Glabrene
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Glabrene
Glabrene is an isoflavonoid that is found in ''Glycyrrhiza glabra'' (licorice). It has estrogenic activity, showing estrogenic effects on breast, vascular, and bone tissue, and hence is a phytoestrogen ( IC50 for estrogen receptor binding = 1 μM). It has also been found to act as a tyrosinase inhibitor ( IC50 = 3.5 μM) and to inhibit the formation of melanin in melanocytes, and for these reasons, has been suggested as a potential skin-lightening agent. See also * Glabridin * Isoliquiritigenin * Liquiritigenin Liquiritigenin is a flavanone that was isolated from ''Glycyrrhiza uralensis'', and is found in a variety of plants, including ''Glycyrrhiza glabra'' (licorice). It is an estrogenic compound which acts as a selective agonist of the ERβ subtype of ... References Isoflavonoids Phytoestrogens {{organic-compound-stub ...
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Glycyrrhiza Glabra
Liquorice (British English) or licorice (American English) ( ; also ) is the common name of ''Glycyrrhiza glabra'', a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring can be extracted. The liquorice plant is an herbaceous perennial legume native to Western Asia, North Africa, and Southern Europe. Botanically, it is not closely related to anise or fennel, which are sources of similar flavouring compounds. (Another such source, star anise, is even more distantly related from anise and fennel than liquorice, despite its similar common name.) Liquorice is used as a flavouring in candies and tobacco, particularly in some European and West Asian countries. Liquorice extracts have been used in herbalism and traditional medicine. Excessive consumption of liquorice (more than per day of pure glycyrrhizinic acid, a liquorice component) may result in adverse effects, and overconsumption should be suspected clinically in patients presentin ...
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Isoflavonoid
Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estrogen receptor. Medically, isoflavonoids and related compounds have been used in many dietary supplements but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including biliatresone which may cause biliary atresia when infants are exposed to the plant product. The isoflavonoid group is broad, and includes many structurally similar groups, including: * isoflavones * isoflavanones * isoflavans * pterocarpans * rotenoids Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin. Chemical makeup While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenyl ...
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Liquiritigenin
Liquiritigenin is a flavanone that was isolated from ''Glycyrrhiza uralensis'', and is found in a variety of plants, including ''Glycyrrhiza glabra'' (licorice). It is an estrogenic compound which acts as a selective agonist of the ERβ subtype of the estrogen receptor (ER), though it is also reported to act as an ERα partial agonist at sufficient concentrations. It also has a choleretic effect. Liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration) is an enzyme that uses liquiritigenin, O2, NADPH and H+ to produce 2,7,4'-trihydroxyisoflavanone, H2O, and NADP+. See also * Menerba * Prinaberel (ERB-041) * Diarylpropionitrile (DPN) * WAY-200070 * PHTPP * (R,R)-Tetrahydrochrysene ((R,R)-THC) * Propylpyrazoletriol (PPT) * Methylpiperidinopyrazole Methylpiperidinopyrazole (MPP) is a synthetic, nonsteroidal, and highly selective antagonist of ERα that is used in scientific research to study the function of this receptor. It has 200-fold selectivity for ER ...
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Isoliquiritigenin
Isoliquiritigenin is a phenolic chemical compound found in licorice. Metabolism The enzyme 6'-deoxychalcone synthase uses malonyl-CoA, 4-coumaroyl-CoA, Nicotinamide adenine dinucleotide phosphate, NADPH, and H+ to produce Coenzyme A, CoA, isoliquiritigenin, Carbon dioxide, CO2, NADP+, and H2O. The enzyme isoliquiritigenin 2'-O-methyltransferase further transforms isoliquiritigenin into 2'-O-methylisoliquiritigenin. Mechanism of action Isoliquiritigenin has been found to be a potent (65 times higher Affinity (pharmacology), affinity than diazepam) GABA-A benzodiapine receptor positive allosteric modulator. It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth ''in vitro''. References

{{chalconoid Chalconoids category:Phenols ...
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Glabridin
Glabridin is a chemical compound that is found in the root extract of licorice (''Glycyrrhiza glabra''). Glabridin is an isoflavane, a type of isoflavonoid. This product is part of a larger family of plant-derived molecules, the natural phenols. Glabridin effectively inhibits platelet activation, so it might become therapeutic agent for thromboembolic disorders. It is used as an ingredient in cosmetics and is listed in International Nomenclature of Cosmetic Ingredients (INCI). Glabridin is yellowish-brown powder. It is insoluble in water, but soluble in organic solvents such as propylene glycol. See also * Glabrene * Isoliquiritigenin * Liquiritigenin Liquiritigenin is a flavanone that was isolated from ''Glycyrrhiza uralensis'', and is found in a variety of plants, including ''Glycyrrhiza glabra'' (licorice). It is an estrogenic compound which acts as a selective agonist of the ERβ subtype ... References {{Isoflavane Isoflavanes ...
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Melanocyte
Melanocytes are melanin-producing neural crest-derived cells located in the bottom layer (the stratum basale) of the skin's epidermis, the middle layer of the eye (the uvea), the inner ear, vaginal epithelium, meninges, bones, and heart. Melanin is a dark pigment primarily responsible for skin color. Once synthesized, melanin is contained in special organelles called melanosomes which can be transported to nearby keratinocytes to induce pigmentation. Thus darker skin tones have more melanosomes present than lighter skin tones. Functionally, melanin serves as protection against UV radiation. Melanocytes also have a role in the immune system. Function Through a process called melanogenesis, melanocytes produce melanin, which is a pigment found in the skin, eyes, hair, nasal cavity, and inner ear. This melanogenesis leads to a long-lasting pigmentation, which is in contrast to the pigmentation that originates from oxidation of already-existing melanin. There are both ...
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Melanin
Melanin (; from el, μέλας, melas, black, dark) is a broad term for a group of natural pigments found in most organisms. Eumelanin is produced through a multistage chemical process known as melanogenesis, where the oxidation of the amino acid tyrosine is followed by polymerization. The melanin pigments are produced in a specialized group of cells known as melanocytes. Functionally, eumelanin serves as protection against Ultraviolet, UV radiation. There are five basic types of melanin: eumelanin, pheomelanin, neuromelanin, allomelanin and pyomelanin. The most common type is eumelanin, of which there are two types— brown eumelanin and black eumelanin. Pheomelanin, which is produced when melanocytes are malfunctioning due to derivation of the gene to its recessive format is a cysteine-derivative that contains polybenzothiazine portions that are largely responsible for the of red yellow tint given to some skin or hair colors. Neuromelanin is found in the brain. Research ha ...
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Enzyme Inhibitor
An enzyme inhibitor is a molecule that binds to an enzyme and blocks its activity. Enzymes are proteins that speed up chemical reactions necessary for life, in which substrate molecules are converted into products. An enzyme facilitates a specific chemical reaction by binding the substrate to its active site, a specialized area on the enzyme that accelerates the most difficult step of the reaction. An enzyme inhibitor stops ("inhibits") this process, either by binding to the enzyme's active site (thus preventing the substrate itself from binding) or by binding to another site on the enzyme such that the enzyme's catalysis of the reaction is blocked. Enzyme inhibitors may bind reversibly or irreversibly. Irreversible inhibitors form a chemical bond with the enzyme such that the enzyme is inhibited until the chemical bond is broken. By contrast, reversible inhibitors bind non-covalently and may spontaneously leave the enzyme, allowing the enzyme to resume its function. Reve ...
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Tyrosinase
Tyrosinase is an oxidase that is the rate-limiting enzyme for controlling the production of melanin. The enzyme is mainly involved in two distinct reactions of melanin synthesis otherwise known as the Raper Mason pathway. Firstly, the hydroxylation of a monophenol and secondly, the conversion of an o-diphenol to the corresponding o-quinone. o-Quinone undergoes several reactions to eventually form melanin. Tyrosinase is a copper-containing enzyme present in plant and animal tissues that catalyzes the production of melanin and other pigments from tyrosine by oxidation. It is found inside melanosomes which are synthesized in the skin melanocytes. In humans, the tyrosinase enzyme is encoded by the ''TYR'' gene. Catalyzed reaction Tyrosinase carries out the oxidation of phenols such as tyrosine and dopamine using dioxygen (O2). In the presence of catechol, benzoquinone is formed (see reaction below). Hydrogens removed from catechol combine with oxygen to form water. The substrate ...
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Estrogen Receptor
Estrogen receptors (ERs) are a group of proteins found inside cells. They are receptors that are activated by the hormone estrogen ( 17β-estradiol). Two classes of ER exist: nuclear estrogen receptors (ERα and ERβ), which are members of the nuclear receptor family of intracellular receptors, and membrane estrogen receptors (mERs) (GPER (GPR30), ER-X, and Gq-mER), which are mostly G protein-coupled receptors. This article refers to the former (ER). Once activated by estrogen, the ER is able to translocate into the nucleus and bind to DNA to regulate the activity of different genes (i.e. it is a DNA-binding transcription factor). However, it also has additional functions independent of DNA binding. As hormone receptors for sex steroids (steroid hormone receptors), ERs, androgen receptors (ARs), and progesterone receptors (PRs) are important in sexual maturation and gestation. Proteomics There are two different forms of the estrogen receptor, usually referred to as α a ...
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IC50
The half maximal inhibitory concentration (IC50) is a measure of the potency of a substance in inhibiting a specific biological or biochemical function. IC50 is a quantitative measure that indicates how much of a particular inhibitory substance (e.g. drug) is needed to inhibit, ''in vitro'', a given biological process or biological component by 50%. The biological component could be an enzyme, cell, cell receptor or microorganism. IC50 values are typically expressed as molar concentration. IC50 is commonly used as a measure of antagonist drug potency in pharmacological research. IC50 is comparable to other measures of potency, such as EC50 for excitatory drugs. EC50 represents the dose or plasma concentration required for obtaining 50% of a maximum effect ''in vivo''. IC50 can be determined with functional assays or with competition binding assays. Sometimes, IC50 values are converted to the pIC50 scale. :\ce = -\log_ \ce Due to the minus sign, higher values of pIC50 indica ...
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Phytoestrogen
A phytoestrogen is a plant-derived xenoestrogen (see estrogen) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity with estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots (see Food Sources section below for bigger list). Its name comes from the Greek ''phyto'' ("plant") and ''estrogen'', the hormone which gives fertility to female mammals. The word "estrus" - Greek οίστρος - means "sexual desire", and "gene" - Greek γόνο - is "to generate". It has been hypothe ...
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