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Enhanced anti-inflammatory activity of curcumin, a naturally occurring pigment in turmeric via cyclodextrin complexation

  • Kohli, K (Department of Pharmaceutics, Faculty of Pharmacy, Jamia Hamdard University) ;
  • Ali, J (Department of Pharmaceutics, Faculty of Pharmacy, Jamia Hamdard University) ;
  • Najmi, AK (Department of Pharmacology, Faculty of Pharmcay, Jamia Hamdard University) ;
  • Anwer, MT (Department of Pharmacology, Faculty of Pharmcay, Jamia Hamdard University) ;
  • Ansari, MJ (Department of Pharmaceutics, Faculty of Pharmacy, Jamia Hamdard University)
  • Published : 2007.06.30

Abstract

Curcumin, a dietary pigment responsible for the yellow color of curry, has been used for the treatment of inflammatory diseases and exhibits a variety of pharmacological effects such as anti- inflammatory, anti-tumor, anti-oxidant, and anti-viral activity. In order to examine the potency of the curcumin in inflammation we used carrageenan induced rat hind paw odema model. As curcumin is practically water insoluble, it is hypothesized that pharmacological activity of curcumin could be improved by enhancing its water solubility. Water soluble complexes of curcumin with cyclodextrins were prepared and screened for greater solubility. Pure curcumin 100 mg/kg body weight along with curcumin complexes equivalent to 100 mg/kg body weight of pure curcumin were tested for the anti-inflammatory activity in Wister rats male rats using carrageenan induced hind paw edema model and compared with that of the reference compound diclofenac sodium at a dose level of 10 mg/kg body weight. Results were statistically analyzed using ANOVA. All the treatment groups showed statistically significant anti-inflammatory activity compared with that of vehicle control and positive control.

Keywords

References

  1. Aktas Y, Unlu N, Orhan M, lrkec M, Hincal AA. (2003) Influence of hydroxypropyl ${\beta}$-cyclodextrin on the corneal permeation of pilocarpine. Drug Dev. Ind. Pharm. 29, 223-230
  2. Ammar HO, Ghorab M, El-nahhas SA, Omar SM, Ghorab MM. (1996) Improvement of some pharmaceutical properties of theophylline by cyclodextrin complexation. Pharmazie 51, 42-46
  3. Arora R, Basu N, Kapoor V. (1971) Anti-inflammatory studies on Curcuma longa (turmeric). Indian J. Med. Res. 59, 1289-1295
  4. Baboota S and Agarwal SP. (2003) Rofecoxib complexation with ${\beta}$-CD: influence on the anti-inflammatory and ulcerogenic activity. Pharmazie 58, 73-74
  5. Brisaert M, Plaizier Vercammen J. (2000) Investigation on the photostability of a tretinoin lotion and stabilization with additives. Int. J. Pharm. 199, 49-57 https://doi.org/10.1016/S0378-5173(00)00366-5
  6. Chandra D, Gupta S. (1972) Anti-inflammatory and anti-arthritic activity of volatile oil of Curcuma longa (Haldi). Indian J. Med. Res. 60,138-142
  7. Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT , Lin BR, Wu MS, Yu HS, Jee SH, Chen GS, Chen TM, Chen CA, Lai MK, Pu YS, Pan MH, Wang YJ, Tsai CC, Hsieh CY. (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high risk or premalignant lesion. Anticancer Res. 21, 2895-9000
  8. Cheng J, Khin KT, Jensen GS, Liu A, Davis ME. (2003) Synthesis of linear, a-cyclodextrin-based polymers and their camptothecin conjugates. Bioconjug. Chem. 14, 1007-1017 https://doi.org/10.1021/bc0340924
  9. Deodhar SD, Sethi R, Srimal RC. (1980) Preliminary study on antirheumatic activity of curcumin (Diferuloyl methane). Indian J. Med. Res. 71, 632-643
  10. Flynn DL, Rafferty MF, Boctor AM. (1986) Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally-occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones. Prostaglandins Leukot. Med. 22, 357-360
  11. Han G, Xu J, Li W, Ning C. (2004) Study on preparation of the inclusion compound of curcumin with beta-cyclodextrin. Zhong Yao Cai 27, 946-948
  12. He ZG, Li YS, Zhang TH, Tang X, Zhao C, Zhang RH. (2004) Effects of 2-hydroxypropyl-${\beta}$-cyclodextrin on pharmacokinetics of digoxin in rabbits and humans. Pharmazie 59, 200-202
  13. Higuchi T, Conners KA. (1965) Phase solubility techniques. Adv. Anal. Chem. Inst. 4, 117-120
  14. Huang MT, Lysz T, Ferraro T, Abidi TF, Laskin JD, Conney AH. (1991) Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Cancer Res. 51, 813-819
  15. Illapakurthy AC, Sabnis YA, Avery BA, Avery MA, Wyandt CM. (2003) Interaction of artemisinin and its related compounds with hydroxypropyl-${\beta}$-cyclodextrin in solution state: experimental and molecular-modeling studies. J. Pharm. Sci. 92, 649-655 https://doi.org/10.1002/jps.10319
  16. Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H. (2003) Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 555, 311-316 https://doi.org/10.1016/S0014-5793(03)01265-1
  17. Kohli K, Ali J, Ansari MJ, Raheman Z. (2005) Curcumin: a natural antiinflammatory agent, Indian J. Pharmacol. 37, 141-147
  18. Kuttan R, Sudheeran PC, Joseph CD. (1987) Turmeric and curcumin as topical agents in cancer therapy. Tumori 73, 29-31
  19. Liu X, Lin HS, Thenmozhiyal JC, Chan SY, Ho PC. (2003) Inclusion of acitretin into cyclodextrins: Phase solubility, photostability, and physicochemical characterization. J. Pharm. Sci. 92, 2449-2457 https://doi.org/10.1002/jps.10495
  20. Miyake K, Arima H, Hirayama F, Yamamoto M, Horikawa T, Sumiyoshi H, Noda S, Uekama K. (2000) Improvement of solubility and oral bioavailability of rutin by complexation with 2-hydroxypropyl-${\beta}$-cyclodextrin. Pharm. Dev. Technol. 5, 399-407 https://doi.org/10.1081/PDT-100100556
  21. Mukhopadhyay A, Basu N and Ghatak N. (1982) Anti-inflammatory and irritant activities of curcumin analogues in rats. Agents Actions 12, 508-515 https://doi.org/10.1007/BF01965935
  22. Paradkar A, Ambike AA, Jadhav BK, Mahadik KR. (2004) Characterization of curcumin-PVP solid dispersion obtained by spray drying. Int. J. Pharm. 271, 281-286 https://doi.org/10.1016/j.ijpharm.2003.11.014
  23. Pralhad T, Rajendrakumar K. (2004) Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J. Pharm. Biomed. Anal. 34, 333-339
  24. Rafatulla S, Tariq M, Alyahya MA. (1990) Evaluation of turmeric (Curcuma longa) for gastric and duodenal antiulcer activity in rats. J. Ethnopharmacol. 29, 25-34 https://doi.org/10.1016/0378-8741(90)90094-A
  25. Rao CV, Rivenson A, Simi B, Reddy BS. (1995) Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound. Cancer Res. 55, 259-266
  26. Rawat S and Jain SK. (2003) Rofecoxib-cyclodextrin inclusion complex for solubility enhancement. Pharmazie 58, 639-641
  27. Satoskar RR, Shah SJ, Shenoy SG. (1986) Evaluation of anti-inflammatory property of curcumin in patients with postoperative inflammation. Int. J. Clin. Pharmacol. Ther. Toxicol. 24, 615-654
  28. Sharma US, Balasubramanian SV, Straubinger RM. (1995) Pharmaceutical and physical properties of paclitaxel (Taxol) complexes with cyclodextrins. J. Pharm. Sci. 84, 1223-1230 https://doi.org/10.1002/jps.2600841015
  29. Sinha M, Sikdar S, DasGupta SR. (1974) Study on the 5-hydroxytryptamine contents in guinea pig stomach with relation to phenylbutazone induced gastric ulcers and the effects of Curcumin thereon. Indian J. Pharmacol. 6, 87-98
  30. Skrzypczak-Jankun E, McCabe NP, Selman SH, Jankun J. (2000) Curcumin inhibits lipoxygenase by binding to its central cavity: theoretical and X-ray evidence. Int. J. Mol. Med. 6, 521-526
  31. Srimal RC, Dhawan BN. (1973) Pharamacology of diferuloyl methane-A non-steroidal anti-inflammatory drug. J. Pharm. Pharmacol. 25, 447-452
  32. Srimal RC, Khanna NM, Dhawan BN. (1971) A preliminary report on anti-inflammatory activity of curcumin. Indian J. Pharmacol. 3, 10-15
  33. Tonnesen HH, Karlsen J, van Henegouwen GB. (1986) Studies on curcumin and curcuminoids. VIII. Photochemical stability of curcumin. Z. Lebensm. Unters. Forsch. 183, 116-122
  34. Uekama K, Fujinaga T, Hirayama F, Otagiri M, Kurono M, Ikeda K. (1982) Effect of cyclodextrins on the acid hydrolysis of digoxin. J. Pharm. Pharmacol. 34, 627-630
  35. Uekama K, Fujinaga T, Otagiri M, Seo H, Tsuruoka M. (1981) Enhanced bioavailability of digoxin by ${\gamma}$-cyclodextrin complexation. J. Pharmacobio-dyn. 4, 735-737
  36. Usuda M, Endo T, Nagase H, Tomono K, Ueda H. (2000) Interaction of antimalarial agent artemisinin with cyclodextrins. Drug Dev. Ind. Pharm. 26, 613-619 https://doi.org/10.1081/DDC-100101276
  37. Vincieri FF, Mazzi G, Mulinacci N, Bambagiotti-Alberti M, DaII Acqua F, Vedaldi D. (1995) Improvement of dissolution characteristics of psoralen by cyclodextrins complexation. Farmaco 50, 543-547
  38. Wallace JM. (2002) Nutritional and botanical modulation of the inflammatory cascade-eicosanoids, cyclooxygenases, and lipoxygenases as an adjunct in cancer therapy. Integr. Cancer Ther. 1, 7-37 https://doi.org/10.1177/153473540200100102
  39. Winter CA, Risley EA, Nuss GW. (1962) Carrageenan-induced oedema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc. Soc. Exp. Biol. Med. 111, 544-547
  40. Wong JW, Yuen KH. (2001) Improved oral bioavailability of artemisinin hrough inclusion complexation with ${\beta}-\;and\;{\gamma}$-cyclodextrins. Int. J. Pharm 227, 177-185 https://doi.org/10.1016/S0378-5173(01)00796-7
  41. Wong JW, Yuen KH. (2003) Inclusion complexation of artemisinin with ${\alpha}-\;and\;{\gamma}$-cyclodextrins. Drug Dev. Ind. Pharm. 29, 1035-1044 https://doi.org/10.1081/DDC-120025460