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Flavanol
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 compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonols. Early use of the term bioflavonoid was imprecisely applied to include the flava ...
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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 compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonols. Early use of the term bioflavonoid was imprecisely applied to include the flava ...
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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 tannic juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene rings (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group 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 ... on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configura ...
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Catechin Molecule File
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 juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene rings (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration and are called ''catechin'' and the other two are in cis configuration and are called ''epicatechin''. The most common catechin isomer is (+)-catechin. The other stereoisomer is (-)-catechin or ''ent''-catechin. The most common epicatechin isomer is (-)-epicatechin (al ...
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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 juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene ring Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atom ...s (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configura ...
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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 juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene ring Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atom ...s (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configura ...
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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 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-phenylcoumarine (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 non ...
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Fluorescence-lifetime Imaging Microscopy
Fluorescence-lifetime imaging microscopy or FLIM is an imaging technique based on the differences in the exponential decay rate of the photon emission of a fluorophore from a sample. It can be used as an imaging technique in confocal microscopy, two-photon excitation microscopy, and multiphoton tomography. The fluorescence lifetime (FLT) of the fluorophore, rather than its intensity, is used to create the image in FLIM. Fluorescence lifetime depends on the local micro-environment of the fluorophore, thus precluding any erroneous measurements in fluorescence intensity due to change in brightness of the light source, background light intensity or limited photo-bleaching. This technique also has the advantage of minimizing the effect of photon scattering in thick layers of sample. Being dependent on the micro-environment, lifetime measurements have been used as an indicator for pH, viscosity and chemical species concentration. Fluorescence lifetimes A fluorophore which is excited b ...
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Pyrocatechol
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Catechol occurs as feathery white crystals that are very rapidly soluble in water. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' (''Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) ...
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Thearubigin
Thearubigins are polymeric polyphenols that are formed during the enzymatic oxidation and condensation of two gallocatechins (epigallocatechin and epigallocatechin gallate) with the participation of polyphenol oxidases during the fermentation reactions in black tea. Thearubigins are red in colour and are responsible for much of the staining effect of tea. Therefore, a black (fully oxidized) tea often appears red while a green or white tea has a much clearer appearance. The colour of a black tea, however, is affected by many other factors as well, such as the amount of theaflavins, another oxidized form of polyphenols. Thearubigins were first studied by Roberts, E. A. H. in the 1960s by the means of spectroscopy or by fractionation or paper chromatography. They have been identified as proanthocyanidins in 1969. The thearubigins formation has been studied in an in vitro model in 1983. Thearubigins from black tea extracts have been studied by degradation in 1996. Quantification metho ...
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Quercitin
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. Occurrence Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived from ''quercetum'' (oak forest), after the oak genus ''Quercus''. It is a naturally occurring polar auxin transport inhibitor. Quercetin is one of the most abundant dietary flavonoids, with an average daily consumption of 25–50 milligrams. In red onions, higher concentrations of quercetin occur in the outermost rings and in the part closest to the root, the latter being the part of the plant with the highest concentration. One study found that organically grown tomatoes had 79% more quercetin than non-organically grown fruit. Quercetin is prese ...
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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. 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 a role along with proanthocyanidins, in the juice's ability to block bacterial adhesion, demonstrated by the compressing the fimbria of ' ...
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Flavan
The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2''H''-chromene skeleton. They may be found in plants. These compounds include the flavan-3-ols, flavan-4-ols and flavan-3,4-diols (leucoanthocyanidin). A ''C''-glycosidic flavan can be isolated from cocoa liquor. ''Casuarina glauca'' is an actinorhizal plant producing root nitrogen-fixing nodules infested by ''Frankia ''Frankia'' is a genus of nitrogen-fixing bacteria that live in symbiosis with actinorhizal plants, similar to the ''Rhizobium'' bacteria found in the root nodules of legumes in the family Fabaceae. ''Frankia'' also initiate the forming of root ...''. There is a regular pattern of cell layers containing flavans. References {{Aromatic-stub ...
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