Preparation and Isolation of Bioactive Sulfated Derivatives from Water-insoluble Glucan in Ganoderma arum

doi:10.7506/spkx1002-6630-201323027

Abstract

Abstract:

Objective: To improve the water solubility of a water-insoluble glucan from Ganoderma atrum by sulfated
modification technique and to investigate the in vitro antitumor activity and properties of sulfated derivatives. Methods: The
water-insoluble glucan was modified using chlorosulfonic acid-pyridine (CSA-Pyr) method to obtain sulfated products with
different degrees of sulfation (DS). The sulfated polysaccharides were characterized by gel filtration chromatography and
FT-IR spectroscopy. The cytotoxicity on S-180 sarcoma cells was measured to screen a fraction with significant antitumor
activity. The separated fraction with high antitumor activity was purified and its solution was subjected to molecular
characterization. Results: Nine sulfated products with different DS were prepared. AGAPS5 (DS 1.14) had significant
antitumor activity. The sugar content of AGAPS5 was 66.3%, and the inhibitory rate of AGAPS5 on the growth of S-180
sarcoma cells was 67.74%. The purified AGAPS5-1 showed a random coil chain in 0.1 mol/L NaNO3 solution. The weight-average
molecular weight (Mw) of AGAPS5-1 was 5.19 × 104 u and the number-average molecular weight (Mn) was 2.63 × 104 u. Conclusion:
Sulfated modification can improve the water-solubility and solution properties, and enhance the in vitro antitumor activity of
glucan from Ganoderma atrum.

Key words: Ganoderma atrum, glucan, sulfated modification, antitumor, isolation

CLC Number:

Q949.32

ZHANG Hui，WANG Jun-qiao，NIE Shao-ping，ZHANG Shen-shen，WANG Yuan-xing，XIE Ming-yong*. Preparation and Isolation of Bioactive Sulfated Derivatives from Water-insoluble Glucan in Ganoderma arum[J]. FOOD SCIENCE, 2013, 34(23): 128-132.

References

[1]SULLIVAN R, SMITH J E, ROWAN N J.Medicinal Mushrooms and Cancer Therapy: Translating a Traditional Practice into Western Medicine[J].Perspectives in Biology and Medicine, 2006, 49(2):159-170

[2]LI Wenjuan, CHEN Yi, NIE Shaoping, et al.Ganoderma atrum Polysaccharide Induces Anti-tumor Activity Via the Mitochondrial Apoptotic PathwayRelated to Activation of Host Immune Response[J].Journal of Cellular Biochemistry, 2011, 112(3):860-871

[3]ZHANG Shenshen, NIE Shaoping, HUANG Danfei, et al.Immunomodulatory Effect of Ganoderma atrum Polysaccharide on CT26 Tumor-bearing Mice[J].Food Chemistry, 2012, 136(3-4):1213-1219

[4]CHEN Yi, XIE Mingyong, NIE Shaoping, et al.Purification,Composition Analysis and Antioxidant Activity of a Polysaccharide from the Fruiting Bodies of Ganoderma atrum[J].Food Chemistry, 2008, 107(1):231-241

[5]张汇, 鄢嫣, 聂少平等.黑灵芝不同部位多糖成分分析及抗氧化活性[J].食品科学, 2011, 32(1):56-61

[6]ZHANG Mei, CUI S W, CHEUNG P C K, et al.Antitumor Polysaccharides from Mushrooms: a Review on Their Isolation Process,Structural Characteristics and Antitumor Activity[J].Trends in Food Science & Technology, 2007, 18(1):4-19

[7] 李盛, 许淑琴, 张俐娜.菌类多糖链构象及其表征方法研究进展[J][J].高分子学报, 2010, (12):1359-1375

[8]BAO Xingfeng, DUAN Jinyou, FANG Xuya, et al.Chemical Modifications of the (1→3)-α-d-Glucan from Spores of Ganoderma lucidum and Investigation of Their Physicochemical Properties and Immunological Activity[J].Carbohydrate research, 2001, 336(2):127-140

[9]ZHANG Pingyi, ZHANG Lina, CHENG Shuyao.Chemical Structure and Molecular Weights of α-(1→3)-D-Glucan from Lentinus Edodes[J].Bioscience, Biotechnology, and Biochemistry, 1999, 63(7):1197-1202

[10]ZHANG Pingyi, Cheung P C K.Evaluation of Sulfated Lentinus Edodesα-(1→3)-D-Glucan as a Potential Antitumor Agent[J].Bioscience, Biotechnology, and Biochemistry, 2002, 66(5):1052-1056

[11]WANG Li, LI Xiaoxuan, CHEN Zhengxing.Sulfated Modification of the Polysaccharides Obtained from Defatted Rice Bran and Their Antitumor Activities[J].International Journal of Biological Macromolecules, 2009, 44(2):211-214

[12]方积年.硫酸酯化多糖的研究进展[J].中国药学杂志, 1993, 28(7):393-395

[13]LU Yu, WANG Deyun, HU Yuanliang, et al.Sulfated Modification of Epimedium Polysaccharide and Effects of the Modifiers on Cellular Infectivity of IBDV[J].Carbohydrate Polymers, 2008, 71(2):180-186

[14]WANG Junlong, GUO Hongyun, ZHANG Ji, et al.Sulfated Modification,Characterization and Structure–antioxidant Relationships of Artemisia sphaerocephala Polysaccharides[J].Carbohydrate Polymers, 2010, 81(4):897-905

[15]王顺春, 方积年.香菇多糖硫酸化衍生物的制备及其结构分析[J].生物化学与生物物理学报: 英文版, 1999, 31(5):594-597

[16]黄小燕, 孔祥峰, 王德云等.多糖硫酸化修饰和多糖硫酸酯的研究进展[J].天然产物研究与开发, 2007, 19(2):328-332

[17] 陶咏真, 张俐娜, 韩露等.水溶性高支化多糖及硫酸酯衍生物抗癌活性研究[J][J].高分子学报, 2009, (9):582-859

[18]史宝军, 聂小华, 许泓渝等.灰树花多糖硫酸酯的制备及其抗肿瘤活性[J].中国医药工业杂志, 2003, 34(8):383-385

[19]Gaborieau M, Castignolles P.Size-exclusion Chromatography (SEC) of Branched Polymers and Polysaccharides[J].Analytical and Bioanalytical Chemistry, 2011, 399(4):1413-1423

[20]张丽萍, 张翼伸.硫酸化对金顶侧耳多糖构象及生物活性的影响[J].生物化学与生物物理学报: 英文版, 1994, 26(4):417-421