Phytoestrogen

A phytoestrogen is a plant-derived xenoestrogen (see estrogen) not generated within the endocrine system, but consumed by eating
phytoestrogenic plants. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds
that, because of its structural similarity with estradiol (17-β-estradiol), have the ability to cause estrogenic and/or antiestrogenic
effects.[1] Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known
to participate in any normal biological function.[1]

Its name comes from the 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
.[2][3]
a phytoestrogen as part of their natural defence against the overpopulation of herbivore animals by controlling female fertility

The similarities, at molecular level, of a estrogen and a phytoestrogen allow them to mildly mimic and sometimes act as a antagonist
of estrogen.[1] Phytoestrogens were first observed in 1926,[1][4] 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.[1][5][6][7]

Contents
Structure
Mechanism of action
Ecology
Avian studies
Food sources
Effects on humans
Males
Females
Infant formula
Ethnopharmacology
See also
External links Chemical structures of the most common phytoestrogens found in
References plants (top and middle) compared with estrogen (bottom) found in
animals.

Structure
Phytoestrogens mainly belong to a large group of substituted natural phenolic compounds: the coumestans, prenylflavonoids and
isoflavones are three of the most active in estrogenic effects in this class. The best-researched are isoflavones, which are commonly
found in soy and red clover. Lignans have also been identified as phytoestrogens, although they are not flavonoids.[1] Mycoestrogens
have similar structures and effects, but are not components of plants; these are mold metabolites of Fusarium, especially common on
cereal grains,[8][9][10] but also occurring elsewhere, e.g. on various forages.
[11] Although mycoestrogens are rarely taken into account
[12]
in discussions about phytoestrogens, these are the compounds that initially generated the interest on the topic.

Mechanism of action
Phytoestrogens exert their effects primarily through binding to estrogen receptors (ER).[13] There are two variants of the estrogen
receptor, alpha (ER-α) and beta (ER-β) and many phytoestrogens display somewhat higheraffinity for ER-β compared to ER-α.[13]
The key structural elements that enable phytoestrogens to bind with high affinity to estrogen receptors and display estradiol-like
effects are:[1]

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).[7]

Emerging evidence shows that some phytoestrogens bind to and transactivate peroxisome proliferator-activated receptors
(PPARs).[14][15] In vitro studies show an activation of PPARs at concentrations above 1 μM, which is higher than the activation level
of ERs.[16][17] 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.[14][15][16]

Ecology
[18]
These compounds in plants are an important part of their defense system, mainly against fungi.

Phytoestrogens are ancient naturally occurring substances, and as dietary phytochemicals they are considered as co-evolutive with
mammals. In the human diet, phytoestrogens are not the only source of exogenous estrogens. Xenoestrogens (novel, man-made), are
found as food additives[19] 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 done on
populations.[20]

Avian studies
The consumption of plants with unusual content of phytoestrogens under drought conditions, has been shown to decrease fertility in
quail.[21] 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 to enable reproduction of
endangered species.[22]

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, legumes, 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.[23] 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:

Soybeans and soy products Sesame seeds

Tempeh Wheat berries
Linseed (flax)
 Fenugreek (contains diosgenin, but also used to make Rice bran
Testofen, a compound taken by men to increase Lupin
testosterone).
Kudzu
Oats
Coffee
Barley
Licorice root
Beans
Mint
Lentils
Ginseng
Yams
Hops,[25]
Rice
Bourbon whiskey
Alfalfa
Beer,[26]
Mung beans
Fennel
Apples
Carrots Anise.[27]
Red clover (sometimes a constituent ofgreen
Pomegranates[24]
manure).
Wheat germ
An epidemiological study of women in the United States found that the dietary intake of phytoestrogens in healthy post-menopausal
.[28]
Caucasian women is less than one milligram daily

Effects on humans
In human beings, phytoestrogens are readily 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.[20]

A wide range of beneficial effects of phytoestrogens on the cardiovascular, metabolic, central nervous systems as well as reduction of
risk of cancer and post menopausal symptoms have been claimed. However, there is also concern that phytoestrogens may act as
endocrine disruptors that adversely affect health. Based on currently available evidence, it is not clear whether the potential health
benefits of phytoestrogens outweigh their risks.[29]

Males
It is unclear if phytoestrogens have any effect on male sexuality, with conflicting results about the potential effects of isoflavones
originating from soy. A 2010 meta-analysis of fifteen placebo-controlled studies said that "neither soy foods nor isoflavone
supplements alter measures of bioavailable testosterone concentrations in men."[30] Some studies showed that isoflavone
supplementation had no effect on sperm concentration, count, or motility, and had no effects on testicular or ejaculate volume.[31][32]
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, but such a link has not been definitively proven.[33] Furthermore, there is some evidence that
[34]
phytoestrogens may affect male fertility, but "further investigation is needed before a firm conclusion can be drawn".

Females
It is unclear if phytoestrogens have any effect on the cause or prevention of cancer in females.[35] Some epidemiological studies have
suggested a protective effect against breast cancer.[35][36] Other epidemiological studies found that consumption of soy estrogens is
safe for patients with breast cancer, and that it may decrease mortality and recurrence rates.[37][38] It remains unclear if
phytoestrogens can minimize some of the deleterious effects of low estrogen levels (hypoestrogenism) resulting from oophorectomy,
menopause, or other causes.[35] A Cochrane Review of the use of phytoestrogens to relieve the vasomotor symptoms of menopause
(hot flashes) stated that there was no conclusive evidence to suggest any benefit to their use, although genistein effects should be
further investigated.[39]

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.[40] Some reviews express the opinion that more research is
needed to answer the question of what effect phytoestrogens may have on infants,[41][42] 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.[43][44][45] 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
[46]
hereditary lactase deficiency (rare) and (b) in situations in which a vegetarian diet is preferred."

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.[47] Plants used that have been shown to contain phytoestrogens include Pueraria mirifica,[48] and its
close relative, kudzu,[49] Angelica,[50] fennel and anise.[27] In a rigorous study, the use of one such source of phytoestrogen, red
clover, has been shown to be safe, but ineffective in relieving menopausal symptoms[51] (black cohosh is also used for menopausal
symptoms, but does not contain phytoestrogens.[52] ) Panax Ginseng contains phytoestrogens and has been used for menopausal
symptoms .

See also
Ethnopharmacology
Isoflavones
Lignan
Mycoestrogens
Phytoandrogens
Soy
Xenoestrogens

External links
Phytoestrogen food sources
Phytoestrogen content in food
Phytoestrogens at e.hormone, a website of the Tulane/Xavier Center for Bioenvironmental Research

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