禹州漏芦均一多糖的结构分析及其硫酸化衍生物的抗补体活性

doi:10.7503/cjcu20140089

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (10): 2119.doi: 10.7503/cjcu20140089

禹州漏芦均一多糖的结构分析及其硫酸化衍生物的抗补体活性

鲍斌, 王辉俊, 王宏伟, 施松善, 王顺春()

上海中医药大学中药研究所, 中药标准化教育部重点实验室,中药新资源与质量标准综合评价国家中医药管理局重点研究室, 上海 201203

收稿日期:2014-01-27 出版日期:2014-10-10 发布日期:2014-09-15
作者简介:联系人简介: 王顺春, 男, 博士, 研究员, 博士生导师, 主要从事糖化学和糖生物学研究. E-mail: shunchunwang@126.com
基金资助:
国家自然科学基金(批准号: 81373951)和重大新药创制专项(批准号: 2012ZX09301001-003)资助

Structural Characterization of One Homogeneous Polysaccharide from Echinops latifolius Tausch. and Anti-complementary Activity of Its Sulfated Derivatives^†

BAO Bin, WANG Huijun, WANG Hongwei, SHI Songshan, WANG Shunchun^*()

Key Laboratory for Standardization of Chinese Medicines, Ministry of Education, Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines of SATCM, Institute of Chinese, Institute of Chinese Materia Medica,Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

Received:2014-01-27 Online:2014-10-10 Published:2014-09-15
Contact: WANG Shunchun E-mail:shunchunwang@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.81373951) and the Key New Drug Creation and Manufacturing Program of China(No.2012ZX09301001-003)

摘要/Abstract

摘要：

以禹州漏芦为原料, 经沸水提取、乙醇沉淀、 DEAE-Cellulose和Superdex^TM75凝胶柱层析分离纯化, 得到一种水溶性的酸性均一多糖(EPS-2A). 采用单糖组成、甲基化及绝对构型等方法对其进行了结构解析. 结果表明, 该均一多糖主要由D-半乳糖醛酸组成, 并含有少量的Rha和Ara. 该均一多糖经不同条件硫酸衍生化后的衍生物(Sul-2A-1和Sul-2A-2)与阳性药肝素[CH₅₀=(103.0±9.0) μg/mL(mean±SD, n=3), CH₅₀为出现50%溶血时的样品浓度]相比, 均表现出很强的抗补体活性[Sul-2A-1的CH₅₀=(74.1±4.6) μg/mL; Sul-2A-2 的CH₅₀=(35.7±2.8) μg/mL].

关键词: 禹州漏芦, 多糖, 结构分析, 硫酸衍生化, 抗补体

Abstract:

To isolate and characterize the anti-complementary polysaccharide from the root of Echinops latifolius Tausch., bioactivity-guided fractionation and purification was used to obtain the anti-complementary polysaccharide from the hot-water extract of the root of Echinops latifolius Tausch. The polysaccharide was characterized by various chemical and spectral analyses. The anti-complementary activities were evaluated by hemolytic assay in vitro. The action targets were identified in the system with individual complement-depleted sera. A homogenous water-soluble polysaccharide(EPS-2A) was obtained from Echinops latifolius Tausch., which average molecular weight was estimated to be 118000. A combination of monosaccharide composition, methylation and configuration analysis, as well as NMR spectroscopy, indicated that EPS-2A was poly-(1-4)-α-D-galactopyranosyluronic acid in which (87.8±0.5)% of uronic acid existed as methylester. Two sulfated derivatives(Sul-2A-1 and Sul-2A-2) from EPS-2A were prepared after sulfation with 1∶1 and 2∶1 of chlorosulfonic acid and pyridine, respectively. The anti-complementary assay showed that Sul-2A-1 and Sul-2A-2 demonstrated a stronger inhibitory effect [CH₅₀=(74.1±4.6) μg/mL for Sul-2A-1; CH₅₀=(35.7±2.8) μg/mL for Sul-2A-2] on the complement activation through the classic pathway, compared to that of heparin [CH₅₀=(103.0±9.0) μg/mL]. The results suggested that the sulfated derivatives Sul-2A-1 and Sul-2A-2 might be promising drug candidates in case of necessary therapeutic complement inhibition.

Key words: Echinops latifolius Tausch., Polysaccharide, Structure analysis, Sulfated derivative, Anti-complement

中图分类号:

O629.12

TrendMD:

鲍斌, 王辉俊, 王宏伟, 施松善, 王顺春. 禹州漏芦均一多糖的结构分析及其硫酸化衍生物的抗补体活性. 高等学校化学学报, 2014, 35(10): 2119.

BAO Bin, WANG Huijun, WANG Hongwei, SHI Songshan, WANG Shunchun. Structural Characterization of One Homogeneous Polysaccharide from Echinops latifolius Tausch. and Anti-complementary Activity of Its Sulfated Derivatives^†. Chem. J. Chinese Universities, 2014, 35(10): 2119.

图/表 2

参考文献 23

[1]	Wang Y., Li X., Zhang P., Chinese Traditional and Herbal Drugs,2005, 36(2), 309—311
	(汪毅, 李铣, 张鹏. 中草药, 2005, 36(2), 309—311)
[2]	Li F. S., Xu H. G., Yan X. M., Li M. Y., Liu H., China Journal of Chinese Materia Medica,2008, 33(11), 1284—1286
	(李发胜, 徐恒瑰, 燕小梅, 李明阳, 刘辉. 中国中药杂志, 2008, 33(11), 1284—1286)
[3]	Zhang X. L., Chinese Journal of Immunology, 2004, 20, 290—293
	(章晓联. 中国免疫学杂志, 2004, 20, 290—293)
[4]	Sturfelt G., Scandinavian Journal of Rheumatology, 2002, 31(3), 129—132
[5]	Di H. Y., Zhang Y. Y., Chen D. F., Chinese Natural Medicine,2013, 11(2), 177—184
	(狄宏晔, 章蕴毅, 陈道峰. 中国天然药物, 2013, 11(2), 177—184)
[6]	Zhang Q., Lin Q. B., Pharmacology and Clinics of Chinese Materia Medica,1998, 14(5), 19—21
	(张庆, 林勤保. 中药药理与临床, 1998, 14(5), 19—21)
[7]	Huang X. Y., Kong X. F., Wang D. Y., Hu Y. L., Nutural Product Research and Development,2007, 19(2), 328—332
	(黄小燕, 孔祥峰, 王德云, 胡云亮. 天然产物研究与开发, 2007, 19(2), 328—332)
[8]	Wang C., Shi S. S., Hong Q. M., Wang S. C., Wang Z. T., Hu Z. B., Chem. J. Chinese Universites,2009, 30(11), 2189—2192
	(王彩, 施松善, 洪其明, 王顺春, 王峥涛, 胡之壁. 高等学校化学学报, 2009, 30(11), 2189—2192)
[9]	Stevenson T. T., Furneaux R. H., Carbohydrate Research,1991, 210, 277—298
[10]	Senchenkova S. N., Knirel Y. A., Likhosherstov L. M., Shashkov A. S., Shibaev V. N., Starukhina L. A., Deryabin V. V., Carbohydrate Research,1995, 266(1), 103—113
[11]	Taylor R. L., Conrad H. E., Biochemistry,1972, 11(8), 1383—1388
[12]	Hakomori S. I., Journal of Biochemistry, 1964, 55(2), 205—208
[13]	Cases M. R., Cerezo A. S., Stortz C. A., Carbohydrate Research,1995, 269(2), 333—341
[14]	Navarro D. A., Stortz C. A., Carbohydrate Research,2003, 338(20), 2111—2118
[15]	Jin H. Y., Shi S. S., Wang S. C., Wang Z. T., Hu Z. B., Chem. J. Chinese Universities,2012, 33(4), 755—760
	(金红英, 施松善, 王顺春, 王峥涛, 胡之壁. 高等学校化学学报, 2012, 33(4), 755—760)
[16]	Inoue K., Kawamoto K., Nakajima H., Kohno M., Kadoya S., Mizuno D., Carbohydrate Research,1983, 115, 199—208
[17]	Chaidedgumjorn A., Toyoda H., Woo E. R., Lee K. B., Kim Y. S., Toida T., Imanari T., Carbohydrate Research,2002, 337, 925—933
[18]	Fang J. N., Chin. Pharm. J., 1993, 28(7), 393—395
	(方积年. 中国药学杂志, 1993, 28(7), 393—395)
[19]	Duan J. Y., Zheng Y., Dong Q., Fang J. N., Phytochemistry,2004, 65, 609—615
[20]	Cozzolino R., Malvagna P., Spina E., Giori A., Fuzzati N., Anelli A., Garozzo D., Impallomeni G., Carbohydrate Polymers,2006, 65, 263—272
[21]	Wang H. J., Wang H. W., Shi S. S., Duan J. Y., Wang S. C., Glycoconjugate,2012, 29, 379—387
[22]	Vityazew F. V., Golovchenko V. V., Patova O. A., Drozd N. N., Makarov V. A., Shashkov A. S., Ovodov Y. S., Biochemistry,2010, 75(6), 759—768
[23]	Weiler J. M., Yurt R. W., Fearon D. T., Austen K. F., The Journal of Experimental Medicine,1978, 147(2), 409—421

禹州漏芦均一多糖的结构分析及其硫酸化衍生物的抗补体活性

Structural Characterization of One Homogeneous Polysaccharide from Echinops latifolius Tausch. and Anti-complementary Activity of Its Sulfated Derivatives^†

RichHTML

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

图/表 2

参考文献 23

相关文章 15

编辑推荐

Metrics

本文评价

[1]	包寒, 罗静, 时连鑫, 徐福建, 王树涛. 采用超疏水微柱阵列模板法制备多糖凝胶微米颗粒[J]. 高等学校化学学报, 2020, 41(7): 1484.
[2]	王婷婷, 李元, 杨莉莉, 鲍昌昊, 程寒. 碳纤维微电极负载金纳米粒子用于芦荟多糖的在体动态监测[J]. 高等学校化学学报, 2020, 41(1): 87.
[3]	金鑫, 嵇国利, 赵小亮, 李国云, 于广利. 一种刺松藻来源的硫酸阿拉伯聚糖的制备及特征结构表征[J]. 高等学校化学学报, 2019, 40(4): 733.
[4]	高云霄, 胡小龙, 王月荣, 姜志宏, 章弘扬, 张敏, 胡坪. 铁皮石斛多糖的初级结构分析[J]. 高等学校化学学报, 2018, 39(5): 934.
[5]	耿丽华, 金维华, 王晶, 张全斌. 海带褐藻多糖硫酸酯的降解与岩藻寡糖的制备[J]. 高等学校化学学报, 2017, 38(12): 2193.
[6]	沈艳红, 陈林枭, 张文清, 徐志珍, 宛燕飞, 张力, 夏玮. 甘露聚糖肽的结构鉴定[J]. 高等学校化学学报, 2016, 37(6): 1088.
[7]	支梓鉴, 邹明明, 李珊, 陈健乐, 叶兴乾, 陈士国. 柑橘果肉果胶的流变和结构特性[J]. 高等学校化学学报, 2016, 37(6): 1175.
[8]	刘洋, 殷璐, 龚桂萍, 彭艺芳, 黄琳娟, 王仲孚. 黑果枸杞叶多糖LRLP3的结构、抗氧化活性及免疫活性[J]. 高等学校化学学报, 2016, 37(2): 261.
[9]	刘磊, 李科, 郝霞, 王桂臻, 秦雪梅, 杜冠华, 张翔. 黄芪药渣中阿拉伯木聚糖(AX-Ⅰ-1)的提取纯化、结构分析及体外抗氧化作用[J]. 高等学校化学学报, 2016, 37(12): 2168.
[10]	冯纪璐, 齐军茹, 刘倩茹. 基于糖基化反应及自组装法制备大豆分离蛋白-可溶性大豆多糖核壳结构纳米凝胶[J]. 高等学校化学学报, 2016, 37(11): 1999.
[11]	管清香, 张广远, 孙丹丹, 孙士淋, 孙诚, 刘昕, 韩冰. 白芨多糖两亲性聚合物的合成及载药纳米体系[J]. 高等学校化学学报, 2016, 37(10): 1915.
[12]	殷军艺, 刘晓莹, 聂少平, 谢明勇. 脱除阿魏酸后车前子多糖的溶液性质、构象特征及固体形貌[J]. 高等学校化学学报, 2016, 37(1): 43.
[13]	王一寓, 刘嘉炜, 司马贞华, 宋厚盼, 李茹柳, 蔡佳仲, 陈蔚文. 白术多糖调节IEC-6细胞迁移活性成分的分离和表征[J]. 高等学校化学学报, 2015, 36(2): 299.
[14]	张霞, 周浩, 杨宇红, 黄郁芳, 陈新. 氧化纤维素增强胶原水凝胶[J]. 高等学校化学学报, 2015, 36(10): 2040.
[15]	李晓军, 蒋嘉烨, 施松善, 栗源, 江永波, 可燕, 王顺春. 关白附中1,6-葡聚糖及其硫酸酯的抗补体活性[J]. 高等学校化学学报, 2014, 35(7): 1423.

Sample	V(Pyridine)∶V(Chlorosulfonic acid)	Reaction temperature/℃	Reaction time/h
Sul-2A-1	1∶1	20	3
Sul-2A-2	1∶2	20	3

Sample	V(Pyridine)∶V(Chlorosulfonic acid)	Reaction temperature/℃	Reaction time/h
Sul-2A-1	1∶1	20	3
Sul-2A-2	1∶2	20	3

禹州漏芦均一多糖的结构分析及其硫酸化衍生物的抗补体活性

Structural Characterization of One Homogeneous Polysaccharide from Echinops latifolius Tausch. and Anti-complementary Activity of Its Sulfated Derivatives†

RichHTML

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

图/表 2

参考文献 23

相关文章 15

编辑推荐

Metrics

本文评价

Structural Characterization of One Homogeneous Polysaccharide from Echinops latifolius Tausch. and Anti-complementary Activity of Its Sulfated Derivatives^†