Genistein (C₁₅H₁₀O₅) is a plant-derived,

aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...

isoflavone Isoflavones are a type of naturally-occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans. Although isoflavones and closely-related phytoestrogens ar ...

. Genistein has the highest content of all isoflavones in soybeans and soy products, such as

tempeh Tempe or tempeh (; , ) is a traditional Indonesian food made from fermented soybeans. It is made by a natural culturing and controlled fermentation process that binds soybeans into a cake form. A fungus, '' Rhizopus oligosporus'' or '' Rhizopu ...

. As a type of

phytoestrogen 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. Also called a "dietary estrogen", it ...

, genistein has estrogenic activity in vitro; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as the

uterus The uterus (from Latin ''uterus'', : uteri or uteruses) or womb () is the hollow organ, organ in the reproductive system of most female mammals, including humans, that accommodates the embryonic development, embryonic and prenatal development, f ...

and

breast The breasts are two prominences located on the upper ventral region of the torso among humans and other primates. Both sexes develop breasts from the same embryology, embryological tissues. The relative size and development of the breasts is ...

. It was first isolated in 1899 from the dyer's broom, ''Genista tinctoria''; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928. Genistein is a primary secondary metabolite of the ''

Trifolium Clovers, also called trefoils, are plants of the genus ''Trifolium'' (), consisting of about 300 species of flowering plants in the legume family Fabaceae originating in Europe. The genus has a cosmopolitan distribution with the highest diversity ...

'' species and '' Glycine max'' (soy).

Natural occurrences

Isoflavones, such as genistein and

daidzein Daidzein (7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one) is a naturally occurring compound found exclusively in soybeans and other legumes, and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones a ...

, occur in soybeans and various other plants, including

lupin ''Lupinus'', commonly known as lupin, lupine, or regionally bluebonnet, is a genus of plants in the legume family Fabaceae. The genus includes over 199 species, with centres of diversity in North and South America. Smaller centres occur in No ...

, fava beans,

kudzu Kudzu (), also called Japanese arrowroot or Chinese arrowroot, is a group of climbing, coiling, and trailing deciduous perennial vines native to much of East Asia, Southeast Asia, and some Pacific islands. It is invasive species, invasive in ...

, psoralea, '' Flemingia vestita'', and

coffee Coffee is a beverage brewed from roasted, ground coffee beans. Darkly colored, bitter, and slightly acidic, coffee has a stimulating effect on humans, primarily due to its caffeine content, but decaffeinated coffee is also commercially a ...

. It is present in

red clover ''Trifolium pratense'' (from Latin prātum, meaning meadow), red clover, is a herbaceous plant, herbaceous species of flowering plant in the bean family, Fabaceae. It is native to the Old World, but planted and naturalised in many other regions ...

In soybean products

Isoflavone intake from consuming soy products may be as high as 50 mg per day in Asian cuisines, although it is considerably lower in Western diets. Genistein has the highest percentage among isoflavones in various soy foods, such as protein concentrate, mature soybeans, and tempeh.

Dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

s and

infant formula Infant formula, also called baby formula, simply formula (American English), formula milk, baby milk, or infant milk (British English), is a manufactured food designed and marketed for feeding to babies and infants under 12 months of age, ...

s containing isoflavone

extract An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered. The aromatic principles of ma ...

s are marketed in some countries.

Metabolism, bioavailability, and safety

Pharmacokinetics Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to describing how the body affects a specific su ...

studies indicate that genistein blood concentrations peak about 6 hours after a meal containing isoflavones, which are hydrolized in the

small intestine The small intestine or small bowel is an organ (anatomy), organ in the human gastrointestinal tract, gastrointestinal tract where most of the #Absorption, absorption of nutrients from food takes place. It lies between the stomach and large intes ...

and colon. The colonic

microbiota Microbiota are the range of microorganisms that may be commensal, mutualistic, or pathogenic found in and on all multicellular organisms, including plants. Microbiota include bacteria, archaea, protists, fungi, and viruses, and have been found ...

during

digestion Digestion is the breakdown of large insoluble food compounds into small water-soluble components so that they can be absorbed into the blood plasma. In certain organisms, these smaller substances are absorbed through the small intestine into th ...

influences the

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

of genistein and other isoflavones, converting them to metabolites having potential biological effects, such as the extent of estrogenic activity. Although soy products are

generally recognized as safe Generally recognized as safe (GRAS) is a United States Food and Drug Administration (FDA) designation that a chemical or substance added to food is considered safe by experts under the conditions of its intended use. An ingredient with a GRAS d ...

(GRAS), a GRAS determination specifically for genistein has not been reported.

Potential for estrogenic activity

Because soy isoflavones have similar chemical structure to 17-β-estradiol, the potential for genistein as an estrogenic (

hormone A hormone (from the Ancient Greek, Greek participle , "setting in motion") is a class of cell signaling, signaling molecules in multicellular organisms that are sent to distant organs or tissues by complex biological processes to regulate physio ...

-like)

signaling molecule In biology, cell signaling (cell signalling in British English) is the Biological process, process by which a Cell (biology), cell interacts with itself, other cells, and the environment. Cell signaling is a fundamental property of all Cell (biol ...

that binds to estrogen receptors within cells, mimicking the action of

estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

, has been the subject of research. Estrogenic effects by genistein may affect the risk of hormone-associated cancers in reproductive tissues, such as the breast,

prostate gland The prostate is an male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found in all male mammals. It differs between species anatomically, chemica ...

, while it may also influence

bone density Bone density, or bone mineral density, is the amount of bone mineral in bone tissue. The concept is of mass of mineral per volume of bone (relating to density in the physics sense), although medicine#Clinical practice, clinically it is measured by ...

and levels of blood lipids.

Human research

Although the potential for genistein to have diverse biological activity in humans has been extensively studied, there is only limited evidence of its specific effects. In a 2011-12 analysis, a scientific panel for the

European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002 ...

found that there was no evidence for a cause-and-effect relationship between the consumption of genistein with other soy isoflavones and 1) protection of

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...

s and lipids from

oxidative Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

damage, 2) maintenance of normal blood LDL-cholesterol concentrations, 3) changes in vascular function associated with menopause, 4) normal hair growth or 5) bone mineral density. The panel further concluded that there was insufficient evidence that soy isoflavones could affect normal skin tone, respiratory functions, cardiovascular health, or prostate cancer. There is preliminary evidence that consuming soy foods rich in genistein and isoflavones may improve cardiovascular function in

postmenopausal Menopause, also known as the climacteric, is the time when menstrual periods permanently stop, marking the end of the reproductive stage for the female human. It typically occurs between the ages of 45 and 55, although the exact timing can ...

women and lower the risk of

breast cancer Breast cancer is a cancer that develops from breast tissue. Signs of breast cancer may include a Breast lump, lump in the breast, a change in breast shape, dimpling of the skin, Milk-rejection sign, milk rejection, fluid coming from the nipp ...

in premenopausal and postmenopausal women. Some studies indicate that supplementation with genistein and soy isoflavones may reduce

hot flash Hot flushes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from t ...

es and

night sweats Night sweats or nocturnal hyperhydrosis is the repeated occurrence of excessive sweating during sleep. The person may or may not also perspire excessively while awake. One of the most common causes of night sweats in women over 40 is the horm ...

during menopause, while there is insufficient evidence for an effect on

osteoporosis Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in Bone fracture, fracture risk. It is the most common reason f ...

and

cognitive function Cognitive skills are skills of the mind, as opposed to other types of skills such as motor skills, social skills or life skills. Some examples of cognitive skills are literacy, self-reflection, logical reasoning, abstract thinking, critical th ...

Laboratory research

In vitro, genistein is an

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

of the G protein-coupled estrogen receptor, and binds to and activates all three

peroxisome proliferator-activated receptor In the field of molecular biology, the peroxisome proliferator–activated receptors (PPARs) are a group of nuclear receptor proteins that function as transcription factors regulating gene expression. PPARs play essential roles in regulating cel ...

isoforms, α, δ, and γ. Genistein is a tyrosine kinase inhibitor, mostly of

epidermal growth factor receptor The epidermal growth factor receptor (EGFR; ErbB-1; HER1 in humans) is a transmembrane protein that is a receptor (biochemistry), receptor for members of the epidermal growth factor family (EGF family) of extracellular protein ligand (biochemistry ...

Anthelmintic

The root-tuber peel extract of ''Flemingia vestita'' is a

traditional medicine Traditional medicine (also known as indigenous medicine or folk medicine) refers to the knowledge, skills, and practices rooted in the cultural beliefs of various societies, especially Indigenous groups, used for maintaining health and treatin ...

anthelmintic Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them without causing significant damage to the host. They may also ...

of the Khasi tribes of India. In research, genistein was found to be the major isoflavone responsible for a deworming property. Genistein was subsequently demonstrated to be effective against intestinal parasites, such as the

poultry Poultry () are domesticated birds kept by humans for the purpose of harvesting animal products such as meat, Eggs as food, eggs or feathers. The practice of animal husbandry, raising poultry is known as poultry farming. These birds are most typ ...

cestode Cestoda is a class of parasitic worms in the flatworm phylum (Platyhelminthes). Most of the species—and the best-known—are those in the subclass Eucestoda; they are ribbon-like worms as adults, commonly known as tapeworms. Their bodies co ...

'' Raillietina echinobothrida'', the

pork Pork is the culinary name for the meat of the pig (''Sus domesticus''). It is the most commonly consumed meat worldwide, with evidence of pig animal husbandry, husbandry dating back to 8000–9000 BCE. Pork is eaten both freshly cooke ...

trematode Trematoda is a Class (biology), class of flatworms known as trematodes, and commonly as flukes. They are obligate parasite, obligate Endoparasites, internal parasites with a complex biological life cycle, life cycle requiring at least two Host ( ...

'' Fasciolopsis buski'', and the sheep liver fluke ''Fasciola hepatica''. It exerts its anthelmintic activity by inhibiting

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

s of

glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...

and

glycogenolysis Glycogenolysis is the breakdown of glycogen (n) to glucose-1-phosphate and glycogen (n-1). Glycogen branches are catabolized by the sequential removal of glucose monomers via phosphorolysis, by the enzyme glycogen phosphorylase. Mechanis ...

in the parasites.

Related compounds

Genistin Genistin is an isoflavone found in a number of dietary plants like soy and kudzu. It was first isolated in 1931 from the 90% methanol extract of a soybean meal, when it was found that hydrolysis with hydrochloric acid produced 1 mole (unit), mole ...

is the 7-O-beta-D- glucoside of genistein. * Wighteone can be described as 6- isopentenyl genistein

References

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Pharmacodynamics Pharmacodynamics (PD) is the study of the biochemistry, biochemical and physiology, physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or comb ...

, titlestyle = background:#ccccff , list1 = {{Estrogen receptor modulators {{Estrogen-related receptor modulators {{Glycine receptor modulators {{Monoamine metabolism modulators {{PPAR modulators {{Thyroid hormone receptor modulators 3α-Hydroxysteroid dehydrogenase inhibitors 21-Hydroxylase inhibitors Dietary supplements Flavonoid antioxidants GPER agonists Isoflavones Protein kinase inhibitors Phytoestrogens Glycine receptor antagonists Selective ERβ agonists Steroid sulfotransferase inhibitors