Structural Characterization of Mannatide†

doi:10.7503/cjcu20160138

Abstract

Abstract:

DEAE-52 cellulose column and Sephacryl S-300 gel column were used to isolate and purify mannatide to give four homogeneous glycopeptides termed as MT1-A, MT1-B, MT2-A and MT2-B. The chemical structure of MT1-A, MT1-B and MT2-B were elucidated using monosaccharide composition analysis, methylation analysis, ¹H-nuclear magnetic resonance(¹H NMR) spectroscopy, infrared(IR) spectroscopy and amino acids analysis. It was concluded that the monosaccharide composition and connection type of sugar residues of MT1-A, MT1-B and MT2-A were the same as MT2-A reported before while the molecular weight and amino acid content of four homogeneous glycopeptides were slightly different. The ¹H NMR spectrum of MT2-A was regarded as the standard reference spectrum and the anomeric region of each spectrum(δ 4.89—5.90) was selected as the identification region. The ¹H NMR spectra of MT1-A, MT1-B, MT2-A and different batches of mannatide were compared with the standard reference spectrum, using the correlation coefficient to quantitatively calculate the similarity. The results showed that mannatide was a mixture of several kinds of homoge-neous glycopeptides with the same glycan structure but different molecular weight and amino acid content.

Key words: Mannatide, Polysaccharide, Structure

CLC Number:

O629.12

TrendMD:

SHEN Yanhong, CHEN Linxiao, ZHANG Wenqing, XU Zhizhen, WAN Yanfei, ZHANG Li, XIA Wei. Structural Characterization of Mannatide^†[J]. Chem. J. Chinese Universities, 2016, 37(6): 1088.

Figures/Tables 2

References 20

[1]	Hu Q. L.,Wang Y. S., Chinese Journal of Antibiotics, 1991, 16(2), 151—156
	(胡其乐, 王浴生.中国抗生素杂志, 1991, 16(2), 151—156)
[2]	Zhang Z. H., Xie W., Ji R., Guo Y. F., Sheng Y. C., Mei Q. B., Chinese Journal of Hospital Pharmacy, 2012, 32(1), 35—40
	(张朕华, 谢炜, 吉蕊, 郭月芳, 盛雨辰, 梅其炳. 中国医院药学杂志, 2012, 32(1), 35—40)
[3]	Wang Y. S., Wang X. Y., China Pharmacist, 2014, 7(4), 302—305
	(王允生, 王晓燕. 中国药师, 2014, 7(4), 302—305)
[4]	Liu Z. S., Wang T. J., Wu G. M., Han C. M., Chinese Journal of Gerontology, 2011, 31(22), 4356—4357
	(刘忠山, 王铁君, 吴国民, 韩成敏. 中国老年学杂志, 2011, 31(22), 4356—4357)
[5]	Liu Y., Huang J., Lu Y. H., Shu Y., Bian C. Y., Fang J. R., Hu T., Medical Recapitulate, 2012, 18(18), 3071—3074
	(刘艳, 黄晶, 路永红, 树瑜, 卞彩云, 方建蓉, 胡涛. 医学综述, 2012, 18(18), 3071—3074)
[6]	Huang J., Lu Y., Chinese Journal of Medicinal Guide, 2015, 17(2), 156—158
	(黄瑾, 芦源. 中国医药导刊, 2015, 17(2), 156—158)
[7]	Su Q. L., Liu F., Wang D. N., Yuan B., Luo F. M., Chinese Journal of Evidence-Based Medicine, 2014, 14(6), 759—764
	(苏巧俐, 刘峰, 王多宁, 袁波, 罗凤鸣. 中国循证医学杂志, 2014, 14(6), 759—764)
[8]	Wang W., Shen Y., Wu J., Chinese Journal of Medicinal Guide, 2014, 16(11), 1414—1415
	(王伟, 沈勇, 武洁. 中国医药导刊, 2014, 16(11), 1414—1415)
[9]	Song G., Gan X., Chemistry & Bioengineering, 2007, 24(4), 14—16
	(宋刚, 干信. 化学与生物工程, 2007, 24(4), 14—16)
[10]	Wang H. Y., Journal of Modern Medicine & Health, 2010, 26(21), 3284—3286
	(王红雁. 现代医药卫生, 2010, 26(21), 3284—3286)
[11]	Zhang X. G., Shi J. G., Yan Q. G., Hu H. Y., Li Y. F., Zhang R., Modern Oncology, 2006, 14(13), 264—266
	(张希国, 师建国, 阎庆国, 胡海洋, 李焱峰, 张蕊. 现代肿瘤医学, 2006, 14(13), 264—266)
[12]	Chen D. Y., Tan D. Y., Chinese Journal of Medicinal Guide, 2014, 16(5), 856—857
	(陈德意, 谭定勇. 中国医药导刊, 2014, 16(5), 856—857)
[13]	Zou J. Y., Xu Y. Z., Chinese Journal of Antibiotics, 1991, 16(6), 419—426
	(邹敬源, 徐寅正. 中国抗生素杂志, 1991, 16(6), 419—426)
[14]	Li S., Pan C., Xia W., Zhang W. Q., Wu S. Y., International Journal of Biological Macromolecules, 2014, 67, 351—359
[15]	Wang Y., Gao Q. P., Li G. R., Chen Y. H., Luo H. M., Gao Y., Jiang R. Z., Chem. Res. Chinese Universities, 2011, 27(1), 104—107
[16]	Zhang N., Liu Y., Lu J. H., Wang J., Yang S., Zhang N., Meng Q. F., Teng L.R., Chem. Res. Chinese Universities, 2012, 28(2), 249—254
[17]	Zhang X. H., Liu L. N., Lin C. W., International Journal of Biological Macromolecules, 2013, 59, 184—191
[18]	Liu Y., Li Y. F., Zheng K. Y., Fei X. F., Chem. Res. Chinese Universities, 2012, 28(3), 449—453
[19]	Liu Y., Yin L., Gong G. P., Peng Y. F., Huang L. J., Wang Z. F., Chem. J. Chinese Universities, 2016, 37(2), 261—268
	(刘洋, 殷璐, 龚桂萍, 彭艺芳, 黄琳娟, 王仲孚. 高等学校化学学报, 2016, 37(2), 261—268)
[20]	Wang J. H., Zha X. Q., Pan L. H., Luo J. P., Chem. J. Chinese Universities, 2013, 34(4), 881—885
	(王军辉, 查学强, 潘利华, 罗建平. 高等学校化学学报, 2013, 34(4), 881—885)

Amino acid	Amino acids content/(g·100 g^-1)
Amino acid	MT1-A	MT1-B	MT2-A	MT2-B
Asparaginic acid	0.393	0.482	0.449	0.745
Threonine	0.655	0.780	0.870	1.480
Serine	0.672	1.392	0.700	1.921
Glutamic acid	0.350	0.529	0.389	0.972
Glycine	0.138	0.188	0.152	0.273
Alanine	0.477	1.036	0.470	1.254
Valine	0.219	0.287	0.258	0.534
Methionine	0.023	0.023	0.010	0.027
Isoleucine	0.087	0.130	0.112	0.207
Leucine	0.102	0.157	0.125	0.202
Tyrosine	0.078	0.097	0.102	0.165
Phenylalanine	0.067	0.090	0.0798	0.117
Histidine	0.037	0.056	0.037	0.055
Lysine	0.194	0.372	0.175	0.359
Arginine	0.047	0.087	0.036	0.066
Proline	0.340	0.444	0.447	0.734
Total content of amino acids	3.88	6.15	4.41	9.11

Amino acid	Amino acids content/(g·100 g^-1)
Amino acid	MT1-A	MT1-B	MT2-A	MT2-B
Asparaginic acid	0.393	0.482	0.449	0.745
Threonine	0.655	0.780	0.870	1.480
Serine	0.672	1.392	0.700	1.921
Glutamic acid	0.350	0.529	0.389	0.972
Glycine	0.138	0.188	0.152	0.273
Alanine	0.477	1.036	0.470	1.254
Valine	0.219	0.287	0.258	0.534
Methionine	0.023	0.023	0.010	0.027
Isoleucine	0.087	0.130	0.112	0.207
Leucine	0.102	0.157	0.125	0.202
Tyrosine	0.078	0.097	0.102	0.165
Phenylalanine	0.067	0.090	0.0798	0.117
Histidine	0.037	0.056	0.037	0.055
Lysine	0.194	0.372	0.175	0.359
Arginine	0.047	0.087	0.036	0.066
Proline	0.340	0.444	0.447	0.734
Total content of amino acids	3.88	6.15	4.41	9.11

Sample	Correlation efficient	Sample	Correlation efficient
Mannatide(G100102)	0.9937	Mannatide(140502)	0.9951
Mannatide(091202)	0.9942	MT1-A	0.9955
Mannatide(140401)	0.9761	MT1-B	0.9959
Mannatide(140501)	0.9783	MT2-B	0.9945

Sample	Correlation efficient	Sample	Correlation efficient
Mannatide(G100102)	0.9937	Mannatide(140502)	0.9951
Mannatide(091202)	0.9942	MT1-A	0.9955
Mannatide(140401)	0.9761	MT1-B	0.9959
Mannatide(140501)	0.9783	MT2-B	0.9945