first isolated in 1828 by French chemist M. Lebreton from the white inner layer of citrus peels (mesocarp, albedo). Hesperidin is believed to play a role in plant defense. Sources ''Rutaceae'' * 700–2,500 ppm in fruit of ''Citrus aurantium'' (bitter orange, petitgrain) * in orange juice (''Citrus sinensis'') * in '' Zanthoxylum gilletii'' * in lemon * in lime * in leaves of '' Agathosma serratifolia'' ''Lamiaceae'' Peppermint contains hesperidin. Content in foods Approximate hesperidin content per 100 ml or 100 g * 481 mg peppermint, dried * 44 mg blood orange, pure juice * 26 mg orange, pure juice * 18 mg lemon, pure juice * 14 mg lime, pure juice * 1 mg grapefruit, pure juice Metabolism Hesperidin 6-''O''-α--rhamnosyl-β--glucosidase, an en ...
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Neohesperidin
Neohesperidin is a flavanone glycoside found in citrus fruits. It is the 7-O- neohesperidose derivative of hesperetin, which in turn is the 4'-methoxy derivative of eriodictyol. Neohesperidin dihydrochalcone has an intense sweet taste, and is listed as a generally recognized as safe Generally recognized as safe (GRAS) is a United States Food and Drug Administration (FDA) designation that a chemical or substance added to food is considered safe by experts under the conditions of its intended use. An ingredient with a GRAS d ... flavour enhancer by the Flavor and Extract Manufacturers Association. References External links * {{Glycosides Flavanone glycosides Flavonoids found in Rutaceae ...
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Chalconoids
Chalconoids (Greek: χαλκός ''khalkós'', "copper", due to its color), also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important biological compounds. They show antibacterial, antifungal, antitumor and anti-inflammatory properties. Some chalconoids demonstrated the ability to block voltage-dependent potassium channels. Chalcones are also natural aromatase inhibitors. Chalcones are aromatic ketones with two phenyl rings that are also intermediates in the synthesis of many biological compounds. The closure of hydroxy chalcones causes the formation of the flavonoid structure. Flavonoids are substances in the plant's secondary metabolism with an array of biological activities. Chalconoids are also intermediating in the Auwers synthesis of flavones. Biosynthesis and metabolism Chalcone synthase is an enzyme responsible for the production of chalconoids in plants. Chalcone isomerase is responsible for their c ...
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4-phenylcoumarin
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 Neoflavonoids include 4-arylcoumarins (neoflavones), 4-arylchromanes, dalbergiones and dalbergiquinols. * Neoflavones are derived from the 4-phenylcoumarin (or 4-aryl-coumarin) backbone (C15H12O2). The first neoflavone isolated from natural sources was calophyllolide from ''Calophyllum inophyllum'' seeds (1951). It is also found in the bark and timber of the plant '' Mesua thwaitesii'', endemic to Sri Lanka. * Neoflavenes possess the 4-phenylchromen backbone (C15H10O2). Dalbergichromene, extracted from the stem-bark and heartwood of ''Dalbergia sissoo'', is an example of such compounds Other examples * Coutareagenin (5-hydroxy-7-methoxy-4-(3,4-dihydroxyphenyl)-2H-benzo-1-pyran-2-on) found in ''Hintonia latiflora ''Hintonia latiflora'' is a pl ...
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Eriodictyol
Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa ('' Eriodictyon californicum''), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin. Eriodictyol has garnered scientific attention for its strong antioxidant, anti-inflammatory, and neuroprotective properties. Structurally similar to other flavonoids, such as hesperidin and naringenin, eriodictyol scavenges free radicals and regulates inflammatory responses. Eriodictyol was also found in the twigs of '' Millettia duchesnei'', in '' Eupatorium arnottianum'', and its glycosides ( eriocitrin) in lemons and rose hips (''Rosa canina''). Eriodictyol belongs to the 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 * ...
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