Comparison of the Permeability of Stilbene Analogues in Caco-2 Cells

  • Kim, Su-Na (Food Function Research Group, Korea Food Research Institute) ;
  • Ahn, Ji-Yun (Food Function Research Group, Korea Food Research Institute) ;
  • Shon, Dong-Wha (Food Function Research Group, Korea Food Research Institute) ;
  • Kim, Ji-Sun (Food Function Research Group, Korea Food Research Institute) ;
  • Kim, Mi-Hye (Food Function Research Group, Korea Food Research Institute) ;
  • Ha, Tye-Youl (Food Function Research Group, Korea Food Research Institute)
  • Published : 2008.06.30

Abstract

Permeability of resveratrol, piceid, rhapontigenin, and rhaponticin in Caco-2 cell assays using high-performance liquid chromatography were compared. Caco-2 cell monolayers were used to evaluate the transport rates of stilbene analogues from the apical to the basolateral sides. All stilbenes experimented in this study were transported to the basolateral side by times. For comparing the permeability of 4 stilbenes, we calculated the slope of the cumulative concentration of each stilbene in basolateral sides over time, resulting in those values of resveratrol, piceid, rhapontigenin, and rhaponticin with $3.766{\times}10^{-5}$, $4.330{\times}10^{-6}$, $5.430{\times}10^{-5}$, and $2.458{\times}10^{-5}\;{\mu}M/sec$, respectively. Apparent permeability coefficient of resveratrol and rhapontigenin were calculated to $9.994{\times}10^{-6}$ and $1.441{\times}10^{-6}\;cm/sec$, respectively, while those of piceid and rhaponticin were to $1.149{\times}10^{-7}$ and $6.523{\times}10^{-7}\;cm/sec$, respectively. These results suggest that aglycones would be absorbed more effectively than glycosides in stilbenoids.

Keywords

References

  1. Roupe KA, Remsberg C, Yanez JA, Davies NM. Pharmacometrics of stilbenes: Seguing towards the clinc. Curr. Clin. Pharmacol. 1: 81-101 (2006) https://doi.org/10.2174/157488406775268246
  2. Cabrera SG, Moon KD. A study of the physicochemical, functional, and sensory properties of farm produced and commercially produced grape juice in the Korean market. Food Sci. Biotechnol. 16: 740-746 (2007)
  3. Yoo MA, Kim JS, Chung HK, Park WJ, Kang MH. The antioxidant activity of various cultivars of grape skin extract. Food Sci. Biotechnol. 16: 884-888 (2007)
  4. Jeandet P, Bessis R, Sbaghi M, Meunier P, Trollat P. Production of phytoalexin resveratrol by grapes in response to botryis attack under natural conditions. J. Phytopathol. 143: 135-139 (1995) https://doi.org/10.1111/j.1439-0434.1995.tb00246.x
  5. Cantos E, Espin JC, Fernandez MJ, Oliva J, Tomas-Barberan FA. Postharvest UV-C-irradiated grapes as a potential source for producing stilbene-enriched red wines. J. Agr. Food Chem. 51: 1208-1214 (2003) https://doi.org/10.1021/jf020939z
  6. Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y. Role of resveratrol in prevention and therapy of cancer: Preclinical and clinical studies. Anticancer Res. 24: 2783-2840 (2004)
  7. Stojanovic S, Sprinz H, Brede O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch. Biochem. Biophys. 391: 79-89 (2001) https://doi.org/10.1006/abbi.2001.2388
  8. Koh KH, Lee JH. Phenolic content and superoxide radical intensity of Korean wines. Food Sci. Biotechnol. 5: 338-342 (1996)
  9. Koh KH, Lee JH, Yoon KR, Choi SY, Seo KL. Phenolic compounds of Korean red wine and their superoxide radical scavenging activity. Food Sci. Biotechnol. 7: 131-136 (1998)
  10. Lee HS, Sur EY, Kim WK. Resveratrol induces apoptosis in SW480 human colon cancer cell lines. Food Sci. Biotechnol. 13: 80-84 (2004)
  11. Rivière C, Richard T, Quentin L, Krisa S, Mérillon JM, Monti JP. Inhibitory activity of stilbenes on Alzheimer's $\beta$-amyloid fibrils in vitro. Bioorgan. Med. Chem. 15: 1160-1167 (2007) https://doi.org/10.1016/j.bmc.2006.09.069
  12. Matsuda H, Tomohiro N, Hiraba K, Harima S, Ko S, Matsuo K, Yoshikawa M, Kubo M. Study on anti-Oketsu activity of rhubarb II. Anti-allergic effects of stilbene components from Rhei undulati Rhizoma (Dried Rhizome of Rheum undulatum cultivated in Korea). Biol. Pharm. Bull. 24: 264-267 (2001) https://doi.org/10.1248/bpb.24.264
  13. Matsuda H, Kageura T, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg. Med. Chem. Lett. 10: 323-327 (2000) https://doi.org/10.1016/S0960-894X(99)00702-7
  14. Liu Y, Hu M. Absorption and metabolism of flavonoids in the Caco-2 cell culture model and a perused rat intestinal model. Drug Metab. Dispos. 30: 370-377 (2002) https://doi.org/10.1124/dmd.30.4.370
  15. Artursson P, Palm K, Luthman K. Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv. Drug Deliver. Rev. 46: 27-43 (2001) https://doi.org/10.1016/S0169-409X(00)00128-9
  16. Li Y, Shin YG, Kosmeder JW, Hirschelman WH, Pezzuto JM, van Breemen RB. Increasing the throughput and productivity of Caco-2 cell permeability assays using liquid chromatography-mass spectrometry: Application to resveratrol absorption and metabolism. Comb. Chem. High T. Scr. 6: 757-767 (2003)
  17. Hilgers AR, Conradi RA, Burton PS. Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa. Pharm. Res. 7: 902-910 (1990) https://doi.org/10.1023/A:1015937605100
  18. Hunter J, Jepson MA, Tsuruo T, Simmons NL, Hirst BH. Functional expression of P-glycoprotein in apical membranes of human intestinal Caco-2 cells. Kinetics of vinblastine secretion and interaction with modulators. J. Biol. Chem. 268: 14991-14997 (1993)
  19. Walle UK, Galijatovic A, Walle T. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2. Biochem. Pharmacol. 58: 431-438 (1999) https://doi.org/10.1016/S0006-2952(99)00133-1
  20. Artursson P, Karlsson J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Bioph. Res. Co. 175: 880-885 (1991) https://doi.org/10.1016/0006-291X(91)91647-U
  21. Gres MC, Julian B, Bourrie M, Meunier V, Roques C, Berger M, Boulenc X, Berger Y, Fabre G. Correlation between oral drug absorption in humans, and apparent drug permeability in TC-7 cells, a human epithelial intestinal cell line: Comparison with the parental Caco-2 cell line. Pharm. Res. 15: 726-733 (1998) https://doi.org/10.1023/A:1011919003030
  22. Misiti F, Sampaolese B, Mezzogori D, Orsini F, Pezzotti M, Giardina B, Clementi ME. Protective effect of rhubarb derivatives on amyloid beta (1-42) peptide-induced apoptosis in IMR-32 cells: A case of nutrigenomic. Brain Res. Bull. 71: 29-36 (2006) https://doi.org/10.1016/j.brainresbull.2006.07.012