Daidzein

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title: "Daidzein" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3α-hydroxysteroid-dehydrogenase-inhibitors", "isoflavones", "glycine-receptor-antagonists", "gper-agonists", "phytoestrogens", "selective-erβ-agonists"] topic_path: "general/3a-hydroxysteroid-dehydrogenase-inhibitors" source: "https://en.wikipedia.org/wiki/Daidzein" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443560562 | Reference = | ImageFile = Daidzein.svg | ImageClass = skin-invert-image | ImageSize = 220px | ImageFile1 = Daidzein-3D-balls.png | ImageClass1 = bg-transparent | ImageSize1 = 220 | ImageAlt1 = Diazein molecule | IUPACName = 4′,7-Dihydroxyisoflavone | SystematicName = 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | OtherNames = 7-Hydroxy-3-(4-hydroxyphenyl)chromen-4-one Daidzeol Isoaurostatin |Section1={{Chembox Identifiers | IUPHAR_ligand = 2828 | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 4445025 | UNII_Ref = | UNII = 6287WC5J2L | InChIKey = ZQSIJRDFPHDXIC-UHFFFAOYAG | ChEMBL_Ref = | ChEMBL = 8145 | StdInChI_Ref = | StdInChI = 1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H | StdInChIKey_Ref = | StdInChIKey = ZQSIJRDFPHDXIC-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 486-66-8 | EINECS = | PubChem = 5281708 | SMILES = O=C\1c3c(O/C=C/1c2ccc(O)cc2)cc(O)cc3 | InChI = 1/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H | RTECS = | MeSHName = | ChEBI_Ref = | ChEBI = 28197 | KEGG_Ref = | KEGG = C10208 |Section2={{Chembox Properties | Formula = C15H10O4 | MolarMass = 254.23 g/mol | Appearance = Pale yellow prisms | Density = | MeltingPtC = 315 to 323 | MeltingPt_notes = (decomposes) | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }}

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. Upon consumption of isoflavone-rich foods, daidzein has poor bioavailability and low water solubility.{{ cite journal | last1 = Wang Y.C. | last2=Yang M. | last3 = Qin J.J. | last4 = Wa W.Q. | date = 2022 | title = Interactions between puerarin/daidzein and micellar casein | journal = Journal of Food Biochemistry | volume = 46 | issue = 2 | article-number = e14048 | doi = 10.1111/jfbc.14048 | pmid=34981538 | s2cid=245670986 | doi-access = free

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 genistein and 6 percent glycitein, according to USDA data. Soy germ contains 41.7 percent daidzein.

Biosynthesis

History

The isoflavonoid pathway has long been studied because of its prevalence in a wide variety of plant species, including as pigmentation in many flowers, as well as serving as signals in plants and microbes. The isoflavone synthase (IFS) enzyme was suggested to be a P-450 oxygenase family, and this was confirmed by Shinichi Ayabe's laboratory in 1999. IFS exists in two isoforms that can use both liquiritigenin and naringenin to give daidzein and genistein respectively.{{ cite journal | last = Winkel-Shirley | first = B. | date = 2001 | title = Flavonoid Biosynthesis. A Colorful Model for Genetics, Biochemistry, Cell Biology, and Biotechnology | journal = Plant Physiology | volume = 126 | issue = 2 | pages = 485–493 | doi = 10.1104/pp.126.2.485 | pmid = 11402179 | pmc = 1540115 | doi-access = free

Pathway

Daidzein is an isoflavonoid derived from the shikimate pathway that forms an oxygen containing heterocycle through a cytochrome P-450-dependent enzyme that is NADPH dependent.

The biosynthesis of daidzein begins with L-phenylalanine and undergoes a general phenylpropanoid pathway where the shikimate derived aromatic ring is shifted to the adjacent carbon of the heterocycle. The process begins with phenylalanine ligase (PAL) cleaving the amino group from L-Phe forming the unsaturated carboxylic acid, cinnamic acid. Cinnamic acid is then hydroxylated by membrane protein cinnamate-4-hydroxylase (C4H) to form p-coumaric acid. P-coumaric acid then acts as the starter unit which gets loaded with coenzyme A by 4-coumaroyl:CoA-ligase (4CL). The starter unit (A) then undergoes three iterations of malonyl-CoA resulting in (B), which enzymes chalcone synthase (CHS) and chalcone reductase (CHR) modify to obtain trihydroxychalcone. CHR is NADPH dependent. Chalcone isomerase (CHI) then isomerizes trihydroxychalcone to liquiritigenin, the precursor to daidzein.

A radical mechanism has been proposed in order to obtain daidzein from liquiritigenin, where an iron-containing enzyme, as well as NADPH and oxygen cofactors are used by a 2-hydroxyisoflavone synthase to oxidize liquiritigenin to a radical intermediate (C). A 1,2 aryl migration follows to form (D), which is subsequently oxidized to (E). Lastly, dehydration of the hydroxy group on C2 occurs through a 2-hydroxyisoflavanone dehydratase (specifically GmHID1) to give daidzein.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/7/7b/Daidzein_v2.gif" caption="Proposed daidzein biosynthesis"] ::

Research

There is preliminary evidence that consuming soy foods rich in daidzein and isoflavones may improve cardiovascular function in postmenopausal women

Pathogen interactions

Because daidzein is a defensive factor, Pseudomonas syringae produces the HopZ1b effector which degrades a GmHID1 product.

Derivatives

Glycosides

Plants containing daidzein

References

References

  1. ''Merck Index'', 11th Edition, '''2805'''.
  2. (2016). "Soy isoflavones". Micronutrient Information Center, Linus Pauling Institute, Oregon State University.
  3. (2000). "Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes". Nature Biotechnology.
  4. (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia.
  5. "Isoflavones contents of food". Top Cultures.
  6. Zhang, Y.. (1999). "Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity". The Journal of Nutrition.
  7. Dewick, P.M.. (2009). "Medicinal Natural Products: A Biosynthetic Approach". Wiley.
  8. (2022). "Soy Isoflavones and Breast Cancer Risk: A Meta-analysis". In Vivo.
  9. (2021). "Pathogens pulling the strings: Effectors manipulating salicylic acid and phenylpropanoid biosynthesis in plants". [[British Society for Plant Pathology]] ([[Wiley-Blackwell.
  10. Chen G.. (2001). "Determination of Puerarin, Daidzein and Rutin in ''Pueraria lobata'' (Willd.) Ohwi by Capillary Electrophoresis with Electrochemical Detection". [[Journal of Chromatography A]].
  11. Xu H.N.. (2007). "Extraction of Isoflavones from Stem of ''Pueraria lobata'' (Willd.) Ohwi Using n-Butanol / Water Two-Phase Solvent System and Separation of Daidzein". Separation and Purification Technology.
  12. Zhou H.Y.. (2007). "[Separation and Determination of Puerarin, Daidzin and Daidzein in Stems and Leaves of ''Pueraria thomsonii'' by RP-HPLC]". Zhongguo Zhong Yao Za Zhi.

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3α-hydroxysteroid-dehydrogenase-inhibitorsisoflavonesglycine-receptor-antagonistsgper-agonistsphytoestrogensselective-erβ-agonists