Investigation of the inclusion behavior of chlorogenic acid with hydroxypropyl-β-cyclodextrin

被引：51

作者：

Chao, Jianbin ^{[1
]}

Wang, Hongfang ^{[1
]}

Zhao, Wei ^{[1
]}

Zhang, Min ^{[1
]}

Zhang, Liwei ^{[1
]}

机构：

[1] Shanxi Univ, Res Inst Appl Chem, Taiyuan 030006, Peoples R China

来源：

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES | 2012年 / 50卷 / 01期

关键词：

Inclusion complex; Chlorogenic acid; Hydroxypropyl-beta-cyclodextrin; Fluorescence; NMR; CAFFEIC ACID; ANTIOXIDANT; COMPLEX;

D O I：

10.1016/j.ijbiomac.2011.11.008

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

The inclusion complexation behavior of chlorogenic acid (CGA) with the hydroxypropyl-beta-cyclodextrin (HP-beta-CD) was investigated in both solution and the solid state by UV-vis and fluorescence spectroscopy, infrared spectroscopy (IR), NMR spectroscopy as well as differential scanning calorimetry (DSC). The experimental results indicate that CGA is able to form an inclusion complex with HP-beta-CD. The inclusion complex has a stoichiometry of 1:1 and the formation constant was calculated to be 155.7 M-1. The antioxidant activity of CGA on complexation with HP-beta-CD increased as compared to uncomplexed CGA. NMR spectroscopic studies show that the aromatic ring and the vinyl group of CGA are deeply included inside the (C) cavity. 2011 Elsevier B.V. All rights reserved.

引用

页码：277 / 282

页数：6

共 20 条

[1]

Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques [J].

Al-Marzouqi, Ali H. ;

Elwy, Hanan M. ;

Shehadi, Ihsan ;

Adem, Abdu .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2009, 49 (02) :227-233

[2]

Inhibitory effects of dimethylacetyl-β-cyclodextrin on lipopolysaccharide-induced macrophage activation and endotoxin shock in mice [J].

Arima, H ;

Motoyama, K ;

Matsukawa, A ;

Nishimoto, Y ;

Hirayama, F ;

Uekama, K .

BIOCHEMICAL PHARMACOLOGY, 2005, 70 (10) :1506-1517

[3]

Experimental study of chemical kinetics and simulation of 5-O-caffeoylquinic acid oxidation during manufacturing of mate (Ilex Paraquariensis) [J].

Beninca, Cristina ;

Kaskantzis, Georges ;

Zanoelo, Everton Fernando .

BIOSYSTEMS ENGINEERING, 2009, 104 (04) :503-509

[4]

Cyclodextrins as pharmaccutical solubilizers [J].

Brewster, Marcus E. ;

Loftsson, Thorsteinn .

ADVANCED DRUG DELIVERY REVIEWS, 2007, 59 (07) :645-666

[5]

Macrocyclic anion receptors based on directed hydrogen bonding interactions [J].

Choi, KH ;

Hamilton, AD .

COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :101-110

[6]

Direct lipase-catalyzed lipophilization of chlorogenic acid from coffee pulp in supercritical carbon dioxide [J].

Hernandez, Carlos E. ;

Chen, Ho-Hsien ;

Chang, Chi-I. ;

Huang, Tzou-Chi .

INDUSTRIAL CROPS AND PRODUCTS, 2009, 30 (03) :359-365

[7]

CDs as solubilizers: Effects of excipients and competing drugs [J].

Jansook, Phatsawee ;

Loftsson, Thorsteinn .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2009, 379 (01) :32-40

[8]

Cyclodextrin conjugate-based controlled release system: repeated- and prolonged-releases of ketoprofen after oral administration in rats [J].

Kamada, M ;

Hirayama, F ;

Udo, K ;

Yano, H ;

Arima, H ;

Uekama, K .

JOURNAL OF CONTROLLED RELEASE, 2002, 82 (2-3) :407-416

[9]

DIFFERENTIAL-EFFECTS OF LIGHT AND FUNGAL ELICITOR ON CHLOROGENIC ACID AND CAFFEOYLSHIKIMIC ACID METABOLISM [J].

KOCH, U ;

KUHNL, T ;

CONRADT, W ;

WELLMANN, E .

PLANT SCIENCE, 1990, 70 (02) :167-174

[10]

Antioxidant activity of polyphenolics in diets - Rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen [J].

Kono, Y ;

Kobayashi, K ;

Tagawa, S ;

Adachi, K ;

Ueda, A ;

Sawa, Y ;

Shibata, H .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1997, 1335 (03) :335-342

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