硫酸化杏鲍菇多糖的理化特性及体外生物活性研究
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摘要
本文采用氯磺酸-吡啶法修饰杏鲍菇多糖(Pleurotus eryngii polysaccharide,PEP),根据加入氯磺酸与吡啶的体积比(1:2,1:5和1:8)不同得到三种硫酸化杏鲍菇多糖(sulfatedPleurotuseryngiipolysaccharide,SPEP),分别记为SPEP-601:2,SPEP-601:5和SPEP-601:8,并通过化学分析法、气相色谱、凝胶渗透色谱对PEP修饰前后的理化性质进行了比较研究,同时对PEP和SPEP的抗氧化性(DPPH·清除能力、O_2~-·清除力)以及对碳水化合物消化与吸收的关键酶(α-淀粉酶和α-葡萄糖苷酶)抑制作用进行了研究。结果表明,SPEP-601:2,SPEP-601:5与SPEP-601:8的取代度依次为0.26±0.00、0.21±0.00与0.19±0.00;三种SPEP均比PEP的总糖、糖醛酸含量少、分子量低,单糖组成的种类相同但单糖的摩尔比不同;在所有的SPEP中,SPEP-601:8对DPPH·清除能力最佳;SPEP-601:2对O_2~-·清除力最强。SPEP对α-淀粉酶和α-葡萄糖苷酶活性抑制活性均有明显增强,对两种酶的抑制活性分别至少提高了834.33%和97.66%。除DPPH·清除能力外,在相同剂量下,SPEP比PEP表现出更强的生物活性,表明硫酸化修饰是提高多糖抗氧化及对α-淀粉酶和α-葡萄糖苷酶的抑制作用的有效途径。
In this work, Pleurotuseryngii polysaccharide(PEP) was chemically modified by chlorosulfonic acid-pyridine method, and three kinds of sulfated Pleurotuseryngiipolysaccharides(SPEP) were obtained. According to the volume ratio of chlorosulfonic acid to pyridine(1:2, 1:5 and 1:8), the three kinds of SPEP were recorded as SPEP-601:2, SPEP-601:5 and SPEP-601:8, respectively. The physicochemical properties of PEP and SPEP were detected by chemical methods, gas chromatography and gel permeation chromatography. In addition, the antioxidant activities(DPPH· scavenging ability and O_2~-· scavenging power) and the inhibitory effect on key enzymes(α-amylase andα-glucosidase) for carbohydrate digestion and absorption of PEP and SPEP were also determined. The results showed that the degree of substitution of SPEP-601:2, SPEP-601:5 and SPEP-601:8 were 0.26±0.00, 0.21±0.00 and 0.19±0.00, respectively. All the SPEP had less total sugar,uronic acid and lower molecular weight than the PEP. They had the same monosaccharide composition with different molar ratio. Moreover,SPEP-601:8 possessed the best scavenging capacity for DPPH compared with other SPEP. SPEP-601:2 showed the strongest scavenging effect on O_2~-·. All the SPEP had higher α-amylase and α-glucosidase inhibitory activity than the PEP, increasing at least by 834.33% and 97.66%,respectively. In addition to DPPH radical scavenging capacity, SPEP exhibited stronger biological activity than PEP at the same dose. These results suggested that sulfation modification might be an effective way to enhance antioxidant and hypoglycemic activities of the polysaccharide.
In this work, Pleurotuseryngii polysaccharide(PEP) was chemically modified by chlorosulfonic acid-pyridine method, and three kinds of sulfated Pleurotuseryngiipolysaccharides(SPEP) were obtained. According to the volume ratio of chlorosulfonic acid to pyridine(1:2, 1:5 and 1:8), the three kinds of SPEP were recorded as SPEP-601:2, SPEP-601:5 and SPEP-601:8, respectively. The physicochemical properties of PEP and SPEP were detected by chemical methods, gas chromatography and gel permeation chromatography. In addition, the antioxidant activities(DPPH· scavenging ability and O_2~-· scavenging power) and the inhibitory effect on key enzymes(α-amylase andα-glucosidase) for carbohydrate digestion and absorption of PEP and SPEP were also determined. The results showed that the degree of substitution of SPEP-601:2, SPEP-601:5 and SPEP-601:8 were 0.26±0.00, 0.21±0.00 and 0.19±0.00, respectively. All the SPEP had less total sugar,uronic acid and lower molecular weight than the PEP. They had the same monosaccharide composition with different molar ratio. Moreover,SPEP-601:8 possessed the best scavenging capacity for DPPH compared with other SPEP. SPEP-601:2 showed the strongest scavenging effect on O_2~-·. All the SPEP had higher α-amylase and α-glucosidase inhibitory activity than the PEP, increasing at least by 834.33% and 97.66%,respectively. In addition to DPPH radical scavenging capacity, SPEP exhibited stronger biological activity than PEP at the same dose. These results suggested that sulfation modification might be an effective way to enhance antioxidant and hypoglycemic activities of the polysaccharide.
引文
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[30]张海平,郑明明,黄凤洪,等.多糖酯的制备与活性研究进展[J].中国油脂,2017,42(11):116-120ZHANG Hai-ping,ZHENG Ming-ming,HUANGFeng-hong,et al.Advance in preparation and bioactivity of polysaccharose ester[J].China Oils and Fats,2017,42(11):116-120
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[2]申进文,王瑞瑞,许春平.秀珍菇多糖的硫酸化及其生物活性研究[J].河南农业科学,2014,43(7):102-106SHEN Jin-wen,WANG Rui-rui,XU Chun-pin.Study on preparation and bioactivity of sulfated saccharides of Pleurotus geesteranus[J].Journal of Henan Agricultural Sciences,2014,43(7):102-106
[3]Asker M S,Shawky B T.Structural characterization and antioxidant activity of an extracellular polysaccharide isolated from Brevibacterium otitidis BTS 44[J].Food Chemistry,2010,123(2):315-320
[4]WANG Z,XIE J,SHEN M,et al.Sulfated modification of polysaccharides:Synthesis,characterization and bioactivities[J].Trends in Food Science and Technology,2018,74:147-157
[5]孟思彤,徐艳芝,王振月.多糖的化学修饰对其生物活性影响研究进展[J].天然产物研究与开发,2014,11:1901-1905MENG Si-tong,XU Yan-zhi,WANG Zhen-yue.Research progress on chemical modification of polysaccharide and their biological activities[J].Natural Product Research and Development,2014,11:1901-1905
[6]XIE J,WANG Z,SHEN M,et al.Sulfated modification,characterization and antioxidant activities of polysaccharide from Cyclocaryapaliurus[J].Food Hydrocolloids,2016,53(53):7-15
[7]CHEN Y,ZHANG H,WANG Y,et al.Sulfated modification of the polysaccharides from Ganoderma atrum and their antioxidant and immunomodulating activities[J].Food Chemistry,2015,186:231-238
[8]王凯,王中红,李芳萍,等.孔石莼多糖及其硫酸酯化衍生物降血脂机制的体外研究[J].中国海洋药物,2018,37(2):81-87WANG Kai,WANG Zhong-hong,LI Fang-ping,et al.The mechanism of Ulva pertusa and its derivative on decreasing blood-lipid in vitro[J].Chinese Journal of Marine Drugs,2018,37(2):81-87
[9]HOANG M H,KIM J Y,LEE J H,et al.Antioxidative,hypolipidemic,and anti-inflammatory activities of sulfated polysaccharides from Monostroma nitidum[J].Food Science and Biotechnology,2015,24(1):199-205
[10]Roman Y,Iacomini M,Sassaki G L,et al.Optimization of chemical sulfation,structural characterization and anticoagulant activity of Agaricus bisporus fucogalactan[J].Carbohydrate Polymers,2016,146:345-352
[11]罗懿洋,任道远,陈丽芳,等.杏鲍菇多糖的单糖组成分析及其抗氧化活性研究[J].食品工业科技,2015,36(8):158-161LUO Yi-yang,REN Dao-yuan,CHEN Li-fang,et al.Study on analysis and antioxidant activity in vitro of the monosaccharide composition of Pleurotus eryngii[J].Science and Technology of Food Industry,2015,36(8):158-161
[12]ZHANG C,LI J,WANG J,et al.Antihyperlipidaemic and hepatoprotective activities of acidic and enzymatic hydrolysis exopolysaccharides from Pleurotus eryngii SI-04[J].Bmc Complementary&Alternative Medicine,2017,17(1):403
[13]Alfred Mugambi Mariga,Wen-Jian Yang,Dorothy Kemuma Mugambi,et al.Antiproliferative and immunostimulatory activity of a protein from Pleurotus eryngii[J].Journal of the Science of Food and Agriculture.2014,94(15):3152-3162
[14]蒋俊,罗珍,刘艳芳,等.醇沉条件对猴头菌多糖得率和品质的影响[J].食用菌学报,2011,18(2):57-61JIANG Jun,LUO Zhen,LIU Yan-fang,et al.Effect of precipitation conditions on the yield and quality of Hericium erinaceus polysaccharides[J].Acta Edulis Fungi,2011,18(2):57-61
[15]杨军国,陈键,王丽丽,等.醇沉分级粗茶多糖的抗氧化活性比较及变化机制[J].食品工业科技,2016,37(17):96-100YANG Jun-guo,CHEN Jian,WANG Li-li,et al.Comparison of the antioxidant activity of tea polysaccharide samples by precipitation fractionation with ethanol and the related mechanism analysis[J].Science and Technology of Food Industry,2016,37(17):96-100
[16]LI J E,WANG W J,ZHENG G D,et al.Physicochemical properties and antioxidant activities of polysaccharides from Gynura procumbens leaves by fractional precipitation[J].International Journal of Biological Macromolecules,2017,95:719-724
[17]GUO X,MENG H,ZHU S,et al.Stepwise ethanolic precipitation of sugar beet pectins from the acidic extract[J].Carbohydrate Polymers,2016,136(2):316-321
[18]ZHANG H,WANG J,NIE S,et al.Sulfated modification,characterization and property of a water-insoluble polysaccharide from Ganoderma atrum[J].International Journal of Biological Macromolecules,2015,79:248-255
[19]WANG J,ZHANG L,YU Y,et al.Enhancement of antitumor activities in sulfated and carboxymethylated polysaccharides of Ganoderma lucidum[J].Journal of Agricultural and Food Chemistry,2009,57(22):10565-10572
[20]WANG Y,SHEN X,LIAO W,et al.A heteropolysaccharide,L-fuco-D-manno-1,6-α-D-galactan extracted from Grifolafrondosa and antiangiogenic activity of its sulfated derivative[J].Carbohydrate Polymers,2014,101(1):631-641
[21]Yuqing CAI,Peng CHEN,Cuiyun WU,et al.Sulfated modification and biological activities of polysaccharides derived from Zizyphusjujuba cv.Jinchangzao[J].International Journal of Biological Macromolecules,2018,120:1149-1155
[22]XU Y,GAO Y,LIU F,et al.Sulfated modification of the polysaccharides from blackcurrant and their antioxidant andα-amylase inhibitory activities[J].International Journal of Biological Macromolecules,2018,109:1344-1354
[23]Dubois M,Gilles K A,Hamilton J K,et al.Colorimetric method for determination of sugars and related substances[J].Analytical Chemistry,1956,28(3):350-356
[24]Blumenkrantz N,Asboe-Hansen G.New method for quantitative determination of uronic acids[J].Analytical Biochemistry,1973,54(2):484-489
[25]WANG X,CHEN Q,LU X,et al.Pectin extracted from apple pomace and citrus peel by subcritical water[J].Food Hydrocolloids,2014,38(3):129-137
[26]WANG X,ZHANG L H,WU J L,et al.Improvement of simultaneous determination of neutral monosaccharides and uronic acids by gas chromatography[J].Food Chemistry,2017,220(1):198-207
[27]SUN Y,HU X,LI W,et al.Antioxidant,antitumor and immunostimulatory activities of the polypeptide from Pleurotus eryngii mycelium[J].International Journal of Biological Macromolecules,2017,97:323-330
[28]Udupa S L,Prabhakar A R,Tandon S.α-amylase inhibitors in foodstuffs[J].Food Chemistry,1989,34(2):95-101
[29]Chapdelaine P,Tremblay R R,Dube J Y.P-Nitrophenol-alpha-D-glucopyranoside as substrate for measurement of maltase activity in human semen[J].Clinical Chemistry,1978,24(2):208-211
[30]张海平,郑明明,黄凤洪,等.多糖酯的制备与活性研究进展[J].中国油脂,2017,42(11):116-120ZHANG Hai-ping,ZHENG Ming-ming,HUANGFeng-hong,et al.Advance in preparation and bioactivity of polysaccharose ester[J].China Oils and Fats,2017,42(11):116-120
[31]卢可可,张月巧,袁娅,等.硫酸化修饰多糖抗肿瘤活性构效关系及分子机制研究进展[J].食品科学,2014,35(23):297-302LU Ke-ke,ZHANG Yue-qiao,YUAN Ya,et al.Progress in the studies of the structure-antitumor activity relationship of sulfated polysaccharides and its molecular mechanisms[J].Food Science,2014,35(23):297-302
[32]WANG J,HU S,NIE S,et al.Reviews on mechanisms of in vitro antioxidant activity of polysaccharides[J].Oxidative Medicine and Cellular Longevity,2016,64:1-13
[33]杜湛湛,张嫱,徐平,等.粒毛盘菌多糖纯化、硫酸酯化修饰及抗氧化活性评价[J].合肥工业大学学报(自然科学版),2016,39(1):134-139DU Zhan-zhan,ZHANG Qiang,XU Ping,et al.Purification and sulfated modification of a Lachnum polysaccharides and evaluation of its antioxidant activity[J].Journal of Hefei University of Technology(Natural Science),2016,39(1):134-139
[34]JUNG H Y,BAE I Y,LEE S,et al.Effect of the degree of sulfation on the physicochemical and biological properties of Pleurotus eryngii polysaccharides[J].Food Hydrocolloids,2011,25(5):1291-1295
[35]贾红倩,刘嵬,颜军,等.杏鲍菇多糖的分离纯化、乙酰化修饰及其抗氧化活性[J].食品工业科技,2018,3:39-44JIA Hong-qian,LIU Wei,YAN Jun,et al.Isolation and purification,acetylation modification and antioxidant activity of polysaccharides of Pleurotus eryngii Quel[J].Science and Technology of Food Industry,2018,3:39-44
[36]WANG J,GUO H,ZHANG J,et al.Sulfated modification,characterization and structure-antioxidant relationships of Artemisia sphaerocephala polysaccharides[J].Carbohydrate Polymers,2010,81(4):897-905
[37]ZHU X Y,JIAN MIN W U.Superoxide anion radical scavenging ability of quaternary ammonium salt of chitosan[J].Chinese Chemical Letters,2004,15(7):808-810
[38]李东文,苏明声,龙凯,等.桦褐孔菌菌质提取物对α-淀粉酶和α-葡萄糖苷酶的抑制作用研究[J].食用菌,2017,39(2):14-16LI Dong-wen,SU Ming-sheng,LONG Kai,et al.Inhibition ofα-amylase andα-glucosidase by the extract of Inonotus obliquus[J].Edible Fungi,2017,39(2):14-16
[39]季芳,肖国春,董莉,等.药用植物来源的α-葡萄糖苷酶抑制剂研究进展[J].中国中药杂志,2010,35(12):1633-1640JI Fang,XIAO Guo-chun,DONG Li,et al.Development ofα-glucosidase inhibitor from medicinal herbs[J].China Journal of Chinese Materia Medica,2010,35(12):1633-1640