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Hesperetin
Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin (and naringenin, the parent flavanone of naringin) are not found to a significant extent in ''Citrus'' spp. Glycosides A variety of glycosides of hesperetin are known, including: * Hesperidin (hesperetin-7-''O''-rutinoside) is a water-insoluble flavonoid glycoside whose solubility is below 5 μg/ml in water. Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. * Neohesperidin is the 7-''O''-neohesperidoside of hesperetin. * Hesperetin-7-''O''-α-L-Rhamnopyranoside (CAS 66513-83-5) is found in the roots of clammy cherry (''Cordia obliqua'' a.k.a. ''Cordia obliqua'' var. ''wallichii''). Metabolism Hesperidin 6-''O''-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. It ...
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Naringenin
Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Structure Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4', 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable. Racemization of S(-)-naringenin has been shown to occur fairly quickly. Sources and bioavailability Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit, bergamot, sour orange, tart cherries, tomatoes, cocoa, Greek oregano, water mint, as well as in beans. Ratios of naringenin to naringin vary among sources, as do enantiomeric rati ...
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Hesperidin
Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called 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 * 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 enzyme ...
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Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase
Hesperidin 6-''O''-alpha--rhamnosyl-beta--glucosidase () is an enzyme with systematic name hesperetin 7-(6-''O''-alpha--rhamnopyranosyl-beta--glucopyranoside) 6-''O''-alpha-rhamnopyranosyl-beta-glucohydrolase. This enzyme catalyses the following chemical reaction : hesperidin + H2O hesperetin + rutinose Rutinose is the disaccharide also known as 6-''O''-α-L-rhamnose, rhamnosyl-D-glucose (C12H22O10) that is present in some flavonoid glycosides. It is prepared from rutin by hydrolysis with the enzyme rhamnodiastase. References * Disaccharide ... The enzyme exhibits high specificity towards 7-''O''-linked flavonoid beta-rutinosides. The enzyme is produced by the fungus ''Acremonium'' sp. DSM24697. The genera ''Acremonium'' and morphologically similar ''Stilbella'' have not yet been fully studied on a molecular basis. Under the morphological basis, the fungus ''Stilbella fimetaria'' SES201 was reidentified as ''Acremonium'' sp. SES201 = DSM24697. References External link ...
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Hesperidin
Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called 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 * 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 enzyme ...
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Flavonoids Found In Rutaceae
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-k ...
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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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TRPM3
Transient receptor potential cation channel subfamily M member 3 is a protein that in humans is encoded by the ''TRPM3'' gene. Function The product of this gene belongs to the family of transient receptor potential (TRP) channels. TRP channels are Ca2+ permeable non-selective cation channels that play roles in a wide variety of physiological processes, including calcium signaling, heat and cold sensation, calcium and magnesium homeostasis. TRPMs mediates sodium and calcium entry, which induces depolarization and a cytoplasmic Ca2+ signal. Alternatively spliced transcript variants encoding different isoforms have been -identified. TRPM3 was shown to be activated by the neurosteroid pregnenolone sulfate as well as the synthetic compound CIM0216. Peripheral heat sensation TRPM3 is expressed in peripheral sensory neurons of the dorsal root ganglia, and they are activated by high temperatures. Genetic deletion of TRPM3 in mice reduces sensitivity to noxious heat, as well as in ...
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Cordia Obliqua
''Cordia obliqua'', the clammy cherry, is a flowering plant species in the genus ''Cordia''. The larvae of '' Brenthia coronigera'', a species of moth found in Bengal, India, feeds on ''Cordia obliqua''. Hesperetin 7-rhamnoside, a glycoside of hesperetin Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin (and naringenin, the parent flavan ..., can be isolated from the plant.Hesperetin 7-rhamnoside from Cordia obliqua. J.S. Chauhan, S.K. Srivastava and M. Sultan, Phytochemistry, 1978, Volume 17, Issue 2, Page 334, References External links obliqua Plants described in 1798 {{Asterid-stub ...
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Neohesperidoside
Neohesperidose is the disaccharide which is present in some flavonoids. It can be found in species of ''Typha.'' ''Delphinidin-3-neohesperidoside and cyanidin-3- neohesperidoside from receptacles of Podocarpus species, Oyvind M. Andersen, Phytochemistry, 1989, Volume 28, Issue 2, Pages 495–497, Neohesperidosides * Cyanidin-3-neohesperidoside * Delphinidin-3-neohesperidoside * Rhoifolin or apigenin 7-''O''-neohesperidoside * Myricetin-3-''O''-neohesperidoside found in ''Physalis angulata''A novel cytotoxic flavonoid glycoside from Physalis angulata. N. Ismail and M. Alam, Fitoterapia, Volume 72, Issue 6, August 2001, Pages 676-679, * Neohesperidin (hesperetin 7-''O''-neohesperidoside) * Neoeriocitrin (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 proper ... 7-''O''-neoh ...
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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 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 proper .... Neohesperidin dihydrochalcone has an intense sweet taste, and is listed as a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association. References External links * {{Glycosides Flavanone glycosides Flavonoids found in Rutaceae ...
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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. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of ''Heliconius'' butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a '' C-glycoside'') glycosidic bond. According to th ...
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Aglycone
An aglycone (aglycon or genin) is the 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 molecule. Detection A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone. Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate and detect them at a sensitivity of 0.25-0.50 µg. Clinical significance A study on molecular markers in human aortic endothelial cells published that aglycone stopped cell migration but not monocyte adhesion, which is the initial step of atherosclerotic plaq ...
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