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{{Short description|Plant-derived xenoestrogen}}
A '''phytoestrogen''' is a  plant-derived [[xenoestrogen]] (a type of [[estrogen]] produced by organisms other than humans) not generated within the [[endocrine system]], but consumed by eating plants or manufactured foods.<ref name="lpi">{{cite web |date=October 2016 |title=Isoflavones |url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/soy-isoflavones |access-date=6 August 2022 |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis}}</ref> Also called a "dietary estrogen", it is a diverse group of naturally occurring  nonsteroidal plant compounds that, because of its structural similarity to [[estradiol]] (17-β-estradiol), have the ability to cause [[estrogenic]] or antiestrogenic effects.<ref name= "Yil">{{cite book | last = Yildiz | first = Fatih | name-list-style = vanc | title = Phytoestrogens in Functional Foods| publisher = Taylor & Francis Ltd | year = 2005 |pages = 3–5, 210–211 | isbn  = 978-1-57444-508-4 }}</ref> Phytoestrogens are not essential [[nutrient]]s because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function.<ref name= "Yil"/> Common foods containing phytoestrogens are [[soy protein]], [[bean]]s, [[oat]]s, [[barley]], [[rice]], [[coffee]], [[apple]]s, [[carrot]]s (see Food Sources section below for bigger list).

Its name comes from the [[Greek language|Greek]] ''phyto'' ("plant") and ''estrogen'', the hormone which gives fertility to [[female mammals]]. The word "[[estrus]]" (Greek οίστρος) means "[[sexual desire]]", and "gene" (Greek γόνο) is "to generate". It has been hypothesized that plants use a phytoestrogen as part of their natural defense against the overpopulation of herbivore animals by controlling female fertility.<ref name="pmid3203635">{{cite journal | vauthors = Hughes CL | title = Phytochemical mimicry of reproductive hormones and modulation of herbivore fertility by phytoestrogens | journal = Environmental Health Perspectives | volume = 78 | pages = 171–4 | date = Jun 1988 | pmid = 3203635 | pmc = 1474615 | doi = 10.1289/ehp.8878171 }}</ref><ref name="isbn0-521-64387-2">{{cite book | last1 = Bentley | first1 = Gillian R. | last2 = Mascie-Taylor | first2 = C. G. N. | name-list-style = vanc |  title = Infertility in the modern world: present and future prospects | url = https://archive.org/details/infertilitymoder00bent | url-access = limited | publisher = Cambridge University Press | location = Cambridge, UK | year = 2000 | isbn = 978-0-521-64387-0 | pages = [https://archive.org/details/infertilitymoder00bent/page/n111 99]–100 }}</ref>

The similarities, at molecular level, of an [[estrogen]] and a phytoestrogen allow them to mildly mimic and sometimes act as an antagonist of estrogen.<ref name= "Yil"/> Phytoestrogens were first observed in 1926,<ref name= "Yil"/><ref>{{cite book | last1 = Varner | first1 = JE | last2 = Bonner | first2 = J | name-list-style = vanc | title =  Plant Biochemistry| publisher = Academic Press| year = 1966 | isbn = 978-0-12-114856-0  }}</ref> but it was unknown if they could have any effect in human or animal metabolism. In the 1940s and early 1950s, it was noticed that some pastures of subterranean clover and [[red clover]] (phytoestrogen-rich plants) had adverse effects on the [[fecundity]] of grazing sheep.<ref name= "Yil"/><ref name="pmid21028682">{{cite journal | vauthors = Bennetts HW, Underwood EJ, Shier FL | title = A specific breeding problem of sheep on subterranean clover pastures in Western Australia | journal = Australian Veterinary Journal | volume = 22 | issue = 1| pages = 2–12 | year = 1946 | pmid = 21028682 | doi = 10.1111/j.1751-0813.1946.tb15473.x}}</ref><ref>{{cite journal | vauthors = Cunningham IJ, Hogan KG | year =  1954 | title = Oestrogens in New Zealand pasture plants.  | journal = N. Z. Vet. J. | volume = 2 | issue = 4 | pages = 128–134 | doi=10.1080/00480169.1954.33166}}</ref><ref name= "Jon">{{cite book | last = Johnston | first = I | name-list-style = vanc | title = Phytochem Functional Foods| publisher = CRC Press Inc|year=2003| pages =  66–68| isbn  = 978-0-8493-1754-5}}</ref>

[[File:Phytoestrogens2.png|thumb|Chemical structures of the most common phytoestrogens found in plants (top and middle) compared with estrogen (bottom) found in animals|400px|right]]

== Structure ==

Phytoestrogens mainly belong to a large group of substituted [[natural phenol]]ic compounds: the [[coumestan]]s, [[prenylflavonoid]]s and [[isoflavone]]s are three of the most active in estrogenic effects in this class.<ref name=lpi/> The best-researched are isoflavones, which are commonly found in [[soy]] and [[red clover]]. [[Lignan]]s have also been identified as phytoestrogens, although they are not flavonoids.<ref name= "Yil"/> [[Mycoestrogens]] have similar structures and effects, but are not components of plants; these are mold metabolites of ''[[Fusarium]]'', especially common on cereal grains,<ref>{{cite journal | vauthors = Bennett GA, Shotwell OI | year = 1979 | title = Zearalenone in cereal grains | journal = J. Amer. Oil. Chemists Soc. | volume = 56 | issue = 9 | pages = 812–819 | doi = 10.1007/bf02909525 | s2cid = 39917693 | url = https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=26065&content=PDF }}{{Dead link|date=October 2022 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref name="pmid2961013">{{cite journal | vauthors = Kuiper-Goodman T, Scott PM, Watanabe H | title = Risk assessment of the mycotoxin zearalenone | journal = Regul. Toxicol. Pharmacol. | volume = 7 | issue = 3 | pages = 253–306 | year = 1987 | pmid = 2961013 | doi = 10.1016/0273-2300(87)90037-7}}</ref><ref name="pmid17045381">{{cite journal | vauthors = Zinedine A, Soriano JM, Moltó JC, Mañes J | title = Review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin | journal = Food Chem. Toxicol. | volume = 45 | issue = 1 | pages = 1–18 | year = 2007 | pmid = 17045381 | doi = 10.1016/j.fct.2006.07.030 }}</ref> but also occurring elsewhere, e.g. on various forages.<ref name="pmid26274974">{{cite journal | vauthors = Gallo A, Giuberti G, Frisvad JC, Bertuzzi T, Nielsen KF | title = Review on Mycotoxin Issues in Ruminants: Occurrence in Forages, Effects of Mycotoxin Ingestion on Health Status and Animal Performance and Practical Strategies to Counteract Their Negative Effects | journal = Toxins (Basel) | volume = 7 | issue = 8 | pages = 3057–111 | year = 2015 | pmid = 26274974 | pmc = 4549740 | doi = 10.3390/toxins7083057 | doi-access = free }}</ref> Although mycoestrogens are rarely taken into account in discussions about phytoestrogens, these are the compounds that initially generated the interest on the topic.<ref>{{cite book | last = Naz| first =  Rajesh K. | name-list-style = vanc | title = Endocrine Disruptors: Effects on Male and Female Reproductive Systems| publisher = CRC Press Inc | year = 1999 | isbn  = 978-0-8493-3164-0| page = 90 }}</ref>

== Mechanism of action ==
Phytoestrogens exert their effects primarily through binding to [[estrogen receptor]]s (ER).<ref name="pmid17518366">{{cite journal | vauthors = Turner JV, Agatonovic-Kustrin S, Glass BD | title = Molecular aspects of phytoestrogen selective binding at estrogen receptors | journal = Journal of Pharmaceutical Sciences | volume = 96 | issue = 8 | pages = 1879–85 | date = Aug 2007 | pmid = 17518366 | doi = 10.1002/jps.20987 }}</ref>  There are two variants of the estrogen receptor, alpha ([[estrogen receptor alpha|ER-α]]) and beta ([[estrogen receptor beta|ER-β]]) and many phytoestrogens display somewhat higher [[Ligand (biochemistry)#Receptor/ligand binding affinity|affinity]] for ER-β compared to ER-α.<ref name="pmid17518366"/>

The key structural elements that enable phytoestrogens to bind with high affinity to estrogen receptors and display estradiol-like effects are:<ref name= "Yil"/>
* The phenolic ring that is indispensable for binding to estrogen receptor
* The ring of isoflavones mimicking a ring of estrogens at the receptors binding site
* Low molecular weight similar to estrogens (MW=272)
* Distance between two hydroxyl groups at the isoflavones nucleus similar to that occurring in estradiol
* Optimal hydroxylation pattern

In addition to interaction with ERs, phytoestrogens may also modulate the concentration of endogenous estrogens by binding or inactivating some enzymes, and may affect the bioavailability of sex hormones by depressing or stimulating the synthesis of sex hormone-binding globulin (SHBG).<ref name= "Jon"/>

Emerging evidence shows that some phytoestrogens bind to and transactivate [[peroxisome proliferator-activated receptor]]s (PPARs).<ref name="pmid15922618">{{cite journal | vauthors = Dang ZC, Lowik C | title = Dose-dependent effects of phytoestrogens on bone | journal = Trends in Endocrinology and Metabolism | volume = 16 | issue = 5 | pages = 207–13 | date = Jul 2005 | pmid = 15922618 | doi = 10.1016/j.tem.2005.05.001 | s2cid = 35366615 }}</ref><ref name="pmid19207876">{{cite journal | vauthors = Dang ZC | title = Dose-dependent effects of soy phyto-oestrogen genistein on adipocytes: mechanisms of action | journal = Obesity Reviews | volume = 10 | issue = 3 | pages = 342–9 | date = May 2009 | pmid = 19207876 | doi = 10.1111/j.1467-789X.2008.00554.x | s2cid = 13804244 }}</ref> In vitro studies show an activation of PPARs at concentrations above 1 μM, which is higher than the activation level of ERs.<ref name="pmid12421816">{{cite journal | vauthors = Dang ZC, Audinot V, Papapoulos SE, Boutin JA, Löwik CW | title = Peroxisome proliferator-activated receptor gamma (PPARgamma ) as a molecular target for the soy phytoestrogen genistein | journal = The Journal of Biological Chemistry | volume = 278 | issue = 2 | pages = 962–7 | date = Jan 2003 | pmid = 12421816 | doi = 10.1074/jbc.M209483200 | doi-access = free }}</ref><ref name="pmid15068509">{{cite journal | vauthors = Dang Z, Löwik CW | title = The balance between concurrent activation of ERs and PPARs determines daidzein-induced osteogenesis and adipogenesis | journal = Journal of Bone and Mineral Research | volume = 19 | issue = 5 | pages = 853–61 | date = May 2004 | pmid = 15068509 | doi = 10.1359/jbmr.040120 | doi-access = free }}</ref> At the concentration below 1 μM, activation of ERs may play a dominant role. At higher concentrations (>1 μM), both ERs and PPARs are activated. Studies have shown that both ERs and PPARs influence each other and therefore induce differential effects in a dose-dependent way. The final biological effects of [[genistein]] are determined by the balance among these pleiotrophic actions.<ref name="pmid15922618"/><ref name="pmid19207876"/><ref name="pmid12421816"/>

{{Affinities of estrogen receptor ligands for the ERα and ERβ}}

== Ecology ==

Phytoestrogens are involved in the synthesis of antifungal [[benzofuran]]s and [[phytoalexin]]s, such as [[medicarpin]] (common in [[legume]]s), and [[sesquiterpene]]s, such as [[capsidiol]] in tobacco.<ref>{{cite book | first1 = Richard C. | last1 = Leegood | first2 = Per | last2 = Lea | name-list-style = vanc | title = Plant Biochemistry and Molecular Biology| publisher = John Wiley & Sons | year = 1998 | isbn = 978-0-471-97683-7| pages = 204,211–213 }}</ref> Soybeans naturally produce isoflavones, and are therefore a dietary source for isoflavones.

Phytoestrogens are ancient naturally occurring substances, and as dietary phytochemicals they are considered to have coevolved with mammals. In the human diet, phytoestrogens are not the only source of exogenous estrogens. [[Xenoestrogens]] (novel, man-made), are found as [[food additive]]s<ref name="pmid19063592">{{cite journal | vauthors = Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P | title = Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach | journal = Chem. Res. Toxicol. | volume = 22 | issue = 1 | pages = 52–63 | year = 2009 | pmid = 19063592 | pmc = 2758355 | doi = 10.1021/tx800048m }}</ref> and ingredients, and also in cosmetics, plastics, and insecticides.  Environmentally, they have similar effects as phytoestrogens, making it difficult to clearly separate the action of these two kind of agents in studies.<ref name= "Repro">{{cite book | last = Korach | first = Kenneth S. | name-list-style = vanc | title = Reproductive and Developmental Toxicology | publisher = Marcel Dekker Ltd | year  =1998 | pages =  278–279| isbn = 978-0-8247-9857-4 }}</ref>

==Avian studies==
The consumption of plants with unusual content of phytoestrogens, under drought conditions, has been shown to decrease fertility in [[quail]].<ref name="pmid1246602">{{cite journal | vauthors = Leopold AS, Erwin M, Oh J, Browning B | title = Phytoestrogens: adverse effects on reproduction in California quail | journal = Science | volume = 191 | issue = 4222 | pages = 98–100 | date = January 1976 | pmid = 1246602 | doi = 10.1126/science.1246602 | bibcode = 1976Sci...191...98S }}</ref> [[Parrot]] food as available in nature has shown only weak estrogenic activity. Studies have been conducted on screening methods for environmental estrogens present in manufactured supplementary food, with the purpose of aiding reproduction of endangered species.<ref name="pmid11302429">{{cite journal | vauthors = Fidler AE, Zwart S, Pharis RP, Weston RJ, Lawrence SB, Jansen P, Elliott G, Merton DV | title = Screening the foods of an endangered parrot, the kakapo (Strigops habroptilus), for oestrogenic activity using a recombinant yeast bioassay | journal = Reproduction, Fertility, and Development | volume = 12 | issue = 3–4 | pages = 191–9 | year = 2000 | pmid = 11302429 | doi = 10.1071/RD00041 }}</ref>

== Food sources ==

According to one study of nine common phytoestrogens in a Western diet, foods with the highest relative phytoestrogen content were nuts and oilseeds, followed by soy products, cereals and breads, [[legume]]s, meat products, and other processed foods that may contain soy, vegetables, fruits, alcoholic, and nonalcoholic beverages. [[Flax]] seed and other oilseeds contained the highest total phytoestrogen content, followed by soybeans and [[tofu]].<ref>{{cite journal | vauthors = Thompson LU, Boucher BA, Liu Z, Cotterchio M, Kreiger N | title = Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan | journal = Nutrition and Cancer | volume = 54 | issue = 2 | pages = 184–201 | year = 2006 | pmid = 16898863 | doi = 10.1207/s15327914nc5402_5 | s2cid = 60328 }}</ref> The highest concentrations of isoflavones are found in soybeans and soybean products followed by legumes, whereas lignans are the primary source of phytoestrogens found in nuts and oilseeds (e.g. flax) and also found in cereals, legumes, fruits and vegetables. Phytoestrogen content varies in different foods, and may vary significantly within the same group of foods (e.g. soy beverages, tofu) depending on processing mechanisms and type of soybean used. Legumes (in particular soybeans), whole grain cereals, and some seeds are high in phytoestrogens.

A more comprehensive list of foods known to contain phytoestrogens includes:
{{div col|colwidth=20em}}
* [[Soybean]]s and soy products
* [[Tempeh]]
* [[Flax|Linseed]] (flax)
* [[Sesame seeds]]
* [[Wheat berry|Wheat berries]]
* [[Fenugreek]] (contains [[diosgenin]], but also used to make [[Testofen]], a compound taken by men to increase testosterone).
* [[Oat]]s
* [[Barley]]
* [[Bean]]s
* [[Lentil]]s
* [[Yam (vegetable)|Yams]]
* [[Rice]]
* [[Alfalfa]]
* [[Mung bean]]s
* [[Apple]]s
* [[Carrot]]s
* [[Pomegranate]]s<ref name="pmid14732284">{{cite journal | vauthors = van Elswijk DA, Schobel UP, Lansky EP, Irth H, van der Greef J | title = Rapid dereplication of estrogenic compounds in pomegranate (Punica granatum) using on-line biochemical detection coupled to mass spectrometry | journal = Phytochemistry | volume = 65 | issue = 2 | pages = 233–41 | date = Jan 2004 | pmid = 14732284 | doi = 10.1016/j.phytochem.2003.07.001 | bibcode = 2004PChem..65..233V }}</ref>
* [[Wheat germ]]
* [[Rice bran]]
* [[Lupin]]
* [[Kudzu]]
* [[Coffee]]
* [[Licorice root]]
* [[Mentha|Mint]]
* [[Ginseng]]
* [[Hops]],<ref name="pmid15620245">{{cite journal | vauthors = Chadwick LR, Nikolic D, Burdette JE, Overk CR, Bolton JL, van Breemen RB, Fröhlich R, Fong HH, Farnsworth NR, Pauli GF | title = Estrogens and congeners from spent hops (Humulus lupulus) | journal = Journal of Natural Products | volume = 67 | issue = 12 | pages = 2024–32 | date = Dec 2004 | pmid = 15620245 | doi = 10.1021/np049783i | pmc = 7418824 }}</ref>
* [[Bourbon whiskey]]
* [[Beer]],<ref name="pmid8116832">{{cite journal | vauthors = Rosenblum ER, Stauber RE, Van Thiel DH, Campbell IM, Gavaler JS | title = Assessment of the estrogenic activity of phytoestrogens isolated from bourbon and beer | journal = Alcoholism: Clinical and Experimental Research | volume = 17 | issue = 6 | pages = 1207–9 | date = Dec 1993 | pmid = 8116832 | doi = 10.1111/j.1530-0277.1993.tb05230.x }}</ref>
* [[Fennel]]
* [[Anise]].<ref name= "fen">{{cite journal | vauthors = Albert-Puleo M | title = Fennel and anise as estrogenic agents | journal = Journal of Ethnopharmacology | volume = 2 | issue = 4 | pages = 337–44 | date = Dec 1980 | pmid = 6999244 | doi = 10.1016/S0378-8741(80)81015-4 }}</ref>
* [[Red clover]] (sometimes a constituent of [[green manure]]).
* [[Spinach]]<ref>{{Cite journal|last1=Bacciottini|first1=Lucia|last2=Falchetti|first2=Alberto|last3=Pampaloni|first3=Barbara|last4=Bartolini|first4=Elisa|last5=Carossino|first5=Anna Maria|last6=Brandi|first6=Maria Luisa|date=2007|title=Phytoestrogens: food or drug?|journal=Clinical Cases in Mineral and Bone Metabolism|volume=4|issue=2|pages=123–130|issn=1724-8914|pmc=2781234|pmid=22461212}}</ref>
{{Div col end}}
* [[Lavender]]<ref>{{cite journal |last1=Ramsey |first1=Tyler |last2=Li |first2=Yin |last3=Yukitomo |first3=Arao |title=Lavender Products Associated With Premature Thelarche and Prepubertal Gynecomastia: Case Reports and Endocrine-Disrupting Chemical Activities |journal=J Clin Endocrinol Metab |date=Nov 1, 2019 |volume=104 |issue=11 |pages=5393–5405 |doi=10.1210/jc.2018-01880 |pmid=31393563 |pmc=6773459 }}</ref>

Food content of phytoestrogens is very variable and accurate estimates of intake are therefore difficult and depends on the databases used.<ref>{{Cite journal |last1=Kuhnle |first1=Gunter G.C. |last2=Dell’Aquila |first2=Caterina |last3=Runswick |first3=Shirley A. |last4=Bingham |first4=Sheila A. |date=2008 |title=Variability of phytoestrogen content in foods from different sources |url=https://linkinghub.elsevier.com/retrieve/pii/S0308814608009679 |journal=Food Chemistry |language=en |volume=113 |issue=4 |pages=1184–1187 |doi=10.1016/j.foodchem.2008.08.004}}</ref>  Data from the [[European Prospective Investigation into Cancer and Nutrition]] found intakes between 1&nbsp;mg/d in [[Mediterranean Countries]] and more than 20&nbsp;mg/d in the [[United Kingdom]].<ref>{{Cite journal |last1=Zamora-Ros |first1=R |last2=Knaze |first2=V |last3=Luján-Barroso |first3=L |last4=Kuhnle |first4=G G C |last5=Mulligan |first5=A A |last6=Touillaud |first6=M |last7=Slimani |first7=N |last8=Romieu |first8=I |last9=Powell |first9=N |last10=Tumino |first10=R |last11=Peeters |first11=P H M |last12=de Magistris |first12=M S |last13=Ricceri |first13=F |last14=Sonestedt |first14=E |last15=Drake |first15=I |date=2012 |title=Dietary intakes and food sources of phytoestrogens in the European Prospective Investigation into Cancer and Nutrition (EPIC) 24-hour dietary recall cohort |journal=European Journal of Clinical Nutrition |language=en |volume=66 |issue=8 |pages=932–941 |doi=10.1038/ejcn.2012.36 |pmid=22510793 |s2cid=24241153 |issn=0954-3007|doi-access=free }}</ref> The high intake in the UK is partly explained by the use of soy in the [[Chorleywood bread process]].<ref>{{Cite book |last=Cauvain |first=Stanley P. |url=https://www.worldcat.org/oclc/236341936 |title=The Chorleywood bread process |date=2006 |publisher=CRC Press |others=Linda S. Young |isbn=1-84569-143-1 |location=Boca Raton, FL |oclc=236341936}}</ref> A 2001 epidemiological study of women in the United States found that the dietary intake of phytoestrogens in healthy post-menopausal Caucasian women is less than one milligram daily.<ref name="pmid11385074">{{cite journal | vauthors = de Kleijn MJ, van der Schouw YT, Wilson PW, Adlercreutz H, Mazur W, Grobbee DE, Jacques PF | title = Intake of dietary phytoestrogens is low in postmenopausal women in the United States: the Framingham study(1-4) | journal = The Journal of Nutrition | volume = 131 | issue = 6 | pages = 1826–32 | date = Jun 2001 | pmid = 11385074 | doi =  10.1093/jn/131.6.1826| url = http://jn.nutrition.org/cgi/content/abstract/131/6/1826 | doi-access = free }}</ref>

== Effects on humans ==
<!-- "Isoflavones" links here -->{{Self-contradictory|about=whether humans are affected by phytoestrogens.|date=May 2023}}

In humans, phytoestrogens are digested in the small intestine, poorly absorbed into the circulatory system, circulate in plasma, and are excreted in the urine. Metabolic influence is different from that of grazing animals due to the differences between ruminant versus monogastric digestive systems.<ref name= "Repro"/>

As of 2020, there is insufficient [[evidence-based medicine|clinical evidence]] to determine that phytoestrogens have effects in humans.<ref>{{Cite journal |last1=Domínguez-López |first1=Inés |last2=Yago-Aragón |first2=Maria |last3=Salas-Huetos |first3=Albert |last4=Tresserra-Rimbau |first4=Anna |last5=Hurtado-Barroso |first5=Sara |date=August 2020 |title=Effects of Dietary Phytoestrogens on Hormones throughout a Human Lifespan: A Review |journal=Nutrients |language=en |volume=12 |issue=8 |pages=2456 |doi=10.3390/nu12082456 |pmid=32824177 |pmc=7468963 |issn=2072-6643 |doi-access=free }}</ref>

=== Females ===

It is unclear if phytoestrogens have any effect on the cause or prevention of cancer in women.<ref name=lpi/><ref name="bilal">{{cite journal | vauthors = Bilal I, Chowdhury A, Davidson J, Whitehead S | title = Phytoestrogens and prevention of breast cancer: The contentious debate | journal = World Journal of Clinical Oncology | volume = 5 | issue = 4 | pages = 705–12 | year = 2014 | pmid = 25302172 | pmc = 4129534 | doi = 10.5306/wjco.v5.i4.705 | doi-access = free }}</ref> Some epidemiological studies have suggested a protective effect against breast cancer.<ref name=lpi/><ref name=bilal/><ref name="pmid9329514">{{cite journal | vauthors = Ingram D, Sanders K, Kolybaba M, Lopez D | title = Case-control study of phyto-oestrogens and breast cancer | journal = Lancet | volume = 350 | issue = 9083 | pages = 990–4 | date = Oct 1997 | pmid = 9329514 | doi = 10.1016/S0140-6736(97)01339-1 | s2cid = 12158051 }}</ref> Additionally, other [[epidemiology|epidemiological]] studies found that consumption of soy estrogens is safe for patients with breast cancer, and that it may decrease mortality and recurrence rates.<ref name=lpi/><ref name="pmid19996398">{{cite journal | vauthors = Shu XO, Zheng Y, Cai H, Gu K, Chen Z, Zheng W, Lu W | title = Soy food intake and breast cancer survival | journal = JAMA | volume = 302 | issue = 22 | pages = 2437–43 | date = Dec 2009 | pmid = 19996398 | pmc = 2874068 | doi = 10.1001/jama.2009.1783 }}</ref><ref name="fritz">{{cite journal|vauthors=Fritz H, Seely D, Flower G, Skidmore B, Fernandes R, Vadeboncoeur S, Kennedy D, Cooley K, Wong R, Sagar S, Sabri E, Fergusson D|title=Soy, red clover, and isoflavones and breast cancer: a systematic review|journal=PLOS ONE|date=2013|volume=8|issue=11|page=e81968|doi=10.1371/journal.pone.0081968|pmid=24312387|pmc=3842968|bibcode=2013PLoSO...881968F|doi-access=free}}</ref> It remains unclear if phytoestrogens can minimize some of the deleterious effects of low estrogen levels ([[hypoestrogenism]]) resulting from [[oophorectomy]], [[menopause]], or other causes.<ref name=bilal/> A [[Cochrane Library|Cochrane review]] of the use of phytoestrogens to relieve the vasomotor symptoms of menopause ([[hot flash]]es) stated that there was no conclusive evidence to suggest any benefit to their use, although [[genistein]] effects should be further investigated.<ref name="Lethaby_2013">{{cite journal | vauthors = Lethaby A, Marjoribanks J, Kronenberg F, Roberts H, Eden J, Brown J | title = Phytoestrogens for menopausal vasomotor symptoms | journal = The Cochrane Database of Systematic Reviews | issue = 12 | pages = CD001395 | year = 2013 | volume = 2013 | pmid = 24323914 | doi = 10.1002/14651858.CD001395.pub4 | pmc = 10247921 }}</ref>

=== Males ===

It is unclear if phytoestrogens have any effect on male sexuality, with conflicting results about the potential effects of isoflavones originating from soy.<ref name=lpi/> Some studies showed that isoflavone supplementation had a positive effect on sperm concentration, count, or [[motility]], and increased ejaculate volume.<ref name= "tox">{{cite book | last = Dabrowski| first = Waldemar M. | name-list-style = vanc | title = Toxins in Food | publisher = CRC Press Inc | year = 2004 | isbn = 978-0-8493-1904-4 | page = 95 }}</ref><ref name="pmid11352776">{{cite journal | vauthors = Mitchell JH, Cawood E, Kinniburgh D, Provan A, Collins AR, Irvine DS | title = Effect of a phytoestrogen food supplement on reproductive health in normal males | journal = Clinical Science | volume = 100 | issue = 6 | pages = 613–8 | date = Jun 2001 | pmid = 11352776 | doi = 10.1042/CS20000212 | url = http://www.clinsci.org/content/100/6/613 }}</ref> Sperm count decline and increasing rate of testicular cancers in the West may be linked to a higher presence of isoflavone phytoestrogens in the diet while in utero, but such a link has not been definitively proven.<ref name="pmid20347861">{{cite journal | vauthors = Patisaul HB, Jefferson W | title = The pros and cons of phytoestrogens | journal = Frontiers in Neuroendocrinology | volume = 31 | issue = 4 | pages = 400–19 | year = 2010 | pmid = 20347861 | pmc = 3074428 | doi = 10.1016/j.yfrne.2010.03.003 }}</ref> Furthermore, while there is some evidence that phytoestrogens may affect male fertility, more recent reviews of available studies found no link,<ref name=":0">{{Cite journal|last1=Messina|first1=Mark|last2=Mejia|first2=Sonia Blanco|last3=Cassidy|first3=Aedin|last4=Duncan|first4=Alison|last5=Kurzer|first5=Mindy|last6=Nagato|first6=Chisato|last7=Ronis|first7=Martin|last8=Rowland|first8=Ian|last9=Sievenpiper|first9=John|last10=Barnes|first10=Stephen|date=2021-03-27|title=Neither soyfoods nor isoflavones warrant classification as endocrine disruptors: a technical review of the observational and clinical data|journal=Critical Reviews in Food Science and Nutrition|volume=62 |issue=21 |pages=5824–5885|doi=10.1080/10408398.2021.1895054|issn=1040-8398|pmid=33775173|s2cid=232408113|doi-access=free}}</ref><ref name=":1">{{Cite journal|last1=Nassan|first1=Feiby L.|last2=Chavarro|first2=Jorge E.|last3=Tanrikut|first3=Cigdem|date=2018-09-01|title=Diet and men's fertility: does diet affect sperm quality?|url=https://www.fertstert.org/article/S0015-0282(18)30426-6/abstract|journal=Fertility and Sterility|language=English|volume=110|issue=4|pages=570–577|doi=10.1016/j.fertnstert.2018.05.025|issn=0015-0282|pmid=30196939|s2cid=52179133|doi-access=free}}</ref> and instead suggests that healthier diets such as the [[Mediterranean diet]] might have a positive effect on male fertility.<ref name=":1" /> Neither isoflavones nor soy have been shown to affect male reproductive hormones in healthy individuals.<ref name=":0" /><ref name="pmid33383165">{{cite journal | vauthors=Reed KE, Camargo J, Messina M| title=Neither soy nor isoflavone intake affects male reproductive hormones: An expanded and updated meta-analysis of clinical studies | journal=Reproductive Toxicology | volume=100 | pages=60–67 | year=2020 | doi=10.1016/j.reprotox.2020.12.019 | pmid=33383165| doi-access=free }}</ref>

=== Infant formula ===

Some studies have found that some concentrations of isoflavones may have effects on intestinal cells. At low doses, genistein acted as a weak estrogen and stimulated cell growth; at high doses, it inhibited proliferation and altered cell cycle dynamics. This biphasic response correlates with how genistein is thought to exert its effects.<ref name="pmid15173388">{{cite journal | vauthors = Chen AC, Donovan SM | title = Genistein at a concentration present in soy infant formula inhibits Caco-2BBe cell proliferation by causing G2/M cell cycle arrest | journal = The Journal of Nutrition | volume = 134 | issue = 6 | pages = 1303–8 | date = Jun 2004 | pmid = 15173388 | doi =  10.1093/jn/134.6.1303| doi-access = free }}</ref>
Some reviews express the opinion that more research is needed to answer the question of what effect phytoestrogens may have on infants,<ref name="pmid14599051">{{cite journal | vauthors = Miniello VL, Moro GE, Tarantino M, Natile M, Granieri L, Armenio L | title = Soy-based formulas and phyto-oestrogens: a safety profile | journal = Acta Paediatrica | volume = 91 | issue = 441 | pages = 93–100 | date = Sep 2003 | pmid = 14599051 | doi = 10.1111/j.1651-2227.2003.tb00655.x | s2cid = 25762109 }}</ref><ref name="pmid15189112">{{cite journal | vauthors = Chen A, Rogan WJ | title = Isoflavones in soy infant formula: a review of evidence for endocrine and other activity in infants | journal = Annual Review of Nutrition | volume = 24 | issue = 1 | pages = 33–54 | year = 2004 | pmid = 15189112 | doi = 10.1146/annurev.nutr.24.101603.064950 | url = https://zenodo.org/record/1235043 }}</ref> but their authors did not find any adverse effects. Studies conclude there are no adverse effects in human growth, development, or reproduction as a result of the consumption of soy-based infant formula compared to conventional cow-milk formula.<ref name="pmid11497534">{{cite journal | vauthors = Strom BL, Schinnar R, Ziegler EE, Barnhart KT, Sammel MD, Macones GA, Stallings VA, Drulis JM, Nelson SE, Hanson SA | title = Exposure to soy-based formula in infancy and endocrinological and reproductive outcomes in young adulthood | journal = JAMA | volume = 286 | issue = 7 | pages = 807–14 | date = Aug 2001 | pmid = 11497534 | doi = 10.1001/jama.286.7.807 | doi-access = free }}</ref><ref name="pmid15055353">{{cite journal | vauthors = Giampietro PG, Bruno G, Furcolo G, Casati A, Brunetti E, Spadoni GL, Galli E | title = Soy protein formulas in children: no hormonal effects in long-term feeding | journal = Journal of Pediatric Endocrinology & Metabolism | volume = 17 | issue = 2 | pages = 191–6 | date = Feb 2004 | pmid = 15055353 | doi = 10.1515/JPEM.2004.17.2.191 | s2cid = 43304969 }}</ref><ref name= "Nutri">{{cite journal | vauthors = Merritt RJ, Jenks BH | title = Safety of soy-based infant formulas containing isoflavones: the clinical evidence | journal = The Journal of Nutrition | volume = 134 | issue = 5 | pages = 1220S–1224S | date = May 2004 | pmid = 15113975 | doi =  10.1093/jn/134.5.1220S| doi-access = free }}</ref> The [[American Academy of Pediatrics]] states: "although isolated soy protein-based formulas may be used to provide nutrition for normal growth and development, there are few indications for their use in place of cow milk-based formula. These indications include (a) for infants with galactosemia and hereditary lactase deficiency (rare) and (b) in situations in which a vegetarian diet is preferred."<ref name="pmid18450914">{{cite journal | vauthors = Bhatia J, Greer F | title = Use of soy protein-based formulas in infant feeding | journal = Pediatrics | volume = 121 | issue = 5 | pages = 1062–8 | date = May 2008 | pmid = 18450914 | doi = 10.1542/peds.2008-0564 | s2cid = 1482728 | url = http://pediatrics.aappublications.org/cgi/pmidlookup?view=long&pmid=18450914 | doi-access =  }}</ref>

==Ethnopharmacology==

In some countries, phytoestrogenic plants have been used for centuries in the treatment of menstrual and menopausal problems, as well as for fertility problems.<ref>{{cite book |last=Muller-Schwarze |first=Dietland |title=Chemical Ecology of Vertebrates |publisher=Cambridge University Press |year=2006 |isbn=978-0-521-36377-8 |page=287 |name-list-style=vanc}}</ref> Plants used that have been shown to contain phytoestrogens include ''[[Pueraria mirifica]]''<ref name="pmid12819377">{{cite journal |vauthors=Lee YS, Park JS, Cho SD, Son JK, Cherdshewasart W, Kang KS |title=Requirement of metabolic activation for estrogenic activity of Pueraria mirifica |journal=Journal of Veterinary Science |volume=3 |issue=4 |pages=273–277 |date=Dec 2002 |pmid=12819377 |doi=10.4142/jvs.2002.3.4.273 |df=dmy-all|doi-access=free }}</ref> and its close relative [[kudzu]],<ref name="pmid16915857">{{cite journal |vauthors=Delmonte P, Rader JI |title=Analysis of isoflavones in foods and dietary supplements |journal=Journal of AOAC International |volume=89 |issue=4 |pages=1138–1146 |year=2006 |doi=10.1093/jaoac/89.4.1138 |pmid=16915857|doi-access=free }}</ref> [[Angelica]],<ref>{{cite book |first1=D.E. |last1=Brown |first2=N.J. |last2=Walton |name-list-style=vanc |title=Chemicals from plants: Perspectives on plant secondary products |publisher=World Scientific Publishing |year=1999 |pages=21, 141 |isbn=978-981-02-2773-9}}</ref> [[fennel]],<ref name= "fen"/> and [[anise]].
In a rigorous study, the use of one such source of phytoestrogen, [[Trifolium pratense|red clover]], has been shown to be safe, but ineffective in relieving menopausal symptoms<ref name="pmid19609225">{{cite journal |vauthors=Geller SE, Shulman LP, van Breemen RB, Banuvar S, Zhou Y, Epstein G, Hedayat S, Nikolic D, Krause EC, Piersen CE, Bolton JL, Pauli GF, Farnsworth NR |title=Safety and efficacy of black cohosh and red clover for the management of vasomotor symptoms: A randomized controlled trial |journal=Menopause |volume=16 |issue=6 |pages=1156–1166 |year=2009 |pmid=19609225 |pmc=2783540 |doi=10.1097/gme.0b013e3181ace49b }}</ref> ([[Actaea racemosa|black cohosh]] is also used for menopausal symptoms, but does not contain phytoestrogens<ref name="pmid12222669">{{cite journal |vauthors=Kennelly EJ, Baggett S, Nuntanakorn P, Ososki AL, Mori SA, Duke J, Coleton M, Kronenberg F |title=Analysis of thirteen populations of black cohosh for formononetin |journal=Phytomedicine |volume=9 |issue=5 |pages=461–467 |date=Jul 2002 |pmid=12222669 |doi=10.1078/09447110260571733 |s2cid=24786174 }}</ref>).

== See also ==
{{div col|colwidth=20em}}
* [[Ethnopharmacology]]
* [[Isoflavones]]
* [[Lignan]]
* [[Mycoestrogens]]
* [[Phytoandrogens]]
* [[Plant hormone]]
* [[Soy]]
{{div col end}}

== References ==
{{Reflist}}

{{Xenoestrogens}}
{{Estrogenics}}

[[Category:Phytoestrogens]]
[[Category:Phytochemicals]]
[[Category:Endocrinology]]
[[Category:Estrogens]]
[[Category:Nutrients]]
[[Category:Nutrition]]
[[Category:Endocrine disruptors]]

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