Synthesis of curdlan sulfates having inhibitory effects in vitro against AIDS viruses HIV-1 and HIV-2

Yoshida, Takashi; Yasuda, Yuki; Mimura, Toru; Kaneko, Yutaro; Nakashima, Hideki; Yamamoto, Naoki; Uryu, Toshiyuki

doi:10.1016/0008-6215(95)00186-w

Cited by 87 publications

(63 citation statements)

References 20 publications

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“…Chemical Characterization of Sulfated Derivatives of (Table 1), according to the method of Yoshida et al 28) The DS that designated the average number of sulfate (SA) groups in each glucosyl residue was calculated from the data obtained by sulfur content analysis. As shown in Table 1, the apparent molecular weight of the derivatives decreased sharply with the increasing DS values in the range from 2.0ϫ10 5 to 0.4ϫ10 5 , while their water solubility was considerably increased in comparison with that of the native glucan.…”

Section: Resultsmentioning

confidence: 99%

Purification, Characterization, and Modification of T Lymphocyte-Stimulating Polysaccharide from Spores of <i>Ganoderma lucidum</i>

et al. 2002

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Ganoderma lucidum, a well-known Chinese medicinal fungus, has been used to promote health and longevity in East Asian countries. Its medical effects on cancer, hypertension, hepatitis, and hypercholesterolemia have been demonstrated by pharmacological studies in the past two decades. [1][2][3][4] This fungus has attracted considerable attention partly because the polysaccharides isolated from the fruit bodies and the mycelium have shown antitumor and hyperglycemic activity. 3,5,6) However, the active components in the spores of G. lucidum have rarely been studied owing to the difficulty in collection and sporoderm-breaking of the spores. Recently, with the successful cultivation of G. lucidum indoors on a large scale and a breakthrough in sporodermbreaking technology, much attention has been paid to chemical components of G. lucidum spores 7,8) and their versatile biological activities.9,10) More recently, we have reported an immunomodulating polysaccharide from the spores of G. lucidum. 11) In the present study, we deal with the purification and characterization of the T lymphocyte-stimulating polysaccharide, based on the activity-guided principle, from the hot-water extract of the sporoderm-broken spores of G. lucidum. A series of sulfated or carboxymethylated derivatives of the polysaccharide were successively prepared and their structures were elucidated by chemical and spectral methods. The solution conformation and T lymphocyte proliferation effect of the polysaccharide and its derivatives are compared and discussed. ExperimentalMaterials Spores of G. lucidum were collected in Shanxi Province, PR China. It was identified by Dr. Xiu-Lan Huang and stored as a voucher specimen (no. 99064) in the Herbarium of Phytochemistry Department of Shanghai Institute of Materia Medica, Shanghai, PR China. Before use, the sporoderm of the spores was ultrasonographically broken and the broken ratio was estimated about 60-80% by electronic microscopy. T-Dextran in a series of different molecular weights was obtained from Pharmacia. Concanavalin (Con A) was from Sigma and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was from Fluka. Medium RPMI-1640 was purchased from Gibco Laboratories. All other reagents were of the highest quality available and were used without further purification.Isolation and Purification of the T Lymphocyte-Stimulating Polysaccharide The sporoderm-broken spores of G. lucidum (1.0 kg), previously defatted with 95% alcohol, were decocted for 6 h with 10 l of water to half the original volume, and the residue was again decocted with 8 l of water. The combined aqueous extract was deproteinated with trichloroacetic acid, and the resulting aqueous fraction was extensively dialyzed against running water for 3 d and then against distilled water for 1 d (molecular weight cutoff 3000-5000 Da). The retentate was concentrated under reduced pressure to a small volume (1.8 l), and 4 volumes of ethanol were added stepwise with stirring at 4°C. Then the mixture was stored overnight at Ϫ10°C. T...

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Section: Resultsmentioning

confidence: 99%

Purification, Characterization, and Modification of T Lymphocyte-Stimulating Polysaccharide from Spores of <i>Ganoderma lucidum</i>

et al. 2002

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“…The sulfating agent was prepared using dry pyridine and chlorosulfonic acid on the basis of the CSA method described by Yoshida et al 13…”

Section: Methodsmentioning

confidence: 99%

“…It was very difficult completely to separate -and -glucans from the extract. 17) Compared with the 13 Figure 5 shows the SEC chromatograms of the native -glucans in 0. …”

Section: Chemical Structurementioning

confidence: 99%

Antitumor Activities ofO-Sulfonated Derivatives of (1→3)-α-D-Glucan from DifferentLentinus edodes

Surenjav

Zeng

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…Assignment of the peaks was carried out by reference to the previous work. 26 The comparison of intensity of methylene group (2.8 ppm, 4H) of the succinyl 34 moiety with that of methyl group (1.8 ppm, 3H) of AZT moiety revealed that the linkage between AZT and curdlan was not broken during the sulfation. Therefore, the degree of AZT substitution to a glucose unit of curdlan did not change by the sulfation.…”

Section: Synthesis and Structure Analysismentioning

confidence: 99%

Synthesis of Azidothymidine-Bound Curdlan Sulfate with Anti-Human Immunodeficiency Virus Activity in vitro

Gao

Katsuraya

Kaneko

et al. 1998

Polym J

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ABSTRACT:Azidothymidine (AZT) was introduced into curdlan by biodegradable ester bond to give AZT-bound curdlan (AZT-curdlan) in order to aim at releasing AZT from the polymer backbone by an enzymatic hydrolysis in living organs. Structure of the AZT-curdlan was analyzed by 13 C NMR and 1 H-13 C COSY-FG 2D-NMR spectroscopy, indicating that AZT was bound to C6 hydroxyl group of curdlan as designed. Subsequently, the AZT-curdlan was sulfated with sulfur trioxide-pyridine complex to give sulfated AZT-curdlans (AZT-curdlan sulfates). AZT-curdlan sulfates, in vitro, exhibited anti-HIV activities in the EC 50 range of 0.20 to 0.60/lgml-1 , corresponding to that (EC50 =0.50!lgml-1 ) of highly active curdlan sulfate. They possessed low cytotoxicities of CC50 more than I 000 !lg ml-1 in vitro, indicating that AZT was not released in vitro. However, an increase in the anti-HIV activity and the cytotoxicity was observed when the AZT-curdlan sulfate solution in 90% buffer at pH 7.4 and 10% dimethyl sulfoxide mixture was kept in a refrigerator for a few weeks. The phenomenon indicates that an anti-HIV active AZT was released slowly from the curdlan sulfate carrier. Furthermore, the AZT-curdlan sulfates exhibited low to moderate anticoagulant activities in vitro.

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Synthesis of curdlan sulfates having inhibitory effects in vitro against AIDS viruses HIV-1 and HIV-2

Cited by 87 publications

References 20 publications

Purification, Characterization, and Modification of T Lymphocyte-Stimulating Polysaccharide from Spores of <i>Ganoderma lucidum</i>

Purification, Characterization, and Modification of T Lymphocyte-Stimulating Polysaccharide from Spores of <i>Ganoderma lucidum</i>

Antitumor Activities ofO-Sulfonated Derivatives of (1→3)-α-D-Glucan from DifferentLentinus edodes

Synthesis of Azidothymidine-Bound Curdlan Sulfate with Anti-Human Immunodeficiency Virus Activity in vitro

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