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Published in: Journal of Inflammation 1/2007

Open Access 01-12-2007 | Research

Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids

Authors: Lucia Rackova, Marek Oblozinsky, Daniela Kostalova, Viktor Kettmann, Lydia Bezakova

Published in: Journal of Inflammation | Issue 1/2007

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Abstract

Roots and stem-bark of Mahonia aquifolium (Oregon grape) (Berberidaceae) are effectively used in the treatment of skin inflammatory conditions.
In the present study, the effect of Mahonia aquifolium crude extract and its two representative alkaloid fractions containing protoberberine and bisbenzylisoquinoline (BBIQ) alkaloids on activity of 12-lipoxygenase (12-LOX), was studied. The reactivity with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), a free stable radical, was evaluated to elucidate the rate of possible lipid-derived radical scavenging in the mechanism of the enzyme inhibition.
The results indicate that although the direct radical scavenging mechanism cannot be ruled out in the lipoxygenase inhibition by Mahonia aquifolium and its constituents, other mechanisms based on specific interaction between enzyme and alkaloids could play the critical role in the lipoxygenase inhibition rather than non-specific reactivity with free radicals.
Literature
1.
go back to reference Muller K, Ziereis K: The antipsoriatic Mahonia aquifolium and its active constituents. I. Pro-antioxidant properties and inhibition of 5-lipoxygenase. Planta Med. 1994, 60: 421-424. 10.1055/s-2006-959523.PubMedCrossRef Muller K, Ziereis K: The antipsoriatic Mahonia aquifolium and its active constituents. I. Pro-antioxidant properties and inhibition of 5-lipoxygenase. Planta Med. 1994, 60: 421-424. 10.1055/s-2006-959523.PubMedCrossRef
2.
go back to reference Volleková A, Košťálová D, Sochorová R: Isoquinoline alkaloids from Mahonia aquifolium stem bark are active against Malassezia spp. Folia Microbiol. 2001, 46: 107-111.CrossRef Volleková A, Košťálová D, Sochorová R: Isoquinoline alkaloids from Mahonia aquifolium stem bark are active against Malassezia spp. Folia Microbiol. 2001, 46: 107-111.CrossRef
3.
go back to reference Galle K, Muller-Jakic B, Proebstle A: Analytical and pharmacological studies on Mahonia aquifolium. Int J Phytomed. 1994, 1: 59-62.CrossRef Galle K, Muller-Jakic B, Proebstle A: Analytical and pharmacological studies on Mahonia aquifolium. Int J Phytomed. 1994, 1: 59-62.CrossRef
4.
go back to reference Amin AH, Subhaiah TV, Abbasi KM: Berberine sulfate: antimicrobial activity, bioassay, and mode of action. Can J Microbiol. 1969, 15: 1067-1076.PubMedCrossRef Amin AH, Subhaiah TV, Abbasi KM: Berberine sulfate: antimicrobial activity, bioassay, and mode of action. Can J Microbiol. 1969, 15: 1067-1076.PubMedCrossRef
5.
go back to reference Gieler U, von der Weth A, Heger M: Mahonia aquifolium – a new type of topical treatment for psoriasis. J Dermatol Treatment. 1995, 6: 31-34.CrossRef Gieler U, von der Weth A, Heger M: Mahonia aquifolium – a new type of topical treatment for psoriasis. J Dermatol Treatment. 1995, 6: 31-34.CrossRef
6.
go back to reference Iwasa K, Moriyasu M, Tachibana Y, Kim HS, Wataya Y, Wiegrebe W, Bastow KF, Cosentino LM, Kozuka M, Lee KH: Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. Bioorg Med Chem. 2001, 9: 2871-84. 10.1016/S0968-0896(01)00154-7.PubMedCrossRef Iwasa K, Moriyasu M, Tachibana Y, Kim HS, Wataya Y, Wiegrebe W, Bastow KF, Cosentino LM, Kozuka M, Lee KH: Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. Bioorg Med Chem. 2001, 9: 2871-84. 10.1016/S0968-0896(01)00154-7.PubMedCrossRef
7.
go back to reference Iwasa K, Moriyasu M, Yamori T, Turuo T, Lee DU, Wiegrebe W: In vitro cytotoxicity of the protoberberine-type alkaloids. J Nat Prod. 2001, 64: 896-98. 10.1021/np000554f.PubMedCrossRef Iwasa K, Moriyasu M, Yamori T, Turuo T, Lee DU, Wiegrebe W: In vitro cytotoxicity of the protoberberine-type alkaloids. J Nat Prod. 2001, 64: 896-98. 10.1021/np000554f.PubMedCrossRef
8.
go back to reference Cernakova M, Kost'alova D, Kettmann V, Plodova M, Toth J, Drimal J: Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium. BMC Complementary and Alternative Medicine. 2002, 2: 2-10.1186/1472-6882-2-2.PubMedPubMedCentralCrossRef Cernakova M, Kost'alova D, Kettmann V, Plodova M, Toth J, Drimal J: Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium. BMC Complementary and Alternative Medicine. 2002, 2: 2-10.1186/1472-6882-2-2.PubMedPubMedCentralCrossRef
9.
go back to reference Choi DS, Kim SJ, Jung MY: Inhibitory activity of berberine on DNA strand cleveage induced by hydrogen peroxide and cytochrome c. Biosci Biotech Biochem. 2001, 65: 452-455. 10.1271/bbb.65.452.CrossRef Choi DS, Kim SJ, Jung MY: Inhibitory activity of berberine on DNA strand cleveage induced by hydrogen peroxide and cytochrome c. Biosci Biotech Biochem. 2001, 65: 452-455. 10.1271/bbb.65.452.CrossRef
10.
go back to reference Yokozawa T, Ishida A, Kashiwada Y, Cho EJ, Kim HY, Ikeshiro Y: Coptidis rhizoma: protective effects against peroxynitrite-induced oxidative damage and elucidation of its active components. J Pharm Pharmacol. 2003, 56: 547-556. 10.1211/0022357023024.CrossRef Yokozawa T, Ishida A, Kashiwada Y, Cho EJ, Kim HY, Ikeshiro Y: Coptidis rhizoma: protective effects against peroxynitrite-induced oxidative damage and elucidation of its active components. J Pharm Pharmacol. 2003, 56: 547-556. 10.1211/0022357023024.CrossRef
11.
go back to reference Akiba S, Kato E, Sato T, Fuji T: Biscoclaurine alkaloids inhibit receptor mediated phospholipase A2 activation probably through uncoupling of a GTP-binding protein from the enzyme in rat peritoneal mast cells. Biochem Pharmacol. 1992, 44: 49-50. 10.1016/0006-2952(92)90036-I.CrossRef Akiba S, Kato E, Sato T, Fuji T: Biscoclaurine alkaloids inhibit receptor mediated phospholipase A2 activation probably through uncoupling of a GTP-binding protein from the enzyme in rat peritoneal mast cells. Biochem Pharmacol. 1992, 44: 49-50. 10.1016/0006-2952(92)90036-I.CrossRef
12.
go back to reference Teh BS, Seow WK, Thong YH: Inhibition of prostaglandins and leukotriene generation by the plant alkaloids tetrandrine and berbamine. Int J Immunopharmac. 1990, 12: 321-26. 10.1016/0192-0561(90)90088-5.CrossRef Teh BS, Seow WK, Thong YH: Inhibition of prostaglandins and leukotriene generation by the plant alkaloids tetrandrine and berbamine. Int J Immunopharmac. 1990, 12: 321-26. 10.1016/0192-0561(90)90088-5.CrossRef
13.
go back to reference Young RN: Inhibition of 5-lipoxygenase: a therapeutic potential yet to be fully realized?. Eur J Med Chem. 1999, 34: 671-685. 10.1016/S0223-5234(99)00225-1.CrossRef Young RN: Inhibition of 5-lipoxygenase: a therapeutic potential yet to be fully realized?. Eur J Med Chem. 1999, 34: 671-685. 10.1016/S0223-5234(99)00225-1.CrossRef
14.
go back to reference Kemal C, Louis-Flamberg P, Krupinsky-Olsen R, Shorter AL: Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry. 1987, 26: 7064-7072. 10.1021/bi00396a031.PubMedCrossRef Kemal C, Louis-Flamberg P, Krupinsky-Olsen R, Shorter AL: Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry. 1987, 26: 7064-7072. 10.1021/bi00396a031.PubMedCrossRef
15.
go back to reference Košťálová D, Brázdovièová B, Tomko J: Isolation of quarternary alkaloids from Mahonia aquifolium (PURSH) Nutt. I. Chem Papers. 1981, 35: 279-283. Košťálová D, Brázdovièová B, Tomko J: Isolation of quarternary alkaloids from Mahonia aquifolium (PURSH) Nutt. I. Chem Papers. 1981, 35: 279-283.
16.
go back to reference Bezakova L, Misik V, Malekova L, Svajdlenka E, Kostalova D: Lipoxygenase inhibition and antioxidant properties of bisbenzylisoquinoline alkaloids isolated from Mahonia aquifolium. Pharmazie. 1996, 5: 758-760. Bezakova L, Misik V, Malekova L, Svajdlenka E, Kostalova D: Lipoxygenase inhibition and antioxidant properties of bisbenzylisoquinoline alkaloids isolated from Mahonia aquifolium. Pharmazie. 1996, 5: 758-760.
17.
go back to reference Kulkarni AP, Cai Y, Richards IS: Rat pulmonary lipoxygenase: dioxygenase activity and role in xenobiotic metabolism. Int J Biochem. 1992, 24: 255-261. 10.1016/0020-711X(92)90255-Y.PubMedCrossRef Kulkarni AP, Cai Y, Richards IS: Rat pulmonary lipoxygenase: dioxygenase activity and role in xenobiotic metabolism. Int J Biochem. 1992, 24: 255-261. 10.1016/0020-711X(92)90255-Y.PubMedCrossRef
18.
go back to reference Blois MS: Antioxidant determination by the use of a stable free radical. Nature. 1958, 181: 1199-1200. 10.1038/1811199a0.CrossRef Blois MS: Antioxidant determination by the use of a stable free radical. Nature. 1958, 181: 1199-1200. 10.1038/1811199a0.CrossRef
19.
go back to reference Mellors A, Tappel AL: The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol. J Biol Chem. 1966, 241: 4353-4356.PubMed Mellors A, Tappel AL: The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol. J Biol Chem. 1966, 241: 4353-4356.PubMed
20.
go back to reference Ratty AK, Sunammoto J, Das NP: Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem Pharmacol. 1988, 37: 989-995. 10.1016/0006-2952(88)90499-6.PubMedCrossRef Ratty AK, Sunammoto J, Das NP: Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem Pharmacol. 1988, 37: 989-995. 10.1016/0006-2952(88)90499-6.PubMedCrossRef
21.
go back to reference Bolivar A, Cevallos-Casals , Cisneros-Zevallos L: Stoichiometric and kinetic studies of phenolic antioxidants from andean purple corn and red-fleshed sweetpotato. J Agricultural Food Chem. 2003, 51: 3313-3319. 10.1021/jf034109c.CrossRef Bolivar A, Cevallos-Casals , Cisneros-Zevallos L: Stoichiometric and kinetic studies of phenolic antioxidants from andean purple corn and red-fleshed sweetpotato. J Agricultural Food Chem. 2003, 51: 3313-3319. 10.1021/jf034109c.CrossRef
22.
go back to reference Yamamoto S: Mammalian lipoxygenases: molecular structures and functions. Biochim Biophys Acta. 1992, 1128: 117-131.PubMedCrossRef Yamamoto S: Mammalian lipoxygenases: molecular structures and functions. Biochim Biophys Acta. 1992, 1128: 117-131.PubMedCrossRef
23.
go back to reference Ibe BO, Raj JU: Developmental differences in production of lipoxygenase metabolites by ovine lungs. Exp Lung Res. 1995, 21 (3): 385-405.PubMedCrossRef Ibe BO, Raj JU: Developmental differences in production of lipoxygenase metabolites by ovine lungs. Exp Lung Res. 1995, 21 (3): 385-405.PubMedCrossRef
24.
go back to reference Lin JK, Tsai SH, Lin-Shiau SY: Antiinflammatory and antitumor effects of flavonoids and flavanoids. Drugs of the Future. 2001, 26: 145-157. 10.1358/dof.2001.026.02.858703.CrossRef Lin JK, Tsai SH, Lin-Shiau SY: Antiinflammatory and antitumor effects of flavonoids and flavanoids. Drugs of the Future. 2001, 26: 145-157. 10.1358/dof.2001.026.02.858703.CrossRef
25.
go back to reference Bezáková L, Muèaji P, Eisenreichová E, Haladová M, Pauliková I, Obložinský M: Effect of different compound from Lilium candidum L. on lipoxygenase activity. Acta Facult Pharm Univ Comenianae. 2004, 51: 45-50. Bezáková L, Muèaji P, Eisenreichová E, Haladová M, Pauliková I, Obložinský M: Effect of different compound from Lilium candidum L. on lipoxygenase activity. Acta Facult Pharm Univ Comenianae. 2004, 51: 45-50.
26.
go back to reference Prieto JM, Recio MC, Giner RM, Manez S, Giner-Larza EM, Rios JL: Influence of traditional Chinese anti-inflammatory medicinal plants on leukocyte and platelet functions. J Pharm Pharmacol. 2003, 55: 1275-1282. 10.1211/0022357021620.PubMedCrossRef Prieto JM, Recio MC, Giner RM, Manez S, Giner-Larza EM, Rios JL: Influence of traditional Chinese anti-inflammatory medicinal plants on leukocyte and platelet functions. J Pharm Pharmacol. 2003, 55: 1275-1282. 10.1211/0022357021620.PubMedCrossRef
27.
go back to reference Gutierrez-Lugo MT, Deschamps JD, Holman TR, Suarez E, Timmermann BN: Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina. Planta Med. 2004, 70: 263-265. 10.1055/s-2004-818920.PubMedCrossRef Gutierrez-Lugo MT, Deschamps JD, Holman TR, Suarez E, Timmermann BN: Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina. Planta Med. 2004, 70: 263-265. 10.1055/s-2004-818920.PubMedCrossRef
28.
go back to reference Lomnitski L, Bar-Natan R, Sklan D, Grossman S: The interaction between beta-carotene and lipoxygenase in plant and animal systems. Biochim Biophys Acta. 1993, 1167 (3): 331-338.PubMedCrossRef Lomnitski L, Bar-Natan R, Sklan D, Grossman S: The interaction between beta-carotene and lipoxygenase in plant and animal systems. Biochim Biophys Acta. 1993, 1167 (3): 331-338.PubMedCrossRef
29.
go back to reference Misik V, Bezakova L, Malekova L, Kostalova D: Lipoxygenase inhibition and antioxidant properties of protoberberine and aporphine alkaloids isolated from Mahonia aquifolium. Planta Med. 1995, 61 (4): 372-373. 10.1055/s-2006-958107.PubMedCrossRef Misik V, Bezakova L, Malekova L, Kostalova D: Lipoxygenase inhibition and antioxidant properties of protoberberine and aporphine alkaloids isolated from Mahonia aquifolium. Planta Med. 1995, 61 (4): 372-373. 10.1055/s-2006-958107.PubMedCrossRef
30.
go back to reference Raèková L, Májeková M, Košťálová D, Štefek M: Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorg Med Chem. 2004, 12: 4709-4715. 10.1016/j.bmc.2004.06.035.CrossRef Raèková L, Májeková M, Košťálová D, Štefek M: Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorg Med Chem. 2004, 12: 4709-4715. 10.1016/j.bmc.2004.06.035.CrossRef
31.
go back to reference Youdim MB, Gassen M, Gross A, Mandel S, Grunblatt E: Iron chelating, antioxidant and cytoprotective properties of dopamine receptor agonist; apomorphine. J Neural Transm Suppl. 2000, 83-96. 58 Youdim MB, Gassen M, Gross A, Mandel S, Grunblatt E: Iron chelating, antioxidant and cytoprotective properties of dopamine receptor agonist; apomorphine. J Neural Transm Suppl. 2000, 83-96. 58
Metadata
Title
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids
Authors
Lucia Rackova
Marek Oblozinsky
Daniela Kostalova
Viktor Kettmann
Lydia Bezakova
Publication date
01-12-2007
Publisher
BioMed Central
Published in
Journal of Inflammation / Issue 1/2007
Electronic ISSN: 1476-9255
DOI
https://doi.org/10.1186/1476-9255-4-15

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