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Oxyresveratrol (trans-Oxyresveratrol) Sale

(Synonyms: 氧化白藜芦醇; trans-Oxyresveratrol) 目录号 : GC33464

A resveratrol analog

Oxyresveratrol (trans-Oxyresveratrol) Chemical Structure

Cas No.:29700-22-9

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10mM (in 1mL DMSO)
¥385.00
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100mg
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500mg
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1g
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产品描述

Resveratrol is a potent phenolic antioxidant found in the skin of grapes and red wine that has anti-proliferative, anti-inflammatory, and cardioprotective properties.1 Oxyresveratrol is a naturally occurring analog of resveratrol found in mulberry wood. It effectively scavenges H2O2, NO (IC50 = 45.3 μM), and the artificial free radical 2,2-diphenyl-l-picrylhydrazyl (IC50 = 28.9 μM).2 At 10 mg/kg, oxyresveratrol acts as a neuroprotectant, reducing brain infarct volume and reducing cytochrome c release and caspase-3 activation in an in vivo model of stroke.3 Oxyresveratrol also has depigmenting effects by effectively inhibiting tyrosinase activity, which catalyzes the rate-limiting step in synthesizing melanin pigments (IC50s = 1.2 and 52.7 μM in mushroom and mouse melanoma B-16 cells, respectively).4 It is 32-fold more potent than kojic acid, a depigmenting agent used in cosmetic materials with skin-whitening effects and medical agents used to treat hyperpigmentation disorders.4

1.Rotondo, S., Rajtar, G., Manarini, S., et al.Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte functionBr. J. Pharmacol.123(8)1691-1699(1998) 2.Lorenz, P., Roychowdhury, S., Engelmann, M., et al.Oxyresveratrol and resveratrol are potent antioxidants and free radical scavengers: Effect on nitrosative and oxidative stress derived from microglial cellsNitric Oxide9(2)64-76(2003) 3.Andrabi, S.A., Spina, M.G., Lorenz, P., et al.Oxyresveratrol (trans-2,3',4,5'-tetrahydroxystilbene) is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemiaBrain Res.101798-107(2004) 4.Kim, Y.M., Yun, J., Lee, C.K., et al.Oxyresveratrol and hydroxystilbene compounds. Inhbitory effect on tyrosinase and mechanism of actionJ. Biol. Chem.277(18)16340-16344(2002)

Chemical Properties

Cas No. 29700-22-9 SDF
别名 氧化白藜芦醇; trans-Oxyresveratrol
Canonical SMILES OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C(O)=C1
分子式 C14H12O4 分子量 244.24
溶解度 DMSO : ≥ 34 mg/mL (139.21 mM) 储存条件 Store at -20°C
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1 mM 4.0943 mL 20.4717 mL 40.9433 mL
5 mM 0.8189 mL 4.0943 mL 8.1887 mL
10 mM 0.4094 mL 2.0472 mL 4.0943 mL
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Research Update

Stir bar sorptive extraction with gas chromatography-mass spectrometry for the determination of resveratrol, piceatannol and Oxyresveratrol isomers in wines

J Chromatogr A 2013 Nov 8;1315:21-7.PMID:24075014DOI:10.1016/j.chroma.2013.09.045.

A simple and highly sensitive procedure based on stir bar sorptive extraction coupled to gas chromatography-mass spectrometry by means of a thermal desorption unit (SBSE-TD-GC-MS) has been optimized for the determination of cis/trans isomers of resveratrol, piceatannol and Oxyresveratrol in wine samples. Quantification of the cis-isomers was carried out by generating the standards from the corresponding trans-species once they had been preconcentrated on the SBSE extracting phase. The optimization of the acetylation derivatization, SBSE extraction and thermal desorption steps was investigated using Plackett-Burman designs, taking into account the high number of variables to be considered. The use of bisphenol F as internal standard allowed quantification of the samples against aqueous standards. Repeatability, expressed as relative standard deviation of 10 successive analyses was between 5% and 9%, confirming the high precision attained under the optimized conditions. Satisfactory recovery values of between 79% and 109% were obtained for spiked samples in the 0.2-1.0 μgL(-1) concentration range, depending on the compound. The main compound determined in the analyzed samples was trans-resveratrol, with concentrations in the range of 3-230 μgL(-1), depending on the type of wine.

Cytotoxic apigenin derivatives from Chrysopogon aciculatis

J Nat Prod 2012 Feb 24;75(2):198-201.PMID:22272829DOI:10.1021/np2007796.

Four new apigenin derivatives, 7-de-O-methylaciculatin, 8-C-β-D-boivinopyranosylapigenin, aciculatinone, and 4'-O-glucosylaciculatin, along with eight known compounds, apigenin-8-carbaldehyde, kaempferol, tricin, taxifolin, 6,7,4'-trihydroxyflavone, trans-Oxyresveratrol, aciculatin, and luteolin-7-sulfate, were isolated from an ethanolic extract of Chrysopogon aciculatis. Their chemical structures were elucidated by spectroscopic methods. Among the known compounds, the natural occurrence of apigenin-8-carbaldehyde and luteolin-7-sulfate is demonstrated for the first time. Some of the isolates were evaluated for cytotoxic activity against human cancer cell lines including MCF-7, H460, HT-29, and CEM.

Genistein, daidzein, and resveratrols stimulate PGC-1β-mediated gene expression

Biochem Biophys Rep 2018 Dec 6;17:51-55.PMID:30582007DOI:10.1016/j.bbrep.2018.11.009.

PGC-1β is a transcriptional co-activator of nuclear receptors such as the estrogen receptor-related receptor (ERR). Transgenic overexpression of PGC-1β in mice increases energy expenditure and suppresses high-fat diet-induced obesity. In this study, we screened various food-derived and natural compounds using a reporter assay system to measure the transcriptional activity of PGC-1β. Soy-derived isoflavones, genistein and daidzein, and several resveratrols activated PGC-1β. Genistein, daidzein, and trans-Oxyresveratrol activated ERR-responsive element-mediated reporter activity in the presence of PGC-1β. Stable overexpression of PGC-1β in C2C12 myoblasts increased the expression of medium-chain acyl-CoA dehydrogenase (MCAD), an important enzyme in fatty acid β-oxidation. Genistein and daidzein increased MCAD mRNA levels and mitochondrial content in PGC-1β-expressing C2C12 cells. These compounds activated ERR/PGC-1β complex-mediated gene expression, and our findings may be a practical foundation for developing functional foods targeting obesity.

Secondary metabolites of Bagassa guianensis Aubl. wood: a study of the chemotaxonomy of the Moraceae family

Phytochemistry 2010 Oct;71(14-15):1708-13.PMID:20655556DOI:10.1016/j.phytochem.2010.06.020.

In order to explain the durability of the Moraceae plant family, phytochemistry of Bagassa guianensis was performed. Ethyl acetate extract was obtained from the heartwood and 18 secondary metabolites were isolated, including 6 moracins [6-O-methyl-moracin M, 6-O-methyl-moracin N and moracin Z; previously identified: moracin M, moracin N and moracin P], 8 stilbenoids [presently identified: (-)-epialboctalol and arachidin 4; previously identified: alboctalol, trans-resveratrol, arachidin 2, trans-Oxyresveratrol and artogomezianol], 3 previously identified flavonoids, steppogenin, katuranin and dihydromorin, beta-sitosterol and resorcinol. Previous studies suggest that stilbenoids are responsible for the natural durability of wood. Our study has determined that B. guianensis is closely related to Morus sp. in phylogeny and should be included in the Moreae sensu stricto tribe of the Moraceae family.

Secondary metabolites from Spirotropis longifolia (DC) Baill and their antifungal activity against human pathogenic fungi

Phytochemistry 2012 Feb;74:166-72.PMID:22137037DOI:10.1016/j.phytochem.2011.10.011.

A phytochemical study of the ethyl acetate extract of the roots and adventitious roots of Spirotropis longifolia, a monodominant tree species of the Guianan rainforest, has allowed the isolation of three compounds: 2-hydroxy-8,9-methylenedioxy-2',2'-dimethylpyrano-[5',6':4,3]-6a-prenyl-[6aS,11aS]-pterocarpan (spirotropin A), 2-hydroxy-8,9-methylenedioxy-2',2'-dimethyl-3',4'-dihydropyrano-[5',6':4,3]-6a-prenyl-[6aS,11aS]-pterocarpan (spirotropin B), and 5,7-dihydroxy-6,8-diprenyl-2'''',2''''-dimethylpyrano[5'''',6'''': 3',4']-isoflavone (spirotropone). In addition, 10 known compounds, trans-Oxyresveratrol, trans-resveratrol, piceatannol, daidzein, genistein, isoprunetin, lupeol, latifolol, gnetin D and gnetin E, were also isolated. These compounds were evaluated for their antifungal activity and their cytotoxicity, and their structures were established by 1D and 2D NMR, HRMS, CD and optical rotation measurements.