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Isoflavonoids
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-phenyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 compound, 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-phenylchromone, chromen-4-one (3-phenyl-1,4-benzopyran, benzopyrone) structure *neoflavonoids, derived from 4-phenylcoumarin (4-phenyl-1,2-benzopyran, 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 bioflavo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isoflavon Num
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 are sold as dietary supplements, there is little scientific evidence for either the safety of long-term supplementation or of health benefits from these compounds. Some studies indicate that isoflavone supplementation may help lower the risk of hormone-related cancers. Organic chemistry and biosynthesis Isoflavone is an isomer of flavone, which is chromone substituted with a phenyl group in the 2-position. In isoflavone, the phenyl group is in the 3-position. Substituted isoflavone derivatives are related to the parent by the replacement of two or three hydrogen atoms with hydroxyl groups. Isoflavone differs from flavone (2-phenyl-4''H''-1-benzopyr-4-one) in location of the phenyl group. Isoflavones are produced via a branch of the genera ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Naringenin
Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs. Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications. 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 disac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Homoisoflavonoid
Homoisoflavonoids (3-benzylidenechroman-4-ones) are a type of phenolic compounds occurring naturally in plants. Chemically, they have the general structure of a 16-carbon skeleton, which consists of two phenyl rings (A and B) and heterocyclic ring (C). Synthesis Homoisoflavones can be synthesized from 2'-hydroxy dihydrochalcones. Homoisoflavanones can be synthesized from 3,5-methoxy phenols via chroman-4-one in three steps or from phloroglucinol. ;Conversion Homoisoflavanes can be obtained from the conversion of homoisoflavonoids. Natural occurrences The homoisoflavonoids portulacanones A, B, C and D can be found in ''Portulaca oleracea'' (common purslane, Caryophyllales, Portulacaceae). The 3,4-dihydroxyhomoisoflavans sappanol, episappanol, 3'-deoxysappanol, 3'-O-methylsappanol and 3'-O-methylepisappanol can be found in ''Caesalpinia sappan''. The homoisoflavones scillavones A and B can be isolated from the bulbs of ''Scilla scilloides'' ('' Barnardia japonica'') ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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-''O''-glucoside) can be transformed to glycetein by human intestinal flora. References O-methylated isoflavones {{aromatic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as the uterus and breast. It was first isolated in 1899 from the dyer's broom, ''Genista tinctoria''; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928. Genistein is a primary secondary metabolite of the ''Trifolium'' species and '' Glycine max'' (soy). Natural occurrences Isoflavones, such as genistein and daidzein, occur in soybeans and various other plants, including lupin, fava beans, kudzu, psoralea, '' Flemingia vestita'', and coffee. It is present in red clover. In soybean products Isoflavone intake from consuming soy pro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Equol
Equol (4',7-isoflavandiol) is an isoflavandiolThe structures of 7,4’-dihydroxy-isoflavan and its precursors is shown iStructural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MSby Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in ''Drug Metabolism and Disposition'' (2005, electronic publication). estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol. History (''S'')-Equol was first isolated from horse urine in 1932, and the name was suggested by this equine connection. Since then, equol has been found in the urine or plasma of many other animal species, although these animals have significant differences in their ability to metabolize daidzein into equol. In 1980, scientists rep ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 are produced in plants through the Phenylpropanoids metabolism, phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. Upon consumption of isoflavone-rich foods, daidzein has poor bioavailability and low water solubility. Natural occurrence Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs like kwao krua (''Pueraria mirifica'') and kudzu. It can also be found in ''Maackia amurensis'' cell cultures. Daidzein can be found in food such as mature soybeans and soy products like soy protein concentrate, tofu and textured vegetable protein. Total isoflavones in soybeans are—in general—37 percent daidzein, 57 percent ge ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Equol
Equol (4',7-isoflavandiol) is an isoflavandiolThe structures of 7,4’-dihydroxy-isoflavan and its precursors is shown iStructural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MSby Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in ''Drug Metabolism and Disposition'' (2005, electronic publication). estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol. History (''S'')-Equol was first isolated from horse urine in 1932, and the name was suggested by this equine connection. Since then, equol has been found in the urine or plasma of many other animal species, although these animals have significant differences in their ability to metabolize daidzein into equol. In 1980, scientists rep ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rotenoids
Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal and piscicidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones. Natural occurrences Many plants in the subfamily Faboideae contain rotenoids. Rotenoids can be found in ''Lonchocarpus sp''. Deguelin and tephrosin can be found in ''Tephrosia vogelii''. 6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of ''Amorpha fruticosa''. Elliptol, 12-deoxo-12alpha-methoxyelliptone, 6-methoxy-6a,12a-dehydrodeguelin, 6a,12a-dehydrodeguelin, 6-hydroxy-6a,12a-dehydrodeguelin, 6-oxo-6a,12a-dehydrodeguelin and 12a-hydroxyelliptone can be isolated from the twigs of ''Millettia duchesnei''. Deguelin, dehydrodeguelin, rotenol, rotenone, tephrosin and sumatrol can be found in ''Indigofera tinctoria''. 6aα,12aα-12a-hydroxyelliptone can be found in the stems of ''Derris trifoliata''. Amorp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
