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Published by Deepankar Srigyan

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Published by: Deepankar Srigyan on Apr 07, 2010
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, sometimes called "dietary estrogens", are a diverse group of naturally occurringnonsteroidal plant compounds that, because of their structural similarity withestradiol(17-β-estradiol), have the ability to causeestrogenicor/and antiestrogenic effects.
Chemical structures of the most common phytoestrogens found in plants (top and middle)compared with estrogen (bottom) found in animals.Their name comes from
= plant and
= estrus (period of fertility for femalemammals) +
= to generate.The similarities, at molecular level, of estrogens and phytoestrogens allow them to mildly mimic and sometimes act as antagonists of  estrogen
 . Phytoestrogens were first observed in 1926
,  but it was unknown if they could have any effect in human or animal metabolism. In the 1940s itwas noticed for the first time thatred clover (a phytoestrogens-rich plant) pastures had effects onthe fertility of grazing sheep.
 Researchers are exploring the nutritionalrole of these substances in the regulation of cholesterol, and the maintenance of proper bone density post-menopause. Evidence is accruing that phytoestrogens may have protective action against diversehealth disorders, such as prostate,  breast, bowel,and other cancers, cardiovascular  disease, brain  function disorders andosteoporosis,
though there is no evidence to support their use inalleviating the symptoms of menopause.
Phytoestrogens cannot be considered as nutrients, given that the lack of these in diet does not produce any characteristic deficiency syndrome, nor do they participate in any essential biological function.
ACOTdraft report from the UK Food Standards Agencypresents an update of methods for a more accurate analysis of phytoestrogen content in plants and food, concluding that research inrecent years is more reliable than previous studies.
[edit] Structure
Phytoestrogens mainly belong to a large group of substituted polyphenoliccompounds : thecoumestans, prenylated flavonoids andisoflavones are three of the most active in estrogenic effects in this class. The best-researched are isoflavones, which are commonly found insoyandred clover . Lignanshave also been identified as phytoestrogens, although they are not flavonoids
.Mycoestrogenshave similar structures and effects, but are not components of  plants; these are mold metabolites of 
, a fungus that is frequently found in pastures aswell as inalfalfaand clover. Although mycoestrogens are rarely taken into account indiscussions about phytoestrogens, these are the compounds that initially generated the interest onthe topic.
[edit] Mechanism of action
Phytoestrogens exert their effects primarily through binding toestrogen receptors(ER).
Thereare two variants of the estrogen receptor, alpha (ER-α) and beta (ER-β) and many phytoestrogens display somewhat higher affinity for ER-β compared to ER-α.
The key structural elements that enable phytoestrogens to bind with high affinity to estrogenreceptors and display estradiol-like effects are:
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 thatoccurring in estradiol
Optimal hydroxylation patternIn 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 binding or stimulating the synthesis of sex hormone bindingglobuline (SHBG).
[edit] Ecology
These compounds in plants are an important part of their defense system, mainly against fungi.
Phytoestrogens are considered archiestrogens (ancient, naturally occurring) 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 asfood additives 
and ingredients, and also in cosmetics, plastics, andinsecticides. Environmentally, they have similar effects as phytoestrogens, making it difficult toclearly separate the action of these two kind of agents in studies done on populations.
[edit] Avian studies
The consumption of plants with unusual content of phytoestrogens under drought conditions, has been shown to decrease fertility in quail.
Parrot food as available in nature has shown onlyweak estrogenic activity. Studies have been conducted on screening methods for environmentalestrogens present in manufactured supplementary food, with the purpose to enable reproductionof endangered species.
[edit] Food sources
According to a study by Canadian researchers about the content of nine common phytoestrogensin 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 andtofu.
The highest concentrations of isoflavones are found in soybeans and soybean productsfollowed by legumes, whereas lignans are the primary source of phytoestrogens found in nutsand 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 samegroup 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 highin phytoestrogens. A more comprehensive list of foods known to contain phytoestrogens

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