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Glycinol (pterocarpan)
Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (''Glycine max''). It is formed by the cyclisation of daidzein. More recent literature supports that glycinol has potent phytoestrogenic activity. The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis. It can be synthethised chemically and possesses two chiral centers. Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase. Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen There are several known allotropes of oxygen. The most familiar is molecular oxygen (O2), present at significant levels in Earth's atmosphere and also known as dioxygen or triplet oxygen. Another is the highly reactive ozone (O3). Others are: *A .... References Pterocarpans Phytoalexins {{aromatic-stub ...
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Pterocarpan
Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6''H''- enzofuro ,2-chromene skeleton) which can be formed by coupling of the B ring to the 4-one position. 2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in ''Cicer arietinum'' and glyceollin synthase for the production of glyceollins, phytoalexins in soybean. Known compounds * Bitucarpin A and B, isolated from the aerial parts of Mediterranean plants ''Bituminaria morisiana'' and ''Bituminaria bituminosa'' * Erybraedin A and B, isolated from the stems of ''Erythrina subumbrans'' and C, isolated from the leaves of ''Bituminaria morisiana'' * Erythrabyssin II, erystagallin A, erythrabissin-1, and erycristagallin isolated from the stems of ''Erythrina subumbrans'' * Glycinol, glyceollidin I and II, glyceollins (glyceollin I, II, III and IV), found in the soybean (''Glycin ...
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Phytoalexin
Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized ''de novo'' by plants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular plant taxa. Phytoalexins tend to fall into several chemical classes, including terpenoids, glyco steroids and alkaloids, however the term applies to any phytochemicals that are induced by microbial infection. Function Phytoalexins are produced in plants to act as toxins to the attacking organism. They may puncture the cell wall, delay maturation, disrupt metabolism or prevent reproduction of the pathogen in question. Their importance in plant defense is indicated by an increase in susceptibility of plant tissue ...
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Soybean
The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu and tofu skin are made. Fermented soy foods include soy sauce, fermented bean paste, nattō, and tempeh. Fat-free (defatted) soybean meal is a significant and cheap source of protein for animal feeds and many packaged meals. For example, soybean products, such as textured vegetable protein (TVP), are ingredients in many meat and dairy substitutes. Soybeans contain significant amounts of phytic acid, dietary minerals and B vitamins. Soy vegetable oil, used in food and industrial applications, is another product of processing the soybean crop. Soybean is the most important protein source for feed farm animals (that in turn yields animal protein for human consumption). Etymology The word "soy" originated as a corruption of the Cantonese or ...
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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 are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility. Natural occurrence Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs like kwao krua (''Pueraria mirifica'') and kudzu. It can also be found in ''Maackia amurensis'' cell cultures. Daid ...
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Osteogenesis
Osteoblasts (from the Greek combining forms for "bone", ὀστέο-, ''osteo-'' and βλαστάνω, ''blastanō'' "germinate") are cells with a single nucleus that synthesize bone. However, in the process of bone formation, osteoblasts function in groups of connected cells. Individual cells cannot make bone. A group of organized osteoblasts together with the bone made by a unit of cells is usually called the osteon. Osteoblasts are specialized, terminally differentiated products of mesenchymal stem cells. They synthesize dense, crosslinked collagen and specialized proteins in much smaller quantities, including osteocalcin and osteopontin, which compose the organic matrix of bone. In organized groups of disconnected cells, osteoblasts produce hydroxylapatite, the bone mineral, that is deposited in a highly regulated manner, into the organic matrix forming a strong and dense mineralized tissue, the mineralized matrix. The mineralized skeleton is the main support for the bodies of ...
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Glyceollin
Glyceollins are a family of prenylated pterocarpans found in ineffective types of nodule in soybean in response to symbiotic infection. It possesses two chiral centers and can be asymmetrically synthesized chemically at a gram level scale. Molecules found in the family are : * Glyceollin I * Glyceollin II * Glyceollin III * Glyceollin IV Effects They are phytoalexins with an antiestrogenic activity.Glyceollins, a Novel Class of Antiestrogenic Phytoalexins. Syreeta L. Tilghman, Stephen M. Boué and Matthew E. Burow, Mol Cell Pharmacol 2010;2(4), pp. 155-160, Lygin ''et al.'' 2013 finds antifungal activity against ''Phytophthora sojae'' and ''Macrophomina phaseolina'', and Kim ''et al.'' 2010 against ''Aspergillus sojae''. Kaplan ''et al.'' 1980 finds nematicidal activity against ''Meloidogyne incognita''. Parniske ''et al.'' 1991 finds an antibacterial effect. Glyceollin is a vital part of soybean immunity. Metabolism Lygin ''et al.'' 2013 find that daidzein is a precursor. . ...
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Prenyltransferase
Prenyltransferases (PTs) are a class of enzymes that transfer allylic prenyl groups to acceptor molecules. Prenyl transferases commonly refer to isoprenyl diphosphate syntheses (IPPSs). Prenyltransferases are a functional category and include several enzyme groups that are evolutionarily independent. Prenyltransferases are commonly divided into two classes, cis (or Z) and trans (or E), depending upon the stereochemistry of the resulting products. Examples of trans-prenyltranferases include dimethylallyltranstransferase, and geranylgeranyl pyrophosphate synthase. Cis-prenyltransferases include dehydrodolichol diphosphate synthase (involved in the production of a precursor to dolichol). Trans- and cis-prenyltransferases are evolutionarily unrelated to each other and there is no sequential and structural similarity. The beta subunit of the farnesyltransferases is responsible for peptide binding. Squalene-hopene cyclase is a bacterial enzyme that catalyzes the cyclization of squalene ...
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Molecular Oxygen
There are several known allotropes of oxygen. The most familiar is molecular oxygen (O2), present at significant levels in Earth's atmosphere and also known as dioxygen or triplet oxygen. Another is the highly reactive ozone (O3). Others are: *Atomic oxygen (O1), a free radical. *Singlet oxygen (O2*), one of two metastable states of molecular oxygen. *Tetraoxygen (O4), another metastable form. *Solid oxygen, existing in six variously colored phases, of which one is and another one metallic. Atomic oxygen Atomic oxygen, denoted O(3P) or O(3P), is very reactive, as the single atoms of oxygen tend to quickly bond with nearby molecules. On Earth's surface, it exists naturally for a very short time. In outer space, the presence of ample ultraviolet radiation results in a low Earth orbit atmosphere in which 96% of the oxygen occurs in atomic form. Ryan D. McCulla, Saint Louis University (2010). /acswebcontent.acs.org/prfar/2010/reports/P11141.html "Atomic Oxygen O(3P): Photog ...
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Pterocarpans
Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6''H''-[1]benzofuro[3,2-c]chromene skeleton) which can be formed by coupling of the B ring to the 4-one position. 2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in ''Cicer arietinum'' and glyceollin synthase for the production of glyceollins, phytoalexins in soybean. Known compounds * Bitucarpin A and Bitucarpin B, B, isolated from the aerial parts of Mediterranean plants ''Bituminaria morisiana'' and ''Bituminaria bituminosa'' * Erybraedin A and erybraedin B, B, isolated from the stems of ''Erythrina subumbrans'' and Erybraedin C, C, isolated from the leaves of ''Bituminaria morisiana'' * Erythrabyssin II, erystagallin A, erythrabissin-1, and erycristagallin isolated from the stems of ''Erythrina subumbrans'' * Glycinol (pterocarpan), Glycinol, glyceollidin I and Glyceollidin II, II, g ...
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