Solubilization of resveratrol in micellar solutions of different bile acids

被引:56
作者
Atanackovic, Milica [1 ]
Posa, Mihalj [2 ]
Heinle, Helmut [3 ]
Gojkovic-Bukarica, Ljiljana [4 ]
Cvejic, Jelena [1 ]
机构
[1] Univ Novi Sad, Fac Med, Dept Pharm, Lab Pharmaceut & Nat Prod Anal, Novi Sad 21000, Serbia
[2] Univ Novi Sad, Fac Med, Dept Pharm, Lab Phys Pharm, Novi Sad 21000, Serbia
[3] Univ Tubingen, Inst Physiol, D-72076 Tubingen, Germany
[4] Univ Belgrade, Fac Med, Dept Pharmacol & Toxicol & Clin Pharmacol, Belgrade 11129, Serbia
关键词
Bile acids; Resveratrol; Solubilization; Critical micellar concentration; AQUEOUS-SOLUTIONS; KETO DERIVATIVES; CHOLIC-ACID; TRANS-RESVERATROL; WINE POLYPHENOL; DIABETIC-RATS; SALTS; RED; ABSORPTION; ENHANCEMENT;
D O I
10.1016/j.colsurfb.2009.03.029
中图分类号
Q6 [生物物理学];
学科分类号
071011 ;
摘要
Bile acids are a special group of biological surfactants which can express different physiological and pharmacological effects. Micellar solutions of bile acids can solubilizate poorly soluble organic substances and improve their resorbtion. Above their critical micellar concentration (CMC) values, bile acids can cause interruption of membrane's integrity. Resveratrol (trans-3,5,4'-trihydroxystilbene) is a stilbene phytoalexine and studies reported that it can prevent or reduce diseases Such as cancer and coronary heart disease. In this study, we examined affinity of different bile acids (CA, 12-MDCA, 12-MCA, 7-MCA, 7,12-DCA, 3,7,12-TCA) micellar solutions for resveratrol solubilization. CMC values for bile acids were determined by conductivity measurements. Concentration of micellar Solutions were 0.25, 0.5, 0.75, 1.0, 1.25, 1.5, 1.75, 2.0 CMC value, for each acid respectively. At the same time, we investigated membranolytical potential of each acid. Solubilizated resveratrol was quantified using HPLC system with UV detection. Membranolytical potential was determined from citrate rabbit blood. Structures of mixed micelles of each bile acid and resveratrol were explained, and multiple linear regression equations for solubilization of resveratrol on different concentrations of bile acids were obtained. Micellar solution of 3,7,12-TCA had the biggest affinity for resveratrol solubilization and then, in decreasing order 7-MCA > 7, 12-DCA > 12-MCA > 12-MDCA > CA. Also, 3,7,12-TCA had the lowest membranolytical potential. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:148 / 154
页数:7
相关论文
共 37 条
[1]   Influence of the semisynthetic bile acid MKC on the ileal permeation of Gliclazide in vitro in healthy and diabetic rats treated with probiotics [J].
Al-Salami, H. ;
Butt, G. ;
Tucker, I. ;
Mikov, M. .
METHODS AND FINDINGS IN EXPERIMENTAL AND CLINICAL PHARMACOLOGY, 2008, 30 (02) :107-113
[2]  
ARMSTRONG MJ, 1982, J LIPID RES, V23, P70
[3]   Bile salt-phospholipid aggregation at submicellar concentrations [J].
Baskin, Rebekah ;
Frost, Laura D. .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2008, 62 (02) :238-242
[4]   Hydrogen-bonded aggregations of oxo-cholic acids [J].
Bertolasi, V ;
Ferretti, V ;
Pretto, L ;
Fantin, G ;
Fogagnolo, M ;
Bortolini, O .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2005, 61 :346-356
[5]   Design of compounds that increase the absorption of polar molecules [J].
Bowe, CL ;
Mokhtarzadeh, L ;
Venkatesan, P ;
Babu, S ;
Axelrod, HR ;
Sofia, MJ ;
Kakarla, R ;
Chan, TY ;
Kim, JS ;
Lee, HJ ;
Amidon, GL ;
Choe, SY ;
Walker, S ;
Kahne, D .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (22) :12218-12223
[6]   Nutraceuticals:: Facts and fiction [J].
Carlos Espin, Juan ;
Teresa Garcia-Conesa, Maria ;
Tomas-Barberan, Francisco A. .
PHYTOCHEMISTRY, 2007, 68 (22-24) :2986-3008
[7]   OXIDATION OF STEROIDS .3. SELECTIVE OXIDATIONS AND ACYLATIONS IN THE BILE ACID SERIES [J].
FIESER, LF ;
RAJAGOPALAN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (12) :5530-5536
[8]   Resveratrol and its antioxidant and antimicrobial effectiveness [J].
Filip, V ;
Plocková, M ;
Smidrkal, J ;
Spicková, Z ;
Melzoch, K ;
Schmidt, S .
FOOD CHEMISTRY, 2003, 83 (04) :585-593
[9]   trans-resveratrol in wines from the major Greek red and white grape varieties [J].
Gerogiannaki-Christopoulou, M ;
Athanasopoulos, P ;
Kyriakidis, N ;
Gerogiannaki, IA ;
Spanos, M .
FOOD CONTROL, 2006, 17 (09) :700-706
[10]  
GOLDBERG DM, 1995, CLIN CHEM, V41, P14