# Genistin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Genistin
> Markdown URL: https://mediated.wiki/source/Genistin.md
> Source: https://en.wikipedia.org/wiki/Genistin
> Source revision: 1268799372
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{distinguish|Genistein}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443833872
| Name = Genistin
| Reference =
| ImageFile = Genistin.svg
| ImageClass = skin-invert-image
| ImageSize = 300px
| IUPACName = 7-(β-<small>D</small>-Glucopyranosyloxy)-4′,5-dihydroxyisoflavone
| SystematicName = 5-Hydroxy-3-(4-hydroxyphenyl)-7-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4''H''-1-benzopyran-4-one
| OtherNames = Genistoside<br>Genistine<br>Genistein 7-glucoside<br>Genistein glucoside<br>Genistein-7-glucoside<br>Genisteol 7-monoglucoside<br>Glucosyl-7-genistein<br>Genistein 7-O-beta-D-glucoside
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444736
| InChIKey = ZCOLJUOHXJRHDI-CMWLGVBABE
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 486625
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZCOLJUOHXJRHDI-CMWLGVBASA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 529-59-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1POG3SCN5T
| EINECS =
| PubChem = 5281377
| SMILES = O=C3c4c(O)cc(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C=C3/c2ccc(O)cc2
| InChI = 1/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1
| RTECS =
| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27514
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09126
}}
|Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>20</sub>O<sub>10</sub>
| MolarMass = 432.37 g/mol
| Appearance =
| Density =
| MeltingPt =
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility =
| SolubleOther =
| Solvent =
| pKa =
| pKb = }}
|Section7={{Chembox Hazards
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
}}
'''Genistin''' is an [isoflavone](/source/isoflavone) found in a number of dietary plants like [soy](/source/soy) and [kudzu](/source/kudzu). It was first isolated in 1931 from the 90% [methanol](/source/methanol) extract of a [soybean](/source/soybean) meal, when it was found that [hydrolysis](/source/hydrolysis) with [hydrochloric acid](/source/hydrochloric_acid) produced 1 [mole](/source/mole_(unit)) each of [genistein](/source/genistein) and [glucose](/source/glucose).<ref>{{cite journal |author=Walter ED |year=1941 |title=Genistin (an isoflavone glucoside) and its aglucone, genistein, from soybeans |journal=J Am Chem Soc |volume=62 |issue=12 |pages=3273–3276 |doi=10.1021/ja01857a013}}</ref> Chemically it is the 7-O-beta-D-[glucoside](/source/glucoside) form of [genistein](/source/genistein) and is the predominant form of the [isoflavone](/source/isoflavone) naturally occurring in plants. In fact, studies in the 1970s revealed that 99% of the [isoflavonoid compounds](/source/isoflavonoid) in [soy](/source/soy) are present as their [glucoside](/source/glucoside)s. The [glucoside](/source/glucoside)s are converted by [digestive enzymes](/source/digestive_enzymes) in the [digestive system](/source/digestive_system) to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic, [estrogenic](/source/estrogenic) and [anticancer](/source/anticancer) effects are analogous.

==Metabolism==
When ingested along the diet, genistin is readily converted to its [aglycone](/source/aglycone) form, [genistein](/source/genistein). It is [hydrolyzed](/source/hydrolysis) by removing the [covalently bound](/source/covalent_bond) [glucose](/source/glucose) to form [genistein](/source/genistein) and that [genistein](/source/genistein) is the form of the compound that is absorbed in the [intestine](/source/intestine) and is the form responsible for the biological activities of the [isoflavone](/source/isoflavone). The digestive metabolism was first demonstrated in 2002 that the gut microflora played a large role in the conversion of genistin to [genistein](/source/genistein).<ref name="Coldham2001">{{cite journal |vauthors=Coldham NG, Darby C, Hows M, King LJ, Zhang AQ, Sauer MJ |year=2001 |title=Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism |journal=[Xenobiotica](/source/Xenobiotica) |volume= 32|issue=10 |pages=45–62 |pmid=11820509 |doi=10.1080/00498250110085809}}</ref> It was later found that [enzyme](/source/enzyme)s present in the human [small intestine](/source/small_intestine) and [liver](/source/liver) also have the ability to convert the [isoflavone](/source/isoflavone). [Hydrolysis](/source/Hydrolysis) actually starts very quickly in the [digestive system](/source/digestive_system) once genistin is ingested, conversion begins in the mouth and then continues in the [small intestine](/source/small_intestine). Moreover, both human [saliva](/source/saliva) and the intestinal cell-free extract from [mice](/source/mice) can cause the complete conversion.<ref name="Coldham2001" />

==Biological importance==

===Estrogenic activity===
Genistin, like genistein, is a [phytoestrogen](/source/phytoestrogen) as it was shown to stimulate [estrogen](/source/estrogen)-dependent [breast cancer](/source/cancer) cell growth in vivo. At a concentration of 1200 [ppm](/source/Parts_per_million), genistin caused significant increase of growth of [breast tumors (MCF-7)](/source/MCF-7), [cellular proliferation](/source/cell_proliferation) and estrogen-responsive pS2 gene expression in [mice](/source/mice). Removal of genistin or [genistein](/source/genistein) from the diet caused [tumor](/source/tumor)s to regress.<ref>{{cite journal |doi=10.1093/carcin/22.10.1667 |vauthors=Allred CD, Ju YH, Allred KF, Chang J, Helferich WG |year=2001 |title=Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein |journal=Carcinogenesis |volume=22 |issue=10 |pages=1667–1673 |pmid=11577007 |doi-access=free }}</ref>

===Antiviral activity===
Genistin and other [isoflavone](/source/isoflavone)s are demonstrated to be bioactive within the neonatal intestine and may reduce the severity of [rotavirus](/source/rotavirus) infections; genistin alone shows inhibition of the viral infectivity by 40-60%.<ref>{{cite journal |vauthors=Donovan SM, Andres A, Mathai RA, Kuhlenschmidt TB, Kuhlenschmidt MS |year=2009 |title=Soy formula and isoflavones and the developing intestine |journal=Nutr. Rev. |volume=67 |issue=S2 |pages=192–200 |pmid=19906223 |doi=10.1111/j.1753-4887.2009.00240.x}}</ref>

===Bone metabolism===
In vitro study have shown that both genistin and [genistein](/source/genistein) are capable of enhancing [bone](/source/bone) [metabolism](/source/metabolism) in the femoral-metaphyseal tissues of elderly [rat](/source/rat)s.<ref>{{cite journal |vauthors=Yamaguchi M, Gao YH |title=Anabolic effect of genistein and genistin on bone metabolism in the femoral-metaphyseal tissues of elderly rats: the genistein effect is enhanced by zinc |journal=Mol. Cell. Biochem. |volume=178 |issue=1–2 |pages=377–82 |date=January 1998 |pmid=9546622 |doi= 10.1023/A:1006809031836 }}</ref> The presence of genistein or genistin in the [tissue culture](/source/tissue_culture) caused a significant increase in [alkaline phosphatase activity](/source/phosphatase), [deoxyribonucleic acid (DNA)](/source/DNA) and [calcium](/source/calcium) contents. The effect of genistein was greater than that of genistin. It is also revealed that genistin has a strong bone loss preventive activity on experimental rats, and is especially enhanced by combination with [fructooligosaccharides](/source/fructooligosaccharides).<ref>{{cite journal |vauthors=Hooshmand S, Juma S, Arjmandi BH |year=2010 |title=Combination of Genistin and Fructooligosaccharides Prevents Bone Loss in Ovarian Hormone Deficiency |journal=J Med Food |volume= 13|issue= 2|pages= 320–5|pmid=20132047 |doi=10.1089/jmf.2009.0059}}</ref> The amount of new bone produced by grafting genistin in [collagen](/source/collagen) matrix was compared to the bone produced by collagen matrix alone in [New Zealand white rabbits](/source/New_Zealand_rabbit), and was observed that genistin caused significant increase in bone formation.<ref>{{cite journal |vauthors=Wong RW, Rabie AB |year=2010 |title=Effect of genistin on bone formation |journal=Front Biosci |volume=2 |issue=1 |pages=764–770 |pmid=20036920}}</ref>
<!-- ==Metabolism==
The enzyme [[ -->
<!-- ==Glycosides==
[[]] is the 7-O-[glucoside](/source/glucoside) of . -->

== References ==
{{reflist}}

== External links ==
* {{cite book|doi=10.1007/978-1-4614-0535-1_808 |chapter=Genistin (Genistein-7-O-β-D-glucoside) |title=Natural Compounds |date=2013 |page=362 |isbn=978-1-4614-0534-4 }}
*[https://web.archive.org/web/20140726143649/http://www.wikigenes.org/e/chem/e/5281377.html Chemical compound Review at Wikigenes]

{{Isoflavone}}

Category:Isoflavone glucosides

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Adapted from the Wikipedia article [Genistin](https://en.wikipedia.org/wiki/Genistin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Genistin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.