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{{Distinguish|Daidzin}}
{{chembox new
{{Lead too short|date=April 2013}}
| reference = <ref>''Merck Index'', 11th Edition, '''2805'''.</ref>
{{Use dmy dates|date=March 2020}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 443560562
| Reference = <ref>''Merck Index'', 11th Edition, '''2805'''.</ref>
| ImageFile = Daidzein.svg
| ImageFile = Daidzein.svg
| ImageSize = 300px
| ImageSize = 220px
| ImageFile1 = Daidzein-3D-balls.png
| IUPACName = 7-Hydroxy-3-(4-hydroxyphenyl) chromen-4-one
| ImageSize1 = 220
| OtherNames = 4',7-Dihydroxyisoflavone<br>Daidzeol<br>Isoaurostatin
| ImageAlt1 = Diazein molecule
| Section1 = {{Chembox Identifiers
| IUPACName = 4′,7-Dihydroxyisoflavone
| Abbreviations =
| SystematicName = 7-Hydroxy-3-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one
| OtherNames = 7-Hydroxy-3-(4-hydroxyphenyl)chromen-4-one<br />Daidzeol<br />Isoaurostatin
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 2828
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4445025
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6287WC5J2L
| InChIKey = ZQSIJRDFPHDXIC-UHFFFAOYAG
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 8145
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZQSIJRDFPHDXIC-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 486-66-8
| CASNo = 486-66-8
| EINECS =
| EINECS =
| PubChem = 5281708
| PubChem = 5281708
| SMILES = C1=CC(=CC=C1C2=COC3=C(C2=O) C=CC(=C3)O)O
| 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
| InChI =
| RTECS =
| RTECS =
| MeSHName =
| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| KEGG =
| ChEBI = 28197
| KEGG_Ref = {{keggcite|correct|kegg}}
| ATCCode_prefix =
| KEGG = C10208
| ATCCode_suffix =
}}
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>4</sub>
| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>4</sub>
| MolarMass = 254.237 g/mol
| MolarMass = 254.23 g/mol
| Appearance = Pale yellow prisms
| Appearance = Pale yellow prisms
| Density =
| Density =
| MeltingPt = 315-323 °C
| MeltingPtC = 315 to 323
| Melting_notes = decomposes
| MeltingPt_notes = (decomposes)
| BoilingPt =
| BoilingPt =
| BoilingPt_notes =
| Boiling_notes =
| Solubility =
| Solubility =
| SolubleOther =
| SolubleOther =
| Solvent =
| Solvent =
| pKa =
| pKa =
| pKb = }}
| pKb = }}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| EUClass =
| MainHazards =
| EUIndex =
| NFPA-H =
| MainHazards =
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-F =
| NFPA-S =
| NFPA-R =
| FlashPt =
| NFPA-O =
| AutoignitionPt =
| RPhrases =
| ExploLimits =
| SPhrases =
| RSPhrases =
| FlashPt =
| Autoignition =
| ExploLimits =
| PEL = }}
| 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 [[Phenylpropanoids metabolism|phenylpropanoid pathway]] of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks.<ref name=Jung>{{Cite journal |last1=Jung W.S. |last2=Yu |first2=O. |last3=Lau, C., S.M. |last4=O'Keefe |first4=D.P. |last5=Odell |first5=J. |last6=Fader |first6=G. |last7=McGonigle |first7=B. |date=2000 |title=Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes |url=https://www.nature.com/articles/nbt0200_208 |journal=Nature Biotechnology |volume=18 |issue=2 |pages=208–212 |doi=10.1038/72671 |pmid=10657130 |s2cid=1717934 |issn=1546-1696}}</ref> 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 [[cancer]]s, 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]].<ref>{{ cite journal
'''Daidzein''' is one of several known [[isoflavone]]s. Isoflavones compounds, such as daidzein and [[genistein]], are found in a number of [[plant]]s and herbs like the Thai [[Kwao Krua]] or Pueraria Mirifica, but [[soybean]]s and soy products like [[tofu]] and [[textured vegetable protein]] are the primary food source. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as [[antioxidant]]s, many isoflavones have been shown to interact with [[animal]] and [[human]] [[estrogen receptor]]s, and are therefore known as [[phytoestrogens]]. Soy isoflavones also produce non-hormonal effects.
| 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
| page = e14048
| doi = 10.1111/jfbc.14048
| pmid=34981538
| s2cid=245670986
| doi-access = free
}}</ref>


==Natural occurrence==
Isoflavones act as antioxidants to counteract damaging effects of free radicals in tissues. Isoflavones can act like estrogen in stimulating development and maintenance of female characteristics or they can block cells from using other forms of estrogen{{Fact|date=June 2007}}. Isoflavones also have been found to have antiangiogenic effects (blocking formation of new blood vessels){{Fact|date=June 2007}}, and may block the uncontrolled cell growth associated with cancer, most likely by inhibiting the activity of substances in the body that regulate cell division and cell survival (growth factors){{Fact|date=June 2007}}.
Daidzein and other isoflavone compounds, such as [[genistein]], are present in a number of [[plant]]s and [[herb]]s like kwao krua (''[[Pueraria mirifica]]'') and [[kudzu]]. It can also be found in ''[[Maackia amurensis]]'' cell cultures.<ref>{{Cite journal |last1=Fedoreyev |first1=S.A. |last2=Pokushalova |first2=T.V. |last3=Veselova |first3=M.V. |last4=Glebko |first4=L.I. |last5=Kulesh |first5=N.I. |last6=Muzarok |first6=T.I. |last7=Seletskaya |first7=L.D. |last8=Bulgakov |first8=V.P. |last9=Zhuravlev |first9=Y.N. |date=2000 |title=Isoflavonoid production by callus cultures of Maackia amurensis |url=https://www.sciencedirect.com/science/article/pii/S0367326X00001295 |journal=Fitoterapia |volume=71 |issue=4 |pages=365–372 |doi=10.1016/S0367-326X(00)00129-5|pmid=10925005 }}</ref> Daidzein can be found in food such as [[soybean]]s and soy products like [[tofu]] and [[textured vegetable protein]]. Soy isoflavones are a group of compounds found in and isolated from the soybean. Of note, total isoflavones in soybeans are—in general—37 percent daidzein, 57 percent genistein and 6 percent [[glycitein]], according to [[United States Department of Agriculture|USDA]] data.<ref>{{ cite web | title = Isoflavones contents of food | url = http://www.isoflavones.info/isoflavones-content.php | publisher = Top Cultures | access-date = 2012-05-15 }}</ref> Soy germ contains 41.7 percent daidzein.<ref>{{cite journal | last = Zhang | first = Y. |author2=Wang, G. J. |author3=Song, T. T. |author4=Murphy, P. A. |author5=Hendrich, S. | title = Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity | journal = The Journal of Nutrition | year = 1999 | volume = 129 | issue = 5 | pages = 957–962 | pmid = 10222386 | doi = 10.1093/jn/129.5.957 | doi-access = free }}</ref>


== Biosynthesis ==
Studies show that groups of people who eat large amounts of soy-based products have lower incidences of breast, colon, endometrial, and prostate cancers than the general (US) population{{Fact|date=June 2007}}. Initial studies of soy and Kwao Krua isoflavone mixtures containing genistein, daidzein, and glycitein have found them safe for human use<ref>Safety of soy-based infant formulas containing isoflavones PMID 15113975</ref>. Laboratory studies using animals models have shown that both soy and isoflavones can be protective against cancer when given during early life but can stimulate response to cancer-causing chemicals when given during fetal development or when circulating levels of estrogen are low (menopause){{Fact|date=June 2007}}.


===History===
'''[[Pueraria mirifica]]''' or White Kawo Krua has been found to contain concentrations of daidzein where the Cu²+ at 300 ppm is shown to contain as much as 44.69 ppm of daidzein. Another source of daidzein is Kudzu also known as Pueraria Lobata.
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.<ref name =Winkel>{{ 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
}}</ref>

===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 [[Nicotinamide adenine dinucleotide phosphate|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.<ref name=Dewick>{{Cite book |last=Dewick |first=P.M. |title=Medicinal Natural Products: A Biosynthetic Approach |publisher=Wiley |year=2009 |isbn=978-0-470-74168-9 |edition=3rd |pages=137–175 |type=E-book |oclc=259265604}}</ref> 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.<ref name =Winkel />

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.<ref name=Dewick /><ref name=Jung />

[[File:Daidzein v2.gif|thumb|Proposed daidzein biosynthesis]]

==Research==
Daidzein has been found to act as an [[agonist]] of the [[GPER]] (GPR30).<ref name="ProssnitzBarton2014">{{cite journal|last1=Prossnitz|first1=E.R. |last2=Barton|first2=M. |title=Estrogen biology: New insights into GPER function and clinical opportunities|journal=Molecular and Cellular Endocrinology|volume=389|issue=1–2|year=2014|pages=71–83|doi=10.1016/j.mce.2014.02.002|pmid=24530924|pmc=4040308}}</ref>

==Pathogen interactions==
Because daidzein is a defensive factor, ''[[Pseudomonas syringae]]'' produces the [[HopZ1b]] effector which degrades a ''GmHID1'' product.<ref name="Bauters-et-al-2021">{{cite journal | last1=Bauters | first1= L. | last2= Stojilković | first2 = B. | last3 =Gheysen | first3 = G. | title=Pathogens pulling the strings: Effectors manipulating salicylic acid and phenylpropanoid biosynthesis in plants | journal=[[Molecular Plant Pathology]] | publisher=[[British Society for Plant Pathology]] ([[Wiley-Blackwell|Wiley]]) | date=2021 | volume= 22 | issue= 11 | pmid=34414650 | doi=10.1111/mpp.13123 |pmc=8518561 | pages=1436–1448| doi-access=free }}</ref>

==Derivatives==
* [[Glyceollin]], a type of [[phytoalexin]]<ref name="Bauters-et-al-2021" />

===Glycosides===
* [[Daidzin]] is the 7-O-[[glucoside]] of daidzein.
* [[Puerarin]] is the 8-C-glucoside of daidzein.

==Plants containing daidzein==
* ''Maackia amurensis''
* [[Pueraria montana var. lobata|''Pueraria montana'' var. ''lobata'']]''{{ space | thin }}<ref name= Chen >{{ cite journal | author = Chen G. | author2 = Zhang J.X. | author3 = Ye J.N. | year = 2001 | title = Determination of Puerarin, Daidzein and Rutin in ''Pueraria lobata'' (Willd.) Ohwi by Capillary Electrophoresis with Electrochemical Detection | journal = [[Journal of Chromatography A]] | volume = 923 | issue = 1–2 | pages = 255–262 | doi = 10.1016/S0021-9673(01)00996-7 | pmid = 11510548 }}</ref>''<ref name="eisp">{{ cite journal | author = Xu H.N. | author2 = He C.H. | date = 2007 | title = Extraction of Isoflavones from Stem of ''Pueraria lobata'' (Willd.) Ohwi Using n-Butanol / Water Two-Phase Solvent System and Separation of Daidzein | journal = Separation and Purification Technology | volume = 56 | issue = 1 | pages = 255–262 | doi = 10.1016/j.seppur.2007.01.027 }}</ref>
* ''[[Pueraria thomsonii]]''{{ space | thin }}<ref name="sdpd">{{cite journal |author=Zhou H.Y. |author2=Wang J.H. |author3=Yan F.Y. |date=2007 |title=[Separation and Determination of Puerarin, Daidzin and Daidzein in Stems and Leaves of ''Pueraria thomsonii'' by RP-HPLC] |journal=Zhongguo Zhong Yao Za Zhi |language=zh |volume=32 |issue=10 |pages=937–939 |pmid=17655152}}</ref>


==References==
==References==
{{Reflist}}
<references/>


{{Isoflavones}}
==External links==
{{Phytoestrogens}}
[[Category:Flavonoids]]
{{Navboxes
| title = [[Pharmacodynamics]]
| titlestyle = background:#ccccff
| list1 =
{{Estrogen receptor modulators}}
{{Estrogen-related receptor modulators}}
{{Glycine receptor modulators}}
{{PPAR modulators}}
}}


[[Category:3α-Hydroxysteroid dehydrogenase inhibitors]]
[[de:Daidzein]]
[[Category:Isoflavones]]
[[Category:Glycine receptor antagonists]]
[[Category:GPER agonists]]
[[Category:Phytoestrogens]]
[[Category:Selective ERβ agonists]]

Latest revision as of 17:48, 30 April 2023

Not to be confused with Daidzin.

Daidzein[1]
Diazein molecule
Names
IUPAC name
4′,7-Dihydroxyisoflavone
Systematic IUPAC name
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
7-Hydroxy-3-(4-hydroxyphenyl)chromen-4-one
Daidzeol
Isoaurostatin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.942 Edit this at Wikidata
KEGG
UNII
  • InChI=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 checkY
    Key: ZQSIJRDFPHDXIC-UHFFFAOYSA-N checkY
  • 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
    Key: ZQSIJRDFPHDXIC-UHFFFAOYAG
  • O=C\1c3c(O/C=C/1c2ccc(O)cc2)cc(O)cc3
Properties
C15H10O4
Molar mass 254.23 g/mol
Appearance Pale yellow prisms
Melting point 315 to 323 °C (599 to 613 °F; 588 to 596 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[2] 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.[3]

Natural occurrence

[edit]

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.[4] Daidzein can be found in food such as soybeans and soy products like tofu and textured vegetable protein. Soy isoflavones are a group of compounds found in and isolated from the soybean. Of note, total isoflavones in soybeans are—in general—37 percent daidzein, 57 percent genistein and 6 percent glycitein, according to USDA data.[5] Soy germ contains 41.7 percent daidzein.[6]

Biosynthesis

[edit]

History

[edit]

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.[7]

Pathway

[edit]

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.[8] 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.[7]

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.[8][2]

Proposed daidzein biosynthesis

Research

[edit]

Daidzein has been found to act as an agonist of the GPER (GPR30).[9]

Pathogen interactions

[edit]

Because daidzein is a defensive factor, Pseudomonas syringae produces the HopZ1b effector which degrades a GmHID1 product.[10]

Derivatives

[edit]

Glycosides

[edit]

Plants containing daidzein

[edit]

References

[edit]
  1. ^ Merck Index, 11th Edition, 2805.
  2. ^ a b Jung W.S.; Yu, O.; Lau, C., S.M.; O'Keefe, D.P.; Odell, J.; Fader, G.; McGonigle, B. (2000). "Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes". Nature Biotechnology. 18 (2): 208–212. doi:10.1038/72671. ISSN 1546-1696. PMID 10657130. S2CID 1717934.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Wang Y.C.; Yang M.; Qin J.J.; Wa W.Q. (2022). "Interactions between puerarin/daidzein and micellar casein". Journal of Food Biochemistry. 46 (2): e14048. doi:10.1111/jfbc.14048. PMID 34981538. S2CID 245670986.
  4. ^ Fedoreyev, S.A.; Pokushalova, T.V.; Veselova, M.V.; Glebko, L.I.; Kulesh, N.I.; Muzarok, T.I.; Seletskaya, L.D.; Bulgakov, V.P.; Zhuravlev, Y.N. (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia. 71 (4): 365–372. doi:10.1016/S0367-326X(00)00129-5. PMID 10925005.
  5. ^ "Isoflavones contents of food". Top Cultures. Retrieved 15 May 2012.
  6. ^ Zhang, Y.; Wang, G. J.; Song, T. T.; Murphy, P. A.; Hendrich, S. (1999). "Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity". The Journal of Nutrition. 129 (5): 957–962. doi:10.1093/jn/129.5.957. PMID 10222386.
  7. ^ a b Winkel-Shirley, B. (2001). "Flavonoid Biosynthesis. A Colorful Model for Genetics, Biochemistry, Cell Biology, and Biotechnology". Plant Physiology. 126 (2): 485–493. doi:10.1104/pp.126.2.485. PMC 1540115. PMID 11402179.
  8. ^ a b Dewick, P.M. (2009). Medicinal Natural Products: A Biosynthetic Approach (E-book) (3rd ed.). Wiley. pp. 137–175. ISBN 978-0-470-74168-9. OCLC 259265604.
  9. ^ Prossnitz, E.R.; Barton, M. (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. PMC 4040308. PMID 24530924.
  10. ^ a b Bauters, L.; Stojilković, B.; Gheysen, G. (2021). "Pathogens pulling the strings: Effectors manipulating salicylic acid and phenylpropanoid biosynthesis in plants". Molecular Plant Pathology. 22 (11). British Society for Plant Pathology (Wiley): 1436–1448. doi:10.1111/mpp.13123. PMC 8518561. PMID 34414650.
  11. ^ Chen G.; Zhang J.X.; Ye J.N. (2001). "Determination of Puerarin, Daidzein and Rutin in Pueraria lobata (Willd.) Ohwi by Capillary Electrophoresis with Electrochemical Detection". Journal of Chromatography A. 923 (1–2): 255–262. doi:10.1016/S0021-9673(01)00996-7. PMID 11510548.
  12. ^ Xu H.N.; He C.H. (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. 56 (1): 255–262. doi:10.1016/j.seppur.2007.01.027.
  13. ^ Zhou H.Y.; Wang J.H.; Yan F.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 (in Chinese). 32 (10): 937–939. PMID 17655152.
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