CN114163546B - 一种橄榄白蜡伞多糖、制备方法及应用 - Google Patents
一种橄榄白蜡伞多糖、制备方法及应用 Download PDFInfo
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- CN114163546B CN114163546B CN202210060299.4A CN202210060299A CN114163546B CN 114163546 B CN114163546 B CN 114163546B CN 202210060299 A CN202210060299 A CN 202210060299A CN 114163546 B CN114163546 B CN 114163546B
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
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Abstract
本发明公开了一种橄榄白蜡伞多糖、制备方法及应用。橄榄白蜡伞多糖由甘露糖、葡萄糖和半乳糖组成,其中甘露糖残基、葡萄糖残基和半乳糖残基之间的摩尔比为1:2:1。该多糖的制备过程包括热水浸提、醇沉、除蛋白、纯化等步骤,操作简单,方便。本发明揭示了橄榄白蜡伞多糖的结构,同时研究了该多糖的免疫调节活性,为进一步研究、开发橄榄白蜡伞多糖产品提供了技术基础。
Description
技术领域
本发明属于食用菌多糖技术领域,具体涉及一种橄榄白蜡伞多糖、制备方法及应用。
背景技术
食用真菌一般为高等真菌的子实体,味道鲜美,富含有丰富的蛋白质、糖、维生素等成分,具有较高的营养价值和药用价值。多糖是食用真菌最主要的活性成分之一,其不仅参与食用菌的生长,还具有多种生物活性。多糖是通过糖苷键复杂聚合而成的碳水化合物长链,不同类型的单糖单元和糖苷键都会导致其结构的多样性。食用菌多糖大多为杂多糖,分子量、单糖组成和糖苷键的连接方式的差异都会导致其生物活性的不同。因此,真菌多糖因其独特的生物活性被国际公认为生物调节效应剂。
橄榄白蜡伞(Hygrophours olivaceoalbus)隶属担子菌纲、伞菌目、蜡伞科、蜡伞属。野生的橄榄白蜡伞,子实体为中等大,菌盖直径约4-9.8cm,扁半球形近乎于平展,中部稍有凸起,颜色介于茶褐色与橄榄灰色之间,颜色最深部分为中部,它的表面有一层粘液。菌肉白色,中部厚,柔软。菌柄长度在7-10cm范围内,粗约1.5-2cm,呈圆柱形,向上稍细而具一层粘液,有黑褐色纤毛,菌环以上白色,菌环以下有黑褐色纤维状同心环带,内部实心。夏秋季在林中地上群生或散生。可以食用,主要分布在我国的四川、贵州、吉林、黑龙江等地。
目前,对橄榄白蜡伞多糖(HO-P)的精细结构及其免疫活性的研究尚未见任何报道。
发明内容
为了填补橄榄白蜡伞多糖的研究空白和开发利用橄榄白蜡伞多糖,发明人首次对橄榄白蜡伞中的多糖进行了长期研究,特别针对该多糖的结构、提取工艺以及生理活性开展了大量的实验。为橄榄白蜡伞多糖的应用奠定了坚实的基础。
第一方面,本发明提供了一种橄榄白蜡伞多糖,其由甘露糖、葡萄糖和半乳糖组成,其中甘露糖残基、葡萄糖残基和半乳糖残基之间的摩尔比为1:2:1。该多糖的化学结构如下:
其中,n为整数,5≤n≤20。
优选地,所述多糖的重均分子量为20000-30000Da,进一步优选为24481Da。
第二方面,本发明还提供了上述橄榄白蜡伞多糖的制备方法,具体制备过程包括以下步骤:
步骤1,将橄榄白蜡伞子实体粉末依次经过热水浸提、醇沉、杂蛋白去除,得到粗多糖;
步骤2,将步骤1制得的粗多糖经过离子交换柱层析,洗脱,收集洗脱液;
步骤3,将步骤2制得的洗脱液用透析袋进行浓缩;
步骤4,将步骤3制得的浓缩液冷冻干燥,得到所述的多糖。
优选地,在步骤(1)中,热水浸提时,所述橄榄白蜡伞子实体粉末与水的料液比为1:1-10,例如1:1,1:2,1:3,1:4,1:5,1:6,1:7,1:8,1:9,1:10。进一步优选为1:3。
优选地,在步骤(1)中,热水浸提的温度为85-100℃,例如85℃、90℃、95℃、100℃。进一步优选为95℃。
优选地,在步骤(1)中,热水浸提的次数为1-5次,例如1次、2次、3次、4次、5次。进一步优选为3次。每次浸提时间优选为1-10小时,例如1小时、2小时、3小时、4小时、5小时、6小时、7小时、8小时、9小时、10小时。进一步优选为6小时。
优选地,在步骤(1)中的醇沉操作时,乙醇与水提物浓缩液的体积比为1-10:1,例如1:1,2:1,3:1,4:1,5:1,6:1,7:1,8:1,9:1,10:1。进一步优选为4:1。
优选地,在步骤(1)中,除蛋白的方法选自Sevag法、三氟三氯乙烷法或三氯醋酸法中的一种,进一步优选为Sevag法。
优选地,在步骤(2)中,离子交换柱层析的填料为纤维素,进一步优选为DEAE-32或DEAE-52,更优选为DEAE-52。
优选地,在步骤(2)中,洗脱液选自蒸馏水、纯化水或注射用水中至少一种,进一步优选为蒸馏水。
优选地,在步骤(3)中,透析袋的截留分子量为5000-10000Da,例如5000Da,6000Da、7000Da、8000Da、9000Da、10000Da。进一步优选为7000Da。
优选地,在步骤(3)中,透析时间为1.5-4天,进一步优选为2-4天,例如2天、2.5天、3天、3.5天、4天。更优选为2天。
第三方面,本发明还提供上述橄榄白蜡伞多糖(HO-P)的应用。例如将该多糖开发为增强机体免疫力的产品,将该多糖用作细胞培养的活性成分,将该多糖用于细胞培养试剂的开发等。
优选地,所述应用为多糖在增强机体免疫力的产品中的应用。
更优选地,所述产品包括药物、食品或保健品中的至少一种。
本发明的有益效果如下;
一、本发明揭示了橄榄白蜡伞多糖的结构,为进一步研究、开发橄榄白蜡伞多糖产品提供了技术基础。
二、本发明对橄榄白蜡伞多糖的免疫调节活性进行了研究,为开发增强机体免疫力的产品(如药品、食品或保健品)提供了技术基础。
三、本发明还提供了橄榄白蜡伞多糖的提取方法,为其它食用菌多糖的提取和研究提供了技术参考。
附图说明
图1橄榄白蜡伞多糖HO-P的HPGPC图谱;
图2橄榄白蜡伞多糖HO-P的红外图谱;
图3橄榄白蜡伞多糖HO-P的HPLC图谱;
图4橄榄白蜡伞多糖HO-P的1H NMR图谱;
图5橄榄白蜡伞多糖HO-P的13C NMR图谱;
图6橄榄白蜡伞多糖HO-P的1H-1H COSY图谱;
图7橄榄白蜡伞多糖HO-P的HMQC图谱;
图8橄榄白蜡伞多糖HO-P的HMBC图谱;
图9橄榄白蜡伞多糖HO-P的化学结构;
图10橄榄白蜡伞多糖HO-P对T细胞增殖的影响的实验结果;
图11橄榄白蜡伞多糖HO-P对T细胞周期的影响的实验结果;
图12橄榄白蜡伞多糖HO-P对T细胞分泌TNF-α的影响的实验结果;
图13橄榄白蜡伞多糖HO-P对B细胞增殖的影响的实验结果;
图14橄榄白蜡伞多糖HO-P对B细胞周期的影响的实验结果;
图15橄榄白蜡伞多糖HO-P对B细胞分泌免疫球蛋白的影响的实验结果;
图16橄榄白蜡伞多糖HO-P对RAW264.7细胞增殖的影响的实验结果;
图17橄榄白蜡伞多糖HO-P对RAW264.7细胞周期的影响的实验结果。
具体实施方式
下面结合实施例来进一步描述本发明的技术方案,本发明的优点和特点将会随着描述而更为清楚。但是应当理解,实施例仅是示例性的,不对本发明的范围构成限制。
需要说明的是,本发明中的HO-P为(Hygrophours olivaceoalbusPolysaccharide)的字头缩写。
实施例1橄榄白蜡伞多糖HO-P的提取与分离纯化
1.橄榄白蜡伞多糖HO-P的提取
1.1橄榄白蜡伞粗多糖的提取
称取200g干燥的橄榄白蜡伞子实体,粉碎成子实体粉末,然后将粉末与蒸馏水按1:3的料液比置于烧杯中,95℃水浴6小时,将浸提混合液在5000r/min下离心10min,收集上清液后再次离心浓缩,重复3次,最终将全部的上清液浓缩至200mL。再将浓缩液和800mL无水乙醇混合、静置、沉淀,将沉淀收集后于40-50℃下烘干。然后采用Sevag法除去干燥样品中的蛋白质,从而获得橄榄白蜡伞粗多糖。
1.2DEAE-纤维素柱层析法分离纯化橄榄白蜡伞粗多糖
精确称取50g DEAE-52纤维素,并将其溶解在超纯水中,充分搅拌,待纤维素不成块状且无明显颗粒时,停止搅拌。静置过夜,将上清液弃去后加入0.5mol/L的NaOH浸泡纤维素6h,然后弃去上清液,用超纯水洗涤至中性。再弃去上清液后加入0.5mol/LHCl浸泡纤维素6h,然后弃去上清液,用超纯水洗涤至中性。再弃去上清液后加入0.5mol/LNaOH浸泡纤维素6h,然后弃去上清液,用超纯水洗涤至中性。将活化后的DEAE-52纤维素装柱,以蒸馏水为流动相压柱平衡3h。
将步骤1.1制备的橄榄白蜡伞粗多糖加入200mL蒸馏水中,混合均匀。然后将混合液在12000r/min下离心10min,再取12mL上清液均匀加入平衡后的DEAE-52纤维素柱中,以蒸馏水为流动相进行洗脱。采用硫酸-苯酚法对多糖进行测定。收集洗脱液,将洗脱液浓缩至5mL。
将洗脱浓缩液使用透析袋(Mw≥7000Da)进行透析,持续48h,然后在12000r/min下离心10min,离心后收集沉淀,然后将沉淀冷冻干燥,得到橄榄白蜡伞多糖,命名为HO-P。
2.橄榄白蜡伞多糖HO-P的结构鉴定
2.1分子量的测定
精确称取10mg橄榄白蜡伞多糖HO-P样品,加1mL ddH2O溶解,超声处理5min,进行高效凝胶渗透色谱(HPGPC)分析。HPGPC图谱(见图1)显示,橄榄白蜡伞多糖HO-P的重均分子量约为24481Da。
2.2橄榄白蜡伞多糖HO-P的傅里叶红外光谱分析
精确称取2mg橄榄白蜡伞多糖HO-P样品,与KBr进行混匀、研磨、压片,红外光谱仪中在4000cm-1-400cm-1范围内扫描。红外光谱图谱(见图2)显示,波数在3428.87cm-1、2923.60cm-1以及1402.02cm-1等处具有典型的多糖吸收峰。橄榄白蜡伞多糖HO-P在红外谱中显示3428.87cm-1的宽吸收峰指定为O-H的伸缩振动峰,2923.60cm-1的吸收峰C-H伸缩振动峰,1402.02cm-1的吸收峰C-H弯曲振动峰,1049.10cm-1的吸收峰C-O伸缩振动峰,673.05cm-1的吸收峰C-H摇摆振动峰。此外,在1730cm-1附近无吸收峰,说明橄榄白蜡伞多糖HO-P不含糖醛酸。
2.3橄榄白蜡伞多糖HO-P的单糖组成成分分析
将7种单糖标准品(鼠李糖、岩藻糖、阿拉伯糖、木糖、甘露糖、葡萄糖、半乳糖)和通过三氟乙酸(TFA)水解后的10mg橄榄白蜡伞多糖HO-P样品,以75%乙腈作为流动相进行高效液相色谱(HPLC)分析。HPLC结果(见图3)显示:峰1为甘露糖(Man),保留时间为5.908min;峰2为葡萄糖(Glc),保留时间为6.600min;峰3为半乳糖(Gal),保留时间6.845min。且甘露糖、葡萄糖和半乳糖的比例为1:2:1
2.4橄榄白蜡伞多糖HO-P的核磁共振分析
精确称取50mg橄榄白蜡伞多糖HO-P样品,溶于0.6mL重水(D2O)中,装入核磁管中,在核磁共振仪上检测。
2.4.1橄榄白蜡伞多糖HO-P的1HNMR结果(见图4)显示,橄榄白蜡伞多糖HO-P有三个异头氢信号,分别为δ5.03ppm、δ4.96ppm、δ4.91ppm,δ3.0~4.2ppm之间的信号归属为糖残基中C2-C6上的氢信号。
2.4.2橄榄白蜡伞多糖HO-P的13C NMR结果(见图5)显示,橄榄白蜡伞多糖HO-P有三个异头碳信号,分别为δ101.67ppm、δ98.25ppm、δ97.85ppm。δ60~78ppm之间的信号归属为糖残基中C2-C6信号。
2.4.3橄榄白蜡伞多糖HO-P的1H-1H COSY结果(见图6)反映相邻氢核之间的耦合关系。图6显示:A部分H1/H2的信号为δ5.03/3.86ppm,A部分H2/H3的信号为3.86/4.09ppm,A部分H3/H4的信号为δ4.09/3.63ppm,A部分H4/H5的信号为δ3.63/3.87ppm,A部分H5/H6的信号为δ3.87/3.29ppm。
所有氢的化学位移结果见表1。
表1 HO-P的1H的化学位移
2.4.4橄榄白蜡伞多糖HO-P的HMQC结果(见图7)反映了直接相连的氢核与碳核之间的耦合关系。图7显示:A部分H1/C1的信号为δ5.03/98.25ppm,A部分H2/C2的信号为δ3.86/77.05ppm,A部分H3/C3的信号为δ4.09/68.25ppm,A部分H4/C4的信号为δ3.63/70.39ppm,A部分H5/C5的信号为δ3.87/66.85ppm,A部分H6/C6的信号为δ3.29/76.21ppm。
2.4.5橄榄白蜡伞多糖HO-P的HMBC结果(见图8)反映了氢核与远程碳核之间的耦合关系。图8显示:A残基的H1/C3的信号为δ5.03/68.25ppm,B残基的H3/C5的信号为δ4.00/72.88ppm,C残基的H1/C3的信号为δ4.96/68.74ppm,D残基的H1/C3的信号为δ4.91/69.13ppm。
所有碳的化学位移结果见表2。
表2 HO-P中13C的化学位移
2.5橄榄白蜡伞多糖HO-P的硅烷化衍生与甲基化分析
精确称取20mg橄榄白蜡伞多糖HO-P样品,加2mLDMSO(二甲基亚矾),混匀后加200mg的NaOH,至不溶解为止。摇床振动1h,加1.5mL碘甲烷,避光反应1h,加水终止反应。用氯仿萃取产物,萃取三次,干燥后得甲基化多糖。
将甲基化多糖用三氟乙酸(TFA)进行水解,水解完全后水洗三次,得甲基化完全酸水解产物。然后将水解产物干燥,再加2mL吡啶充分溶解,然后加入2mL的六甲基二硅烷胺和1mL的三甲基氯硅烷,充分反应,并在50℃条件下水浴20min,12000r/min离心20min,取上清液,置样品瓶中用于GC-MS分析,结果见表3。
表3甲基化分析结果
表3的数据表明,橄榄白蜡伞多糖HO-P主链由(1→2,6)-半乳糖残基、(1→4)-葡萄糖残基和(1→4,6)-D-甘露糖残基构成,支链由(1→2,6)-半乳糖残基、(1→4,6)-甘露糖残基,→1)葡萄糖残基构成。
根据2.1-2.5的结果得到橄榄白蜡伞多糖HO-P的化学结构(见图9)。
实施例2橄榄白蜡伞多糖HO-P的免疫调节活性研究
1实验操作
1.1橄榄白蜡伞多糖HO-P对T、B和RAW264.7细胞增殖的影响
用CCK-8试剂盒测定橄榄白蜡伞多糖HO-P对T细胞、B细胞和巨噬细胞的增殖影响。将生长状况良好的细胞(浓度为1×105个/mL),接种在96孔培养板中,每孔加100μL,置于37℃、5%CO2的培养箱中进行培养。培养24h后,分别加100μL细胞培养液(空白对照)、4个不同浓度的HO-P溶液以及脂多糖(LPS)(终质量浓度5μg/mL,阳性对照),置于37℃、5%CO2的培养箱中进行培养继续培养24h。然后每孔加入5μL CCK-8溶液继续培养3小时,放置酶标仪在波长450nm处测定,记录测定结果。
1.2橄榄白蜡伞多糖HO-P对T、B和RAW264.7细胞周期的影响
细胞周期与细胞凋亡检测试剂盒检测橄榄白蜡伞多糖HO-P对T、B和RAW264.7细胞的细胞周期影响。将生长状况良好的细胞(浓度为1×105个/mL),接种在6孔培养板中,每孔加1mL,置于37℃、5%CO2的培养箱中进行培养。培养24h后,分别加1mL细胞培养液(空白对照)、HO-P溶液以及LPS(终质量浓度5μg/mL,阳性对照),置于37℃、5%CO2的培养箱中进行培养继续培养24h。将细胞收集起来,按照细胞周期试剂盒说明书对细胞进行固定、碘化丙啶染色后,用流式细胞仪(S3eTM CellSorter,BIO-RAD)进行检测,记录检测结果。
1.3橄榄白蜡伞多糖HO-P对T、B和RAW264.7细胞功能的影响
将生长状况良好的细胞(浓度为1×105个/mL),接种在6孔培养板中,每孔加2mL,置于37℃、5%CO2的培养箱中进行培养。培养24h后,分别加2mL细胞培养液(空白对照)、HO-P溶液以及LPS(终质量浓度5μg/mL,阳性对照),置于37℃、5%CO2的培养箱中进行培养继续培养24h。根据ELISA试剂盒说明书检测细胞因子,记录检测结果。
1.4统计与分析
将实验数据用t-test检验差异的显著性,与对照组对比显著用*表示,P<0.05,极显著用**表示,P<0.01。
2实验结果
2.1橄榄白蜡伞多糖HO-P对T细胞增殖的影响
橄榄白蜡伞多糖HO-P对T细胞增殖效果如图10所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度在2.5-10μg/mL浓度范围内,T细胞增殖效应极显著(P<0.01),且当HO-P浓度为5μg/mL时达到最大值,增殖率达35.80%。
2.2橄榄白蜡伞多糖HO-P对T细胞周期的影响
橄榄白蜡伞多糖HO-P对T细胞周期效果如图11所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度为5μg/mL时,G0/G1期细胞百分比显著(P<0.05)降低。
2.3橄榄白蜡伞多糖HO-P对T细胞分泌TNF-α的影响
橄榄白蜡伞多糖HO-P对T细胞分泌TNF-α的影响效果如图12所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度为5μg/mL时,不能促进T细胞分泌TNF-α。
2.4橄榄白蜡伞多糖HO-P对B细胞增殖的影响
橄榄白蜡伞多糖HO-P对B细胞增殖效果如图13所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度在1.25-10μg/mL之间时,B细胞增殖效应极显著(P<0.01)。且当HO-P浓度为2.5μg/mL时达到最大值,增殖率达48.61%。
2.5橄榄白蜡伞多糖HO-P对B细胞周期的影响
橄榄白蜡伞多糖HO-P对B细胞周期效果如图14所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度为2.5μg/mL时,G0/G1期细胞百分比极显著(P<0.01)降低,S期细胞百分比显著(P<0.05)增加,G2/M细胞百分比显著(P<0.05)增加。
2.6橄榄白蜡伞多糖HO-P对B细胞分泌免疫球蛋白的影响
橄榄白蜡伞多糖HO-P对B细胞分泌免疫球蛋白的影响效果如图15所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度为2.5μg/mL时,极显著(P<0.01)促进B细胞分泌IgA、IgD、IgE、IgG,显著(P<0.05)促进B细胞分泌IgM。
2.7橄榄白蜡伞多糖HO-P对RAW264.7细胞增殖的影响
橄榄白蜡伞多糖HO-P对RAW264.7细胞增殖效果如图16所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度在2.5-10μg/mL之间时,RAW264.7细胞增殖效应极显著(P<0.01),且当HO-P浓度为5μg/mL时达到最大值,增殖率达38.59%。
2.8橄榄白蜡伞多糖HO-P对RAW264.7细胞周期的影响
橄榄白蜡伞多糖HO-P对RAW264.7细胞周期效果如图17所示,与空白组相比,当橄榄白蜡伞多糖HO-P浓度为10μg/mL时,G0/G1期细胞百分比显著(P<0.05)降低,S期细胞百分比显著(P<0.05)增加。
以上所述仅为本发明的实施例,并非因此限制本发明的专利范围,凡是利用本发明说明书内容所作的等效结构变换,或直接或间接运用在其他相关的技术领域,均同理包括在本发明的专利保护范围内。
Claims (7)
2.根据权利要求1所述的多糖,其特征在于:
所述多糖的重均分子量为20000-30000Da。
3.根据权利要求2所述的多糖,其特征在于:
所述多糖的重均分子量为24481Da。
4.权利要求1-3中任一项所述多糖的制备方法,其特征在于:
所述多糖的制备过程包括以下步骤:
步骤1,将橄榄白蜡伞子实体粉末依次经过热水浸提、醇沉、杂蛋白去除,得到粗多糖;
步骤2,将步骤1制得的粗多糖经过离子交换柱层析,洗脱,收集洗脱液;
步骤3,将步骤2制得的洗脱液用透析袋进行浓缩;
步骤4,将步骤3制得的浓缩液冷冻干燥,得到所述的多糖。
5.根据权利要求4所述的制备方法,其特征在于:
所述热水浸提的温度为85-100℃,所述热水浸提的次数为1-5次,每次浸提时间为1-10小时;
所述醇沉中乙醇与水提物的浓缩液的体积比为1-10:1。
6.根据权利要求4所述的制备方法,其特征在于:
所述离子交换柱层析的填料为纤维素。
7.根据权利要求6所述的制备方法,其特征在于:
所述纤维素为DEAE-52或DEAE-32。
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