Absorption mechanism of ginsenoside compound K and its butyl and octyl ester prodrugs in caco-2 cells

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 41, 2012, Pages 10278-10284

  Zhang, Bing ^a   Zhu, Xue Mei ^a   Hu, Jiang Ning ^a   Ye, Hui ^a   Luo, Ting ^a   Liu, Xiao Ru ^a   Li, Hong Yan ^a   Li, Wei ^b   Zheng, Yi Nan ^b   Deng, Ze Yuan ^a  

^a NANCHANG UNIVERSITY   (China)

^b JILIN AGRICULTURAL UNIVERSITY   (China)

Author keywords

butyl and octyl ester; Caco 2 cells; compound K; ginsenosides; intestinal absorption; P glycoprotein

Indexed keywords

CACO-2 CELLS; COMPOUND K; GINSENOSIDES; INTESTINAL ABSORPTION; P-GLYCOPROTEIN;

BIOCHEMISTRY; ESTERIFICATION; ESTERS; GLYCOPROTEINS; PHARMACODYNAMICS;

CELLS;

GINSENOSIDE; GINSENOSIDE M1; PRODRUG; PROPIONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; VERAPAMIL; VERLUKAST;

ABSORPTION; ACYLATION; ARTICLE; BIOAVAILABILITY; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; HUMAN; INTESTINE ABSORPTION; METABOLISM; PANAX; STRUCTURE ACTIVITY RELATION; TRANSPORT AT THE CELLULAR LEVEL;

ABSORPTION; ACYLATION; BIOLOGICAL AVAILABILITY; BIOLOGICAL TRANSPORT; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; GINSENOSIDES; HUMANS; INTESTINAL ABSORPTION; PANAX; PRODRUGS; PROPIONATES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; VERAPAMIL;

EID: 84867632570     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf303160y     Document Type: Article

References (37)

1. Yuan, C. S.; Wang, C. Z.; Wicks, S. M.; Qi, L. W. Chemical and pharmacological studies of saponins with a focus on American ginseng J. Ginseng Res. 2010, 34, 160-167
2. Li, Q. Y.; Chen, L.; Fu, W. H.; Li, Z. D.; Wang, B.; Shi, X. J.; Zhong, M. K. Ginsenoside Rb1 inhibits proliferation and inflammatory responses in rat aortic smooth muscle cells J. Agric. Food Chem. 2011, 59, 6312-6318
3. Yoon, S. R.; Lee, G. D.; Park, J. H.; Lee, I. S.; Kwon, J. H. Ginsenoside composition and antiproliferative activities of explosively puffed ginseng (Panax ginseng C.A. Meyer) J. Food Sci. 2010, 75, 378-382
4. Christensen, L. P. Ginsenosides chemistry, biosynthesis, analysis, and potential health effects Adv. Food. Nutr. Res. 2009, 55, 1-99
5. Wakabayashi, C.; Hasegawa, H.; Murata, J.; Saiki, I. In vivo antimetastatic action of ginseng protopanaxadiol saponins is based on their intestinal bacterial metabolites after oral administration Oncol. Res. 1998, 9, 411-417
6. Bae., E. A.; Han., M. J.; Choo., M. K.; Park., S. Y.; Kim., D. H. Metabolism of 20(S)-and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities Biol. Pharm. Bull. 2002, 25, 58-63
7. Yan, Q.; Zhou, W.; Shi, X. L.; Zhou, P.; Ju, D. W.; Feng, M. Q. Biotransformation pathways of ginsenoside Rb1 to compound K by β-glucosidases in fungus Paecilomyces Bainier sp. 229 Process Biochem. 2010, 45, 1550-1556
8. Hasegawa, H.; Sung, J. H.; Benno, Y. Role of human intestinal prevotella oris in hydrolyzing ginseng saponins Planta Med. 1997, 63, 436-440
9. Choo, M. K.; Park, E. K.; Han, M. J.; Kim, D. H. Antiallergic activity of ginseng and its ginsenoside Planta Med. 2003, 69, 518-522
10. Park, E. K.; Choo, M. K.; Han, M. J.; Kim, D. H. Ginsensodide Rh1 possesses antiallergic and anti-inflammatory activities Int. Arch. Allergy Immunol. 2004, 133, 113-120
11. Hasegawa, H.; Lee, K. S.; Nagaoka, T.; Tezuka, Y.; Uchiyama, M.; Kadota, S.; Saiki, I. Pharmacokinetics of ginsenoside deglycosylated by intestinal bacteria and its transformation to biologically active fatty acid esters Biol. Pharm. Bull. 2000, 23, 298-304
12. Odani, T.; Tanizawa, H.; Takino, Y. Studies on the absorpation, distribution, excretion and metabolism of ginseng saponins: II. The absorption, distribution and excretion of ginsenoside Rg1 in the rats Chem. Pharm. Bull. 1983, 31, 292-298
13. Takino, T. Studies on the pharmacodynamics of ginsenoside Rg1, Rb1, and Rb2 in rats Yakugaku Zasshi 1994, 114, 550-564
14. Soumyajit, M.; Sridhar, D.; Ashim, K. M. Membrane transporter/receptor- targeted prodrug design: strategies for human and veterinary drug development Adv. Drug Delivery Rev. 2004, 56, 1437-1452
15. Cao, F.; Guo, J. X.; Ping, Q. N.; Liao, Z. G. Prodrugs of scutellarin: ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats Eur. J. Pharm. Sci. 2006, 29, 385-393
16. Taylor, M. D. Improved passive oral drug delivery via prodrugs Adv. Drug Delivery Rev. 1996, 19, 131-148
17. Abuo-Rahma, G. E.; Sarhan, H. A.; Gad, G. F. Design, synthesis, antibacterial activity and physicochemical parameters of novel N-4-piperazinyl derivatives of norfloxacin Bioorg. Med. Chem. 2009, 17, 3879-3886
18. Hirosato, K.; Fumio, S.; Toshio, U.; Yoshihiro, K.; Goro, T. Studies on prodrugs. 11. Synthesis and antimicrobial activity of N-[(4-methyl-5-methylene- 2-oxo-1,3-dioxolan-4-yl) oxy] norfloxacin J. Med. Chem. 1989, 32, 671-674
19. Teng, R. w.; Ang, C. s.; David, M.; David, A.; Shaiolim, M.; Antony, B. Regioselective acylation of ginsenosides by Novozyme 435 Tetrahedron Lett. 2003, 44, 5661-5664
20. Melzig, M. F.; Bader, G.; Loose, R. Investigations of the mechanism of membrane activity of selected triterpenoid saponins Planta Med. 2001, 67, 43-48
21. Pinto, M.; Robine-Leon, S.; Appay, M. D.; Kedinger, M.; Triadou, N.; Dussaulx, E.; Lacroix, B.; Simon-Assmann, P.; Haffen, K.; Fogh, J.; Zweibaum, A. Enterocyte-like differentiation and polarization of the human colon carcinoma cell line Caco-2 in culture Biol. Cell. 1983, 47, 323-330
22. Grasset, E.; Pinto, M.; Dussaulx, E.; Zweibaum, A.; Desjeux, J. F. Epithelial properties of human colonic carcinoma cell line Caco-2: electrical parameters Am. J. Physiol. 1984, 247, 260-267
23. Borlak, J.; Zwadlo, C. Expression of drug-metabolizing enzymes, nuclear transcription factors and ABC transporters in Caco-2 cells Xenobiotica 2005, 33, 927-943
24. Fischer, D.; Li, Y.; Krieglstein, J.; Kissel, T. In vitro cytotoxicity testing of polycations: influence of polymer structure on cellviability and hemolysis Biomaterials 2003, 24, 1121-1131
25. Sgouras, D.; Duncan, R. Use of the tetrazolium-based colorimetric assay (MTT) as a preliminary screen for the evaluation of in vitro cytotoxicity J. Mater. Sci.: Mater. Med. 1990, 1, 61-68
26. Li, H.; Chung, S. J.; Kim, D. C.; Kim, H. S.; Lee, J. W.; Shim, C. K. The transport of a reversible proton pump antagonist 5,6-dimethyl-2- (4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinoline-2-yl) pyrimidine hydrochloride (YH1885), across Caco-2 cell monolayers Drug. Metab. Dispos. 2001, 29, 54-59
27. Wahlang, B; Pawar, Y. B; Bansal, A. K. Identification of permeability-related hurdles in oral delivery of curcumin using the Caco-2 cell model Eur. J. Pharm. Biopharm. 2011, 77, 275-282
28. Bromberga, L.; Alakhov, V. Effects of polyether-modified poly (acrylic acid) microgels on doxorubicin transport in human intestinal epithelial Caco-2 cell layers J. Controlled Release 2003, 88, 11-22
29. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. 1991, 175, 880-885
30. Yee, S. In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man: fact or myth Pharm. Res. 1997, 14, 763-766
31. Lee, P. S.; Song, T. W.; Sung, J. H.; Moon, D. C.; Song, S.; Chung, Y. B. Pharmacokinetic characteristics and hepatic distribution of IH-901, a novel intestinal metabolite of ginseng saponin, in rats Planta Med. 2006, 72, 204-210
32. Paek, I. B.; Moon, Y.; Kim, J.; Ji, H. Y.; Kim, S. A.; Sohn, D. H.; Kim, J. B.; Lee, H. S. Pharmacokinetics of a ginseng saponin metabolite compound K in rats Biopharm. Drug Dispos. 2006, 27, 39-45
33. Yang, Z.; Wang, J. R.; Niu, T.; Gao, S.; Yin, T.; You, M.; Jiang, Z. H.; Hu, M. Inhibition of p-glycoprotein leads to improved oral bioavailability of compound k, an anticancer metabolite of red ginseng extract produced by gut microflora Drug Metab. Dispos. 2012, 40, 1538-1544
34. Liu, H.; Yang, J.; Du, F.; Gao, X.; Ma, X.; Huang, Y.; Xu, F.; Niu, W.; Wang, F.; Mao, Y.; Sun, Y.; Lu, T.; Liu, C.; Zhang, B.; Li, C. Absorption and disposition of ginsenosides after oral administration of Panax notoginseng extract to rats Drug Metab. Dispos. 2009, 37, 2290-2298
35. Gan, L. S. L.; Thakker, D. R. Applications of the Caco-2 model in the design and development of orally active drugs: Elucidation of biochemical and physical barriers posed by the intestinal epithelium Adv. Drug Delivery Rev. 1997, 23, 77-98
36. Zhou, L.; Lee, K.; Dhiren, R. T.; David, W. B.; Richard, R. T.; James, E. H. Enhanced permeability of the antimicrobial agent 2, 5-bis(4-amidinophenyl) furan across Caco-2 cell monolayers via its methylamidoxime prodrug Pharm. Res. 2002, 19, 1689-1695
37. Artursson, P.; Magnusson, C. Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells J. Pharm. Sci. 1990, 79, 595-600