Hispidulin: Antioxidant properties and effect on mitochondrial energy metabolism^†

References

• Yuting C, Rongliang Z, Zhong Jian J, Yong J. Flavonoids as superoxide scavengers and antioxidants. Free Rad Biol Med 1990; 9: 19–21
   PubMed Web of Science ®Google Scholar
• Hodnick WF, Milosavljevic EB, Nelson JH, Pardini RS. Relationships between redox potentials, inhibition of mitochondrial respiration, and production of oxygen radicals by flavonoids. Biochem Pharmacol 1988; 37(13)2607–2611
   PubMed Web of Science ®Google Scholar
• Hodnick WF, Dawn LD, Pardini RS. Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids. Biochem Pharmacol 1994; 47(3)537–580
   Web of Science ®Google Scholar
• Syrov VN, Khushbaktova ZA, Ablazora MKH, Sultanov MB, Hazekamp A, Verpoorte R, Panthong A. Isolation of a bronchodilator flavonoid from the Thai medicinal plant Clerodendrum petasites. Ethnopharmacology 2001; 78(1)45–49
   PubMed Web of Science ®Google Scholar
• Liu L, Xiao X, Zhang L, Zheng R, Li Y, Du M, Zhu Z. Effects of flavones from Saussurea involucrata on DNA synthesis by cancer cells. Lanzhou Daxue Xuebao 1985; 21: 80–83
   Google Scholar
• Bourdillat B, Delautier D, Labat C, Benveniste J, Potier P, Brink C. Hispidulin, a natural flavone, inhibits human platelet aggregation by increasing cAMP levels. Eur J Pharmacol 1988; 147: 1–6
   PubMed Web of Science ®Google Scholar
• Soicke H, Leng PE. Characterization of flavonoids from Baccharis trimera and their antihepatotoxic properties. Planta Med 1987; 53(1)37–39
   PubMedGoogle Scholar
• Ferrándiz ML, Bustos G, Payá M, Gunasegaran R, Alcaraz MJ. Hispidulin protection against hepatotoxicity induced by bromobenzene in mice. Pharmacol Lett 1994; 55(8)145–150
   Google Scholar
• Kupchan SM, Sigel CW, Hemingway RJ, Knox JR, Udayamurthy MS. Cytotoxic flavones from Eupatorium species. Tetrahedron 1969; 25(8)1603–1615
   PubMed Web of Science ®Google Scholar
• Sanz MJ, Ferrandiz ML, Cejudo M, Terencio MC, Gil B, Bustos G, Ubeda A, Gunasegaran R, Alcaraz MJ. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica 1994; 24(7)689–699
   PubMed Web of Science ®Google Scholar
• Sang JL, Há YC, In KL, Seung UO, Ick DY. Isolation and identification of flavonoids from ethanol extracts of Artemisia vulgaris and their antioxidant activity. Korean J Food Sci Technol 1999; 31(3)815–822
   Google Scholar
• Sang JL, Há YC, In KL, Seung UO, Ick DY. Phenolics with inhibitory activity on mouse brain monoamine oxidase (MAO) from whole parts of Artemisia vulgaris L. Food Sci Biotechnol 2000; 9(3)179–182
   Google Scholar
• Miura K, Kikuzaki H, Nakatani N. Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method. J Agric Food Chem 2002; 50(7)1845–1851
   PubMed Web of Science ®Google Scholar
• Coleman PC, Potgieter DJJ, van Aswegen CH, Vermeulen NMJ. Flavonoids of Geigeria. Phytochemistry 1984; 23(5)1202–1203
   Web of Science ®Google Scholar
• Mathiesen L, Malterud KE, Sund RB. Hydrogen bond formation as basis for radical scavenging activity: A structure–activity study of C-methylated dihydrochalcones from Myrica gale and structurally related acetophenones. Free Radic Biol Med 1997; 22(1/2)307–311
   PubMed Web of Science ®Google Scholar
• Mora A, Payá M, Ríos JL, Alcaraz MJ. Structure–activity relationships of polymethoxy-flavones and other flavonoids as inhibitors of non-enzymic lipid peroxidation. Biochem Pharmacol 1990; 40: 793–797
   PubMed Web of Science ®Google Scholar
• Arora A, Nair MG, Strasburg GM. Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system. Free Radic Biol Med 2001; 24(9)1355–1363
   Google Scholar
• van Acker SABE, Berg DJ, Tromp MNJL, Griffioen DH, Bennekom WP, Vijgh WJF, Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radic Biol Med. 1996; 20(3)331–342
   PubMed Web of Science ®Google Scholar
• Pannala AS, Chan TS, O'Brien PJ, Rice-Evans CA. Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem Biophys Res Commun 2001; 282(5)1161–1168
   PubMed Web of Science ®Google Scholar
• Puppo A. Effect of flavonoids on hydroxyl radical formation by Fenton-type reactions; influence of the iron chelator. Phytochemistry 1992; 31(1)85–88
   Web of Science ®Google Scholar
• Monteiro HP, Vile GF, Winterbourn CC. Release of iron from ferritin by semiquinone, anthracycline, bipyridyl, and nitroaromatic radicals. Free Radic Biol Med 1988; 6: 587–591
   Web of Science ®Google Scholar
• Oliveira BH, Nakashima T, Filho JDS, Frehse FL. HPLC analysis of flavonoids in Eupatorium litoralle. J Braz Chem Soc 2001; 12(2)243–246
   Web of Science ®Google Scholar
• Voss OD, Campelo AP, Bacila M. The respiration chain and the oxidative phosphorylation of rat brain mitochondria. Biochem Biophys Res Commun 1961; 4(1)48–51
   PubMed Web of Science ®Google Scholar
• Braguini WL, Gomes MAB, Oliveira BH, Carnieri EGS, Rocha MEM, Oliveira MBM. Activity of isosteviol lactone on mitochondrial metabolism. Toxicol Lett 2003; 143: 83–92
   PubMed Web of Science ®Google Scholar
• Estabrook RW. Mitochondrial respiratory control and the polarography measurement of ADP/O ratios. Methods Enzymol 1967; 10: 41–47
   Google Scholar
• Chance B, Williams ER. The respiratory enzymes in oxidative phosphorilation: Kinetics of oxygen utilization. J Biol Chem 1955; 217: 383–393
   PubMed Web of Science ®Google Scholar
• Singer TP. Determination of the activity of succinate, NADH, choline and α-glycerophosphate dehydrogenase. Methods Biochem Anal 1974; 22: 123–175
   PubMedGoogle Scholar
• Somlo M. Induction des lactico-cytocromo c redutases (D-ET L-) de la levure aerobie par les lactates (D-ET L-). Biochim Biophys Acta 1965; 97: 183–201
   PubMed Web of Science ®Google Scholar
• Mason TL, Poyton RO, Wharto DC, Schatz G. Cytochrome c oxidase from bakers yeast. Isolation and properties. J Biol Chem 1973; 248(4)1346–1354
   PubMed Web of Science ®Google Scholar
• Pullman ME, Penefsky HS, Datta A, Racker E. Partial resolution of the enzymes catalysing oxidative phosphorylation. I. Purification and properties of soluble, dinitrophenol-stimulated adenosine triphosphatase. J Biol Chem 1960; 235(11)3322–3329
   PubMed Web of Science ®Google Scholar
• Sumner JB. Scientific apparatus and laboratory methods. A method for the colorimetric determination of phosphorus. Science 1944; 100: 413–414
   PubMedGoogle Scholar
• Mustafa MG, Utsumi K, Packer L. Damped oscillatory control of mitochondrial respiration and volume. Biochem Biophys Res Commun 1966; 24: 381–385
   PubMed Web of Science ®Google Scholar
• Sepalla AJ, Wiktron MKF, Saris NEL. Damping of mitochondrial volume oscillations by propanolol and related compounds. Biological and biochemical oscillators, B Chance, KK Pye, AK Gosh, B HESS. Academic Press, New York 1973
   Google Scholar
• Moreno AJM, Madeira VMC. Interference of parathion with mitochondrial bioenergetics. Biochim Biophys Acta 1990; 1015: 361–367
   PubMed Web of Science ®Google Scholar
• Oteiza PI, Kleinman CG, Demasi M, Bechara EJH. 5-Aminolevulinic acid induces iron release from ferritin. Arch Biochem Biophys 1995; 316: 607–611
   PubMed Web of Science ®Google Scholar
• Blois MS. Antioxidant determinations by the use of a stable free radical. Nature 1958; 181: 1199–1200
   Web of Science ®Google Scholar
• Lowry OH, Rosebrough NJ, Farr AC, Randall RJ. Protein measurement with the polyphenol reagent. J Biol Chem 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Nicholls DG, Ferguson SJ. Bioenergetics 2. Academic Press, San Diego 1992
   Google Scholar
• Nakashima RA, Garlid KD. Quinine inhibitions of Na+e K+ transport provides evidence for two cation/H+ exchange in rat liver mitochondria. J Biol Chem 1982; 287: 9252–9254
   Google Scholar
• Funk F, Lenders JP, Crichton RR, Schneider W. Reductive mobilization of ferritin iron. Eur J Biochem 1985; 152: 167–172
   PubMedGoogle Scholar
• Rocha MEM, Ferreira AMDC, Bechara EJH. Roles of phosphate and enoyl radical in ferritin iron mobilization by 5-aminolevulinic acid. Free Radic Biol Med 2000; 29(12)1272–1279
   PubMed Web of Science ®Google Scholar
• Toyokuni S. Iron-induced carcinogenesis: the role of redox regulation. Free Radic Biol Med 1996; 20: 553–566
   PubMed Web of Science ®Google Scholar
• Monteiro HP, Abdalla DSP, Augusto O, Bechara EJH. Free radical generation during δ-aminolevulinic acid autoxidation: Induction by hemoglobin and connection with porphyrinpathies. Arch Biochem Biophys 1989; 271: 206–216
   PubMed Web of Science ®Google Scholar
• Monteiro HP, Winterbourn CC. 6-hydroxydopamine releases iron from ferritin and promotes ferritin-dependent lipid peroxidation. Biochem Pharmacol 1989; 38: 4177–4182
   PubMed Web of Science ®Google Scholar
• Ohkawa M, Kinjo J, Hagiwara Y, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T. Three new anti-oxidative saponarin analogs from young green barley leaves. Chem Pharm Bull 1998; 46(12)
   PubMed Web of Science ®Google Scholar
• Ohkawa M, Kinjo J, Nohara T, Ono M. DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scaveging activity of flavonoids obtained from some medicinal plants. Biochim Biophys Acta 2001; 1526(2)159–167
   PubMed Web of Science ®Google Scholar
• Hodnick WF, Bohmont CW, Capps C, Pardini RS. Inhibition of the mitochondrial NADH-oxidase (NADH-coenzyme Q oxido-reductase) enzyme system by flavonoids: A structure–activity study. Biochem Pharmacol 1987; 36(17)2873–2874
   PubMed Web of Science ®Google Scholar
• Creuzet S, Ravanel P, Tissut M, Kaouadji M. Uncoupling properties of three flavonols from plane-tree buds. Phytochemistry 1988; 27(10)3093–3099
   Web of Science ®Google Scholar
• Terada H. The interaction of highly active uncouplers with mitochondria. Biochim Biophy Acta 1981; 639: 225–242
   PubMed Web of Science ®Google Scholar
• Ravanel P. Uncoupling activity of a series of flavones and flavonols on isolated plant mitochondria. Phytochemistry 1986; 25(5)1015–1020
   Web of Science ®Google Scholar
• Carpenedo F, Bortignon C, Bruni A, Santi R. Effect of quercetin on membrane-linked activities. Biochem Pharmacol 1969; 18: 1495–1500
   PubMed Web of Science ®Google Scholar
• van Acker SABE, Groot MJ, van der Berg DJ, Tromp MNJL, den Kelder GDO, van der Vijgh WJF, Bast A. A quantum chemical explanation of the antioxidant activity of flavonoids. Chem Res Toxicol 1996; 9: 1305–1312
   PubMed Web of Science ®Google Scholar
• Bandy B, Davison AJ. Interaction between metals, ligands and oxygen in the autooxidation of 6 hydroxy-dopamine: Mechanisms by which metal chelation enhances inhibition by superoxide dismutase. Arch Biochem Biophys 1987; 259(2)305–315
   PubMed Web of Science ®Google Scholar
• Burda S, Oleszek W. Antioxidant and antiradical activities of flavonoids. J Agric Food Chem 2001; 49(6)2774–2779
   PubMed Web of Science ®Google Scholar
• Cadena SMSC, Carnieri EGS, Echevaria A, Oliveira MBM. Effect of MI-D, a new mesoionic compound, on energy-linkes functions of rat liver mitochondria. FEBS Lett 1998; 440: 46–50
   PubMed Web of Science ®Google Scholar
• Senff-Ribeiro A, Echevaria A, Silva EF, Veiga SS, Oliveira MBM. Effect of a new 1,3,4-thiadiazolium mesoionic compound (MI-D) on B16-F10 murine melanoma. Melanoma Res 2003; 13(5)465–472
   PubMed Web of Science ®Google Scholar
• Senff-Ribeiro A, Echevaria A, Silva EF, Veiga SS, Oliveira MBM. Anti melanoma activity of 1,3,5-thiadiazolium mesoionics: A structure–activity relationship study. Anti-cancer Drugs 2004; 15(3)269–275
   PubMed Web of Science ®Google Scholar
• Cortez-Pinto H, Yang SQ, Lin HZ, Costa S, Hwang C-S, Lane D, Bagby G, Diehl AM. Bacterial lipopolysaccharide induces uncoupling protein-2 expression in hepatocytes by a tumor necrosis factor-α-dependent mechanism. Biochem Biophys Res Commun 1998; 251(1)313–319
   PubMed Web of Science ®Google Scholar
• Tsuboyama-Kasaoka N, Takahashi M, Kim H, Ezaki O. Up-regulation of liver uncoupling protein-2 mRNA by either fish oil feeding or fibrate administration in mice. Biochem Biophys Res Commun 1999; 257(3)879–885
   PubMed Web of Science ®Google Scholar
• Uchino S, Yamaguchi Y, Furuhashi T, Wang F-S, Zhang J-L, Okabe K, Kihara S, Yamada S, Mori K, Ogawa M. Steatotic liver allografts up-regulate UCP-2 expression and suffer necrosis in rats. J Surg Res 2004; 120(1)73–82
   PubMed Web of Science ®Google Scholar
• Brand MB, Affourtit C, Esteves TC, Green K, Lambert AJ, Miwa S, Pakay JL, Parker N. Mitochondrial superoxide: Production, biological effects, and activation of uncoupling proteins. Free Radic Biol Med 2004; 37(6)755–767
   PubMed Web of Science ®Google Scholar
• Talbot DA, Lambert AJ, Brand MD. Production of endogenous matrix superoxide from mitochondrial complex I leads to activation of uncoupling protein 3. FEBS Lett 2004; 556: 111–115
   PubMed Web of Science ®Google Scholar
• Williams RJ, Spencer JPE, Rice-Evans C. Flavonoids: Antioxidants or signalling molecules?. Free Radic Biol Med 2004; 36(7)838–849
   PubMed Web of Science ®Google Scholar