Inclusion complexes of azadirachtin with native and methylated cyclodextrins: solubilization and binding ability

被引：59

作者：

Liu, Y ^{[1
]}

Chen, GS

Chen, Y

Lin, J

机构：

[1] Nankai Univ, Dept Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Yunnan Univ, Dept Appl Chem, Kunming 650091, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 12期

基金：

中国国家自然科学基金;

关键词：

azadirachtin; cyclodextrin; inclusion complex; molecular recognition;

D O I：

10.1016/j.bmc.2005.03.051

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The inclusion complexation behavior of azadirachtin with several cyclodextrins and their methylated derivatives has been investigated in both solution and the solid state by means of XRD, TG-DTA, DSC, NMR, and UV-vis spectroscopy. The results show that the water solubility of azadirachtin was obviously increased after resulting inclusion complex with cyclodextrins. Typically, P-cyclodextrin (P-CD), dimethyl-p-cyclodextrin (DM beta CD), permethyl-beta-cyclodextrin (TM beta CD), and hydroxypropyl-beta-cyclodextrin (HP beta CD) are found to be able to solubilize azadirachtin to high levels up to 2.7, 1.3, 3.5, and 1.6 mg/mL (calculated as azadirachtin), respectively. This satisfactory water solubility and high thermal stability of the cyclodextrin-azadirachtin complexes, will be potentially useful for their application as herbal medicine or healthcare products. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4037 / 4042

页数：6

共 37 条

[1] Cytotoxicity of azadirachtin A in human glioblastoma cell lines [J].

Akudugu, J ;

Gäde, G ;

Böhm, L .

LIFE SCIENCES, 2001, 68 (10) :1153-1160

[2]

[Anonymous], 1992, NEEM TREE SOLV GLOB

[3]

[Anonymous], 1996, SUPRAMOL SCI, DOI DOI 10.1016/0968-5677(96)00016-8

[4] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .1. CONVERSION FROM THE AZADIRACHTIN TO THE AZADIRACHTININ SKELETONS [J].

BILTON, JN ;

JONES, PS ;

LEY, SV ;

ROBINSON, NG ;

SHEPPARD, RN .

TETRAHEDRON LETTERS, 1988, 29 (15) :1849-1852

[5] CYCLODEXTRIN CHEMISTRY - SELECTIVE MODIFICATION OF ALL PRIMARY HYDROXYL-GROUPS OF ALPHA-CYCLODEXTRINS AND BETA-CYCLODEXTRINS [J].

BOGER, J ;

CORCORAN, RJ ;

LEHN, JM .

HELVETICA CHIMICA ACTA, 1978, 61 (06) :2190-2218

[6] Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].

Breslow, R ;

Dong, SD .

CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011

[7] Influence of operating parameters on the use of the microwave-assisted process (MAP) for the extraction of azadirachtin-related limonoids from neem (Azadirachta indica) under atmospheric pressure conditions [J].

Dai, JM ;

Yaylayan, VA ;

Raghavan, GSV ;

Paré, JRJ ;

Liu, Z ;

Bélanger, JMR .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (10) :4584-4588

[8] Multivariate calibration for the determination of total azadirachtin-related limonoids and simple terpenoids in neem extracts using vanillin assay [J].

Dai, JM ;

Yaylayan, VA ;

Raghavan, GSV ;

Parè, JR ;

Liu, Z .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (03) :1169-1174

[9] Structure-antifeedant activity relationship of clerodane diterpenoids.: Comparative study with withanolides and azadirachtin [J].

Enriz, RD ;

Baldoni, HA ;

Zamora, MA ;

Jáuregui, EA ;

Sosa, ME ;

Tonn, CE ;

Luco, JM ;

Gordaliza, M .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (04) :1384-1392

[10] STRUCTURE-RELATED INSECT ANTIFEEDANT AND GROWTH-REGULATING ACTIVITIES OF SOME LIMONOIDS [J].

GOVINDACHARI, TR ;

NARASIMHAN, NS ;

SURESH, G ;

PARTHO, PD ;

GOPALAKRISHNAN, G ;

KUMARI, GNK .

JOURNAL OF CHEMICAL ECOLOGY, 1995, 21 (10) :1585-1600

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