Anti-inflammatory activity and percutaneous absorption of quercetin and its polymethoxylated compound and glycosides: The relationships to chemical structures

European Journal of Pharmaceutical Sciences

Volumn 47, Issue 5, 2012, Pages 857-864

  Lin, Chwan Fwu ^a   Leu, Yann Lii ^b   Al Suwayeh, Saleh A ^c   Ku, Ming Chuan ^b   Hwang, Tsong Long ^b   Fang, Jia You ^a,b  

^a CHANG GUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^b CHANG GUNG UNIVERSITY   (Taiwan)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Anti inflammatory activity; Glycosides; Percutaneous absorption; Polymethoxylation; Quercetin

Indexed keywords

QUERCETIN; RUTOSIDE; SUPEROXIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG ABSORPTION; DRUG SOLUBILITY; DRUG STRUCTURE; GLYCOSYLATION; IC 50; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MOLECULAR WEIGHT; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL; SKIN IRRITATION; STRATUM CORNEUM;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELLS, CULTURED; FEMALE; GLYCOSIDES; HUMANS; MICE; MICE, NUDE; MOLECULAR STRUCTURE; NEUTROPHILS; PANCREATIC ELASTASE; QUERCETIN; SKIN; SKIN ABSORPTION; SOLUBILITY; SUPEROXIDES; TRANSITION TEMPERATURE;

EID: 84868711105     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.04.024     Document Type: Article

References (41)

1. S. Ahmed, T. Imai, and M. Otagiri Stereoselective hydrolysis and penetration of propranolol prodrugs: in vitro evaluation using hairless mouse skin J. Pharm. Sci. 84 1995 877 883
2. B.M. Babior, R.S. Kipnes, and J.T. Curnutte Biological defense mechanisms. The production by leukocytes of superoxide, a potential bactericidal agent J. Clin. Invest. 52 1987 741 744
3. N. Bhatia, C. Agarwal, and R. Agarwal Differential responses of skin cancer-chemopreventive agents silibinin, quercetin, and epigallocatechin 3-gallate on mitogenic signaling and cell cycle regulators in human epidermoid carcinoma A431 cells Nutr. Cancer 39 2001 292 299 (Pubitemid 33694049)
4. A. Boyum, D. Lovhaug, L. Tresland, and E.M. Nordlie Separation of leucocytes: improved cell purity by fine adjustments of gradient medium density and osmolality Scand. J. Immunol. 34 1991 697 712
5. K. Cal How dose the type of vehicle influence the in vitro skin absorption and elimination kinetics of terpenes? Arch. Dermatol. Res. 297 2006 311 315 (Pubitemid 41789814)
6. R. Cermak, S. Landgraf, and S. Wolffram The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors J. Nutr. 133 2003 2802 2807 (Pubitemid 37099763)
7. J.J. Chen, Y.C. Tsai, T.L. Hwang, and T.C. Wang Thymol, benzofuranoid, and phenylpropanoid derivatives: anti-inflammatory constituents from Eupatorium cannabinum J. Nat. Prod. 74 2011 1021 1027
8. L. Cole, and C.M. Heard Skin permeation enhancement potential of Aloe Vera and a proposed mechanism of action based upon size exclusion and pull effect Int. J. Pharm. 333 2007 10 16 (Pubitemid 46283265)
9. S.E. dal Belo, L.R. Gaspar, P.M.B.G. Maia Campos, and J.P. Marty Skin penetration of epigallocatechin 3-gallate and quercetin from green tea and Ginkgo biloba extracts vehiculated in cosmetic formulations Skin Pharmacol. Physiol. 22 2009 299 304
10. M.D.L. de la Torre, A.G.P. Rodrigues, A.C. Tomé, A.M.S. Silva, and J.A.S. Cavaleiro [60]fullerene-flavonoid dyads Tetrahedron Lett. 60 2004 3581 3592 (Pubitemid 38429904)
11. J.Y. Fang, C.F. Hung, C.H. Chi, and C.C. Chen Transdermal permeation of selegiline from hydrogel-membrane drug delivery systems Int. J. Pharm. 380 2009 33 39
12. B.C. Finnin, and T.M. Morgan Transdermal penetration enhancers: applications, limitations, and potential J. Pharm. Sci. 88 1999 955 958 (Pubitemid 29480582)
13. D.J. Heal, and D.M. Pierce Methylphenidate and its isomers: their role in the treatment of attention-deficit hyperactivity disorder using a transdermal delivery system CNS Drugs 20 2006 713 738 (Pubitemid 44373701)
14. P.C.H. Hollman, J.H.M. de Vries, S.D. van Leeuwen, M.J.B. Mengelers, and M.B. Katan Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers Am. J. Clin. Nutr. 62 1995 1276 1282
15. C.F. Hung, Y.K. Lin, Z.R. Huang, and J.Y. Fang Delivery of resveratrol, a red wine polyphenol, from solutions and hydrogels via the skin Biol. Pharm. Bull. 31 2008 955 962
16. C.F. Hung, Y.K. Lin, L.W. Zhang, C.H. Chang, and J.Y. Fang Topical delivery of silymarin constituents via the skin route Acta Pharmacol. Sin. 31 2010 118 126
17. T.L. Hwang, Y.C. Su, H.L. Chang, Y.L. Leu, P.J. Chung, L.M. Kuo, and Y.J. Chang Suppression of superoxide anion and elastase release by C18 unsaturated fatty acids in human neutrophils J. Lipid Res. 50 2009 1395 1408
18. T.L. Hwang, C.C. Wang, Y.H. Kuo, H.C. Huang, Y.C. Wu, L.M. Kuo, and Y.H. Wu The hederagenin saponin SMG-1 is a natural FMLP receptor inhibitor that suppresses human neutrophil activation Biochem. Pharmacol. 80 2010 1190 1200
19. Y. Iwase, Y. Takemura, M. Ju-ichi, M. Yano, C. Ito, H. Furukawa, T. Mukainaka, M. Kuchide, H. Tokuda, and H. Nishino Cancer chemopreventive activity of 3,5,6,7,8,3′,4′-hepamethoxyflavone from the peel of citrus plants Cancer Lett. 163 2011 7 9
20. J.M. Jungersted, J.K. Hogh, L.I. Hellgren, G.B.E. Jemec, and T. Agner Skin barrier response to occlusion of healthy and irritated skin: differences in trans-epidermal water loss, erythema, and stratum corneum lipids Contact Dermatitis 63 2010 313 319
21. M.R. Kim, J.Y. Lee, H.H. Lee, D.K. Aryal, Y.G. Kim, S.K. Kim, E.R. Woo, and K.W. Kang Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara L Food Chem. Toxicol. 44 2006 1299 1307
22. J. Lademann, M.C. Meinke, W. Sterry, and M.E. Darvin Carotenoids in human skin Exp. Dermatol. 20 2011 377 382
23. W.R. Lee, T.L. Pan, P.W. Wang, R.Z. Zhuo, C.M. Huang, and J.Y. Fang Erbium: YAG laser enhances transdermal peptide delivery and skin vaccination J. Control. Release 128 2008 200 208
24. Borgia S. Lombardi, P. Schlupp, W. Mehnert, and M. Schäfer-Korting In vitro skin absorption and drug release - a comparison of six commercial prednicarbate preparations for topical use Eur. J. Pharm. Biopharm. 68 2008 380 389
25. J.A. Manthey, and N. Guthrie Antiproliferative activities of citrus flavonoids against six human cancer cell lines J. Agr. Food Chem. 50 2002 5837 5843 (Pubitemid 35155302)
26. 14C]- bisphenol A in rats: a possible extrapolation to human absorption? Arch. Toxicol. 85 2011 1035 1043
27. P.R. Mishra, L. Al Shaal, R.H. Müller, and C.M. Keck Production and characterization of hesperetin nanosuspensions for dermal delivery Int. J. Pharm. 371 2009 182 189
28. N. Nenadis, H.Y. Zhang, and M.Z. Tsimidou Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups J. Agr. Food Chem. 51 2003 1874 1879
29. A. Pȩkal, M. Biesaga, and K. Pyrzynska Interaction of quercetin with copper ions: complexation, oxidation and reactivity towards radicals Biometals 24 2011 41 49
30. M. Reinboth, S. Wolffram, G. Abraham, F.R. Ungemach, and R. Cermak Oral bioavailability of quercetin from different quercetin glycosides in dogs Br. J. Nutr. 104 2010 198 203
31. D. Rigano, C. Formisano, A. Basile, A. Lavitola, F. Senatore, S. Rosselli, and M. Bruno Antibacterial activity of flavonoids and phenylpropanoids from Marrubium globosum ssp. libanoticum Phytother. Res. 21 2007 395 397 (Pubitemid 46595989)
32. F. Rijken, and C.A.F.M. Bruijnzeel-Koomen Photoaged skin: the role of neutrophils, preventive measures, and potential pharmacological targets Nat. Clin. Pharmacol. Ther. 89 2011 120 124
33. M. Schneider, F. Stracke, S. Hansen, and U.F. Schaefer Nanoparticles and their interactions with the dermal barrier Dermato-Endocrinol. 1 2009 197 206
34. K.B. Sloan, and S. Wasdo Designing for topical delivery: prodrugs can make the difference Med. Res. Rev. 23 2003 763 793 (Pubitemid 37306013)
35. R. Suedee, C. Bodhibukkana, N. Tangthong, C. Amnuaikit, S. Kaewnopparat, and T. Srichana Development of a reservoir-type transdermal enantioselective- controlled delivery system for racemic propranolol using a molecularly imprinted polymer composite membrane J. Control. Release 129 2008 170 178
36. H. Takeuchi, T. Gomi, M. Shishido, H. Watanabe, and N. Suenobu Neutrophil elastase contributes to extracellular matrix damage induced by chronic low-dose UV irradiation in a hairless mouse photoaging model J. Dermatol. Sci. 60 2010 151 158
37. D.A. Valério, S.R. Georgetti, D.A. Magro, R. Casagrande, T.M. Cunha, F.T.M.C. Vicentini, S.M. Vieira, M.J.V. Fonseca, S.H. Ferreira, F.Q. Cunha, and W.A. Verri Quercetin reduces inflammatory pain: inhibition of oxidative stress and cytokine production J. Nat. Prod. 72 2009 1975 1979
38. C. Wagner, A.P. Vargas, D.H. Roos, A.F. Morel, M. Farina, C.W. Nogueira, M. Aschner, and J.B. Rocha Comparative study of quercetin and its two glycoside derivatives quercetin and rutin against methylmercury (MgHg)-induced ROS production in rat brain slices Arch. Toxicol. 84 2010 89 97
39. L.H. Wang, and W.H. Li General method for determining flavonoids in medicinal plants and raw cosmetics using HPLC with a photodiode array detector Pharm. Chem. J. 41 2007 225 231
40. J.J. Yourick, C.T. Jung, and R.L. Bronaugh In vitro and in vivo percutaneous absorption of retinol from cosmetic formulations: significance of the skin reservoir and prediction of systemic absorption Toxicol. Appl. Pharmacol. 231 2008 117 121
41. L.W. Zhang, S.A. Al-Suwayeh, P.W. Hsieh, and J.Y. Fang A comparison of skin delivery of ferulic acid and its derivatives: evaluation of their efficacy and safety Int. J. Pharm. 399 2010 44 51