In vitro and in vivo stability of caffeic acid phenethyl ester, a bioactive compound of propolis

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 9, 2007, Pages 3398-3407

  Celli, Nicola ^a   Dragani, Luana K ^a   Murzilli, Stefania ^a   Pagliani, Tommaso ^a   Poggi, Andreina ^a  

^a Consorzio Mario Negri Sud ^*  (Italy)

Author keywords

Caffeic acid phenethyl ester; Carboxylesterase; Ethyl transesterification; Human plasma; Rat plasma

Indexed keywords

CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CAFFEIC ACID PHENETHYL ESTER; CHLOROGENIC ACID; CINNAMIC ACID DERIVATIVE; DEPSIDE; DRUG DERIVATIVE; PHENETHYL ALCOHOL; PROPOLIS; ROSMARINIC ACID; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; BLOOD; CHEMISTRY; COMPARATIVE STUDY; DRUG STABILITY; HUMAN; HYDROLYSIS; RAT;

ANIMALS; CAFFEIC ACIDS; CHLOROGENIC ACID; CINNAMATES; DEPSIDES; DRUG STABILITY; HUMANS; HYDROLYSIS; PHENYLETHYL ALCOHOL; PROPOLIS; RATS;

RATTUS;

EID: 34249340858     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf063477o     Document Type: Article

References (50)

1. Bankova, V.; Dyulgerov, A.; Popov, S.; Marekov, N. A GC/MS study of the propolis phenolic constituents. Z. Naturforsch. C 1987, 42, 147-151.
2. Greenaway, W.; Scaysbrook, T.; Whatley, F. R. The analysis of bud exudate of Populus x euroamericana, and of propolis by gas chromatography-mass spectrometry. Proc. R. Soc. London, Ser. B 1987, 232, 249-272.
3. Burdock, G. A. Review of the biological properties and toxicity of bee propolis (propolis). Food Chem. Toxicol. 1998, 36, 347-363.
4. Banskota, A. H.; Tezuka, Y.; Kadota, S. Recent progress in pharmacological research of propolis. Phytother. Res. 2001, 15, 561-571.
5. Russo, A.; Longo, R.; Vanella, A. Antioxidant activity of propolis: role of caffeic acid phenethyl ester and galangin. Fitoterapia 2002, 73 (Suppl. 1), S21-S29.
6. Grunberger, D.; Banerjee, R.; Eisinger, K.; Oltz, E. M.; Efros, L.; Caldwell, M.; Estevez, V.; Nakanishi, K. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis. Experientia 1988, 44, 230-232.
7. Chiao, C.; Carothers, A. M.; Grunberger, D.; Solomon, G.; Preston, G. A.; Barrett, J. C. Apoptosis and altered redox state induced by caffeic acid phenethyl ester (CAPE) in transformed rat fibroblast cells. Cancer Res. 1995, 55, 3576-3583.
8. Mahmoud, N. N.; Carothers, A. M.; Grunberger, D.; Bilinski, R. T.; Churchill, M. R.; Martucci, C.; Newmark, H. L.; Bertagnolli, M. M. Plant phenolics decrease intestinal tumors in an animal model of familial adenomatous polyposis. Carcinogenesis 2000, 21, 921-927.
9. Fesen, M. R.; Kohn, K. W.; Leteurtre, F.; Pommier, Y. Inhibitors of human immunodeficiency virus integrase. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 2399-2403.
10. Mirzoeva, O. K.; Grishanin, R. N.; Calder, P. C. Antimicrobial action of propolis and some of its components: the effects on growth, membrane potential and motility of bacteria. Microbiol. Res. 1997, 152, 239-246.
11. Huleihel, M.; Isanu, V. Anti-herpes simplex virus effect of an aqueous extract of propolis. Isr. Med. Assoc. J. 2002, 4 (11), 923-927.
12. Borrelli, F.; Posadas, I.; Capasso, R.; Aviello, G.; Ascione, V.; Capasso, F. Effect of caffeic acid phenethyl ester on gastric acid secretion in vitro. Eur. J. Pharmacol. 2005, 521, 139-143.
13. Maffia, P.; Ianaro, A.; Pisano, B.; Borrelli, F.; Capasso, F.; Pinto, A.; Ialenti, A. Beneficial effects of caffeic acid phenethyl ester in a rat model of vascular injury. Br. J. Pharmacol. 2002, 136, 353-360.
14. Liao, H.-F.; Chen, Y.-Y.; Liu, J.-J.; Hsu, M.-L.; Shieh, H.-J.; Liao, H.-J.; Shieh, C.-J.; Shiao, M.-S.; Chen, Y.-J. Inhibitory effect of caffeic acid phenethyl ester on angiogenesis, tumor invasion, and metastasis. J. Agric. Food Chem. 2003, 51, 7907-7912.
15. Carrasco-Legleu, C. E.; Márquez-Rosado, L.; Fattel-Fazenda, S.; Arce-Popoca, E.; Pérez-Carreón, J. I.; Villa-Treviño, S. Chemoprotective effect of caffeic acid phenethyl ester on promotion in a medium-term rat hepatocarcinogenesis assay. Int. J. Cancer 2004, 108, 488-492.
16. Chung, T.-W.; Moon, S.-K.; Chang, Y.-C.; Ko, J.-H.; Lee, Y.-C.; Cho, G.; Kim, S.-H.; Kim, J.-G.; Kim, C.-H. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J. 2004, 18, 1670-1681.
17. Kuo, H.-C.; Kuo, W.-H.; Lee, Y.-J.; Lin, W.-L.; Chou, F.-P.; Tseng, T.-H. Inhibitory effect of caffeic acid phenethyl ester on the growth of C6 glioma cells in vitro and in vivo. Cancer Lett. 2006, 234, 199-208.
18. Celli, N.; Mariani, B.; Dragani, L. K.; Murzilli, S.; Rossi, C.; Rotilio, D. Development and validation of a liquid chromatographic-tandem mass spectrometric method for the determination of caffeic acid phenethyl ester in rat plasma and urine. J. Chromatogr., B 2004, 810, 129-136.
19. Satoh, T.; Taylor, P.; Bosron, W. F.; Sanghani, S. P.; Hosokawa, M.; La Du, B. N. Current progress on esterases: from molecular structure to function. Drug Metab. Dispos. 2002, 30, 488-493.
20. Harel, M.; Aharoni, A.; Gaidukov, L.; Brumshtein, B.; Khersonsky, O.; Meged, R.; Dvir, H.; Ravelli, R. B. G.; McCarthy, A.; Toker, L.; Silman, I.; Sussman, J. L.; Tawfik, D. S. Structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes. Nat. Struct. Mol. Biol. 2004, 11, 412-419.
21. Gan, K. N.; Smolen, A.; Eckerson, H. W.; La Du, B. N. Purification of human serum paraoxonase/arylesterase. Evidence for one esterase catalyzing both activities. Drug Metab. Dispos. 1991, 19, 100-106.
22. Billecke, S.; Draganov, D.; Counsell, R.; Stetson, P.; Watson, C.; Hsu, C.; La Du, B. N. Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab. Dispos. 2000, 28, 1335-1342.
23. Massoulié, J.; Pezzementi, L.; Bon, S.; Krejci, E.; Vallette, F.-M. Molecular and cellular biology of cholinesterases. Prog. Neurobiol. 1993, 41, 31-91.
24. Patocka, J.; Kuca, K.; Jun, D. Acetylcholinesterase and butyrylcholinesterase - important enzymes of human body. Acta Med. (Hradec Králové) 2004, 47, 215-228.
25. Satoh, T.; Hosokawa, M. Structure, function and regulation of carboxylesterases. Chem. Biol. Interact. 2006, 162, 195-211.
26. Redinbo, M. R.; Potter, P. M. Mammalian carboxylesterases: from drug targets to protein therapeutics. Drug Discovery Today 2005, 10, 313-325.
27. Li, B.; Sedlacek, M.; Manoharan, I.; Boopathy, R.; Duysen, E. G.; Masson, P.; Lockridge, O. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem. Pharmacol. 2005, 70, 1673-1684.
28. Clifford, M. N. Chlorogenic acids and other cinnamates - nature, occurence, dietary burden, absorption and metabolism. J. Sci. Food Agric. 2000, 80, 1033-1043.
29. Petersen, M.; Simmonds, M. S. J. Rosmarinic acid. Phytochemistry 2003, 62, 121-125.
30. Eckerson, H. W.; Wyte, C. M.; La Du, B. N. The human serum paraoxonase/arylesterase polymorphism. Am. J. Hum. Genet. 1983, 35, 1126-1138.
31. Ellman, G. L.; Courtney, K. D.; Andres, V., Jr.; Featherstone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
32. Morgan, E. W.; Yan, B.; Greenway, D.; Petersen, D. R.; Parkinson, A. Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B). Arch. Biochem. Biophys. 1994, 315, 495-512.
33. Eckerson, H. W.; Romson, J.; Wyte, C.; La Du, B. N. The human serum paraoxonase polymorphism: identification of phenotypes by their response to salts. Am. J. Hum. Genet. 1983, 35, 214-227.
34. Diczfalusy, M. A.; Björkhem, I.; Einarsson, K.; Alexson, S. E. H. Acyl-coenzyme A:cholesterol O-acyltransferase is not identical to liver microsomal carboxylesterase. Arterioscler. Thromb. Vasc. Biol. 1996, 16, 606-610.
35. Becker, A.; Böttcher, A.; Lackner, K. J.; Fehringer, P.; Notka, F.; Aslanidis, C.; Schmitz, G. Purification, cloning, and expression of a human enzyme with acyl Coenzyme A: cholesterol acyltransferase activity, which is identical to liver carboxylesterase. Arterioscler. Thromb. 1994, 14, 1346-1355.
36. Tsujita, T.; Okuda, H. Fatty acid ethyl ester synthase in rat adipose tissue and its relationship to carboxylesterase. J. Biol. Chem. 1992, 267, 23489-23494.
37. Laposata, E. A.; Lange, L. G. Presence of nonoxidative ethanol metabolism in human organs commonly damaged by ethanol abuse. Science 1986, 231, 497-499.
38. Hearn, W. L.; Rose, S.; Wagner, J.; Ciarleglio, A.; Mash, D. C. Cocaethylene is more potent than cocaine in mediating lethality. Pharmacol. Biochem. Behav. 1991, 39, 531-533.
39. Dean, R. A.; Christian, C. D.; Sample, R. H. B.; Bosron, W. F. Human liver cocaine esterases: ethanol-mediated formation of ethylcocaine. FASEB J. 1991, 5, 2735-2739.
40. Bourland, J. A.; Martin, D. K.; Mayersohn, M. In vitro transesterification of cocaethylene (ethylcocaine) in the presence of ethanol. Esterase-mediated ethyl ester exchange. Drug Metab. Dispos. 1998, 26, 203-206.
41. Dean, R. A.; Zhang, J.; Brzezinski, M. R.; Bosron, W. F. Tissue distribution of cocaine methyl esterase and ethyl transferase activities: correlation with carboxylesterase protein. J. Pharmacol. Exp. Ther. 1995, 275, 965-971.
42. Carmona, G. N.; Jufer, R. A.; Goldberg, S. R.; Gorelick, D. A.; Greig, N. H.; Yu, Q.-S.; Cone, E. J.; Schindler, C. W. Butyrylcholinesterase accelerates cocaine metabolism: in vitro and in vivo effects in nonhuman primates and humans. Drug Metab. Dispos. 2000, 28, 367-371.
43. 6]ethanol: preliminary in vitro findings using a rat liver preparation. J. Pharm. Sci. 1997, 86, 1494-1496.
44. Chen, Z.; Agrawal, A. K.; Franklin, R. B.; Leung, K. H.; Chiu, S.-H. L. In vitro and in vivo trans-esterification of 1-[2(R)-(2- amino-2-methylpropionylamino)-3-(1H-indol-3-yl)propionyl]-3(S) -benzyl-piperidine-3-carboxylic acid ethyl ester and the effects of ethanol on its pharmacokinetics in rats. Pharm. Res. 2004, 21, 996-999.
45. Raneva, V.; Shimasaki, H.; Ishida, Y.; Ueta, N.; Niki, E. Antioxidative activity of 3,4-dihydroxyphenylacetic acid and caffeic acid in rat plasma. Lipids 2001, 36, 1111-1116.
46. Xu, F.; Song, D.; Zhen, Y. Inhibition of tumor metastasis by sodium caffeate and its effect on angiogenesis. Oncology 2004, 67, 88-92.
47. Fiuza, S. M.; Gomes, C.; Teixeira, L. J.; Girão da Cruz, M. T.; Cordeiro, M. N. D. S.; Milhazes, N.; Borges, F.; Marques, M. P. M. Phenolic acid derivatives with potential anticancer properties - a structure-activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids. Bioorg. Med. Chem. 2004, 12, 3581-3589.
48. 2 in vitro or in mouse skin. Br. J. Pharmacol. 2005, 146, 352-363.
49. Cárdenas, M.; Marder, M.; Blank, V. C.; Roguin, L. P. Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines. Bioorg. Med. Chem. 2006, 14, 2966-2971.
50. Jayaprakasam, B.; Vanisree, M.; Zhang, Y.; Dewitt, D. L.; Nair, M. G. Impact of alkyl esters of caffeic and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme, and lipid peroxidation. J. Agric. Food Chem. 2006, 54, 5375-5381.