Xyloketal B exhibits its antioxidant activity through induction of HO-1 in vascular endothelial cells and zebrafish

Marine Drugs

Volumn 11, Issue 2, 2013, Pages 504-522

  Li, Zhen Xing ^a   Chen, Jian Wen ^b   Yuan, Feng ^a   Huang, Yun Ying ^a   Zhao, Li Yan ^a   Li, Jie ^b   Su, Huan Xing ^c   Liu, Jie ^a   Pang, Ji Yan ^b   Lin, Yong Cheng ^b   Lu, Xi Lin ^b   Pei, Zhong ^b   Wang, Guan Lei ^a,b   Guan, Yong Yuan ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

^c University of Macau   (Macao)

Author keywords

Apoptosis; HO 1; Nrf 2; Reactive oxygen species; Xyloketal B

Indexed keywords

1,4 DIAMINO 1,4 BIS(2 AMINOPHENYLTHIO) 2,3 DICYANOBUTADIENE; 2 MORPHOLINO 8 PHENYLCHROMONE; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; ANGIOTENSIN II; ANTIOXIDANT; HEME OXYGENASE 1; LIPOCORTIN 5; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; PROTOPORPHYRIN; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; XYLOKETAL B;

ANTIOXIDANT ACTIVITY; ANTIOXIDANT RESPONSIVE ELEMENT; APOPTOSIS; ARTICLE; CONTROLLED STUDY; EMBRYO; ENDOTHELIUM CELL; ENZYME ACTIVITY; FLOW CYTOMETRY; GENE EXPRESSION; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; OXIDATIVE STRESS; PROTEIN PHOSPHORYLATION; UMBILICAL VEIN ENDOTHELIAL CELL; VASCULAR ENDOTHELIUM; ZEBRA FISH;

EID: 84875787395     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11020504     Document Type: Article

References (38)

1. Wu, Q.; Huang, K. Protective effect of ebselen on cytotoxicity induced by cholestane-3 beta, 5 alpha, 6 beta-triol in ECV-304 cells. Biochim. Biophys. Acta 2006, 1761, 350-359.
2. Yamaguchi, T.; Sano, K.; Takakura, K.; Saito, I.; Shinohara, Y.; Asano, T.; Yasuhara, H. Ebselen in acute ischemic stroke: A placebo-controlled, double-blind clinical trial. Ebselen Study Group. Stroke 1998, 29, 12-17.
3. Lin, Y.; Wu, X.; Feng, S.; Jiang, G.; Luo, J.; Zhou, S.; Vrijmoed, L.L.; Jones, E.B.; Krohn, K.; Steingrover, K.; Zsila, F. Five unique compounds: Xyloketals from mangrove fungus Xylaria sp. from the South China Sea coast. J. Org. Chem. 2001, 66, 6252-6256.
4. Chen, W.L.; Qian, Y.; Meng, W.F.; Pang, J.Y.; Lin, Y.C.; Guan, Y.Y.; Chen, S.P.; Liu, J.; Pei, Z.; Wang, G.L. A novel marine compound xyloketal B protects against oxidized LDL-induced cell injury in vitro. Biochem. Pharmacol. 2009, 78, 941-950.
5. Lu, X.L.; Yao, X.L.; Liu, Z.; Zhang, H.; Li, W.; Li, Z.; Wang, G.L.; Pang, J.; Lin, Y.; Xu, Z.; et al. Protective effects of xyloketal B against MPP+-induced neurotoxicity in Caenorhabditis elegans and PC12 cells. Brain Res. 2010, 1332, 110-119.
6. Zhao, J.; Li, L.; Ling, C.; Li, J.; Pang, J.Y.; Lin, Y.C.; Liu, J.; Huang, R.; Wang, G.L.; Pei, Z.; Zeng, J. Marine compound Xyloketal B protects PC12 cells against OGD-induced cell damage. Brain Res. 2009, 1302, 240-247.
7. Duckers, H.J.; Boehm, M.; True, A.L.; Yet, S.F.; San, H.; Park, J.L.; Clinton Webb, R.; Lee, M.E.; Nabel, G.J.; Nabel, E.G. Heme oxygenase-1 protects against vascular constriction and proliferation. Nat. Med. 2001, 7, 693-698.
8. Buckley, B.J.; Marshall, Z.M.; Whorton, A.R. Nitric oxide stimulates Nrf-2 nuclear translocation in vascular endothelium. Biochem. Biophys. Res. Commun. 2003, 307, 973-979.
9. Chen, J.S.; Huang, P.H.; Wang, C.H.; Lin, F.Y.; Tsai, H.Y.; Wu, T.C.; Lin, S.J.; Chen, J.W. Nrf-2 mediated heme oxygenase-1 expression, an antioxidant-independent mechanism, contributes to anti-atherogenesis and vascular protective effects of Ginkgo biloba extract. Atherosclerosis 2011, 214, 301-309.
10. Kim, Y.M.; Pae, H.O.; Park, J.E.; Lee, Y.C.; Woo, J.M.; Kim, N.H.; Choi, Y.K.; Lee, B.S.; Kim, S.R.; Chung, H.T. Heme oxygenase in the regulation of vascular biology: From molecular mechanisms to therapeutic opportunities. Antioxid. Redox Signal. 2011, 14, 137-167.
11. Abraham, N.G.; Kappas, A. Pharmacological and clinical aspects of heme oxygenase. Pharmacol. Rev. 2008, 60, 79-127.
12. Hosick, P.A.; Stec, D.E. Heme oxygenase, a novel target for the treatment of hypertension and obesity? Am. J. Physiol. Regul. Integr. Comp. Physiol. 2012, 302, R207-R214.
13. Ryter, S.W.; Alam, J.; Choi, A.M. Heme oxygenase-1/carbon monoxide: From basic science to therapeutic applications. Physiol. Rev. 2006, 86, 583-650.
14. Jazwa, A.; Cuadrado, A. Targeting heme oxygenase-1 for neuroprotection and neuroinflammation in neurodegenerative diseases. Curr. Drug Targets 2010, 11, 1517-1531.
15. Ferrandiz, M.L.; Devesa, I. Inducers of heme oxygenase-1. Curr. Pharm. Des. 2008, 14, 473-486.
16. Meijer, A.H.; Spaink, H.P. Host-pathogen interactions made transparent with the zebrafish model. Curr. Drug Targets 2011, 12, 1000-1017.
17. Nayak, A.S.; Lage, C.R.; Kim, C.H. Effects of low concentrations of arsenic on the innate immune system of the zebrafish (Danio rerio). Toxicol. Sci. 2007, 98, 118-124.
18. Phennicie, R.T.; Sullivan, M.J.; Singer, J.T.; Yoder, J.A.; Kim, C.H. Specific resistance to Pseudomonas aeruginosa infection in zebrafish is mediated by the cystic fibrosis transmembrane conductance regulator. Infect. Immun. 2010, 78, 4542-4550.
19. Hermann, A.C.; Millard, P.J.; Blake, S.L.; Kim, C.H. Development of a respiratory burst assay using zebrafish kidneys and embryos. J. Immunol. Methods 2004, 292, 119-129.
20. Datla, S.R.; Dusting, G.J.; Mori, T.A.; Taylor, C.J.; Croft, K.D.; Jiang, F. Induction of heme oxygenase-1 in vivo suppresses NADPH oxidase derived oxidative stress. Hypertension 2007, 50, 636-642.
21. Mazza, F.; Goodman, A.; Lombardo, G.; Vanella, A.; Abraham, N.G. Heme oxygenase-1 gene expression attenuates angiotensin II-mediated DNA damage in endothelial cells. Exp. Biol. Med. (Maywood) 2003, 228, 576-583.
22. Morita, T.; Imai, T.; Sugiyama, T.; Katayama, S.; Yoshino, G. Heme oxygenase-1 in vascular smooth muscle cells counteracts cardiovascular damage induced by angiotensin II. Curr. Neurovasc. Res. 2005, 2, 113-120.
23. Kang, K.W.; Lee, S.J.; Kim, S.G. Molecular mechanism of Nrf-2 activation by oxidative stress. Antioxid. Redox Signal. 2005, 7, 1664-1673.
24. Kim, S.J.; Park, C.; Han, A.L.; Youn, M.J.; Lee, J.H.; Kim, Y.; Kim, E.S.; Kim, H.J.; Kim, J.K.; Lee, H.K.; et al. Ebselen attenuates cisplatin-induced ROS generation through Nrf-2 activation in auditory cells. Hear. Res. 2009, 251, 70-82.
25. Berger, S.P.; Hunger, M.; Yard, B.A.; Schnuelle, P.; van der Woude, F.J. Dopamine induces the expression of heme oxygenase-1 by human endothelial cells in vitro. Kidney Int. 2000, 58, 2314-2319.
26. Yang, L.; Quan, S.; Nasjletti, A.; Laniado-Schwartzman, M.; Abraham, N.G. Heme oxygenase-1 gene expression modulates angiotensin II-induced increase in blood pressure. Hypertension 2004, 43, 1221-1226.
27. Schuhmacher, S.; Wenzel, P.; Schulz, E.; Oelze, M.; Mang, C.; Kamuf, J.; Gori, T.; Jansen, T.; Knorr, M.; Karbach, S.; et al. Pentaerythritol tetranitrate improves angiotensin II-induced vascular dysfunction via induction of heme oxygenase-1. Hypertension 2010, 55, 897-904.
28. Aizawa, T.; Ishizaka, N.; Taguchi, J.; Nagai, R.; Mori, I.; Tang, S.S.; Ingelfinger, J.R.; Ohno, M. Heme oxygenase-1 is upregulated in the kidney of angiotensin II-induced hypertensive rats: Possible role in renoprotection. Hypertension 2000, 35, 800-806.
29. Liu, X.M.; Peyton, K.J.; Shebib, A.R.; Wang, H.; Durante, W. Compound C stimulates heme oxygenase-1 gene expression via the Nrf-2-ARE pathway to preserve human endothelial cell survival. Biochem. Pharmacol. 2011, 82, 371-379.
30. Dikalova, A.; Clempus, R.; Lassegue, B.; Cheng, G.; McCoy, J.; Dikalov, S.; San Martin, A.; Lyle, A.; Weber, D.S.; Weiss, D.; et al. Nox1 overexpression potentiates angiotensin II-induced hypertension and vascular smooth muscle hypertrophy in transgenic mice. Circulation 2005, 112, 2668-2676.
31. Lee, I.T.; Luo, S.F.; Lee, C.W.; Wang, S.W.; Lin, C.C.; Chang, C.C.; Chen, Y.L.; Chau, L.Y.; Yang, C.M. Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress. Am. J. Pathol. 2009, 175, 519-532.
32. Chen, Y.; Junger, W.G. Measurement of oxidative burst in neutrophils. Methods Mol. Biol. 2012, 844, 115-124.
33. Beliaeva, N.F.; Kashirtseva, V.N.; Medvedeva, N.V.; Khudoklinova, I.; Ipatova, O.M.; Archakov, A.I. Zebrafish as a model organism for biomedical studies (in Russian). Biomed. Khim. 2010, 56, 120-131.
34. Dimmeler, S.; Fleming, I.; Fisslthaler, B.; Hermann, C.; Busse, R.; Zeiher, A.M. Activation of nitric oxide synthase in endothelial cells by Akt-dependent phosphorylation. Nature 1999, 399, 601-605.
35. Xu, Z.; Li, Y.; Xiang, Q.; Pei, Z.; Liu, X.; Lu, B.; Chen, L.; Wang, G.; Pang, J.; Lin, Y. Design and synthesis of novel xyloketal derivatives and their vasorelaxing activities in rat thoracic aorta and angiogenic activities in zebrafish angiogenesis screen. J. Med. Chem. 2010, 53, 4642-4653.
36. Bouton, C.; Demple, B. Nitric oxide-inducible expression of heme oxygenase-1 in human cells. Translation-independent stabilization of the mRNA and evidence for direct action of nitric oxide. J. Biol. Chem. 2000, 275, 32688-32693.
37. Morita, T. Heme oxygenase and atherosclerosis. Arterioscler. Thromb. Vasc. Biol. 2005, 25, 1786-1795.
38. Prestera, T.; Talalay, P.; Alam, J.; Ahn, Y.I.; Lee, P.J.; Choi, A.M. Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: Regulation by upstream antioxidant-responsive elements (ARE). Mol. Med. 1995, 1, 827-837.