Inhibition of peroxidase activity and scavenging of reactive oxygen species by astilbin isolated from Dimorphandra mollis (Fabaceae, Caesalpinioideae)

Biological Research

Volumn 43, Issue 1, 2010, Pages 63-74

  Petacci, Fernando ^a   Freitas, Silvia S ^a   Brunetti, Iguatemy L ^b   Khalil, Najeh M ^c  

^a FEDERAL UNIVERSITY OF GOIÁS   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^c Pharmacy Department   (Brazil)

Author keywords

Astilbin; Horseradish peroxidase; Hypochlorous acid; Myeloperoxidase; Reactive oxygen species

Indexed keywords

ARMORACIA RUSTICANA; CAESALPINIOIDEAE; DIMORPHANDRA MOLLIS; FABACEAE;

EID: 77953698629     PISSN: 07169760     EISSN: 07176287     Source Type: Journal    
DOI: 10.4067/S0716-97602010000100008     Document Type: Article

References (48)

1. AUDI EA, TOLEDO DP, PERES PG, KIMURA E, PEREIRA WKV, MELLO JCP, NAKAMURA CV, ALVES DO PRADO W, CUMAN RKN, BERSANI AMADO CA (1999) Gastric antiulcerogenic effects of Stryphnodendron adstringens in rats. Phyt. Res. 13: 264-266.
2. AWAD HM, BOERSMA M G, VERVOORT J, RIETJENS IM (2000) Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts. Arch Bioch Bioph 378: 224-233.
3. BEECHER GR (1999) Phytonutrients' role in metabolism: Effects on resistance to degenerative processes. Nutr Reviews 57: S3-S6.
4. BINSACK R, BOERSMA BJ, PATE RP, KIRK M, WHITE CR, DARLEY-USMAR V, BARNES S, ZHOU F, PARKS DA (2001) Enhanced antioxidant activity after chlorination of quercetin by hypochlorous acid. Alcohol Clin Exper Res 25: 434-443.
5. CAI Y, CHEN T, XU Q (2003) Astilbin suppresses collagen-induced arthritis via the dysfunction of lymphocytes. Inflam Res 52: 334-340.
6. CECHINEL-FILHO V, VAZ ZR, ZUNINO L, CALIXTO JB, YUNES RA (2000) Antinociceptive and antioedematogenic properties of astilbin, taxifolin and some related compounds Arzneimittelforschung 50: 281-285.
7. CHING TL, JONG J, BAST A (1994) A method for screening hypochlorous acid scavengers by inhibition of the oxidation of 5-thio-2-nitrobenzoic acid: application to anti-asthmatic drugs. Anal Biochem 218: 377-381.
8. CINTRA P, PETACCI F, FERNANDES JB, VIEIRA PC, SILVA MFGF, MALASPINA O, BUENO OC (2002) Toxicity of Dimorphandra mollis to workers of Apis mellifera. J Braz Chem Soc 13: 115-118.
9. CINTRA P, PETACCI F, FERNANDES JB, BUENO OC, MALASPINA O, VIEIRA PC, SILVA MFGF (2005a). Oral toxicity of chemical substances found in Dimorphandra mollis (Caesalpiniaceae) against honeybees (Apis mellifera) (Hymenopetra: Apidae). Sociobiology 45: 141-149.
10. CINTRA P, PETACCI F, FERNANDES JB, MALASPINA O, BUENO OC, BUENO FC (2005b) Astilbin toxicity to leaf-cutting ants Atta sexdens rubropilosa (Hymenoptera: Formicidae). Sociobiology 45: 1-7.
11. CLARK SF (2002) The biochemistry of antioxidants revisited. Nutr. Clin. Practice 17: 5-17.
12. CLOSA D, TORRES M, HOTTER G, BIOQUE G, LEON OS, GELPI E, ROSELLO CATAFAU J (1997) Prostanoids and free radicals in CCl4-induced hepatotoxicity in rats: effect of astilbin. Prost Leuk Ess Fat Acids 56: 331-334.
13. DE BRITO J, MANICKAM VS, GOPALAKRISHNAN S, USHIODA T, TANAKA N (1995) Determination of aglycone chirality in dihydroflavonol 3-O-a-L rhamnosides by 1H-NMR spectroscopy. Chem Pharm Bul 43: 338-339.
14. GAZARYAN IG, LAGRIMINI LM, ASHBY GA, THORNELEY NF (1996) Mechanism of indol-3-acetic acid oxidation by plant peroxidases: anaerobic stoppedflow spectrophotometric studies on horseradish and tobacco peroxidases. Biochem J 313: 841-847.
15. GIORDANO FJ (2005) Oxygen, oxidative stress, hypoxia, and heart failure. J Clin Investig 115: 500-508.
16. GUO J, XU K, CHEN T (2004) Quantitative determination of astilbin in rabbit plasma by liquid chromatography. Journal of Chromatography B 805: 357-60.
17. HARAGUCHI H, MOCHIDA Y, SAKAI S, MASUDA H, TAMURA Y, MIZUTANI K, TANAKA O, CHOU WH (1996a) Protection against oxidative damage by dihydroflavonols in Engelhardtia chrysolepis. Biosc Biotech Biochem 60: 945-948.
18. HARAGUCHI H, OHMI I, MASUDA H, TAMURA Y, MIZUTANI K, TANAKA O, CHOU WH (1996b) Inhibition of aldose reductase by dihydroflavonols in Engelhardtia chrysolepis and effects on other enzymes. Experientia 52: 564-567.
19. HAVSTEEN BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Therap 96: 67-202.
20. HERTOG MG, KROMHOUT D, ARAVANIS C, BLACKBURN H, BUZINA R, FIDANZA F (1995) Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Internal Med 155: 381-386.
21. HOSNY M, ROSAZZA JP (2002) Novel oxidations of (+)- catechin by horseradish peroxidase and laccase. J Agric Food Chem 50: 5539-5545.
22. IGARASHI K, UCHIDA Y, MURAKAMI N, MIZUTANI K, MASUDA H (1996) Effect of astilbin in tea processed from leaves of Engelhardtia chrysolepis on the serum and liver lipid concentrations and on the erythrocyte and liver antioxidative enzyme activities of rats. Biosc Biotech Biochem 60: 513-515.
23. JORGE NETO J, FRACASSO JF, CAMARGO NEVES MCL, SANTOS LE, BANUTH VL (1996) Tratamento de úlcera varicosa e lesões de pele com Calendula officinalis L. e/ou com Stryphnodendron barbatiman (Vellozo) Martius. Rev Ciênc Farm 17: 181-186.
24. KHALIL NM, PEPATO MT, BRUNETTI IL (2008) Free radical scavenging profile and myeloperoxidase inhibition of extracts from antidiabetic plants: bauhinia forficata and cissus sicyoides. Biol Res 41: 165-171.
25. KOSTYUK VA, KRAEMER T, SIES H, SCHEWE T (2003) Myeloperoxidase/nitrite-mediated lipid peroxidation of low-density lipoprotein as modulated by flavonoids. FEBS Letters 537: 146-50.
26. LANDRAULT N, LARRONDE F, DELAUNNAY JC, CASTAGNINO C, VERCAUTEREN J, MERILLON JM, GASC F, CROS G, TEISSEDRE PL (2002) Levels of stilbenes oligomers and astilbin in french varietal wines and in grapes during noble rot development. Journal of Agricultural and Food Chemistry 50: 2046-52.
27. LIANG Y, XU Q, KANG A, XIE Y, XIE T, LIU L, HAO H, XIE L, WANG G (2009) Validation and application of an LC-ESI-MS method for simultaneous determination of astilbin and its major metabolite 3'-Omethylastilbin in rat plasma. Journal of Chromatography B 877: 1765-70.
28. LIMA JCS, MARTINS DTO, DE SOUZA JR, PT (1998) Experimental evaluation of stem bark of Stryphnodendron adstringens (Mart.) Coville for antiinflammatory activity. Phyt Res 12: 218-220.
29. LIU RH (2003) Health benefits of fruit and vegetables are from additive and synergistic combinations of phytochemicals. Am J Clin Nutr 78: 517-520.
30. LOPES GC, SANCHES ACC, NAKAMURA CV, DIAS FILHO BP, HERNANDES L, MELLO JCP (2005) Influence of extracts of Stryphnodendron polyphyllum Mart. and Stryphnodendron obovatum Benth. on the cicatrisation of cutaneous wounds in rats. J Ethnopharm 99: 265-272
31. LORENZI H (1992) Árvores Brasileiras: manual de identificação e cultivo de plantas arbóreas nativas do Brasil. Nova Odessa, SP, Editora Plantarum, 352 p.
32. MACHIN M, SIMOYI MF, BLEMINGS KP, KLANDORF H (2004) Increased dietary protein elevates plasma uric acid and is associated with decreased oxidative stress in rapidly-growing broilers. Comp Biochem Physiol B 137: 383-390.
33. MERTENS A, HOLVOET P (2001) Oxidized LDL and HDL: antagonists in atherothrombosis. Faseb J 15: 2073-2084.
34. MIURA T, MURAOKA S, FUJIMOTO Y (2003) Inactivation of creatine kinase induced by quercetin with horseradish peroxidase and hydrogen peroxide: pro-oxidative and anti-oxidative actions of quercetin. Food Chem Toxicol 41: 759-765.
35. MOTOYASHIKI T, MIYAKE M, MORITA T, MIZUTANI K, MASUDA H, UEKI H (1998) Enhancement of the vanadate-stimulated release of lipoprotein lipase activity by astilbin from the leaves of Engelhardtia chrysolepis. Biol Pharm Bul 21: 517-519.
36. PANIZZA S, ROCHA AB, GECCHI R, SILVA RAP. (1988) Stryphnodendron barbadetiman (Vellozo) Martius: teor em tanino na casca e sua propriedade cicatrizante. Rev Ciênc Farm 10: 101-106.
37. PEREIRA LB, PETACCI F, FERNANDES JB, VIEIRA PC, SILVA M. FGF, MALASPINA, O, CORREA AG (2002) Biological activity of astilbin from Dimorphandra mollis Benth. against Anticarsia gemmatalis Hübner and Spodoptera frugiperda Smith. Pest Man Sci 58: 503-507.
38. RAJENDRAN M, MANISANKAR P, GANDHIDASAN R, MURUGESAN R (2004) Free radicals scavenging efficiency of a few naturally occurring flavonoids: a comparative study. J Agric Food Chem 52: 7389-7394.
39. RE R, PELLEGRINI N, PROTEGGENTE A, PANNALA A, YANG M, RICE-EVANS C (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Rad. Biol. Med. 26: 1231-1237.
40. REGASINI LO, VELLOSA JC, SILVA DH, FURLAN M, DE OLIVEIRA OM, KHALIL NM, BRUNETTI IL, YOUNG MC, BARREIRO EJ, BOLZANI VS (2008) Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors. Phytochemistry 69: 1739-44.
41. B.C. SAUNDERS, Peroxidases and catalases, in: G.L. Eichhorn (Ed.), Inorganic Biochemistry, Elsevier, Amsterdam, 1973, pp. 988-1021.
42. STINEFELT B, LEONARD SS, BLEMINGS KP, SHI X, KLANDORF H (2005) Free radical scavenging, DNA protection, and inhibition of lipid peroxidation mediated by uric acid. An. Clin. Lab. Sci. 35: 37-45.
43. URQUIAGA I, LEIGHTON F (2000) Plant polyphenol antioxidants and oxidative stress. Biol. Res. 33: 55-64.
44. VAN ACKER SA, DE GROOT MJ, VAN DEN BERG DJ, TROMP MN, DONNE-OP DEN KELDER G, VAN DER VIJGH WJ, BAST A (1996) A quantum chemical explanation of the antioxidant activity of flavonoids. Chem. Res. Toxicol. 9: 1305-1312.
45. XU Q, WU FG, CAO JS, CHEN T, JIANG JY, SAIKI I, KODA A (1999) Astilbin selectively induces dysfunction of liver-infiltrating cells-novel protection from liver damage. Eur J Pharmacol 377: 93-100.
46. YAN R, XU Q (2001) Astilbin selectively facilitates the apoptosis of interleukin-2-dependent phytohemagglutinin-activated Jurkat cells. Pharmacol Res 44: 135-139.
47. YAO LH, JIANG YM, SHI J, TOMAS-BARBERAN FA, DATTA N, SINGANUSONG R, CHEN SS (2004) Flavonoids in food and their health benefits. Plant Foods Hum Nutr 59: 113-122.
48. YAO LH, JIANG YM, SHI J, TOMAS-BARBERAN FA, DATTA N, SINGANUSONG R, CHEN SS (2004) Flavonoids in food and their health benefits. Plant Foods Hum Nutr 59: 113-122.