Glycinol (pterocarpan)

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Glycinol
Glycinol.svg
Glycinol-3D-balls.png
Names
Preferred IUPAC name
(6aS,11aS)-6H-[1]Benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1 X mark.svgN
    Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N X mark.svgN
  • InChI=1/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1
    Key: QMXOFBXZEKTJIK-LSDHHAIUBH
  • O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3
Properties
C15H12O5
Molar mass 272.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[ citation needed ]

More recent literature supports that glycinol has potent phytoestrogenic activity. [1] [2]

The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis.[ citation needed ]

It can be synthethised chemically and possesses two chiral centers. [3]

Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase.[ citation needed ]

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen. [4]

Related Research Articles

Serine is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group, a carboxyl group, and a side chain consisting of a hydroxymethyl group, classifying it as a polar amino acid. It can be synthesized in the human body under normal physiological circumstances, making it a nonessential amino acid. It is encoded by the codons UCU, UCC, UCA, UCG, AGU and AGC.

<span class="mw-page-title-main">Leghemoglobin</span> Phytoglobin

Leghemoglobin is an oxygen-carrying phytoglobin found in the nitrogen-fixing root nodules of leguminous plants. It is produced by these plants in response to the roots being colonized by nitrogen-fixing bacteria, termed rhizobia, as part of the symbiotic interaction between plant and bacterium: roots not colonized by Rhizobium do not synthesise leghemoglobin. Leghemoglobin has close chemical and structural similarities to hemoglobin, and, like hemoglobin, is red in colour. It was originally thought that the heme prosthetic group for plant leghemoglobin was provided by the bacterial symbiont within symbiotic root nodules. However, subsequent work shows that the plant host strongly expresses heme biosynthesis genes within nodules, and that activation of those genes correlates with leghemoglobin gene expression in developing nodules.

Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicines, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

VO2 max (also maximal oxygen consumption, maximal oxygen uptake or maximal aerobic capacity) is the maximum rate of oxygen consumption attainable during physical exertion. The name is derived from three abbreviations: "V̇" for volume (the dot appears over the V to indicate "per unit of time"), "O2" for oxygen, and "max" for maximum. A similar measure is VO2 peak (peak oxygen consumption), which is the measurable value from a session of physical exercise, be it incremental or otherwise. It could match or underestimate the actual VO2 max. Confusion between the values in older and popular fitness literature is common. The capacity of the lung to exchange oxygen and carbon dioxide is constrained by the rate of blood oxygen transport to active tissue.

<span class="mw-page-title-main">Equol</span> Isoflavandiol estrogen metabolized from daidzein

Equol (4',7-isoflavandiol) is an isoflavandiol estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.

<span class="mw-page-title-main">Allyl isothiocyanate</span> Chemical compound

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of Cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but more soluble in most organic solvents.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

<span class="mw-page-title-main">Fasciation</span> Condition of abnormal growth in vascular plants

Fasciation, also known as cresting, is a relatively rare condition of abnormal growth in vascular plants in which the apical meristem, which normally is concentrated around a single point and produces approximately cylindrical tissue, instead becomes elongated perpendicularly to the direction of growth, thus producing flattened, ribbon-like, crested, or elaborately contorted tissue. Fasciation may also cause plant parts to increase in weight and volume in some instances. The phenomenon may occur in the stem, root, fruit, or flower head.

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein 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.

<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce is referred to as dissociative anesthesia.

In enzymology, a glyceollin synthase is an enzyme that catalyzes the last committed step in glyceollin biosynthesis. This enzyme has been classified as a cytochrome dependent monooxygenase. It uses cyclization of prenyl residue to convert glyceollidins into glyceollins.

<span class="mw-page-title-main">Soybean aphid</span> Species of true bug

The soybean aphid is an insect pest of soybean that is exotic to North America. The soybean aphid is native to Asia. It has been described as a common pest of soybeans in China and as an occasional pest of soybeans in Indonesia, Japan, Korea, Malaysia, the Philippines, and Thailand. The soybean aphid was first documented in North America in Wisconsin in July 2000. Ragsdale et al. (2004) noted that the soybean aphid probably arrived in North America earlier than 2000, but remained undetected for a period of time. Venette and Ragsdale (2004) suggested that Japan probably served as the point of origin for the soybean aphid's North American invasion. By 2003, the soybean aphid had been documented in Delaware, Georgia, Illinois, Indiana, Iowa, Kansas, Kentucky, Michigan, Minnesota, Mississippi, Missouri, Nebraska, New York, North Dakota, Ohio, Pennsylvania, South Dakota, Virginia, West Virginia, and Wisconsin. Together, these states accounted for 89% of the 63,600,000 acres (257,000 km2) of soybean planted in the United States in 2007.

<i>Glycine soja</i> Species of legume

Glycine soja, known as wild soybean, is an annual plant in the legume family. It may be treated as a separate species, the closest living relative of the cultivated soybean, Glycine max, an important crop, or as a subspecies of the cultivated soybean, Glycine max subsp. soja.

<span class="mw-page-title-main">Pterocarpan</span> Class of chemical compounds

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 which can be formed by coupling of the B ring to the 4-one position.

Glyceollins are a family of prenylated pterocarpans found in ineffective types of nodule in soybean in response to symbiotic infection.

<span class="mw-page-title-main">Glyceollin I</span> Chemical compound

Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.

<span class="mw-page-title-main">Glyceollin III</span> Chemical compound

Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean. It has an antiestrogenic effect. In soil, it has an antifungal activity against Aspergillus sojae.

<i>Aspergillus sojae</i> Species of fungus

Aspergillus sojae is a species of fungus in the genus Aspergillus.

<span class="mw-page-title-main">Gelsemine</span> Chemical compound

Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.

Ensifer fredii is a nitrogen fixing bacteria of the genus Sinorhizobium. It is a fast-growing root nodule bacteria. Sinorhizobium fredii exhibit a broad host-range and are able to nodulate both determinant hosts such as soy as well as indeterminate hosts including the pigeon pea. Because of their ease of host infection there is interest in their genetics and the symbiotic role in host infection and nodule formation.

References

  1. Boué, Stephen M.; Tilghman, Syreeta L.; Elliott, Steven; Zimmerman, M. Carla; Williams, K. Y.; Payton-Stewart, Florastina; Miraflor, Allen P.; Howell, Melanie H.; Shih, Betty Y.; Carter-Wientjes, Carol H.; Segar, Chris; Beckman, Barbara S.; Wiese, Thomas E.; Cleveland, Thomas E.; McLachlan, John A.; Burow, Matthew E. (2009). "Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)". Endocrinology. 150 (5): 2446–2453. doi: 10.1210/en.2008-1235 . ISSN   0013-7227. PMC   2671905 . PMID   19116342.
  2. Strong, Amy L; Jones, Robert B; Glowacki, Julie; Boue, Stephen M; Burow, Matthew E; Bunnell, Bruce A (2017). "Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells". Regenerative Medicine. 12 (5): 513–524. doi:10.2217/rme-2016-0148. ISSN   1746-0751. PMID   28718749.
  3. Luniwal Amarjit; Khupse Rahul S; Reese Michael; Lei Fang; Erhardt Paul W (2009). "Total Syntheses of Racemic and Natural Glycinol". Journal of Natural Products. 72 (11): 2072–2075. doi:10.1021/np900509f. PMID   19943626.
  4. Matthews, David E.; Plattner, Ronald D.; Vanetten, Hans D. (1989). "The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen". Phytochemistry. 28 (1): 113–115. Bibcode:1989PChem..28..113M. doi:10.1016/0031-9422(89)85020-4.