Quercetin flavonoids

Flavonoids (Quercetin, Rutin, Hyperoside, Quercitrin) [15] Method... 

Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity, FEBS Letters, 416, 123-9. 

Walle, T. Vincent, T. S. Walle, U. K. Evidence of covalent binding of the dietary flavonoid quercetin to DNA and protein in human intestinal and hepatic cells. Biochem. Pharmacol. 2003, 65, 1603-1610. 

When light from all three channels excites the fluorescence of crystalline individual compounds such as allelochemicals flavonoids quercetin and rutin or pigments of plant cells - azulene, chlorophyll and carotenoids fluoresce in different regions of the spectra in yellow and red or blue, red and yellow-orange, respectively (Fig. 7). It compares the light emission of the substances within cellular structures. 

Colquhoun and Schumacher [98] have shown that y-linolcnic acid and eicosapentaenoic acid, which inhibit Walker tumor growth in vivo, decreased proliferation and apoptotic index in these cells. Development of apoptosis was characterized by the enhancement of the formation of reactive oxygen species and products of lipid peroxidation and was accompanied by a decrease in the activities of mitochondrial complexes I, III, and IV, and the release of cytochrome c and caspase 3-like activation of DNA fragmentation. Earlier, a similar apoptotic mechanism of antitumor activity has been shown for the flavonoid quercetin [99], Kamp et al. [100] suggested that the asbestos-induced apoptosis in alveolar epithelial cells was mediated by iron-derived oxygen species, although authors did not hypothesize about the nature of these species (hydroxyl radicals, hydrogen peroxide, or iron complexes ). 

The ability of flavonoids (quercetin and rutin) to react with superoxide has been shown in both aqueous and aprotic media [59,94]. Then, the inhibitory activity of flavonoids in various enzymatic and nonenzymatic superoxide-producing systems has been studied. It was found that flavonoids may inhibit superoxide production by xanthine oxidase by both the scavenging of superoxide and the inhibition of enzyme activity, with the ratio of these two mechanisms depending on the structures of flavonoids (Table 29.4). As seen from Table 29.4, the data obtained by different authors may significantly differ. For example, in recent work [107] it was found that rutin was ineffective in the inhibition of xanthine oxidase that contradicts the previous results [108,109], The origins of such big differences are unknown. 

It must be noted that the inhibitory effects of flavonoids and other antioxidants in nonhomogenous biological systems can depend not only on their reactivities in reactions with free radicals (the chain-breaking activities) but also on the interaction with biomembranes. Thus, Saija et al. [137] compared the antioxidant effects and the interaction with biomembranes of four flavonoids quercetin, hesperetin, naringen, and rutin in iron-induced... 

Aherne GW, Hardcastle A, Valenti M, Bryant A, Rogers P, Pettit GR, Srirangam JK, Kelland LR (1996) Antitumour evaluation of dolastatins 10 and 15 and their measurement in plasma by radioimmunoassay. Cancer Chemother Pharmacol 38 225-232 Ahmad S, Pardini S (1990) Antioxidant defense of the cabbage looper, Trichoplusia ni enzymatic responses to the superoxide-generating flavonoid, quercetin and photodynamic furanocou-marin, xantotoxin. Photochem Photobiol 51 305-312 Amsler CD, Fairhead VA (2006) Defensive and sensory chemical ecology of brown algae. Adv BotRes 43 1-91... 

Opioid A recent study has shown activity of hypericum extracts at opioid receptors (Simmen et al. 1998). Extracts displace naloxone from p and x opioid receptors in the micromolar range (IC50 25 and 90 pg/ml, respectively). In contrast, extracts of the sedative herb Valeriana officinalis do not have this effect. This effect is due to unidentified constituents and not by the flavonoids quercetin or kaemferol. Opioids are known to have effects on emotion, so it is conceivable that activity of hypericum at p and k receptors contributes to its therapeutic effects (Gerra et al. 1998 Tejedor-Real et al. 1995 Walker and Zacny 1998). Although they are not conventional treatment for depression, opioids such as buprenorphine have been effective in treatment of refractory depression (Bodkin et a. 1995). However, for any further conclusions to be drawn, it would be necessary to further e uddate the opioid effects of hypericum to determine what functional effect, if any, hypericum has on the receptors. 

The flavonoid quercetin suppresses growth somewhat in prairie voles, M. ochrogaster, while tannic acid, a hydrolyzable tannin, has an even stronger effect (Lindroth and Batzli, 1984). Quercetin is toxic, but does not bind with protein and, therefore, does not affect protein digestibility. Tannic acid has some effect on protein digestibility but is also toxic. 

Ferry DR, Smith A, Malkhandi J, F e DW, deTakats PG, Anderson D, Baker J, Kerr DJ (1996) Phase 1 clinical trial of the flavonoid quercetin pharmacokinetics and evidence for in vivo tyrosine kinase inhibition. Clin Cancer Res 2 659-668 Findik D, Song Q, Hidaka H, Lavin M (1995) Protein kinase A inhibitors enhance radiation-induced apoptosis. J Cell Biochem 57 12-21 Fine RL, Patel J, Chabner BA (1988) Phorbol esters induce multidrug resistance in human breast cancer cells. Proc Natl Acad Sci USA, 85 582-586 Finkenzeller G, Marme D, Hug H (1992) Inducible overexpression of human protein kinase C in NIH 3T3 fibroblasts results in growth abnormalities. Cell Signall 4 163-177... 

Mendoza-Wilson, A.M. and Glossman-Mitnik, D., CHIH-DFT determination of the molecular structure, infrared and ultraviolet spectra of the flavonoid quercetin, J. Mol. Struct. (Theochem.), 681, 71, 2004. 

Zsila, F., Bikadi, Z., and Simonyi, M., Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods, Biochem. Pharmacol, 65, 447, 2003. 

Borbulevych, O.Y. et al.. Lipoxygenase interactions with natural flavonoid, quercetin, reveal a complex with protocatechuic acid in its x-ray structure at 2.1 A resolution. Proteins, 54, 13, 2004. 

Ferry, D.R., Smith, A., Malkhandi, J., Fyfe, D.W., deTakats, P.G., Anderson, D., Baker, J., and Kerr, D.J., Phase I clinical trial of the flavonoid quercetin pharmacokinetics and evidence for in vivo tyrosine kinase inhibition, Clin. Cancer Res., 2, 659, 1996. 

Walgren, R.A., Lin, J.T., Kinne, R.K., and Walle, T., Cellular uptake of dietary flavonoid quercetin 4 -(3-glucoside by sodium-dependent glucose transporter SGLTl, J. Pharmacol Exp. Ther., 294, 837, 2000. 

Van Zanden, J.J. et al.. Inhibition of human glutathione S-transferase Pl-1 by the flavonoid quercetin, Chem. Biol. Interact., 145, 139, 2003. 

Ciolino, H.P., Daschner, P.J., and Yeh, G.C., Dietary flavonoids quercetin and kaempferol are ligands of aryl hydrocarbon receptor that affect CYPlAl differentially, Biochem. J., 340, 715, 1999. 

Jatropha podagrica Hooker San Hu You Tong (stem bark) Tetramethylpyrazine, steroids, n-hexacosane, beta-amirine, lupeol palmitate, beta-sitosterol, rutin, flavonoids, quercetin, apigenin, vitexin, isovitexin.57-207 208 This herb is toxic. Detoxicant, hypotensive, neuromuscular and cardiovascular actions, antibacterial, relieve swelling, pain, externally treat snakebite, infection. 

Figure 6.8 Regioselective deacylation of the polyacetilated flavonoid quercetin (28a) by action of different lipases (CalB, lipase from Candida antarctica Mml, lipase from Mucor miehei f-BME, ferf-butyl methyl ether)...

Nicolosi and coworkers have intensively investigated the exploitation of lipases for the selective deprotection of bioactive compounds [90]. For instance, as shown in Figure 6.8, the alternative use of the lipases from Candida antarctica (CalB) and Mucor miehei (Mml) enabled the preparation of different derivatives of the flavonoid quercetin (28) [91]. Similar results, this time exploiting the lipase from Pseudomonas cepacia, were obtained with the polyacetylated catechin 29 [92]. 

The flavonoids quercetin, hyperoside and isoquercetin, present in the ethanolic extract of Drosera madagascariensis, are inducers of spasmolytic and anti-inflammatory effects in guinea-pig ileum by affecting cholinergic M3 and histamine HI receptors [183]. 

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