Complexation of hydroxytyrosol with β-cyclodextrins. An efficient photoprotection

被引：26

作者：

Angeles Lopez-Garcia, M. ^{[1
]}

Lopez, Oscar ^{[1
]}

Maya, Ines ^{[1
]}

Fernandez-Bolanos, Jose G. ^{[1
]}

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, E-41012 Seville, Spain

来源：

TETRAHEDRON | 2010年 / 66卷 / 40期

关键词：

Supramolecular chemistry; Inclusion complex; Hydroxytyrosol; Cyclodextrin; Antioxidant activity; Photoprotection; ANTIOXIDANT ACTIVITY; OLIVE OIL; ALPHA-CYCLODEXTRIN; INCLUSION; CONSTANTS; H-1-NMR;

D O I：

10.1016/j.tet.2010.08.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The complexation of the potent olive oil antioxidant hydroxytyrosol (HT) with commercial beta-cyclodextrin (beta-CD) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) in aqueous solutions has been studied for the first time. The 1:1 stoichiometries of the complexes were evidenced by Job's plot and the association constants were determined by linear regressions from Scott's method. The geometry of the HT/beta-CD complex was elucidated by 2D-ROESY experiments, suggesting insertion of the catechol moiety with the hydroxyalkyl chain directed to the primary rim. The antioxidant activity of encapsulated HT was also evaluated by scavenging of the stable DPPH radical, observing an improvement of the scavenging activity upon increase of the cyclodextrin concentration. Complexation of HT with beta-CD also provided a strong photoprotection of the polyphenolic compound upon irradiation with UV (lambda=254 nm). (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：8006 / 8011

页数：6

共 21 条

[1] Complexation study of midazolam hydrochloride with β-cyclodextrin:: NMR spectroscopic study in solution [J].

Ali, Syed Mashhood ;

Upadhyay, Santosh Kumar .

MAGNETIC RESONANCE IN CHEMISTRY, 2008, 46 (07) :676-679

[2] Inclusion complexes of 2-phenoxyethanol and alkoxyethanols in cyclodextrins:: an 1H NMR study [J].

Andrade-Dias, Cristiano ;

Goodfellow, Brian J. ;

Cunha-Silva, Luis ;

Teixeira-Dias, Jose J. C. .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2007, 57 (1-4) :151-156

[3] Changes in the polyphenolic and volatile content of "Fino" Sherry wine exposed to high temperature and ultraviolet and visible radiation [J].

Benítez, P ;

Castro, R ;

Natera, R ;

Barroso, CG .

EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2006, 222 (3-4) :302-309

[4] Effects of α and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones [J].

Calabrò, ML ;

Tommasini, S ;

Donato, P ;

Raneri, D ;

Stancanelli, R ;

Ficarra, P ;

Ficarra, R ;

Costa, C ;

Catania, S ;

Rustichelli, C ;

Gamberini, G .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2004, 35 (02) :365-377

[5] Cyclodextrin-based bioactive supramolecular assemblies [J].

Chen, Yong ;

Liu, Yu .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :495-505

[6] Nutritional benefit of olive oil: The biological effects of hydroxytyrosol and its arylating quinone adducts [J].

Cornwell, David G. ;

Ma, Jiyan .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (19) :8774-8786

[7] Cyclodextrins and their uses: a review [J].

Del Valle, EMM .

PROCESS BIOCHEMISTRY, 2004, 39 (09) :1033-1046

[8] Hydroxytyrosol and derivatives:: Isolation, synthesis, and biological properties [J].

Fernandez-Bolanos, Jose G. ;

Lopez, Oscar ;

Fernandez-Bolanos, Juan ;

Rodriguez-Gutierrez, Guillermo .

CURRENT ORGANIC CHEMISTRY, 2008, 12 (06) :442-463

[9] Determination of association constants (Ka) from solution NMR data [J].

Fielding, L .

TETRAHEDRON, 2000, 56 (34) :6151-6170

[10] Proton NMR study of α-cyclodextrin inclusion of short-chain surfactants [J].

Funasaki, N ;

Ishikawa, S ;

Neya, S .

JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (37) :10094-10099

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