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).
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.
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.
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