Flavonoids and Polyphenols

<p>Applications Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bcl-2 ratio and by inhibiting the release of cytochrome c.<br>References Zhao, J. et al.: J. Ethnopharmacol., 120, 387 (2008); Liu, R. et al.: Brain Res., 1216, 104 (2008); Gao, M. et al.: Eur. J. Pharmacol., 591, 73 (2008);<br></p>

<p>Applications Naturally occurring flavonic glycoside; rhamnoglycoside of Diosmetin. Capillary protectant.<br>References Damon, M., et al.: Arzneim.-Forsch., 37, 1149 (1987), Laurent, R., et al.: Int. Angiol., 7, 39 (1988), Tajana, A., et al.: Minerva Med., 79, 387 (1988),<br></p>

<p>Applications Labelled Ferulic acid (4-hydroxy-3-methoxycinnamic acid or, in IUPAC nomenclature, 3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid) which is a highly abundant phenolic phytochemical which is present in plant cell walls. It may have significant health benefits through its antioxidant and anti-cancer activity, and may also serve as a precursor in the manufacturing of useful aromatic compounds. Used as an antioxidant.<br>References Smart, M.G., et al.: Aust. J. Plant Physiol., 6, 485 (1979), Chen, C., et al.: J. Food Lipids, 2, 35,1995, Benzie, I., et al.: Anal. Biochem. 239, 70 (1996), Nardini, M., et al.: Food Chem., 79, 119 (2002), Lee, J., et al.: J. Agric. Food Chem., 52, 2647 (2004),<br></p>

<p>Applications Widely distributed in small amounts in plants. Used as an antioxidant and food preservative.<br>References Smart, M.G., et al.: Aust. J. Plant Physiol., 6, 485 (1979), Chen, C., et al.: J. Food Lipids, 2, 35,1995, Benzie, I., et al.: Anal. Biochem. 239, 70 (1996), Nardini, M., et al.: Food Chem., 79, 119 (2002), Lee, J., et al.: J. Agric. Food Chem., 52, 2647 (2004),<br></p>

<p>Applications Bisdemethoxycurcumin is one of the three major forms of curcuminoids found in the rhizomes of turmeric. Bisdemethoxycurcumin displays antioxidant, anti-inflammatory as well as chemotherapeutic activity. Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes .<br>References Ponnusamy, S. et al.: Food Chem., 135, 2638 (2012); Hung, C.-M. et al.: J. Agric. Food. Chem., 60, 8427 (2012); Jayaprakasha, G.K. et al.: Food Chem., 98, 720 (2006);<br></p>

<p>Applications Scopoletin is the aglucone of Scopolin. Used for cosmetics, topical formulations, and foods. Dyes and metabolites.<br></p>

<p>Stability Light Sensitive<br>Applications Tetrahydro Curcumin is a major metabolite of Curcumin (C838500) that has been shown to have protective effects against diabetes and vascular dysfunction via alleviation of oxidative stress.<br>References Namareoung, S. et al.: Naun.-Schmied. Arch. Pharmacol.,383, 519 (2011); Kartileksan, K. et al.: J. Func. Foods, 2, 134 (2009);<br></p>

<p>Applications Triclosan O-β-D-Glucuronide is a metabolite of the bacteriostat, Triclosan (T774250).<br>References Moss, T. et al.: Food Chem. Toxicol., 38, 361 (2000); Wu, J. et al.: Sepu, 27, 724 (2009);<br></p>

<p>Applications Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol<br>References Akiyama, T., et al.: J. Biol. Chem., 262, 5592 (1987), O'Dell, T.J., et al.: Nature, 353, 588 (1991), Aharonovits, O., et al.: Biochim Biophys. Acta, 1112, 181 (1992), Platanias, L.C., et al.: J. Biol. Chem., 267, 24053 (1992), Yoshida, H., et al.: Biochim. Biophys. Acta, 1137, 321 (1992), Uckun, F.M., et al.: Science, 267, 886 (1995)Merck Index 12th ed. 43952. Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)<br></p>

<p>Applications Hexahydrocurcumin-d6 is an isotope labelled degradation product of Curcumin (C838500), a dietary anti-inflammatory and chemopreventive agent consisting of two methoxyphenol rings connected by a conjugated heptadienedione chain.<br>References Gordon, D.N., et al.: J. Biol. Chem., 290, 4817 (2015);<br></p>

<p>Applications A metabolite of trans Resveratrol (150000).<br>References Schroder, H., et al.: Clin. Nutr., 20, 429 (2001), Yu, C., et al.: Pharm. Res., 19, 1907 (2002), Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2004), Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2004), Ito, H., et al.: Br. J. Nutr., 94, 500 (2005),<br></p>

<p>Applications The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions.<br>References Lomovskaya, N., et al.: J. Bacteriol., 181, 305 (1999), Chung, L., et al.: J. Antibiot., 54, 250 (2001), Kim, D., et al.: Biochemistry, 43, 981 (2004), Kumar, S., et al.: J. Biol. Chem., 280, 19569 (2005),<br></p>

<p>Stability Light Sensitive<br>Applications One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the catechins alter gA channel function and modify bilayer properties, with a 500-fold range in potency. The gallate group causes current block, as evident by brief downward current transitions.<br>References Ingolfsson, H., et al.: FEBS Lett., 585, 3101 (2011),<br></p>

<p>Stability Hygroscopic<br>Applications Urolithin B is an intestinal microbial metabolite of ellagitannis and exhibits potent anti-oxidant and pro-oxidant activies depending on the assay system and conditions. Urolithin B can also display estrogenic and/or anti-estrogenic activity.<br>References Kallio, T., et al.: J. Agr. Food Chem., 61, 10720 (2013); Nealmongkol, P., et al.: Tetrahedron, 69, 9277 (2013); Larrosa, M., et al.: J. Agr. Food Chem., 54, 1611 (2006); Bialonska, D., et al.: J. Agr. Food Chem., 57, 10181 (2009)<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of trans Resveratrol (R150000).<br>References Schroder, H., et al.: Clin. Nutr., 20, 429 (2001), Yu, C., et al.: Pharm. Res., 19, 1907 (2002), Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2004), Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2004), Ito, H., et al.: Br. J. Nutr., 94, 500 (2005),<br></p>

<p>Stability Unstable in Solution<br>Applications Kaempferol is a plant flavonoid.<br>References Hertog, M., et al.: Nutr. Cancer, 20, 21 (1993), Peluso, M., et al.: Carcinogenesis, 21, 183 (2000), Briggs, W., et al.: Plant Physiol., 125, 85 (2001),<br></p>

<p>Stability Hygroscopic<br>Applications Urolithin M7 is an intestinal microbial metabolite of ellagitannins.<br>References Garcia-Villalba, R., et al.: J. Agr. Food Chem., 61, 8797 (2013);<br></p>

<p>Applications trans-Caffeic Acid is a useful synthetic intermediate. It was used as a reactant to synthesize N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors. It is also used to prepare caffeic acid phenethyl ester analogs with antitumor structures.<br>References Michalet, S., et al.: Bioorg. Med. Chem. Lett., 17, 1755 (2007); Nagaoka, T., et al.: Bioorg. Med. Chem., 10, 3351 (2002)<br></p>

<p>Applications 7-Hydroxy Coumarin-d5 is the labeled analogue of 7-Hydroxy Coumarin (H924875), a metabolite of Coumarin that is present in many plants and is the aglucon of skimmin.<br>References Schilling, et al.: Nature, 221, 664 (1969); Indahl, S., et al.: Xenobiotica, 1, 13 (1971); Thompson, S.G., et al.: Antimicrob. Agents Chemother., 18, 264 (1980)<br></p>

<p>Fulvic Acid is a natural product of humus produced by microorganisms in soil, sediment or aquatic environments.</p>

<p>Applications Narcissoside is a flavonoid from Nitraria tangutorum. Narcissoside may have antiproliferative activity in human colon cancer cell line (HT29).<br>References Wu, Z., et. al.: Chem. Nat. Compnd., 49, 1125 (2014); Serra, A.T., et. al.: Food Res. Int., 54, 892 (2013)<br></p>

<p>Stability Hygroscopic<br>Applications Feruloylputrescine is an effector of plant root systems, influencing development of nutrient gathering root systems. Inhibition of the formation of this compound causes the development of a dominant or ‘tap’ root.<br>References Ben-Hayyim G. et al.: FEBS Lett., 4, 145 (1994);<br></p>

<p>Stability Hygroscopic<br>Applications Glycyrrhizic Acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory, antiulcerous and antiallergic effects.<br>References Marsh, L., et al.: Biochem. J., 63, 9 (1956), Kitagawa, et al.: Chem. Pharm. Bull., 36, 3710 (1988),<br></p>

<p>Applications Antioxidant.<br>References Arnous, A., et al.: J. Agr. Food Chem., 49, 5736 (2001), Guendez, R., et al.: Food Chem., 89, 1 (2005), Proestos, C., et al.: Food Control,16, 319 (2005)<br></p>

<p>Applications Urolithin M5 is an intestinal microbial metabolite of ellagitannins.<br>References Garcia-Villalba, R., et al.: J. Agr. Food Chem., 61, 8797 (2013);<br></p>

<p>Stability Moisture Sensitive<br>Applications β-Glucogallin is used as a novel aldose reductase (ALR2) inhibitor, one of the factors regulating the secondary complications arising from diabetes mellitus.<br>References Puppala, M. et al.: PLoS. One., 7, 31399 (2012);<br></p>

<p>Applications trans-p-Coumaric Acid is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Studies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.<br>References Kikugawa, K. et al.: J. Agric. Food Chem., 1, 780 (1983); Ferguson, L.R. et al.: Mol. Nutrit. Food Res., 585 (2005); Chung, F.L. et al.: IARC Sci. Pub., 57, 797 (1984);<br></p>

<p>Stability Hygroscopic<br>Applications Found in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.<br>References Harrison, et al.: J. Am. Pharm. Assoc., 39, 557 (1950), Humphreys, et al.: Econ. Bot., 18, 195 (1964), Khalifa, T.I., et al.: Anal. Profiles Drug Subs., 12, 623 (1983).<br></p>