Investigation of cytochrome P450 inhibitory properties of maslinic acid, a bioactive compound from Olea europaea L., and its structure-activity relationship

Phytomedicine

Volumn 22, Issue 1, 2015, Pages 56-65

  Sun, Min ^a   Tang, Yu ^a   Ding, Tonggui ^a   Liu, Mingyao ^a,b   Wang, Xin ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

Cytochrome P450 (CYP); Maslinic acid; Olea europaea; Oleanolic acid; Pentacyclic triterpenes

Indexed keywords

CYTOCHROME P450 2C11; CYTOCHROME P450 2E1; CYTOCHROME P450 3A2; CYTOCHROME P450 3A4; HYDROXYL GROUP; MASLINIC ACID; OLEANOLIC ACID; CYP3A4 PROTEIN, HUMAN; CYTOCHROME P450 3A; CYTOCHROME P450 INHIBITOR; TRITERPENE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; DRUG EFFECT; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME KINETICS; HUMAN; LIVER MICROSOME; MALE; NONHUMAN; OLIVE TREE; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; DRUG EFFECTS; IC50; METABOLISM; SPRAGUE DAWLEY RAT;

OLEA EUROPAEA;

ANIMALS; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MALE; MICROSOMES, LIVER; OLEA; OLEANOLIC ACID; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 84915767812     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2014.10.003     Document Type: Article

References (45)

1. Y. Allouche, F. Warleta, M. Campos, C. Sanchez-Quesada, M. Uceda, and G. Beltran Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage J. Agric. Food Chem. 59 2011 121 130
2. D.G. Bailey, J. Malcolm, O. Arnold, and J.D. Spence Grapefruit juice-drug interactions Br. J. Clin. Pharmacol. 46 1998 101 110
3. Z. Bibi Role of cytochrome P450 in drug interactions Nutr. Metab. 5 2008 27
4. L.F. Blob, M. Sharoky, B.J. Campbell, E.M. Kemper, M.G. Gilmor, and C.M. VanDenberg Effects of a tyramine-enriched meal on blood pressure response in healthy male volunteers treated with selegiline transdermal system 6 mg/24 hour CNS Spectr. 12 2007 25 34
5. R.E. Brown, K.L. Jarvis, and K.J. Hyland Protein measurement using bicinchoninic acid: elimination of interfering substances Anal. Biochem. 180 1989 136 139
6. W.K. Chan, L.T. Nguyen, V.P. Miller, and R.Z. Harris Mechanism-based inactivation of human cytochrome P450 3A4 by grapefruit juice and red wine Life Sci. 62 1998 135 142
7. J.D. Chen, Y.Z. Wu, Z.L. Tao, Z.M. Chen, and X.P. Liu Hawthorn (shan zha) drink and its lowering effect on blood lipid levels in humans and rats World Rev. Nutr. Diet 77 1995 147 154
8. A. Dahan, and G.L. Amidon Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of p-glycoprotein Pharm. Res. 26 2009 883 892
9. M.S. Faber, A. Jetter, and U. Fuhr Assessment of CYP1A2 activity in clinical practice: why, how, and when? Basic Clin. Pharmacol. Toxicol. 97 2005 125 134
10. R. Ghanbari, F. Anwar, K.M. Alkharfy, A.H. Gilani, and N. Saari Valuable nutrients and functional bioactives in different parts of olive (Olea europaea L.)-A review Int. J. Mol. Sci. 13 2012 3291 3340
11. T. Guan, Y. Qian, X. Tang, M. Huang, L. Huang, and Y. Li Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation J. Neurosci. Res. 89 2011 1829 1839
12. L. Huang, T. Guan, Y. Qian, M. Huang, X. Tang, and Y. Li Anti-inflammatory effects of maslinic acid, a natural triterpene, in cultured cortical astrocytes via suppression of nuclear factor-kappa B Eur. J. Pharmacol. 672 2011 169 174
13. Z. Huang, M.J. Fasco, and L.S. Kaminsky Alternative splicing of CYP2D mRNA in human breast tissue Arch. Biochem. Biophys. 343 1997 101 108
14. K. Ikeya, A.K. Jaiswal, R.A. Owens, J.E. Jones, D.W. Nebert, and S. Kimura Human CYP1A2: sequence, gene structure, comparison with the mouse and rat orthologous gene, and differences in liver 1A2 mRNA expression Mol. Endocrinol. 3 1989 1399 1408
15. M.E. Juan, U. Wenzel, V. Ruiz-Gutierrez, H. Daniel, and J.M. Planas Olive fruit extracts inhibit proliferation and induce apoptosis in HT-29 human colon cancer cells J. Nutr. 136 2006 2553 2557
16. E. Kim, A. Sy-Cordero, T.N. Graf, S.J. Brantley, M.F. Paine, and N.H. Oberlies Isolation and identification of intestinal CYP3A inhibitors from cranberry (Vaccinium macrocarpon) using human intestinal microsomes Planta Med. 77 2011 265 270
17. K.A. Kim, J.S. Lee, H.J. Park, J.W. Kim, C.J. Kim, I.S. Shim, N.J. Kim, S.M. Han, and S. Lim Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes Life Sci. 74 2004 2769 2779
18. J. Kirchheiner, and J. Brockmoller Clinical consequences of cytochrome P450 2C9 polymorphisms Clin. Pharmacol. Ther. 77 2005 1 16
19. C. Li, Z. Yang, Z. Li, Y. Ma, L. Zhang, and C. Zheng Maslinic acid suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by regulating RANKL-mediated NF-kappaB and MAPK signaling pathways J. Bone Miner. Res. 26 2011 644 656
20. C. Li, Z. Yang, C. Zhai, W. Qiu, D. Li, and Z. Yi Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor alpha by inhibiting NF-kappaB signaling pathway Mol. Cancer 9 2010 73
21. G. Lozano-Mena, M.E. Juan, A. Garcia-Granados, and J.M. Planas Determination of maslinic acid, a pentacyclic triterpene from olives, in rat plasma by high-performance liquid chromatography J. Agric. Food Chem. 60 2012 10220 10225
22. S. Madani, M.F. Paine, L. Lewis, K.E. Thummel, and D.D. Shen Comparison of CYP2D6 content and metoprolol oxidation between microsomes isolated from human livers and small intestines Pharm. Res. 16 1999 1199 1205
23. R. Martin, J. Carvalho-Tavares, E. Ibeas, M. Hernandez, V. Ruiz-Gutierrez, and M.L. Nieto Acidic triterpenes compromise growth and survival of astrocytoma cell lines by regulating reactive oxygen species accumulation Cancer Res. 67 2007 3741 3751
24. M.P. Montilla, A. Agil, M.C. Navarro, M.I. Jimenez, A. Garcia-Granados, and A. Parra Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea Planta Med. 69 2003 472 474
25. F.R. Nieto, E.J. Cobos, J.M. Entrena, A. Parra, A. Garcia-Granados, and J.M. Baeyens Antiallodynic and analgesic effects of maslinic acid, a pentacyclic triterpenoid from Olea europaea J. Nat. Prod. 76 2013 737 740
26. R.W. Owen, R. Haubner, G. Wurtele, E. Hull, B. Spiegelhalder, and H. Bartsch Olives and olive oil in cancer prevention Eur. J. Cancer Prev. 13 2004 319 326
27. M.F. Paine, H.L. Hart, S.S. Ludington, R.L. Haining, A.E. Rettie, and D.C. Zeldin The human intestinal cytochrome P450 pie Drug Metab. Dispos. 34 2006 880 886
28. S.Y. Park, C.W. Nho, D.Y. Kwon, Y.H. Kang, K.W. Lee, and J.H. Park Maslinic acid inhibits the metastatic capacity of DU145 human prostate cancer cells: possible mediation via hypoxia-inducible factor-1alpha signalling Br. J. Nutr. 109 2013 210 222
29. M.C. Perez-Camino, and A. Cert Quantitative determination of hydroxypentacyclic triterpene acids in vegetable oils J. Agric. Food Chem. 47 1999 1558 1562
30. A.E. Rettie, and J.P. Jones Clinical and toxicological relevance of CYP2C9: drug-drug interactions and pharmacogenetics Annu. Rev. Pharmacol. Toxicol. 45 2005 477 494
31. F.J. Reyes-Zurita, G. Pachon-Pena, D. Lizarraga, E.E. Rufino-Palomares, M. Cascante, and J.A. Lupianez The natural triterpene maslinic acid induces apoptosis in HT29 colon cancer cells by a JNK-p53-dependent mechanism BMC Cancer 11 2011 154
32. F.J. Reyes-Zurita, E.E. Rufino-Palomares, J.A. Lupianez, and M. Cascante Maslinic acid, a natural triterpene from Olea europaea L., induces apoptosis in HT29 human colon-cancer cells via the mitochondrial apoptotic pathway Cancer Lett. 273 2009 44 54
33. J.M. Rigelsky, and B.V. Sweet Hawthorn: pharmacology and therapeutic uses Am. J. Health Syst. Pharm. 59 2002 417 422
34. M. Sanchez-Gonzalez, G. Lozano-Mena, M.E. Juan, A. Garcia-Granados, and J.M. Planas Assessment of the safety of maslinic acid, a bioactive compound from Olea europaea L Mol. Nutr. Food Res. 57 2013 339 346
35. P. Schmiedlin-Ren, D.J. Edwards, M.E. Fitzsimmons, K. He, K.S. Lown, and P.M. Woster Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents, decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins Drug Metab. Dispos. 25 1997 1228 1233
36. M. Sun, Y. Tang, T. Ding, M. Liu, and X. Wang Inhibitory effects of celastrol on rat liver cytochrome P450 1A2, 2C11, 2D6, 2E1 and 3A2 activity Fitoterapia 92 2014 1 8
37. T. Uno, and N. Yasui-Furukori Effect of grapefruit juice in relation to human pharmacokinetic study Curr. Clin. Pharmacol. 1 2006 157 161
38. J. Venhorst, A.M. ter Laak, J.N. Commandeur, Y. Funae, T. Hiroi, and N.P. Vermeulen Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities J. Med. Chem. 46 2003 74 86
39. X. Wang, C.M. Cheung, W.Y. Lee, P.M. Or, and J.H. Yeung Major tanshinones of Danshen (Salvia miltiorrhiza) exhibit different modes of inhibition on human CYP1A2, CYP2C9, CYP2E1 and CYP3A4 activities in vitro Phytomedicine 17 2010 868 875
40. X. Wang, W.Y. Lee, P.M. Or, and J.H. Yeung Effects of major tanshinones isolated from Danshen (Salvia miltiorrhiza) on rat CYP1A2 expression and metabolism of model CYP1A2 probe substrates Phytomedicine 16 2009 712 725
41. X. Wang, W.Y. Lee, P.M. Or, and J.H. Yeung Pharmacokinetic interaction studies of tanshinones with tolbutamide, a model CYP2C11 probe substrate, using liver microsomes, primary hepatocytes and in vivo in the rat Phytomedicine 17 2010 203 211
42. X. Wang, and J.H. Yeung Inhibitory effect of tanshinones on rat CYP3A2 and CYP2C11 activity and its structure-activity relationship Fitoterapia 82 2011 539 545
43. X. Wang, and J.H. Yeung Investigation of cytochrome P450 1A2 and 3A inhibitory properties of Danshen tincture Phytomedicine 19 2012 348 354
44. S. Zhou, S. Yung Chan, B. Cher Goh, E. Chan, W. Duan, and M. Huang Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs Clin. Pharmacokinet. 44 2005 279 304
45. R. Zuber, E. Anzenbacherova, and P. Anzenbacher Cytochromes P450 and experimental models of drug metabolism J. Cell Mol. Med. 6 2002 189 198