Structure elucidation and sulfated derivatives preparation of two α-D-glucans from Gastrodia elata Bl. and their anti-dengue virus bioactivities

被引：88

作者：

Qiu, Hong

Tang, Wei

Tong, Xiankun

Ding, Kan ^{[1
]}

Zuo, Jianping

机构：

[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Materia Med, Glycobiol & Glycochem Lab,State Key Lab Drug Res, Shanghai 201203, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Materia Med, Lab Immunopharmacol,State Key Lab Drug Res, Shanghai 201203, Peoples R China

[3] Shanghai Univ Tradit Chinese Med, Lab Immunol & Virol, Shanghai 201203, Peoples R China

来源：

CARBOHYDRATE RESEARCH | 2007年 / 342卷 / 15期

关键词：

Gastrodia elata; alpha-D-glucan; dengue virus; sulfated polysaccharide;

D O I：

10.1016/j.carres.2007.06.021

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 structures of two glucans, WGEW and AGEW, isolated from Gastrodia elata Bl. were elucidated using monosaccharide composition analysis by gas chromatography (GC), methylation analysis by gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) spectroscopy. Their structures were deduced as an alpha-D-(1 --> 4)-glucan with an alpha-(1 --> 4) linked branch attached to O-6 branch points with different branch degrees. Their sulfate derivatives with distinct degrees of substitution (DS) were prepared. The substitution position was assigned to O-6 according to the C-13 NMR spectra. All sulfated derivatives showed strong anti-dengue virus bioactivities. The structure-activity relationships (SAR) between the polysaccharides and their sulfated derivatives were also investigated. Results showed that the higher the DS is, the more potent the impact on the dengue virus infection would be. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2230 / 2236

页数：7

共 22 条

[1] Chemical modifications of the (1→3)-α-D-glucan from spores of Ganoderma lucidum and investigation of their physicochemical properties and immunological activity [J].

Bao, XF ;

Duan, JY ;

Fang, XY ;

Fang, JN .

CARBOHYDRATE RESEARCH, 2001, 336 (02) :127-140

[2] An α-glucan of Pseudallescheria boydii is involved in fungal phagocytosis and toll-like receptor activation [J].

Bittencourt, Vera Carolina B. ;

Figueiredo, Rodrigo T. ;

da Silva, Rosana B. ;

Mourao-Sa, Diego S. ;

Fernandez, Patricia L. ;

Sassaki, Guilherme L. ;

Mulloy, Barbara ;

Bozza, Marcelo T. ;

Barreto-Bergter, Eliana .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (32) :22614-22623

[3] Effect of (1→3)- and (1→4)-linkages of fully sulfated polysaccharides on their anticoagulant activity [J].

Chaidedgumjorn, A ;

Toyoda, H ;

Woo, ER ;

Lee, KB ;

Kim, YS ;

Toida, T ;

Imanari, T .

CARBOHYDRATE RESEARCH, 2002, 337 (10) :925-933

[4] Dengue virus infectivity depends on envelope protein binding to target cell heparan sulfate [J].

Chen, YP ;

Maguire, T ;

Hileman, RE ;

Fromm, JR ;

Esko, JD ;

Linhardt, RJ ;

Marks, RM .

NATURE MEDICINE, 1997, 3 (08) :866-871

[5] Sulfated seaweed polysaccharides as antiviral agents [J].

Damonte, EB ;

Matulewicz, MC ;

Cerezo, AS .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (18) :2399-2419

[6] A NOTE ON DETERMINATION OF ESTER SULPHATE CONTENT OF SULPHATED POLYSACCHARIDES [J].

DODGSON, KS ;

PRICE, RG .

BIOCHEMICAL JOURNAL, 1962, 84 (01) :106-&

[7] A β-D-glucan isolated from the fruiting bodies of Hericium erinaceus and its aqueous conformation [J].

Dong, Q ;

Jia, LM ;

Fang, JN .

CARBOHYDRATE RESEARCH, 2006, 341 (06) :791-795

[8]

Guzman M G, 1984, Bull Pan Am Health Organ, V18, P213

[9] A colorimetric assay for viral agents that produce cytopathic effects [J].

Heldt, Caryn L. ;

Hernandez, Raquel ;

Mudiganti, Usharani ;

Gurgel, Patrick V. ;

Brown, Dennis T. ;

Carbonell, Ruben G. .

JOURNAL OF VIROLOGICAL METHODS, 2006, 135 (01) :56-65

[10] THE DENGUE VIRUSES [J].

HENCHAL, EA ;

PUTNAK, JR .

CLINICAL MICROBIOLOGY REVIEWS, 1990, 3 (04) :376-396

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