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Isoflavonoid Biosynthesis
The biosynthesis of isoflavonoids involves several enzymes; These are: Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration), also known as Isoflavonoid synthase, is an enzyme that uses liquiritigenin (a flavanone), O2, NADPH and H+ to produce 2,7,4'-trihydroxyisoflavanone (an isoflavonoid), H2O and NADP+. * Biochanin-A reductase * Flavone synthase * 2'-hydroxydaidzein reductase * 2-hydroxyisoflavanone dehydratase * 2-hydroxyisoflavanone synthase * Isoflavone 4'-O-methyltransferase * Isoflavone 7-O-methyltransferase * Isoflavone 2'-hydroxylase * Isoflavone 3'-hydroxylase * Isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase * Isoflavone 7-O-glucosyltransferase * 4'-methoxyisoflavone 2'-hydroxylase Pterocarpans biosynthesis * 3,9-dihydroxypterocarpan 6a-monooxygenase * Glyceollin synthase * Pterocarpin synthase See also * Flavonoid biosynthesis Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylal ...
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Biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. This process often consists of metabolic pathways. Some of these biosynthetic pathways are located within a single cellular organelle, while others involve enzymes that are located within multiple cellular organelles. Examples of these biosynthetic pathways include the production of lipid membrane components and nucleotides. Biosynthesis is usually synonymous with anabolism. The prerequisite elements for biosynthesis include: precursor compounds, chemical energy (e.g. ATP), and catalytic enzymes which may require coenzymes (e.g.NADH, NADPH). These elements create monomers, the building blocks for macromolecules. Some important biological macromolecules include: proteins, which are composed of amino acid monomers joined via peptide bon ...
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Isoflavone 2'-hydroxylase
In enzymology, an isoflavone 2'-hydroxylase (, Formerly ) is an enzyme that catalyzes the chemical reaction :an isoflavone + NADPH + H+ + O2 \rightleftharpoons a 2'-hydroxyisoflavone + NADP+ + H2O The 4 substrates of this enzyme are isoflavone, NADPH, H+, and O2, whereas its 3 products are 2'-hydroxyisoflavone, NADP+, and H2O. This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor. The systematic name of this enzyme class is isoflavone,NADPH:oxygen oxidoreductase (2'-hydroxylating). Other names in common use include isoflavone 2'-monooxygenase, CYP81E1, and CYP Ge-3. This enzyme participates in isoflavonoid biosynthesis The biosynthesis of isoflavonoids involves several enzymes; These are: Liquiritigenin,NADPH:oxygen oxidoredu ...
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Flavonoid Biosynthesis
Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics. Flavanoids can possess chiral carbons. Methods of analysis should take this element into account especially regarding bioactivity or enzyme stereospecificity. Enzymes The biosynthesis of flavonoids involves several enzymes. * Anthocyanidin reductase * Chalcone isomerase * ...
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Pterocarpin Synthase
In enzymology, a pterocarpin synthase () is an enzyme that catalyzes the chemical reaction :medicarpin + NADP+ + H2O \rightleftharpoons vestitone + NADPH + H+ The 3 substrates of this enzyme are medicarpin, NADP+, and H2O, whereas its 3 products are vestitone, NADPH, and H+. This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-OH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is medicarpin:NADP+ 2'-oxidoreductase. This enzyme is also called pterocarpan synthase. This enzyme participates in isoflavonoid biosynthesis The biosynthesis of isoflavonoids involves several enzymes; These are: Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration), also known as Isoflavonoid synthase, is an enzyme that uses liquiritigenin (a flavanone), O2, NADPH .... References * EC 1.1.1 NADPH-dependent enzymes Enzymes of unknown structure Isoflavonoids metabolism {{1.1.1-enzyme-s ...
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Glyceollin Synthase
In enzymology, a glyceollin synthase is an enzyme that catalyzes the last committed step in glyceollin biosynthesis. This enzyme has been classified as a cytochrome dependent monooxygenase. It uses cyclization of prenyl residue to convert glyceollidins (I and II) into glyceollins (I - III). This enzyme catalyzes the following chemical reaction: :2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADPH + H+ + O2 \rightleftharpoons glyceollin + NADP+ + 2 H2O The five substrates of this enzyme are 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, 4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, NADPH, H+, and O2, whereas its three products are glyceollin, NADP+, and H2O. This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o o ...
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3,9-dihydroxypterocarpan 6a-monooxygenase
In enzymology, a 3,9-dihydroxypterocarpan 6a-monooxygenase () is an enzyme that catalyzes the chemical reaction :(6aR,11aR)-3,9-dihydroxypterocarpan + NADPH + H+ + O2 \rightleftharpoons (6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADP+ + H2O The 4 substrates of this enzyme are (6aR,11aR)-3,9-dihydroxypterocarpan, NADPH, H+, and O2, whereas its 3 products are (6aS,11aS)-3,6a,9-trihydroxypterocarpan, NADP+, and H2O. This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor. The systematic name of this enzyme class is (6aR,11aR)-3,9-dihydroxypterocarpan,NADPH:oxygen oxidoreductase (6a-hydroxylating). Other names in common use include 3,9-dihydroxypterocarpan 6a-hydroxylase, and 3,9-dihydroxypterocarpan 6alpha-monooxygenase (erroneous). ...
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4'-methoxyisoflavone 2'-hydroxylase
In enzymology, a 4'-methoxyisoflavone 2'-hydroxylase (, Formerly ) is an enzyme that catalyzes the chemical reaction :formononetin + NADPH + H+ + O2 \rightleftharpoons 2'-hydroxyformononetin + NADP+ + H2O The 4 substrates of this enzyme are formononetin, NADPH, H+, and O2, whereas its 3 products are 2'-hydroxyformononetin, NADP+, and H2O. This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor. The systematic name of this enzyme class is formononetin,NADPH:oxygen oxidoreductase (2'-hydroxylating). Other names in common use include isoflavone 2'-monooxygenase (ambiguous), and isoflavone 2'-hydroxylase (ambiguous). This enzyme participates in isoflavonoid biosynthesis. It employs one cofactor, heme Heme, or haem (pronounced / h ...
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Isoflavone 7-O-glucosyltransferase
In enzymology, an isoflavone 7-O-glucosyltransferase () is an enzyme that catalyzes the chemical reaction :UDP-glucose + an isoflavone \rightleftharpoons UDP + an isoflavone 7-O-beta-D-glucoside Thus, the two substrates of this enzyme are UDP-glucose and isoflavone, whereas its two products are UDP and isoflavone 7-O-beta-D-glucoside. This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase. Other names in common use include uridine diphosphoglucose-isoflavone 7-O-glucosyltransferase, UDPglucose-favonoid 7-O-glucosyltransferase, and UDPglucose:isoflavone 7-O-glucosyltransferase. This enzyme participates in isoflavonoid biosynthesis The biosynthesis of isoflavonoids involves several enzymes; These are: Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration), also known as Isoflavonoid synthase, is an enzyme that uses li ...
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Isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase
In enzymology, an isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase () is an enzyme that catalyzes the chemical reaction :malonyl-CoA + biochanin A 7-O-beta-D-glucoside \rightleftharpoons CoA + biochanin A 7-O-(6-O-malonyl-beta-D-glucoside) Thus, the two substrates of this enzyme are malonyl-CoA and biochanin A 7-O-beta-D-glucoside, whereas its two products are CoA and biochanin A 7-O-(6-O-malonyl-beta-D-glucoside). This enzyme belongs to the family of transferases, specifically those acyltransferases transferring groups other than aminoacyl groups. The systematic name of this enzyme class is malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6"-O-malonyltransferase. Other names in common use include flavone/flavonol 7-O-beta-D-glucoside malonyltransferase, flavone (flavonol) 7-O-glycoside malonyltransferase, malonyl-CoA:flavone/flavonol 7-O-glucoside malonyltransferase, MAT-7, malonyl-coenzyme A:isoflavone 7-O-glucoside-6"-malonyltransferase, and malonyl-coenzyme A:flavone/flav ...
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Isoflavone 3'-hydroxylase
In enzymology, an isoflavone 3'-hydroxylase (, Formerly ) is an enzyme that catalyzes the chemical reaction :formononetin + NADPH + H+ + O2 \rightleftharpoons calycosin + NADP+ + H2O The 4 substrates of this enzyme are formononetin, NADPH, H+, and O2, whereas its 3 products are calycosin, NADP+, and H2O. This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor. The systematic name of this enzyme class is formononetin,NADPH:oxygen oxidoreductase (3'-hydroxylating). This enzyme is also called isoflavone 3'-monooxygenase. This enzyme participates in isoflavonoid biosynthesis. It employs one cofactor, heme Heme, or haem (pronounced / hi:m/ ), is a precursor to hemoglobin, which is necessary to bind oxygen in the bloodstream. Heme i ...
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Isoflavone 7-O-methyltransferase
In enzymology, an isoflavone 7-O-methyltransferase () is an enzyme that catalyzes the chemical reaction :S-adenosyl-L-methionine + a 7-hydroxyisoflavone \rightleftharpoons S-adenosyl-L-homocysteine + a 7-methoxyisoflavone Thus, the two substrates of this enzyme are S-adenosyl methionine and 7-hydroxyisoflavone, whereas its two products are S-adenosylhomocysteine and 7-methoxyisoflavone. This enzyme belongs to the family of transferases, specifically those transferring one-carbon group methyltransferases. The systematic name of this enzyme class is S-adenosyl-L-methionine:hydroxyisoflavone 7-O-methyltransferase. This enzyme participates in isoflavonoid biosynthesis The biosynthesis of isoflavonoids involves several enzymes; These are: Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration), also known as Isoflavonoid synthase, is an enzyme that uses liquiritigenin (a flavanone), O2, NADPH .... References * * * * * * * EC 2.1.1 Enzymes of ...
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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-phenyl ...
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