Antioxidants from Rabdosia japonica

Phytotherapy Research

Volumn 20, Issue 3, 2006, Pages 206-213

  Masuoka, Noriyoshi ^a   Isobe, Takahiko ^b   Kubo, Isao ^c  

^a OKAYAMA UNIVERSITY   (Japan)

^b HYOGO COLLEGE OF MEDICINE   (Japan)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antioxidant; Inhibition kinetics; Pedalitin; Rabdosia japonica; Rosmarinic acid; Xanthine oxidase

Indexed keywords

ANTIOXIDANT; FLAVONOID; ISOQUERCITRIN; PEDALITIN; QUERCETIN; ROSMARINIC ACID; RUTOSIDE; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG; URIC ACID; XANTHINE; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR;

ANTIOXIDANT ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; DRUG EFFECT; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; LINEWEAVER BURK PLOT; PLANT LEAF; PLOTS AND CURVES; RABDOSIA; RABDOSIA JAPONICA;

ANTIOXIDANTS; CINNAMATES; DEPSIDES; FLAVONES; FLAVONOIDS; FLAVONOLS; INHIBITORY CONCENTRATION 50; PICRATES; PLANT EXTRACTS; PLANT LEAVES; RABDOSIA; SUPEROXIDES; URIC ACID; XANTHINE OXIDASE;

JAPONICA; LAMIACEAE; RABDOSIA;

EID: 33645470431     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.1835     Document Type: Article

References (49)

1. Agata I, Hatano T, Nishibe S, Okuda T. 1988. Rabdosiin, a new rosmarinic acid dimer with a lignan skeleton, from Rabdosia japonica. Chem Phar Bull 36: 3223-3225.
2. Awad HM, Boersma MG, Vervoort J, Rietjens IMCM. 2000. Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts. Arch Biochem Biophys 378: 224-233.
3. Boersma MG, Vervoort J, Szymusiak H et al. 2000. Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide. Chem Res Toxicol 13: 185-191.
4. Bray RC. 1975. Molybdenum iron-sulfur flavin hydroxylases and related enzymes. In The Enzymes, Boyer PD (ed.), volume 12. Academic Press: New York, 299-419.
5. Cimanga K, DeBruyen T, Hu JP et al. 1999. Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions. Pharm Pharmacol Commun 5: 419-424.
6. Constantinou A, Mehta R, Runyan C, Rao K, Vaughan A, Moon R. 1995. Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships. J Nat Prod 58: 217-225.
7. Cosentino F, Patton S, D'Uscio LV, Werner ER. 1998. Tetrahydrobiopterin alters superoxide and nitric oxide release in prehypertensive rats. J Clin Invest 101: 1530-1537.
8. Dailey LA, Imming P. 1999. 12-Lipoxygenase: classification, possible therapeutic benefits from inhibition, and inhibitors. Curr Med Chem 6: 389-398.
9. Dangles O, Fargeix G, Dufour C. 1999. One-electron oxidation of quercetin and quercetin derivatives in protic and non protic media. J Chem Soc Perkin Trans 2: 1387-1395.
10. Enforth C, Eger BT, Okamoto K, Nishino T, Nishino T, Pai EF. 2000. Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structure-based mechanism of conversion. Proc Natl Acad Sci 97: 10723-10728.
11. Fernandez MT, Mira ML, Florêncio MH, Jennings KR. 2002. Iron and copper chelation by flavonoids: an electrospray mass spectrometry study. J Inorg Biochem 92: 105-111.
12. Fleming I, Michaelis UR, Bredenkotter D et al. 2001. Endothelium-derived hyperpolarizing factor synthase (cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res 88: 44-51.
13. Fujita E, Node M. 1984. Diterpenoids of Rabdosia species. Prog Chem Org Nat Prod 46: 77-157.
14. Galati G, Teng S, Moridani MY, Chan TS, O'Brien PJ. 2000. Cancer chemoprevention and apoptosis mechanisms induced by dietary polyphenolics. Drug Metabol Drug Interact 17: 311-349.
15. Halliwell B, Gutteridge JMC. 1990. Role of free radicals and catalytic metal ions in human disease: an overview. In Methods in Enzymology, Packer L, Glazer AN (eds), volume 186. Academic Press: New York, 1-85.
16. Hara H. 1972. On the Asiatic species of the genus Rabdosia (Labiatae). J Jpn Bot 47: 193-203.
17. Hara H. 1985. Comments on the east Asiatic plants. 17. J Jpn Bot 60: 230-237.
18. Haraguchi H, Ishikawa H, Sanchez Y, Ogura T, Kubo Y, Kubo I. 1997. Antioxidative constituents in Heterotheca inuloides. Bioorg Med Chem 5: 865-871.
19. Harrison R. 2002. Structure and function of xanthine oxidoreductase: where are we now? Free Radic Biol Med 33: 774-797.
20. Isobe T, Kamikawa T, Kubota T. 1972. Bitter components from the leaves of Isodon species. Nippon Kagaku Kaishi 2143-2148.
21. Isobe T, Noda Y, Kubota T. 1985. Phenolic compounds from Rabdosia japonica. Nippon Kagaku Kaishi 1513-1515.
22. Jungbluth G, Rühling I, Ternes W. 2000. Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media. J Chem Soc Perkin Trans 2: 1946-1952.
23. Knight JA. 1998. Free radicals: their history and current status in aging and disease. Ann Clin Lab Sci 28: 331-346.
24. Kober T, Konig I, Weber M, Kojda G. 2003. Diethyldithiocarbamate inhibits the catalytic activity of xanthine oxidase. FEBS Lett 551: 99-103.
25. Kok FJ, van Popple G, Melse J et al. 1991. Do antioxidants and polyunsaturated fatty acids have a combined association with coronary atherosclerosis? Atherosclerosis 86: 85-90.
26. Krishnamachari V, Levine LH, Paré PW. 2002. Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J Agric Food Chem 50: 4357-4363.
27. Kubo I, Kamikawa T, Kubota T. 1974. Constituents of Isodon japonicus. Structures and absolute stereochemistry of isodonal, trichodonin, and epinodosin. Tetrahedron 30: 615-622.
28. Kubo I, Nihei K, Shimizu K. 2004. Oxidation products of quercetin catalyzed by mushroom tyrosinase. Bioorg Med Chem 12: 5343-5347.
29. Kukreja RC, Kontos HA, Hess ML, Ellis EF. 1986. PGH synthase and lipoxygenase generate superoxide in the presence of NADH or NADPH. Circ Res 59: 612-619.
30. Lee KH, Lin YM, Wu TS et al. 1988. The cytotoxic principles of Prunella vulgaris, Psychotria serpens, and Hyptis capitata: ursolic acid and related derivatives. Planta Med 54: 308-311.
31. Lin T-J, Liu G-T, Liu Y, Xu G-Z. 1992. Protection by salvianolic acid A against adriamycin toxicity on rat heart mitochondria. Free Radic Biol Med 12: 347-351.
32. Lu Y, Foo LY. 2001. Antioxidant activities of polyphenols from sage (Salvia officinalis). Food Chem 75: 197-202.
33. Machlin L, Bendich A. 1987. Free radical tissue damage: protective role of antioxidant nutrients. Fed Am Soc Exp Biol J 1: 441-445.
34. Najid A, Simon A, Cook J et al. 1992. Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL60 leukemic cells. FEBS Lett 299: 213-217.
35. Nakamura Y, Ohto Y, Murakami A, Ohigashi H. 1998. Superoxide scavenging activity of rosmarinic acid from Perilla frutescens Britton Var. acuta f. viridis. J Agric Food Chem 46: 4545-4550.
36. Olthof MR, Hollman PCH, Buijsman MNCP, van Amelsvoort JMM, Katan MB. 2003. Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr 133: 1806-1814.
37. Pagano P, Ito Y, Tomheim K, Gallop P, Tauber A, Cohen RA. 1995. An NADPH oxidase superoxide-generating system in the rabbit aorta. Am J Physiol 268: H2274-H2280.
38. Petersen M, Simmonds MSJ. 2003. Rosmarinic acid. Phytochemistry 62: 121-125.
39. Rice-Evans C, Miller N. 1997. Measurement of the antioxidant status of dietary constituents, low density lipoproteins and plasma. Prostaglandins Leukot Essent Fatty Acids 57: 499-505.
40. Rousseau EJ, Davison AJ, Dunn B. 1992. Protection by beta-carotene and related compounds against oxygen-mediated cytotoxicity and genotoxicity: implications for carcinogenesis and anticarcinogenesis. Free Radic Biol Med 13: 407-433.
41. Slater TF, Cheeseman KH, Davies MJ, Proudfoot K, Xin W. 1987. Free radical mechanisms in relation to tissue injury. Proc Nutr Soc 46: 1-12.
42. Steele VE, Holmes CA, Hawk ET et al. 1999. Lipoxygenase inhibitors as potential cancer chemopreventives. Cancer Epidemiol Biomarkers Prev 8: 467.
43. Sugawara H, Tobise K, Minami H, Uekita K, Yoshie H, Onodera S. 1992. Diabetes mellitus and reperfusion injury increase the level of active oxygen-induced lipid peroxidation in rat cardiac membranes. J Clin Exp Med (Igaku no Ayumi) 163: 237-238.
44. Takeda Y, Otsuka H. 1995. Recent advances in the chemistry of diterpenoids from Rabdosia species. Stud in Nat Prod Chem, Structure and chemistry (Part C) 15: 111-185.
45. Toda S, Kumura M, Ohnishi M. 1991. Effects of phenolcarboxylic acids on superoxide anion and lipid peroxidation induced by superoxide anion. Planta Med 57: 8-10.
46. Tokuda H, Ohigashi H, Koshimizu K, Ito Y. 1986. Inhibitory effects of ursolic and oleanolic acid on skin tumor promotion by 12-O-tetradecanoylphorbol- 13-acetate. Cancer Lett 33: 279-285.
47. Wiswedel I, Ulbricht O, Augustin W. 1989. Studies of lipid peroxidation in isolated rat heart mitochondria. Biomed Biochem Acta 2: S73-S76.
48. Yagi K. 1987. Lipid peroxides and human diseases. Chem Phys Lipids 45: 337-351.
49. Yang CS, Landau JM, Huang MT. 2001. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 21: 381-406.