Oxyresveratrol

Last updated
Oxyresveratrol
Oxyresveratrol.svg
Names
Preferred IUPAC name
4-[(E)-2-(3,5-Dihydroxyphenyl)ethen-1-yl]benzene-1,3-diol
Other names
2,3',4,5'-Tetrahydroxy-trans-stilbene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.108.380 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH C034912
PubChem CID
UNII
  • InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+
    Key: PDHAOJSHSJQANO-OWOJBTEDSA-N
  • C1=CC(=C(C=C1O)O)C=CC2=CC(=CC(=C2)O)O
Properties
C14H12O4
Molar mass 244.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oxyresveratrol is a stilbenoid. It is found in the heartwood of Artocarpus lakoocha and in the traditional drug 'Puag-Haad' made from it. [1] It is also the aglycone of mulberroside A, a compound found in Morus alba , the white mulberry. [2]

Oxyresveratrol is a potent tyrosinase inhibitor. [2]

Related Research Articles

<span class="mw-page-title-main">Moraceae</span> Family of flowering plants

The Moraceae — often called the mulberry family or fig family — are a family of flowering plants comprising about 38 genera and over 1100 species. Most are widespread in tropical and subtropical regions, less so in temperate climates; however, their distribution is cosmopolitan overall. The only synapomorphy within the Moraceae is presence of laticifers and milky sap in all parenchymatous tissues, but generally useful field characters include two carpels sometimes with one reduced, compound inconspicuous flowers, and compound fruits. The family includes well-known plants such as the fig, banyan, breadfruit, jackfruit, mulberry, and Osage orange. The 'flowers' of Moraceae are often pseudanthia.

<i>Morus</i> (plant) Genus of plants

Morus, a genus of flowering plants in the family Moraceae, consists of diverse species of deciduous trees commonly known as mulberries, growing wild and under cultivation in many temperate world regions. Generally, the genus has 64 subordinate taxa, three of which are well-known and are ostensibly named for the fruit color of the best-known cultivar: white, red, and black mulberry, with numerous cultivars and some taxa currently unchecked and awaiting taxonomic scrutiny. M. alba is native to South Asia, but is widely distributed across Europe, Southern Africa, South America, and North America. M. alba is also the species most preferred by the silkworm, and is regarded as an invasive species in Brazil and the United States.

<span class="mw-page-title-main">Resveratrol</span> Polyphenol with a stilbene skeleton

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

<i>Morus alba</i> Species of plant

Morus alba, known as white mulberry, common mulberry and silkworm mulberry, is a fast-growing, small to medium-sized mulberry tree which grows to 10–20 m (33–66 ft) tall. It is generally a short-lived tree with a lifespan comparable to that of humans, although there are some specimens known to be more than 250 years old. The species is native to China and India and is widely cultivated and naturalized elsewhere.

<i>Artocarpus</i> Genus of flowering plants

Artocarpus is a genus of approximately 60 trees and shrubs of Southeast Asian and Pacific origin, belonging to the mulberry family, Moraceae. Most species of Artocarpus are restricted to Southeast Asia; a few cultivated species are more widely distributed, especially A. altilis (breadfruit) and A. heterophyllus (jackfruit), which are cultivated throughout the tropics.

<span class="mw-page-title-main">Tyrosinase</span> Enzyme for controlling the production of melanin

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.

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

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Skin whitening</span> Practice of using chemical substances to lighten the skin

Skin whitening, also known as skin lightening and skin bleaching, is the practice of using chemical substances in an attempt to lighten the skin or provide an even skin color by reducing the melanin concentration in the skin. Several chemicals have been shown to be effective in skin whitening, while some have proven to be toxic or have questionable safety profiles. This includes mercury compounds which may cause neurological problems and kidney problems.

Polyphenol oxidase, an enzyme involved in fruit browning, is a tetramer that contains four atoms of copper per molecule.

<span class="mw-page-title-main">Dopachrome tautomerase</span>

Dopachrome tautomerase , also known as DCT, is a human gene. Its expression is regulated by the microphthalmia-associated transcription factor (MITF).

<span class="mw-page-title-main">Membrane-associated transporter protein</span> Protein

Membrane-associated transporter protein (MATP), also known as solute carrier family 45 member 2 (SLC45A2) or melanoma antigen AIM1, is a protein that in humans is encoded by the SLC45A2 gene.

<span class="mw-page-title-main">BW-723C86</span> Chemical compound

BW-723C86 is a tryptamine derivative drug which acts as a 5-HT2B receptor agonist. It has anxiolytic effects in animal studies, and is also used for investigating the function of the 5-HT2B receptor in a range of other tissues.

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

Dihydromorin is a flavanonol, a type of flavonoid. It can be found in plants of the family Moraceae including Morus nigra, in Morus alba, Maclura pomifera, in the jackfruit and in Artocarpus dadah.

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

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

<i>Artocarpus lacucha</i> Species of flowering plant

Artocarpus lacucha, also known as monkey jack or monkey fruit, is a tropical evergreen tree species of the family Moraceae. It is distributed throughout the Indian Subcontinent and Southeast Asia. The tree is valued for its wood; its fruit is edible and is believed to have medicinal value. In Northeastern Thailand, the wood is used to make pong lang, a local traditional instrument.

<i>Haplorchis taichui</i> Species of fluke

Haplorchis taichui is a species of intestinal fluke in the family Heterophyidae. It is a human parasite.

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

Mulberroside A is a stilbenoid found in Morus alba, the white mulberry. It is the diglucoside of oxyresveratrol.

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

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.

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

Rhododendrol (RD) also called 4-[(3R)-3-hydroxybutyl]phenol (systemic name), is an organic compound with the formula C10H14O2. It is a naturally occurring ingredient present in many plants, such as the Rhododendron. The phenolic compound was first developed in 2010 as a tyrosinase inhibitor for skin-lightening cosmetics. In 2013, after rhododendrol reportedly caused skin depigmentation in consumers using RD-containing skin-brightening cosmetics, the cosmetics were withdrawn from the market. The skin condition, caused by RD, is called RD-induced leukoderma. Rhododendrol exerts melanocyte cytotoxicity via a tyrosinase-dependent mechanism. It has been shown to impair the normal proliferation of melanocytes through reactive oxygen species-dependent activation of GADD45. It is now well established that rhododendrol is a potent tyrosinase inhibitor.

<i>Morus mongolica</i> Species of fruit and plant

Morus mongolica, also described as Morus alba var. mongolica, is a woody plant native to mountain forests in Mongolia, China, Korea, and Japan. Common names include Mongolian mulberry, meng sang (China), and ilama by native people in the namesake region of Mongolia. Similar to M. notabilis, M. mongolica is an uncultivated mulberry.

References

  1. Maneechai, S; Likhitwitayawuid, K; Sritularak, B; Palanuvej, C; Ruangrungsi, N; Sirisa-Ard, P (2009). "Quantitative analysis of oxyresveratrol content in Artocarpus lakoocha and 'Puag-Haad'". Medical Principles and Practice. 18 (3): 223–7. doi:10.1159/000204354. PMID   19349726. S2CID   29232919.
  2. 1 2 Kim, JK; Kim, M; Cho, SG; Kim, MK; Kim, SW; Lim, YH (2010). "Biotransformation of mulberroside a from Morus alba results in enhancement of tyrosinase inhibition". Journal of Industrial Microbiology & Biotechnology. 37 (6): 631–7. doi: 10.1007/s10295-010-0722-9 . PMID   20411402. S2CID   21236818.