Isoflavones comprise a class of organic compounds 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. The distinction between "organic" and ", often naturally occurring, related to the isoflavonoids.[1] Many act as phytoestrogens Phytoestrogens, sometimes called "dietary estrogens", are a diverse group of naturally occurring nonsteroidal plant compounds that, because of their structural similarity with estradiol , have the ability to cause estrogenic or/and antiestrogenic effects in mammals Mammals are a class of vertebrate, air-breathing animals whose females are characterized by the possession of mammary glands while both males and females are characterized by hair and/or fur, three middle ear bones used in hearing, and a neocortex region in the brain. Some mammals have sweat glands, but most do not. Being polyphenols 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. Polyphenols are generally divided into hydrolyzable tannins and phenylpropanoids, such as lignins, flavonoids, and condensed tannins, they are antioxidants An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions that damage cells. Antioxidants terminate these chain reactions by.[citation needed] Some isoflavones and isoflavone-rich foods possess activity against cancer Cancer /ˈkænsər/ (medical term: malignant neoplasm) is a class of diseases in which a group of cells display uncontrolled growth (division beyond the normal limits), invasion (intrusion on and destruction of adjacent tissues), and sometimes metastasis (spread to other locations in the body via lymph or blood). These three malignant properties, including certain types of breast and prostate Prostate cancer is a form of cancer that develops in the prostate, a gland in the male reproductive system. Most prostate cancers are slow growing; however, there are cases of aggressive prostate cancers. The cancer cells may metastasize from the prostate to other parts of the body, particularly the bones and lymph nodes. Prostate cancer may cause cancer.[2] Isoflavones are produced almost exclusively by the members of the 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. The name 'Fabaceae' comes from the defunct genus Faba, now included into Vicia. Leguminosae is an older name still considered valid, and refers to the typical fruit of/Leguminosae (bean) family.

Contents

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, numbering. Genistein Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source. Besides functioning as antioxidants, many isoflavones have been shown to interact with animal and human estrogen receptors, causing effects (5-OH, 7-OH, 4'-OH) or 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. Soy isoflavones are a group of compounds found in and (7-OH, 4'-OH) are e. g. members of the isoflavone family.

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 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 herbivores, 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 Flavonoids , also collectively known as Vitamin P and citrin, are a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into: compounds in higher plants. Soybeans The soybean or soya bean (UK) (Glycine max) 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 to primarily add nitrogen into the soil as part of crop rotation are the most common source of isoflavones in human food; the major isoflavones in soybean The soybean or soya bean (UK) (Glycine max) 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 to primarily add nitrogen into the soil as part of crop rotation are genistein Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source. Besides functioning as antioxidants, many isoflavones have been shown to interact with animal and human estrogen receptors, causing effects and 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. Soy isoflavones are a group of compounds found in and. The phenylpropanoid pathway begins from the amino acid Amino acids are molecules containing an amine group, a carboxylic acid group and a side chain that varies between different amino acids. These molecules contain the key elements of carbon, hydrogen, oxygen, and nitrogen. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula phenylalanine Phenylalanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. L-Phenylalanine (LPA) is an electrically-neutral amino acid, one of the twenty common amino acids used to biochemically form proteins, coded for by DNA. The codons, and an intermediate of the pathway, naringenin, is sequentially converted in to the isoflavone genistein by two legume-specific enzymes Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process are called substrates, and the enzyme converts them into different molecules, called the products. Almost all processes in a biological cell need enzymes to occur at significant rates. Since enzymes are selective for their, isoflavone synthase, and a dehydratase. Similarly, another intermediate naringenin chalcone 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 compounds to ward off disease-causing pathogenic A pathogen, (from Greek πάθος pathos "suffering, passion", and γἰγνομαι gignomai (gen-) "I give birth to") an infectious agent, or more commonly germ, is a biological agent that causes disease to its host. There are several substrates and pathways whereby pathogens can invade a host; the principal pathways have fungi A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. The Fungi (pronounced /ˈfʌndʒaɪ/ or /ˈfʌŋɡaɪ/) are classified as a kingdom that is separate from plants, animals and bacteria. One major difference is that fungal cells have cell and other microbes A microorganism or microbe is an organism that is microscopic (too small to be seen by the naked human eye). The study of microorganisms is called microbiology, a subject that began with Anton van Leeuwenhoek's discovery of microorganisms in 1675, using a microscope of his own design. In addition, soybean uses isoflavones to stimulate soil Soil is a natural body consisting of layers of mineral constituents of variable thicknesses, which differ from the parent materials in their morphological, physical, chemical, and mineralogical characteristics-microbe rhizobium Rhizobium is a genus of Gram-negative soil bacteria that fix nitrogen. Rhizobium forms an endosymbiotic nitrogen fixing association with roots of legumes to form nitrogen-fixing root nodules Root nodules occur on the roots of plants that associate with symbiotic nitrogen-fixing bacteria.

Occurrence

Most members of the 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. The name 'Fabaceae' comes from the defunct genus Faba, now included into Vicia. Leguminosae is an older name still considered valid, and refers to the typical fruit of 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 corylifolia). Various legumes including kudzu Kudzu is a plant in the genus Pueraria in the pea family Fabaceae, subfamily Faboideae. It is a climbing, coiling, and trailing vine native to southern Japan and southeast China. Its name comes from the Japanese name for the plant, Kuzu (クズ or 葛?) (Pueraria lobata), lupine Lupins or lupines are the members of the genus Lupinus in the legume family (Fabaceae). The genus comprises between 200 and 600 species, with major centers of diversity in South America and western North America, in the Mediterranean region and Africa (Lupinus spp), fava Vicia faba, the Broad Bean, Fava Bean, Faba Bean, Field Bean, Bell Bean or Tic Bean is a species of bean native to north Africa and southwest Asia, and extensively cultivated elsewhere. A variety is provisionally recognized: bean (Vicia faba), and soy The soybean or soya bean (UK) (Glycine max) 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 to primarily add nitrogen into the soil as part of crop rotation (Glycine max) contained substantial amounts of isoflavones according to this analysis[citation needed]. 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 The chickpea (also garbanzo bean, Indian pea, ceci bean, Bengal gram) is an edible legume of the family Fabaceae, subfamily Faboideae. Chickpeas are high in protein and one of the earliest cultivated vegetables; 7,500-year-old remains have been found in the Middle East (biochanin A), alfalfa Alfalfa is a flowering plant in the pea family Fabaceae cultivated as an important forage crop. In the UK, Australia, South Africa and New Zealand it is known as lucerne and as lucerne grass in south Asia. It resembles clover with clusters of small purple flowers (formononetin and coumestrol), and peanut The peanut, or groundnut , is a species in the legume "bean" family (Fabaceae). The cultivated peanut was probably first domesticated in the valleys of Perú. It is an annual herbaceous plant growing 30 to 50 cm (0.98 to 1.6 ft) tall. The leaves are opposite, pinnate with four leaflets (two opposite pairs; no terminal leaflet), each (genistein Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source. Besides functioning as antioxidants, many isoflavones have been shown to interact with animal and human estrogen receptors, causing effects).

Health effects

Further information: Phytoestrogens#Health risks and benefits Phytoestrogens, sometimes called "dietary estrogens", are a diverse group of naturally occurring non steroidal plant compounds that, because of their structural similarity with estradiol , have the ability to cause estrogenic or/and antiestrogenic effects

Because of their diversity, isoflavones can have diverse effects on human and animal health.[2] Early evidence that plants Plants are living organisms belonging to the kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The scientific study of plants, known as botany, has identified about 350,000 extant species of plants, defined as seed plants, bryophytes, ferns and fern allies. As of 2004, produced estrogen-like compounds was manifested in the infertility Infertility primarily refers to the biological inability of a person to contribute to conception. Infertility may also refer to the state of a woman who is unable to carry a pregnancy to full term. There are many biological causes of infertility, some which may be bypassed with medical intervention among sheep Domestic sheep are quadrupedal, ruminant mammals typically kept as livestock. Like all ruminants, sheep are members of the order Artiodactyla, the even-toed ungulates. Although the name "sheep" applies to many species, in everyday usage it almost always refers to Ovis aries. Numbering a little over 1 billion, domestic sheep are the most that eat large amounts of 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. They are small annual, biennial, in Australia For at least 40,000 years before European settlement in the late 18th century, Australia was inhabited by indigenous Australians, who belonged to one or more of the roughly 250 language groups. After sporadic visits by fishermen from the immediate north and discovery by Dutch explorers in 1606, Australia's eastern half was claimed by the British.[citation needed] Similarly, California Quails 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. It is the state bird of California fed on the leaves of high-isoflavone desert annuals during periods of food shortage had reduced fertility.[3] 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 [2])

Studies on mice indicate that isoflavones may cause thymic and immune system abnormalities and reduction in immune system activity.[4]

There may be a link between soy and health problems in certain animals.[5]

See also

References

  1. ^ Kaufman PB, Duke JA, Brielmann H, Boik J, Hoyt JE (1997). "A comparative survey of leguminous plants as sources of the isoflavones, genistein and daidzein: implications for human nutrition and health". J Altern Complement Med 3 (1): 7–12. doi A digital object identifier is a character string used to uniquely identify an electronic document or other object. Metadata about the object is stored in association with the DOI name and this metadata may include a location, such as a URL, where the object can be found. The DOI for a document is permanent, whereas its location and other metadata:10.1089/acm.1997.3.7. PMID A PMID is a unique number assigned to each PubMed citation of life sciences and biomedical scientific journal articles. The related Pubmed Central archive may additionally assign a separate number, a PMCID (PubMed Central Identifier), normally written with a PMC prefix 9395689.
  2. ^ a b c Dixon, RA (2004). "Phytoestrogens". Annu Rev Plant Biol. 55: 225–61. doi A digital object identifier is a character string used to uniquely identify an electronic document or other object. Metadata about the object is stored in association with the DOI name and this metadata may include a location, such as a URL, where the object can be found. The DOI for a document is permanent, whereas its location and other metadata:10.1146/annurev.arplant.55.031903.141729. PMID A PMID is a unique number assigned to each PubMed citation of life sciences and biomedical scientific journal articles. The related Pubmed Central archive may additionally assign a separate number, a PMCID (PubMed Central Identifier), normally written with a PMC prefix 15377220.
  3. ^ Leopold AS, Erwin M, Oh J, Browning B (January 1976). "Phytoestrogens: adverse effects on reproduction in California quail". Science 191 (4222): 98–100. doi A digital object identifier is a character string used to uniquely identify an electronic document or other object. Metadata about the object is stored in association with the DOI name and this metadata may include a location, such as a URL, where the object can be found. The DOI for a document is permanent, whereas its location and other metadata:10.1126/science.1246602. PMID A PMID is a unique number assigned to each PubMed citation of life sciences and biomedical scientific journal articles. The related Pubmed Central archive may additionally assign a separate number, a PMCID (PubMed Central Identifier), normally written with a PMC prefix 1246602. http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=1246602.
  4. ^ Yellayi S, Naaz A, Szewczykowski MA, et al. (May 2002). "The phytoestrogen genistein induces thymic and immune changes: a human health concern?". Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7616–21. doi A digital object identifier is a character string used to uniquely identify an electronic document or other object. Metadata about the object is stored in association with the DOI name and this metadata may include a location, such as a URL, where the object can be found. The DOI for a document is permanent, whereas its location and other metadata:10.1073/pnas.102650199. PMID 12032332. PMC 124301. http://www.pnas.org/cgi/content/full/99/11/7616.
  5. ^ FDA Scientists Against Soy. The anti-soy website "Soy Online Service" has the original letter in PDF. [1]

External links

Isoflavones info

Isoflavones and their glycosides
Isoflavones Daidzein | Genistein | Irilone | Orobol | Pratensein | Prunetin
O-methylated isoflavones Biochanin A | Formononetin | Glycitein | Irigenin | Psi-tectorigenin | Retusin | Tectorigenin
Glycosides Daidzin | Genistin | Iridin | Ononin | Puerarin | Tectoridin
Acetylated Derrubone | Luteone | Wighteone
Synthetic Ipriflavone

Categories: Types of Flavonoids | Isoflavones

 

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Natural levels of isoflavones
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