Structural characterization and antiviral effect of a novel polysaccharide PSP-2B from Prunellae Spica

Carbohydrate Polymers

Volumn 152, Issue , 2016, Pages 699-709

  Ma, Feng wei ^a   Kong, Si yuan ^b   Tan, Hong sheng ^b   Wu, Rong ^b   Xia, Bing ^a   Zhou, Yan ^a   Xu, Hong xi ^b  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Against herpes simplex virus activity; Prunellae Spica; Structural characterization; Sulphated polysaccharide

Indexed keywords

CHROMATOGRAPHY; VIRUSES;

ANTI-VIRAL EFFECTS; DIRECT ULTRAFILTRATION; GEL CHROMATOGRAPHY; HERPES SIMPLEX VIRUS; INHIBITORY CONCENTRATION; PRUNELLAE SPICA; STRUCTURAL CHARACTERIZATION; SULPHATED POLYSACCHARIDES;

CHARACTERIZATION;

ANTIVIRUS AGENT; POLYSACCHARIDE;

ANIMAL; CHEMISTRY; CHLOROCEBUS AETHIOPS; CONFORMATION; HERPES SIMPLEX; HUMAN; HUMAN ALPHAHERPESVIRUS 1; ISOLATION AND PURIFICATION; METABOLISM; PATHOLOGY; PRUNELLA; VERO CELL LINE;

ANIMALS; ANTIVIRAL AGENTS; CARBOHYDRATE CONFORMATION; CERCOPITHECUS AETHIOPS; HERPES SIMPLEX; HERPESVIRUS 1, HUMAN; HUMANS; POLYSACCHARIDES; PRUNELLA; VERO CELLS;

EID: 84978878314     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2016.07.062     Document Type: Article

References (76)

1. Andrews, P., The gel-filtration behaviour of proteins related to their molecular weights over a wide range. Biochemical Journal 96 (1965), 595–606.
2. Baba, M., Snoeck, R., Pauwels, R., de Clercq, E., Sulfated polysaccharides are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, and human immunodeficiency virus. Antimicrobial Agents and Chemotherapy 32:11 (1988), 1742–1745.
3. Berg, K., Hansen, M.B., Nielsen, S.E., A new sensitive bioassay for precise quantification of interferon activity as measured via the mitochondrial dehydrogenase function in cells (MTT-method). APMIS 98:1–6 (1990), 156–162.
4. Bitter, T., Muir, H.M., A modified uronic acid carbazole reaction. Analytical Biochemistry 4:4 (1962), 330–334.
5. Blumenkrantz, N., Asboe-Hansen, G., New method for quantitative determination of uronic acids. Analytical Biochemistry 54:2 (1973), 484–489.
6. Bradford, M.M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 72:1–2 (1976), 248–254.
7. Cheang, B., Zydney, A.L., A two-stage ultrafiltration process for fractionation of whey protein isolate. Journal of Membrane Science 231:1–2 (2004), 159–167.
8. Cheung, H.-Y., Zhang, Q.-F., Enhanced analysis of triterpenes, flavonoids and phenolic compounds in Prunella vulgaris L. by capillary zone electrophoresis with the addition of running buffer modifiers. Journal of Chromatography A 1213:2 (2008), 231–238.
9. Chiu, L.C.-M., Zhu, W., Ooi, V.E.-C., A polysaccharide fraction from medicinal herb Prunella vulgaris downregulates the expression of herpes simplex virus antigen in Vero cells. Journal of Ethnopharmacology 93:1 (2004), 63–68.
10. Choi, J.H., Han, E.H., Hwang, Y.P., Choi, J.M., Choi, C.Y., Chung, Y.C., et al. Suppression of PMA-induced tumor cell invasion and metastasis by aqueous extract isolated from Prunella vulgaris via the inhibition of NF-κB-dependent MMP-9 expression. Food and Chemical Toxicology 48:2 (2010), 564–571.
11. Committee, C.P., Pharmacopoeia of the People's Republic of China. 2010, Chinese Medical Science and Technology Press, Beijing.
12. Cong, Q., Shang, M., Dong, Q., Liao, W., Xiao, F., Ding, K., Structure and activities of a novel heteroxylan from Cassia obtusifolia seeds and its sulfated derivative. Carbohydrate Research 393 (2014), 43–50.
13. Cong, Q., Xiao, F., Liao, W., Dong, Q., Ding, K., Structure and biological activities of an alginate from Sargassum fusiforme, and its sulfated derivative. International Journal of Biological Macromolecules 69 (2014), 252–259.
14. Cui, T., Miao, M., Chemistry, pharmacology and clinical applications of selfheal. China Journal of Chinese Medicine 29:3 (2014), 386–388.
15. Cui, Z.F., Wright, K.I.T., Gas—liquid two-phase cross-flow ultrafiltration of BSA and dextran solutions. Journal of Membrane Science 90:1–2 (1994), 183–189.
16. Deng, Q., Zhou, X., Chen, H., Optimization of enzyme assisted extraction of Fructus Mori polysaccharides and its activities on antioxidant and alcohol dehydrogenase. Carbohydrate Polymers 111:0 (2014), 775–782.
17. Diller, I.C., Mankowski, Z.T., Fisher, M.E., The effect of yeast polysaccharides on mouse tumors. Cancer Res 23:2 Part 1 (1963), 201–208.
18. Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides. Biochemical Journal 84:1 (1962), 106–110.
19. Dore, C.M.P.G., Faustino Alves d, M.G.C., Pofírio Will, L.S.E., Costa, T.G., Sabry, D.A., de Souza Rêgo, L.A.R., et al. A sulfated polysaccharide, fucans, isolated from brown algae Sargassum vulgare with anticoagulant, antithrombotic, antioxidant and anti-inflammatory effects. Carbohydrate Polymers 91:1 (2013), 467–475.
20. Feng, L., Jia, X.-B., Shi, F., Chen, Y., Identification of two polysaccharides from Prunella vulgaris L. and evaluation on their anti-lung adenocarcinoma activity. Molecules 15:8 (2010), 5093–5103.
21. Fincher, G.B., Stone, B.A., Clarke, A.E., Arabinogalactan-proteins: Structure, biosynthesis, and function. Annual Review of Plant Physiology 34:1 (1983), 47–70.
22. Gan, D., Ma, L., Jiang, C., Xu, R., Zeng, X., Production, preliminary characterization and antitumor activity in vitro of polysaccharides from the mycelium of Pholiota dinghuensis Bi. Carbohydrate Polymers 84:3 (2011), 997–1003.
23. Gao, X., Dong, S., Prunrllae oral solution for cystic hyperplasia of breast in 100 cases. Shanghai Journal of Traditional Chinese Medicine 37:11 (2003), 27–28.
24. Gelotte, B., Studies on gel filtration: Sorption properties of the bed material Sephadex. Journal of Chromatography A 3 (1960), 330–342.
25. Han, E.H., Choi, J.H., Hwang, Y.P., Park, H.J., Choi, C.Y., Chung, Y.C., et al. Immunostimulatory activity of aqueous extract isolated from Prunella vulgaris. Food and Chemical Toxicology 47:1 (2009), 62–69.
26. Harmsen, M.C., Swart, P.J., de Béthune, M.-P., Pauwels, R., De Clercq, E., Meijer, D.K.F., Antiviral effects of plasma and milk proteins: Lactoferrin shows potent activity against both human immunodeficiency virus and human cytomegalovirus replication in vitro. Journal of Infectious Diseases 172:2 (1995), 380–388.
27. Hasenclever, H.F., Mitchell, W.O., Immunochemical studies on polysaccharides of yeasts. The Journal of Immunology 93:5 (1964), 763–771.
28. Honda, S., Akao, E., Suzuki, S., Okuda, M., Kakehi, K., Nakamura, J., High-performance liquid chromatography of reducing carbohydrates as strongly ultraviolet-absorbing and electrochemically sensitive 1-phenyl-3-methyl5-pyrazolone derivatives. Analytical Biochemistry 180:2 (1989), 351–357.
29. Hong, J.H., Choi, Y.H., Physico-chemical properties of protein-bound polysaccharide from Agaricus blazei Murill prepared by ultrafiltration and spray drying process. International Journal of Food Science & Technology 42:1 (2007), 1–8.
30. Inoue, Y., Nagasawa, K., Selective N-desulfation of heparin with dimethyl sulfoxide containing water or methanol. Carbohydrate Research 46:1 (1976), 87–95.
31. Iyer, A.S., Ohtola, J.A., Westerink, M.A.J., Age-related immune response to pneumococcal polysaccharide vaccination: Lessons for the clinic. Expert Review of Vaccines 0 (2015), 1–13.
32. Jong, S.C., Birmingham, J.M., Medicinal and therapeutic value of the shiitake mushroom. Advances in Applied Microbiology, 39, 1993 153–153.
33. Kojima, H., Ogura, H., Triterpenoids from Prunella vulgaris. Phytochemistry 25:3 (1986), 729–733.
34. Kojima, H., Sato, N., Hatano, A., Ogura, H., Sterol glucosides from Prunella vulgaris. Phytochemistry 29:7 (1990), 2351–2355.
35. Lee, J.-B., Koizumi, S., Hayashi, K., Hayashi, T., Structure of rhamnan sulfate from the green alga Monostroma nitidum and its anti-herpetic effect. Carbohydrate Polymers 81:3 (2010), 572–577.
36. Li, H., Mao, W., Zhang, X., Qi, X., Chen, Y., Chen, Y., et al. Structural characterization of an anticoagulant-active sulfated polysaccharide isolated from green alga Monostroma latissimum. Carbohydrate Polymers 85:2 (2011), 394–400.
37. Li, C., Huang, Q., Fu, X., Yue, X.-J., Liu, R.H., You, L.-J., Characterization: Antioxidant and immunomodulatory activities of polysaccharides from Prunella vulgaris Linn. International Journal of Biological Macromolecules 75 (2015), 298–305.
38. Liu, P., The organs structure feature and the accumulation laws of the main medcinal component study on the Prunella vulgaris Lnn (Vol. Master). 2010, Northwest Agriculture and Forestry University.
39. Luong, J.H.T., Male, K.B., Nguyen, A.L., A continuous affinity ultrafiltration process for trypsin purification. Biotechnology and Bioengineering 31:6 (1988), 516–520.
40. Lyu, S.-Y., Rhim, J.-Y., Park, W.-B., Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2)in vitro. Archives of Pharmacal Research 28:11 (2005), 1293–1301.
41. Ma, S.-C., Du, J., But, P.P.-H., Deng, X.-L., Zhang, Y.-W., Ooi, V.E.-C., et al. Antiviral Chinese medicinal herbs against respiratory syncytial virus. Journal of Ethnopharmacology 79:2 (2002), 205–211.
42. Maes, C., Delcour, J.A., Structural characterisation of water-extractable and water-unextractable arabinoxylans in wheat bran. Journal of Cereal Science 35:3 (2002), 315–326.
43. McCandless, E.L., Craigie, J.S., Sulfated polysaccharides in red and brown algae. Annual Review of Plant Physiology 30:1 (1979), 41–53.
44. Mould, D.L., Synge, R.L.M., Electrokinetic ultrafiltration analysis of polysaccharides. A new approach to the chromatography of large molecules. Analyst 77:921 (1952), 964–969.
45. Nagasawa, K., Inoue, Y., Kamata, T., Solvolytic desulfation of glycosaminoglycuronan sulfates with dimethyl sulfoxide containing water or methanol. Carbohydrate Research 58:1 (1977), 47–55.
46. Nagasawa, K., Inoue, Y., Tokuyasu, T., An improved method for the preparation of chondroitin by solvolytic desulfation of chondroitin sulfates. Journal of Biochemistry 86:5 (1979), 1323–1329.
47. Pauwels, R., Balzarini, J., Baba, M., Snoeck, R., Schols, D., Herdewijn, P., et al. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. Journal of Virological Methods 20:4 (1988), 309–321.
48. Prabasari, I., Pettolino, F., Liao, M.-L., Bacic, A., Pectic polysaccharides from mature orange (Citrus sinensis) fruit albedo cell walls: Sequential extraction and chemical characterization. Carbohydrate Polymers 84:1 (2011), 484–494.
49. Prajapati, V.D., Maheriya, P.M., Jani, G.K., Solanki, H.K., Carrageenan: A natural seaweed polysaccharide and its applications. Carbohydrate Polymers 105:0 (2014), 97–112.
50. Robinson, T., McMullan, G., Marchant, R., Nigam, P., Remediation of dyes in textile effluent: A critical review on current treatment technologies with a proposed alternative. Bioresource Technology 77:3 (2001), 247–255.
51. Ryu, S.Y., Oak, M.H., Yoon, S.K., Cho, D.I., Yoo, G.S., Kim, T.S., et al. Anti-allergic and anti-inflammatory triterpenes from the herb of Prunella vulgaris. Planta Medica 66:4 (2000), 358–360.
52. Şahin, S., Demir, C., Malyer, H., Determination of phenolic compounds in Prunella L. by liquid chromatography-diode array detection. Journal of Pharmaceutical and Biomedical Analysis 55:5 (2011), 1227–1230.
53. Seki, Y., Mizukura, M., Ichimiya, T., Suda, Y., Nishihara, S., Masuda, M., et al. O-sulfate groups of heparin are critical for inhibition of ecotropic murine leukemia virus infection by heparin. Virology 424:1 (2012), 56–66.
54. Slokar, Y.M., Le Marechal, A.M., Methods of decoloration of textile wastewaters. Dyes and Pigments 37:4 (1998), 335–356.
55. Susanto, H., Arafat, H., Janssen, E.M.L., Ulbricht, M., Ultrafiltration of polysaccharide–protein mixtures: Elucidation of fouling mechanisms and fouling control by membrane surface modification. Separation and Purification Technology 63:3 (2008), 558–565.
56. Tabba, H.D., Chang, R.S., Smith, K.M., Isolation, purification, and partial characterization of prunellin, an anti-HIV component from aqueous extracts of Prunella vulgaris. Antiviral Research 11:5–6 (1989), 263–273.
57. Tang, L., Ling, A., Koh, R., Chye, S., Voon, K., Screening of anti-dengue activity in methanolic extracts of medicinal plants. BMC Complementary and Alternative Medicine, 12(1), 2012, 3.
58. Toba, T., Uemura, H., Itoh, T., A new method for the quantitative determination of microbial extracellular polysaccharide production using a disposable ultrafilter membrane unit. Letters in Applied Microbiology 14:2 (1992), 30–32.
59. Tsiountsioura, M., Wong, J.E., Upton, J., McIntyre, K., Dimakou, D., Buchanan, E., et al. Detailed assessment of nutritional status and eating patterns in children with gastrointestinal diseases attending an outpatients clinic and contemporary healthy controls. European Journal of Clinical Nutrition 68:6 (2014), 700–706.
60. Turgeon, S.L., Gauthier, S.F., Whey peptide fractions obtained with a two‐step ultrafiltration process: Production and characterization. Journal of Food Science 55:1 (1990), 106–110.
61. Wang, J., Zhang, Q., Zhang, Z., Li, Z., Antioxidant activity of sulfated polysaccharide fractions extracted from Laminaria japonica. International Journal of Biological Macromolecules 42:2 (2008), 127–132.
62. Wang, Y., Yang, Z., Wei, X., Antioxidant activities potential of tea polysaccharide fractions obtained by ultra filtration. International Journal of Biological Macromolecules 50:3 (2012), 558–564.
63. Wang, Y., Fang, J., Ni, X., Li, J., Liu, Q., Dong, Q., et al. Inducement of cytokine release by GFPBW2, a novel polysaccharide from fruit bodies of Grifola frondosa, through dectin-1 in macrophages. Journal of Agricultural and Food Chemistry 61:47 (2013), 11400–11409.
64. Wang, P., Liao, W., Fang, J., Liu, Q., Yao, J., Hu, M., et al. A glucan isolated from flowers of Lonicera japonica Thunb: Inhibits aggregation and neurotoxicity of Aβ 42. Carbohydrate Polymers 110 (2014), 142–147.
65. Wasser, S., Medicinal mushrooms as a source of antitumor and immunomodulating polysaccharides. Applied Microbiology and Biotechnology 60:3 (2002), 258–274.
66. Wijesinghe, W., Jeon, Y.-J., Biological activities and potential industrial applications of fucose rich sulfated polysaccharides and fucoidans isolated from brown seaweeds: A review. Carbohydrate Polymers 88:1 (2012), 13–20.
67. Wijesinghe, W.A.J.P., Jeon, Y.-J., Biological activities and potential industrial applications of fucose rich sulfated polysaccharides and fucoidans isolated from brown seaweeds: A review. Carbohydrate Polymers 88:1 (2012), 13–20.
68. Xie, J.-H., Shen, M.-Y., Nie, S.-P., Zhao, Q., Li, C., Xie, M.-Y., Separation of water-soluble polysaccharides from Cyclocarya paliurus by ultrafiltration process. Carbohydrate Polymers 101 (2014), 479–483.
69. Xu, H.-X., Lee, S.H.S., Lee, S.F., White, R.L., Blay, J., Isolation and characterization of an anti-HSV polysaccharide from Prunella vulgaris. Antiviral Research 44:1 (1999), 43–54.
70. Yang, L., Zhang, L.-M., Chemical structural and chain conformational characterization of some bioactive polysaccharides isolated from natural sources. Carbohydrate Polymers 76:3 (2009), 349–361.
71. Yang, K., Guo, K., Wu, H., Ye, L., Xia, H., Clinical effect of prunrllae oral solution in treating hyperthyrea. China Journal of Chinese Materia Medica 32:16 (2007), 1706–1708.
72. Yao, X.-J., Wainberg, M.A., Parniak, M.A., Mechanism of inhibition of HIV-1 infection in vitro by purified extract of Prunella vulgaris. Virology 187:1 (1992), 56–62.
73. Ye, H., Wang, K., Zhou, C., Liu, J., Zeng, X., Purification, antitumor and antioxidant activities in vitro of polysaccharides from the brown seaweed Sargassum pallidum. Food Chemistry 111:2 (2008), 428–432.
74. Ye, Y., Study on the extration and isolation of flavonids from Prunella vulgaris (Vol. Master). 2010, Fujian Agriculture and Forestry University.
75. Yin, J.-Y., Chan, B.C.-L., Yu, H., Lau, I.Y.-K., Han, X.-Q., Cheng, S.-W., et al. Separation, structure characterization, conformation and immunomodulating effect of a hyperbranched heteroglycan from Radix Astragali. Carbohydrate Polymers 87:1 (2012), 667–675.
76. Zhang, Y., But, P.P.-H., Ooi, V.E.-C., Xu, H.-X., Delaney, G.D., Lee, S.H.S., et al. Chemical properties, mode of action, and in vivo anti-herpes activities of a lignin-carbohydrate complex from Prunella vulgaris. Antiviral Research 75:3 (2007), 242–249.