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Isoflavones comprise a class of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s, often naturally occurring, related to the flavonoid
Flavonoid

The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
s. Many act as phytoestrogens in mammal
Mammal

Mammals are a class of vertebrate animals whose name is derived from their distinctive feature, mammary glands, with which they feed their young....
s. Being polyphenol
Polyphenol

Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule....
s, they are antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
s. Some isoflavones and isoflavone-rich foods possess activity against cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
, including certain types of breast
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
 and prostate
Prostate cancer

Prostate cancer is a disease in which cancer develops in the prostate, a gland in the male reproductive system. It occurs when cell s of the prostate Mutation and begin to multiply out of control....
 cancer. Isoflavones are produced almost exclusively by the members of the Fabaceae
Fabaceae

Fabaceae or Leguminosae is a large and economically important family of flowering plants, which is commonly known as the legume family, pea family, bean family or pulse family....
/Leguminosae (bean) family.

lavones of nutritional interest are substituted derivatives of isoflavone, being related to the parent by the replacement of two or three hydrogen atoms with hydroxyl groups.






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Encyclopedia


Isoflavones comprise a class of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s, often naturally occurring, related to the flavonoid
Flavonoid

The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
s. Many act as phytoestrogens in mammal
Mammal

Mammals are a class of vertebrate animals whose name is derived from their distinctive feature, mammary glands, with which they feed their young....
s. Being polyphenol
Polyphenol

Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule....
s, they are antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
s. Some isoflavones and isoflavone-rich foods possess activity against cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
, including certain types of breast
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
 and prostate
Prostate cancer

Prostate cancer is a disease in which cancer develops in the prostate, a gland in the male reproductive system. It occurs when cell s of the prostate Mutation and begin to multiply out of control....
 cancer. Isoflavones are produced almost exclusively by the members of the Fabaceae
Fabaceae

Fabaceae or Leguminosae is a large and economically important family of flowering plants, which is commonly known as the legume family, pea family, bean family or pulse family....
/Leguminosae (bean) family.

Organic chemistry and biosynthesis

Isoflavones of nutritional interest are substituted derivatives of isoflavone, being related to the parent by the replacement of two or three hydrogen atoms with hydroxyl groups. The parent isoflavone is of no nutritional interest. Isoflavone differs from flavone (2-phenyl-4H-1-benzopyr-4-one) in location of the phenyl group.

Isoflavones are produced via a branch of the general phenylpropanoid
Phenylpropanoid

Phenylpropanoids are a class of plant-derived organic compounds that are biosynthesized from the amino acid phenylalanine. They have a wide variety of functions, including defense against Herbivory, microbial attack, or other sources of injury; as structural components of cell walls; as protection from ultraviolet light; as pigments; and as...
 pathway that produces flavonoid
Flavonoid

The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
 compounds in higher plants. Soybeans are the most common source of isoflavones in human food; the major isoflavones in soybean
Soybean

The soybean or soya bean is a species of legume native to East Asia. The plant is classed as an oilseed rather than a Pulse . It is an annual plant that has been used in China for 5,000 years as a food and a component of drugs....
 are genistein
Genistein

Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with soybeans and soy products like tofu and textured vegetable protein being the primary food source....
 and daidzein
Daidzein

Daidzein is one of several known isoflavones. Isoflavones compounds, such as daidzein and genistein, are found in a number of plants and herbs like the Thai Kwao Krua or Pueraria Mirifica, but soybeans and soy products like tofu and textured vegetable protein are the primary food source....
. The phenylpropanoid pathway begins from the amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 phenylalanine
Phenylalanine

Phenylalanine is an a-amino acid with the chemical formula HO2CCHCH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects....
, and an intermediate of the pathway, naringenin
Naringenin

Naringenin is a flavonoid that is considered to have a bioactive effect on human health as antioxidant, free radical radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulater....
, is sequentially converted in to the isoflavone genistein by two legume-specific enzymes, isoflavone synthase, and a dehydratase
Dehydratase

Dehydratase is an enzyme that catalyzes the removal of oxygen and hydrogen from organic compounds in the form of water. This process is also known as dehydration....
. Similarly, another intermediate naringenin chalcone
Chalcone

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones....
 is converted to the isoflavone daidzein by sequential action of three legume-specific enzymes: chalcone reductase, type II chalcone isomerase, and isoflavone synthase. Plants use isoflavones and their derivatives as phytoalexin
Phytoalexin

Phytoalexins are antibiotics produced by plants that are under attack. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids and alkaloids; however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal....
 compounds to ward off disease-causing pathogen
Pathogen

A pathogen , infectious agent, or germ, is a biological agent that causes disease or illness to its Host .There are several substrates and pathways whereby pathogens can invade a host; the principal pathways have different episodic time frames, but soil contamination has the longest or most persistent potential for harboring...
ic fungi
Fungus

A fungus is a Eukaryote organism that is a member of the Kingdom Fungi . The fungi are a monophyletic group, also called the Eumycota , that is phylogeny distinct from the morphologically similar slime molds and water molds ....
 and other microbes. In addition, soybean uses isoflavones to stimulate soil
Soil

Soil is the naturally occurring, unconsolidated or loose covering on the Earth's surface. Soil is composed of particles of broken rock that have been altered by chemical and environmental processes including weathering and erosion....
-microbe rhizobium to form nitrogen-fixing root nodule
Root nodule

Root nodules occur on the roots of plants that associate with symbiotic bacterium.Under nitrogen limiting conditions, plants from the pea family Fabaceae form a symbiotic relationship with a host-specific strain of bacteria known as rhizobia....
s.

Occurrence

Most members of the Fabaceae family contain significant quantities of isoflavones. Analysis of levels in various species has found that the highest levels of genistein and daidzein in psoralea
Psoralea

Psoralea is a genus in the legume family . Although most species are poisonous, the starchy roots of Psoralea esculenta and P. hypogaea are edible....
 (Psoralea corylifolia). Various legumes including kudzu
Kudzu

, Pueraria lobata , is one of about 20 species in the genus Pueraria in the pea family Fabaceae, subfamily Faboideae. It is native to southern Japan and southeast China in eastern Asia....
 (Pueraria lobata), lupin
Lupin

Lupin, often spelled lupine in North America, is the common name for members of the genus Lupinus in the legume family . The genus comprises between 200-600 species, with major centers of diversity in South America and western North America - ) and - in the Mediterranean region and Africa....
e (Lupinus spp), fava
Vicia faba

Vicia faba, the Broad Bean, Fava Bean, Faba Bean, Field Bean, Bell Bean or Tic Bean is a species of legume native to north Africa and southwest Asia, and extensively cultivated elsewhere....
 bean (Vicia faba), and soy (Glycine max) contained substantial amounts of isoflavones according to this analysis. Highly processed foods made from legumes, such as tofu, retain most of their isoflavone content, with the exception of fermented miso, which has increased levels.

Other dietary sources of isoflavones include chick pea (biochanin A), alfalfa
Alfalfa

Alfalfa is a flowering plant in the pea family Fabaceae cultivated as an important forage crop. In the United Kingdom, Australia and New Zealand it is known as lucerne and as lucerne grass in south Asia....
 (formononetin and coumestrol
Coumestrol

Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica....
), and peanut
Peanut

The peanut, or groundnut , is a species in the legume Fabaceae native to South America, Mexico and Central America. It is an annual plant herbaceous plant growing to 30 to 50 cm tall....
 (genistein
Genistein

Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with soybeans and soy products like tofu and textured vegetable protein being the primary food source....
).

Health effects


Because of their diversity, isoflavones can have diverse effects on human and animal health. Early evidence that plant
Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
s produced estrogen-like compounds was manifested in the infertility
Infertility

Infertility primarily refers to the biological inability of a person to contribute to fertilization. Infertility may also refer to the state of a woman who is unable to carry a pregnancy to full term....
 among sheep
Sheep

#REDIRECT Domestic sheep...
 that eat large amounts of clover
Clover

Clover , or trefoil, is a genus of about 300 species of plants in the pea family Fabaceae. The genus has a cosmopolitan distribution; the highest diversity is found in the temperate Northern Hemisphere, but many species also occur in South America and Africa, including at high altitudes on mountains in the tropics....
 in Australia
Australia

Australia, officially the Commonwealth of Australia, is a country in the southern hemisphere comprising the Australia of the world's smallest continent, the major island of Tasmania, and numerous list of islands of Australia in the Indian Ocean and Pacific Oceans....
. Similarly, California Quail
California Quail

The California Quail, Callipepla californica, also known as the California Valley Quail or Valley Quail, is a small ground-dwelling bird in the New World quail family....
s fed on the leaves of high-isoflavone desert annuals during periods of food shortage had reduced fertility. Studies using chemically pure isoflavones or plant materials with known concentrations of these compounds have indicated both positive and negative effects of isoflavones on disease progression and fertility. (Reviewed in )

Studies on mice indicate that isoflavones may cause thymic and immune system abnormalities and reduction in immune system activity.

There may be link between soy and health problems in certain animals.

See also

  • Nutrition
    Nutrition

    Nutrition is the provision, to cells and organisms, of the materials necessary to support life. Many common health problems can be prevented or alleviated with good nutrition....
  • Phytonutrients


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