Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 72, Issue 3-4, 2012, Pages 405-411

  Tsao, Jung Ying ^a,b   Wu, Chien Pang ^c   Tsai, Hsieh Ho ^c   Peng, Kuang Chia ^a   Lin, Pi Yun ^d   Su, Shan Yu ^a,b   Chen, Lieh Der ^a   Tsai, Fuu Jen ^a,b,e   Tsai, Yuhsin ^a  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b CHINA MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

^c INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE   (Taiwan)

^d NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^e ASIA UNIVERSITY   (Taiwan)

Author keywords

Chinese traditional medicine; Hydroxypropyl cyclodextrin; Inclusion complex; Paeonol

Indexed keywords

EID: 84862123227     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-0003-x     Document Type: Article

References (37)

1. Uekama, K., Hirayama, F., Irie, T.: Cyclodextrin drug carrier system. Chem. Rev. 98, 2045-2076 (1998)
2. Del Valle, E.M.M.: Cyclodextrins and their uses: a review. Process. Biochem. 39, 1033-1046 (2004) (Pubitemid 38527174)
3. Brewster, M.E., Loftsson, T.: Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev. 59, 645-666 (2007) (Pubitemid 47299263)
4. Li, J., Loh, X.J.: Cyclodextrin-based supramolecular architectures: syntheses, structures, and applications for drug and gene delivery. Adv. Drug Deliv. Rev. 60, 1000-1017 (2008)
5. Vyas, A., Saraf, S.: Cyclodextrin based novel drug delivery systems. J. Incl. Phenom. Macrocycl. Chem. 62, 23-42 (2008)
6. Astray, G., Gonzalez-Barreiro, C., Mejuto, J.C., Rial-Otero, R., Simal-Gándara, J.: A review on the use of cyclodextrins in foods. Food Hydrocolloids 23, 1631-1640 (2009)
7. Cal, K., Centkowska, K.: Use of cyclodextrins in topical formulations: practical aspects. Eur. J. Pharm. Biopharm. 68, 467-478 (2008) (Pubitemid 351318207)
8. Yoshikawa, M., Uchida, E., Kawaguchi, A., Kitagawa, I., Yamahara, J.: Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese Moutan Cortex. Chem. Pharm. Bull. 40, 2248-2250 (1992)
9. Ishiguro, K., Ando, T., Maeda, O., Hasegawa, M., Kadomatsu, K., Ohmiya, N., Niwa, Y., Xavier, R., Goto, H.: Paeonol attenuates TNBS-induced colitis by inhibiting NFkappaB and STAT1 transactivation. Toxicol. Appl. Pharm. 217, 35-42 (2006) (Pubitemid 44635657)
10. Nizamutdinova, I.T., Oh, H.M., Min, Y.N., Park, S.H., Lee, M.J., Kim, J.S., Yean, M.H., Kang, S.S., Kim, Y.S., Chang, K.C., Kim, H.J.: Paeonol suppresses intercellular adhesion molecule-1 expression in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells by blocking p38, ERK and nuclear factor-kappaB signaling pathways. Int. Immunopharmacol. 7, 343-350 (2007) (Pubitemid 46186173)
11. Chou, T.C.: Anti-inflammatory and analgesic effects of paeonol in carrageenanevoked thermal hyperalgesia. Br. J. Pharmacol. 13, 1146-1152 (2003)
12. Tsai, H., Lin, H., Fong, Y., Wu, J., Chen, Y., Tsuzuki, M., Tang, C.: Paeonol inhibits RANKL-induced osteoclastogenesis by inhibiting ERK, p38 and NF-jB pathway. Eur. J. Pharmacol. 588, 124-133 (2008)
13. Chung, J.G.: Paeonol promotion of DNA adduct formation and arylamines Nacetyltransferase activity in human colon tumour cells. Food Chem. Toxicol. 37, 327-334 (1999) (Pubitemid 29335760)
14. Xie, S., Chen, Z., Ma, P.: Down-regulation of melanin synthesis and transfer by paeonol and its mechanisms. Am. J. Chin. Med. 35, 139-151 (2007) (Pubitemid 46206529)
15. Li, Z.X., Ren, R.: The preparation for the inclusion complex of paeonol-bcyclodextrin. Chin. Pharm. J. 39, 305-306 (2004)
16. Sun, D., Li, L., Qiu, X., Liu, F., Yin, B.: Isothermal titration calorimetry and 1H NMR studies on host-guest interaction of paeonol and two of its isomers with β-cyclodextrin. Int. J. Pharm. 316, 7-13 (2006) (Pubitemid 43765694)
17. Sun, D., Li, L., Qiu, X., Liu, M., Yin, B.: Cyclodextrins binding to paeonol and two of its isomers in aqueous solution. Isothermal titration calorimetry and 1H NMR investigations of molecular recognition. J. Solut. Chem. 35, 1537-1549 (2006) (Pubitemid 44748947)
18. Tsao, J., Tsai, H., Wu, C., Lin, P., Su, S., Chen, L., Tsai, F., Tsai, Y.: Release of paeonol-β-CD complex from thermo-sensitive poly(N-isopropylacrylamide) hydrogels. Int. J. Pharm. 402, 123-128 (2010)
19. Tsai, Y., Tsai, H., Wu, C., Tsai, F.: Preparation, characterization and activity of the inclusion complex of paeonol with β-cyclodextrin. Food Chem. 120, 837-841 (2010)
20. Gould, S., Scott, R.C.: 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): a toxicology review. Food Chem. Toxicol. 43, 1451-1459 (2005)
21. Higuchi, T., Connors, K.A.: Phase solubility technique. Adv. Anal. Chem. Instrum. 4, 117-212 (1965)
22. Strazisar, M., Andrensek, S., Smidovnik, A.: Effect of β-cyclodextrin on antioxidant activity of coumaric acids. Food Chem. 110, 636-642 (2008)
23. Jullian, C., Orosteguis, T., P'erez-Cruzb, F., S'anchez, P., Mendizabal, F., Olea-Azar, C.: Complexation of morin with three kinds of cyclodextrin, a thermodynamic and reactivity study. Spectrochim. Acta A 71, 269-275 (2008)
24. Lim, T.Y., Lim, Y.Y., Yule, C.M.: Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four Macaranga species. Food Chem. 114, 594-599 (2009)
25. Meier, M.M., Bordignon Luiz, M.T., Farmer, P.J., Szpoganicz, B.: The influence of beta-and gammacyclodextrin cavity size on the association constant with decanoate and octanoate anions. J. Incl. Phenom. Macrocycl. Chem. 40, 291-295 (2001) (Pubitemid 33380107)
26. Tongiani, S., Velde, D.V., Ozeki, T., Stella, V.J.: Sulfoalkyl ether-alkyl ether cyclodextrin derivatives, their synthesis, NMR characterization, and binding of 6alpha-methylprednisolone. J. Pharm. Sci. 94, 2380-2392 (2005) (Pubitemid 43081936)
27. Axel Castelli, V.V., Trivieri, G., Zucchelli, I., Brambilla, L., Barbuzzi, T., Castiglioni, C., Paci, M., Zerbi, G., Zanol, M.: Characterisation of an inclusion complex between cladribine and 2-hydroxypropyl-β- cyclodextrin. J. Pharm. Sci. 97, 3897-3906 (2008)
28. Koontz, J.L., Marcy, J.E., O'Keefe, S.F., Duncan, S.E.: Cyclodextrin inclusion complex formation and solid-state characterization of the natural antioxidants r-tocopherol and quercetin. J. Agric. Food Chem. 57, 1162-1171 (2009)
29. Parmar, K.R., Patel, K.A., Shah, S.R., Sheth, N.R.: Inclusion complexes of lamotrigine and hydroxy propyl β-cyclodextrin: solid state characterization and dissolution studies. J. Incl. Phenom. Macrocycl. Chem. 65, 263-268 (2009)
30. Calderini, A., Pessine, F.B.T.: Synthesis and characterization of inclusion complex of the vasodilator drug minoxidil with bcyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 60, 369-377 (2008)
31. Tominaga, H., Kobayashi, Y., Goto, T., Kasemura, K., Nomura, M.: DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives. Yakugaku Zasshi 125, 371-375 (2005) (Pubitemid 40628390)
32. Jullian, C., Moyano, L., Yanez, C., Olea-Azar, C.: Complexation of quercetin with three kinds of cyclodextrins: an antioxidant study. Spectrochim. Acta A 67, 230-234 (2007) (Pubitemid 46498954)
33. Lu, Z., Cheng, B., Hu, Y., Zhang, Y., Zou, G.: Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity. Food Chem. 113, 17-20 (2009)
34. Fayad, N., Marchal, L., Billaud, C., Nicolas, J.: Comparison of acyclodextrin effect on polyphenol oxidation catalyzed by purified polyphenol oxidase from different sources. J. Agric. Food Chem. 45, 2442-2446 (1997) (Pubitemid 127476957)
35. Alvarez-Parrilla, E., de la Rosa, L.A., Rodrigo-García, J., Escobedo-González, R., Mercado-Mercado, G., Moyers-Montoya, E., Vázquez-Flores, A., González-Aguilar, G.A.: Dual effect of β-cyclodextrin (β-cD) on the inhibition of apple polyphenol oxidase by 4-hexylresorcinol (HR) and methyl jasmonate (MJ). Food Chem. 101, 1346-1356 (2007) (Pubitemid 44488569)
36. Villalonga, R., Cao, R., Fragoso, A.: Supramolecular chemistry of cyclodextrins in enzyme technology. Chem. Rev. 107, 3088-3116 (2007) (Pubitemid 47162905)
37. Orenes-Pinero, E., García-Carmona, F., Sánchez-Ferrer, A.: Kinetic characterization of diphenolase activity from Streptomyces antibioticus tyrosinase in the presence and absence of cyclodextrins. J. Mol. Catal. B Enzym. 47, 143-148 (2007) (Pubitemid 47031675)