Physicochemical and thermodynamic characterization of hydroxy pentacyclic triterpenoic acid/γ-cyclodextrin inclusion complexes

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 73, Issue 1-4, 2012, Pages 341-347

  Fontanay, Stephane ^a   Kedzierewicz, Francine ^a   Duval, Raphael Emmanuel ^a   Clarot, Igor ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

Cyclodextrin; DSC; HPLC; HPTA; NMR

Indexed keywords

EID: 84862626180     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-0063-y     Document Type: Article

References (33)

1. Z Ali SI Khan D Ferreira IA Khan 2006 Podocarpaside, a triterpenoid possessing a new backbone from Actaea podocarpa Org. Lett. 8 5529 5532 10.1021/ol062212s 1:CAS:528:DC%2BD28Xht1Clu77F
2. SK Han YI Ko SJ Park IJ Jin YM Kim 1997 Oleanolic acid and ursolic acid stabilize liposomal membranes Lipids 32 769 773 10.1007/s11745-997-0098-9 1:CAS:528:DyaK2sXkvFeltrg%3D
3. J Li WJ Guo QY Yang 2002 Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15 World J. Gastroenterol. 8 493 495 1:CAS:528:DC%2BD38XlsF2ksrs%3D
4. S Murakami H Takashima M Sato-Watanabe S Chonan K Yamamoto M Saitoh S Saito H Yoshimura K Sugawara J Yang N Gao X Zhang 2004 Ursolic acid, an antagonist for transforming growth factor (TGF)-beta1 FEBS Lett. 566 55 59 10.1016/j.febslet.2004.04.036 1:CAS:528:DC%2BD2cXktVOltL0%3D
5. Y Tan R Yu JM Pezzuto 2003 Betulinic acid-induced programmed cell death in human melanoma cells involves mitogen-activated protein kinase activation Clin. Cancer Res. 9 2866 2875 1:CAS:528:DC%2BD3sXlt1yrsbk%3D
6. G Altinier S Sosa RP Aquino T Mencherini R Della Loggia A Tubaro 2007 Characterization of topical antiinflammatory compounds in Rosmarinus officinalis J. Agric. Food Chem. 55 1718 1723 10.1021/jf062610+ 1:CAS:528: DC%2BD2sXhsVCgtbg%3D
7. AR Chowdhury S Mandal B Mittra S Sharma S Mukhopadhyay HK Majumder 2002 Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives Med. Sci. Monit. 8 254 265
8. R Saravanan V Pugalendi 2006 Impact of ursolic acid on chronic ethanol-induced oxidative stress in the rat heart Pharmacol. Rep. 58 41 47 1:CAS:528:DC%2BD28XlvVOhur8%3D
9. H Ismaili L Milella S Fkih-Tetouani A Ilidrissi A Camporese S Sosa G Altinier R Della Loggia R Aquino 2004 In vivo topical anti-inflammatory and in vitro antioxidant activities of two extracts of Thymus satureioides leaves J. Ethnopharmacol. 91 31 36 10.1016/j.jep.2003.11.013 1:STN:280: DC%2BD2c7ktlyqug%3D%3D
10. LI Somova FO Shode P Ramnanan A Nadar 2003 Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves J. Ethnopharmacol. 84 299 305 10.1016/S0378-8741(02)00332-X 1:CAS:528:DC%2BD3sXhsleht7w%3D
11. J Liu 1995 Pharmacology of oleanolic acid and ursolic acid J. Ethnopharmacol. 49 57 68 10.1016/0378-8741(95)90032-2 1:CAS:528: DyaK28Xht12gtL4%3D
12. HX Xu FQ Zeng M Wan KY Sim 1996 Anti-HIV triterpene acids from Geum japonicum J. Nat. Prod. 59 643 645 10.1021/np960165e 1:CAS:528: DyaK28XjvVOktr8%3D
13. LO Somova A Nadar P Rammanan FO Shode 2003 Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension Phytomedicine 10 115 121 10.1078/094471103321659807 1:CAS:528:DC%2BD3sXksFGkt7Y%3D
14. N Germonprez L Maes L Van Puyvelde M Van Tri DA Tuan N De Kimpe 2005 In vitro and in vivo anti-leishmanial activity of triterpenoid saponins isolated from Maesa balansae and some chemical derivatives J. Med. Chem. 48 32 37 10.1021/jm031150y 1:CAS:528:DC%2BD2cXhtFSlur%2FK
15. JF Hu E Garo MG Goering M Pasmore HD Yoo T Esser J Sestrich PA Cremin GW Hough P Perrone YS Lee NT Le M O'Neil-Johnson JW Costerton GR Eldridge 2006 Bacterial biofilm inhibitors from Diospyros dendo J. Nat. Prod. 69 118 120 10.1021/np049600s 1:CAS:528:DC%2BD28XjvV2ksg%3D%3D
16. ZD He CY Ma HJ Zhang GT Tan P Tamez K Sydara S Bouamanivong B Southavong DD Soejarto JM Pezzuto HH Fong 2005 Antimalarial constituents from Nauclea orientalis (L.) Chem. Biodivers. 2 1378 1386 10.1002/cbdv.200590110 1:CAS:528:DC%2BD2MXht1Wru7%2FJ
17. Y Kashiwada HK Wang T Nagao S Kitanaka I Yasuda T Fujioka T Yamagishi LM Cosentino M Kozuka H Okabe Y Ikeshiro CQ Hu E Yeh KH Lee 1998 Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoides J. Nat. Prod. 61 1090 1095 10.1021/np9800710 1:CAS:528: DyaK1cXmsVOlt7s%3D
18. J Liu 2005 Oleanolic acid and ursolic acid: research perspectives J. Ethnopharmacol. 100 92 94 10.1016/j.jep.2005.05.024 1:CAS:528: DC%2BD2MXmvVKnsbw%3D
19. WN Setzer GF Rozmus MC Setzer JM Schmidt B Vogler S Reeb BR Jackes AK Irvine 2006 Bioactive principles in the bark of Pilidiostigma tropicum J. Mol. Model. 12 703 711 10.1007/s00894-005-0047-1 1:CAS:528:DC%2BD28XosVKjtLs%3D
20. MM Cowan 1999 Plant products as antimicrobial agents Clin. Microbiol. Rev. 12 564 582 1:CAS:528:DyaK1MXntFSmsLc%3D
21. Szejtli, J.: Cyclodextrin technology. Kluwer Academic Publishers, Dordrecht (1988)
22. AD Procyk M Bissell KW Street Jr WE Acree Jr 1987 Solubility in binary solvent systems: 8. Estimation of binary alkane plus p-dioxane solvent nonideality from measured anthracene solubilities J. Pharm. Sci. 76 621 625 10.1002/jps.2600760807 1:CAS:528:DyaL2sXmtVGjtLg%3D
23. VJ Stella Q He 2008 Cyclodextrins Toxicol. Pathol. 36 30 42 10.1177/0192623307310945 1:CAS:528:DC%2BD1cXkslKgsL4%3D
24. J Szejtli A Gerloczy L Szente E Benky-Elod G Sebestyen A Fonagy M Kurcz 1979 Enhancement of drug absorption with cyclodextrin inclusion complexes Acta. Pharm. Hung. Acad. Sci. Hung. 49 207 221 1:CAS:528:DyaL3cXkslWksw%3D%3D
25. P Jansook SV Kurkov T Loftsson 2010 Cyclodextrins as solubilizers: formation of complex aggregates J. Pharm. Sci. 99 719 729 1:CAS:528: DC%2BD1MXhsF2jsLrN
26. B Claude P Morin M Lafosse P Andre 2004 Evaluation of apparent formation constants of pentacyclic triterpene acids complexes with derivatized beta- and gamma-cyclodextrins by reversed phase liquid chromatography J. Chromatogr. A 1049 37 42 1:CAS:528:DC%2BD2cXnsFGnt7w%3D
27. I Clarot D Clédat YC Guillaume PJP Cardot 2001 Chromatographic study of terpene-β-cyclodextrin complexes on porous graphitic carbon stationary phase Chromatographia 54 447 453 10.1007/BF02491198 1:CAS:528:DC%2BD3MXotlaisbY%3D
28. Higuchi, T., Connors, K.A.: Phase-solubility techniques. In: Reilly, C.N. (ed.) Advances in Analytical Chemistry Instrumentation, vol. 4, pp. 117-212. Wiley-Interscience, New York (1965)
29. Y Matsui K Mochida 1979 Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution Bull. Chem. Soc. Jpn. 52 2808 2814 10.1246/bcsj.52.2808 1:CAS:528:DyaL3cXpsVKmtw%3D%3D
30. K Uekama F Hirayama T Irie 1978 New method for determination of the stability constants of cyclodextrin-prostaglandin inclusion complexes by liquid chromatography Chem. Lett. 7 661 664 10.1246/cl.1978.661
31. C Roussel A Favrou 1993 HPLC separation of the atropisomers of some substituted N-arylthiazoline-2-thiones with γ-cyclodextrin as a chiral mobile phase additive: size and lipophilicity effects of substituents J. lncl. Phenom. Mol. 16 283 296 10.1007/BF00708798 1:CAS:528:DyaK2cXls12hu7w%3D
32. T Pralhad K Rajendrakumar 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 10.1016/S0731-7085(03)00529-6 1:CAS:528:DC%2BD2cXptFarsQ%3D%3D
33. H-J Schneider F Hacket V Rüdiger H Ikeda 1998 NMR studies of cyclodextrins and cyclodextrin complexes Chem. Rev. 98 1755 1786 10.1021/cr970019t 1:CAS:528:DyaK1cXksV2iur0%3D