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Isoflavonoids Metabolism
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] |
Isoflavon Num
Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae). 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 have identified potential risks from high intake of isoflavones, such as in women with a history of breast cancer, but this concern has not been substantiated with high-quality clinical research. 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 4-position. Isoflavone is of liminted interest per se, but substituted derivatives are of nutritional interest. Substituted derivativ ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Liquiritigenin
Liquiritigenin is a flavanone that was isolated from ''Glycyrrhiza uralensis'', and is found in a variety of plants, including ''Glycyrrhiza glabra'' (licorice). It is an estrogenic compound which acts as a selective agonist of the ERβ subtype of the estrogen receptor (ER), though it is also reported to act as an ERα partial agonist at sufficient concentrations. It also has a choleretic effect. Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration) is an enzyme that uses liquiritigenin, O2, NADPH and H+ to produce 2,7,4'-trihydroxyisoflavanone, H2O, and NADP+. See also * Menerba * Prinaberel (ERB-041) * Diarylpropionitrile (DPN) * WAY-200070 * PHTPP * (R,R)-Tetrahydrochrysene ((R,R)-THC) * Propylpyrazoletriol (PPT) * Methylpiperidinopyrazole Methylpiperidinopyrazole (MPP) is a synthetic, nonsteroidal, and highly selective antagonist of ERα that is used in scientific research to study the function of this receptor. It has 200-fold selectivity for ERΠ... [...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 synthetized from 2'-hydroxydihydrochalcones. Homoisoflavanones can be synthetized 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 portulacanone A, portulacanones A, portulacanone B, B, portulacanone C, C and portulacanone D, 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 scillavone A, scillavones A and scillavone ... [...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 A phytoestrogen is a plant-derived xenoestrogen (see estrogen) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonster ... 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 naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen. 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. It has been shown to be the primary secondary metabolite of the ''Trifolium'' species and ''Glycine max L''. Natural occurrences Isoflavones such as genistein and daidzein are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plants, '' Flemingia vestita'' and '' F. macrophylla'', and coffee. It can also be found in ''Maackia amurensis'' cell cultures. Biological effects Besides functioning as an antioxidant and anthelmintic, many isoflavones have been sh ... [...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 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 ... [...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 repo ... [...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 phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their 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. Daid ... [...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 repo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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-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- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rotenoids
Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno ,4-bhromene nucleus. Many have insecticidal 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''. Amo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
