CN113004432A - 一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用 - Google Patents
一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用 Download PDFInfo
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- CN113004432A CN113004432A CN202110247117.XA CN202110247117A CN113004432A CN 113004432 A CN113004432 A CN 113004432A CN 202110247117 A CN202110247117 A CN 202110247117A CN 113004432 A CN113004432 A CN 113004432A
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Abstract
本发明是关于一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用,主要技术为,所述铁皮石斛寡糖含有3‑9个糖苷残基,并在非还原端具有葡萄糖残基;其衍生物是在非还原端被疏水残基取代得到,还提供了二者的制备方法和应用。本发明的有益效果为:首次从铁皮石斛中制备得到了纯度≥99%以上的铁皮石斛寡糖,明确了铁皮石斛寡糖结构、抗衰老活性作用和免疫调节作用,发现其可以很好的抑制胶原蛋白酶,对TNF‑α和IL‑6也具有一定的活性;可应用于医药、食品、日用品开发等领域。
Description
技术领域
本发明涉及天然药物化学技术领域,特别是涉及一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用。
背景技术
铁皮石斛Dendrobium officinale Kimura et Migo为兰科(Orchidaceae)石斛属多年生草本植物,载于各版药典,药典记载其有生津养胃;滋阴清热;润肺益肾;明目强腰等功效。现代药理学研究表明铁皮石斛具有抗氧化,降糖,调节免疫和抗炎等活性。古籍文献中记录铁皮石斛茎可以用于肌肤润泽和消渴症。而研究发现铁皮石斛主要含有多糖、菧类、黄酮、菲类、木质素等化学成分。
衰老是人体生长发育的必然结果而如何延缓衰老则一直是护肤品领域及生物医药大健康领域的终极命题。衰老大体分为两类:生理性衰老和病理性衰老。生理性衰老是指成熟期后出现的生理性退化过程,病理性衰老是由于各种外来因素(包括各种疾病)所导致的老年性变化。两者实际很难区分。而古籍中有记载铁皮石斛具有抗衰老的作用,那么铁皮石斛中天然、绿色、安全、高效的抗衰老物质则是人们关注的研究重点。
目前,国内外多位研究者对铁皮石斛的各个部分进行化学成分提取分离研究,大部分研究者主要得到的多为小分子酚类成分或分子量大于10万的多糖类成分。有研究人员从鉴定铁皮石斛中分离得到了20个化合物,主要为联苄类成分,并通过活性筛选发现铁皮石斛小分子酚类成分具有抗氧化、抗炎、抗肿瘤等作用。还有研究人员从铁皮石斛中提取分离出了2种多糖,其分子量分别为7.4×105,5.4×105。有研究人员利用水提醇沉,硫酸水解方法,得到铁皮石斛中多糖并通过活性筛选发现铁皮石斛多糖类成分对小鼠外围白细胞计数有影响,说明其具有免疫调节的作用。有研究人员通过超声萃取得到铁皮石斛多糖并通过活性筛选发现铁皮石斛多糖类成分对果蝇的SOD,MDA,CAT有影响,说明其具有抗氧化的作用。有研究人员阐明铁皮石斛多糖有4个主要均一多糖,且分子量为6800—1.78×105Da。这些前人的研究工作,大量的集中在小分子酚类成分及多糖类成分的药理活性研究上,对于寡糖的研究鲜有报道。
发明内容
有鉴于此,本发明提供一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用,阐明铁皮石斛寡糖具有抗衰老和免疫调节功效,适用于具有抗衰老免疫调节功效的皮肤化妆品、保健食品及药品中。
为达到上述目的,本发明主要提供如下技术方案:
一方面,一种铁皮石斛寡糖,所述铁皮石斛寡糖含有3-9个糖苷残基,并在非还原端具有葡萄糖残基;优选的,所述铁皮石斛寡糖含有6个糖苷残基;优选的,所述铁皮石斛寡糖的结构如式(I)所示:
另一方面,上述的一种铁皮石斛寡糖,所述糖苷残基包括半乳糖残基、甘露糖残基和葡萄糖残基;优选的,半乳糖残基、甘露糖残基和葡萄糖残基的摩尔比计为(3~2):(2~1):(2~1),优选为2:1:1。
再一方面,一种铁皮石斛寡糖衍生物,所述铁皮石斛寡糖衍生物为上述的铁皮石斛寡糖的葡萄糖残基与疏水残基反应生成的;
优选的,所述疏水残基包括直链或支链C1-C18烷基、C1-C18烷基羧酸、C1-C18烷基胺、C1-C18芳基烷基和C1-C18烷基酰胺中的任意一种,或
所述疏水残基包括包括苯甲酰基、苯乙酰基、苯丙酰基中的任意一种(以苯基取代羟基、甲氧基)。
再一方面,上述的一种铁皮石斛寡糖在制备抗衰老或免疫调节产品中的应用;优选的,所述产品包括药物、食品、制剂及化妆品;优选的,所述化妆品的类型包括面霜、乳剂、化妆水或修复霜。
另一方面,上述的铁皮石斛寡糖衍生物在制备抗衰老或免疫调节产品中的应用;优选的,所述产品包括药物、食品、制剂及化妆品;优选的,所述化妆品的类型包括面霜、乳剂、化妆水或修复霜。
再一方面,上述的一种铁皮石斛寡糖的提取方法,包括以下步骤:
1)制备铁皮石斛粉末:对铁皮石斛茎进行干燥处理后,再将其粉粹过筛,得到铁皮石斛粉末;
2)制备铁皮石斛水提液:将所述铁皮石斛粉末和水混合后,进行至少一次沸水浴,然后合并水提液,得到铁皮石斛水提液;
3)制备铁皮石斛浓缩水提液:将所述铁皮石斛水提液离心后,再减压浓缩,得到铁皮石斛浓缩水提液;
4)制备复溶液:在所述铁皮石斛浓缩水提液中加乙醇,沉淀,然后离心并弃去上清液;在得到的沉淀中加入水复溶,得到复溶液;
5)制备铁皮石斛寡糖水溶液:对所述复溶液除蛋白后,冷冻干燥得铁皮石斛粗多糖;在所述铁皮石斛粗多糖中加水溶解后,再向其中加入纤维素酶进行反应后,灭活并离心,弃去沉淀,得到铁皮石斛寡糖水溶液;
6)制备铁皮石斛寡糖:将铁皮石斛寡糖水溶液纯化,得到铁皮石斛寡糖。
另一方面,上述的一种铁皮石斛寡糖的提取方法,
步骤1)中,优选的,干燥处理的温度为50-60℃;所述干燥处理后的铁皮石斛茎的水分质量含量低于6%;所述过筛的目数为20-40目;
步骤2)中,优选的,所述铁皮石斛粉末和水按照质量体积比1:(50-80)g/mL混合;进行2-3次沸水浴;每次沸水浴的时间为1-2h;
步骤3)中,优选的,离心条件为:3000-4000rpm/min,8-12min,室温;减压浓缩条件为:采用旋转蒸发方式,回收乙醇温度为<50℃,压力为0.7Pa-0.9Pa;铁皮石斛浓缩水提液的料液质量体积比为1:(5-10)g/ml。
另一方面,上述的一种铁皮石斛寡糖的提取方法,
步骤4)中,优选的,在所述铁皮石斛浓缩水提液中加入体积浓度为95%的乙醇至混合液的醇浓度以体积百分比计为70%-80%后,进行隔夜沉淀;离心条件为3500-4500rpm,18-22min,室温;所述沉淀和水的重量体积比1:(4-6)g/ml加入水复溶;
步骤5)中,优选的,以Sevage法对所述复溶液除蛋白;冷冻干燥温度为45℃;在所述铁皮石斛粗多糖中加水溶解至4.5-5.5mg/ml;纤维素酶的加入量为所述铁皮石斛粗多糖重量的2%-4%;加入纤维素酶后,进行反应的反应温度为55-65℃、反应时间为2h-4h;通过煮沸25-35min灭活处理;离心条件为3500-4500rpm,15-25min,室温;所述铁皮石斛寡糖水溶液中的寡糖含量大于80%;
步骤6)中,优选的,纯化是采用过G75凝胶柱的方式;铁皮石斛寡糖的纯度为99.86%。
另一方面,上述的一种铁皮石斛寡糖衍生物的制备方法,包括以下步骤:1)将脂肪酸还原成脂肪醇;
2)脂肪醇与铁皮石斛寡糖进行糖苷化。
另一方面,上述的一种铁皮石斛寡糖衍生物的制备方法,
步骤1)中,优选的,反应过程为:脂肪酸10mmol、NaBH4 20mmol、AlCl3 40mmol、THF27ml、MeOH 3ml,反应温度为100℃,反应时间为8h,产率为90%;
步骤2)中,优选的,利用还原得到的脂肪醇与铁皮石斛寡糖进行糖苷化反应,反应过程为:醇糖摩尔比1:(8~10)、催化剂十六烷基溴化铵,反应温度为110~115℃,反应时间为3h,产率为80%。
上述铁皮石斛中分离纯化寡糖的方法,铁皮石斛多糖的分子量(≥10万)大,难以透过皮肤细胞被吸收,主要作用于皮肤外起到保湿作用,而多糖被酶解后形成的寡糖则分子量小,易于透过皮肤细胞被吸收,起到抗衰老作用,依据二者分子量不同,可以区别应用。
另一方面,还发现铁皮石斛寡糖可以增加Hacat及RAW264.7细胞的存活率及存活时间,考虑到铁皮石斛寡糖可能回具有很好的抗衰老活性及免疫调节活性,故对衰老的几个主要作用靶点蛋白(弹力蛋白酶、胶原蛋白酶,透明质酸)进行了活性验证,结果发现铁皮石斛寡糖对胶原蛋白酶具有很强的抑制作用,能有效的缓解胶原蛋白的降解代谢,维持皮肤年轻态;对弹力蛋白酶也有一定抑制作用,同时也有一定促进透明质酸分泌活性。铁皮石斛寡糖对TNF-α和IL-6也有一定的活性,具有较好的免疫调节作用。
再一方面,一种抗衰老或免疫调节产品,所述抗衰老或免疫调节产品为面霜或乳剂;其中,
按照质量百分比计,所述面霜包括:富含寡糖的铁皮石斛原液0.4-0.6%,硬脂酸7.5-8.5%,C16醇1.5-2.5%,自乳化单甘酯1.5-2.5%,氢化羊毛脂1.5-2.5%,液体石蜡11-13%,甘油6-8%,乳化剂1-2%,防腐剂0.1-0.3%,香精0.1-0.3%,水余量;
按照质量百分比计,所述乳剂包括:富含寡糖的铁皮石斛原液0.4-0.6%,硬脂酸1.3-1.5%,鲸蜡醇0.08-0.12%,2-乙基醇鲸蜡基硬脂酸酯1.7-1.9%,肉豆蔻酸异丙酯0.1-0.3%,2-己基-1-癸醇0.9-1.1%,液体石蜡7-8%,甘油2.5-3.5%,丙二醇7-9%,三乙醇胺0.08-0.12%,羧乙烯基聚合物0.3-0.4%,Arlacel 165 1.5-2.5%,防腐剂0.1-0.3%,香精0.1-0.3%,水余量。
再一方面,一种抗衰老或免疫调节产品,所述抗衰老或免疫调节产品为化妆水;其中,
按照质量百分比计,所述化妆水包括:富含寡糖的铁皮石斛原液1-10%,聚丙烯酸钠0.3-0.4%,甘油3.5-4.5%,1,3-丁二醇2-3%,维生素B5 0.4-0.6%,熊果苷0.4-0.6%,EDTA-Na2 0.04-0.06%,去离子水余量;
优选的,所述化妆水的制备方法为:将聚丙烯酸钠溶入水中,搅拌,充分溶胀,再加入其余成分,持续搅拌;然后再加入富含寡糖的铁皮石斛原液搅拌后,加去离子水定容,得到化妆水。
再一方面,一种抗衰老或免疫调节产品,所述抗衰老或免疫调节产品为修复霜;其中,
按照质量百分比计,所述修复霜包括:甘油5-7%,卡波姆1.4-1.6%,三乙醇胺1.4-1.6%,丙二醇5.5-6.5%,尼伯金乙酯0.15-0.25%,富含寡糖的铁皮石斛原液9-11%,精油0.4-0.6%,去离子水余量;
优选的,所述修复霜的制备方法为:取卡波姆于适量去离子水中,搅匀,静置过夜,使其充分溶胀后,加入甘油,用三乙醇胺调节pH值,使凝胶基质粘稠性增加,得到卡波姆凝胶;
将富含寡糖的铁皮石斛原液、丙二醇及去离子水混合后,再向其中加入卡波姆凝胶、精油和尼伯金乙酯,搅拌至均匀细腻,加蒸镏水至足量,研磨均匀,得到修复霜。
与现有技术相比,本发明的一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用,至少具有下列有益效果:
一方面,本发明首次阐明从铁皮石斛中制备的纯度≥99%以上的铁皮石斛寡糖,并对其进行了结构解析,明确了铁皮石斛寡糖的结构。
进一步地,本发明首次对铁皮石斛寡糖的抗衰老活性进行了系统的研究,研究发现铁皮石斛寡糖可以很好的抑制胶原蛋白酶等具有很强的抗衰老作用,对TNF-α和IL-6也有一定的活性,具有较好的免疫调节作用。
另一方面,本发明所涉及的铁皮石斛寡糖制备方法及活性应用方向,为铁皮石斛在相关方向的应用提供了科学依据。
再一方面,本发明所制备出的铁皮石斛寡糖用途,可作为中间体用于铁皮石斛系列产品的开发(如应用于医药、食品、日用品开发等领域)。
上述说明仅是本发明技术方案的概述,为了能够更清楚了解本发明的技术手段,并可依照说明书的内容予以实施,以下以本发明的较佳实施例并配合附图详细说明如后。
附图说明
图1-3为本发明铁皮石斛寡糖的结构及纯度鉴定HPLC-ELSD,NMR,MS,图谱。
图1为铁皮石斛寡糖的纯度鉴定HPLC-ELSD图谱。
图2为铁皮石斛寡糖的1H,13C-NMR图谱(图2-A为1H,图2-B为13C)。
图3为铁皮石斛寡糖寡糖的MS图谱。
图4至图7为铁皮石斛寡糖的抗衰老活性测试结果图。
图4为以DPPH自由基清除率确定铁皮石斛寡糖的抗氧化率(寡糖浓度为4%、8%、11%、15%、20%)。
其中,纵坐标为DPPH自由基清除率所代表的抗氧化率%,横坐标从1-5分别为寡糖浓度4%、8%、11%、15%、20%。
图5为铁皮石斛寡糖对弹性蛋白酶活性的抑制率(寡糖浓度为4%、8%、11%、15%、20%)。
其中,纵坐标为弹性蛋白酶抑制率%,横坐标从1-5分别为寡糖浓度4%、8%、11%、15%、20%。
图6为铁皮石斛寡糖对胶原蛋白酶活性的抑制率(寡糖浓度为0.4%、0.8%、1%、2%、4%)。
其中,纵坐标为胶原蛋白酶抑制率%,横坐标从1-5分别为寡糖浓度0.4%、0.8%、1%、2%、4%。
图7为铁皮石斛寡糖对透明质酸分泌的促进活性(寡糖浓度为4%、8%、11%、15%、20%)。
其中,纵坐标为透明质酸分泌量(ng/ml),横坐标从1-5分别为寡糖浓度4%、8%、11%、15%、20%。
图8为铁皮石斛寡糖对RAW264.7细胞免疫调节活性的影响(寡糖浓度为3.125μg/mL、6.25μg/mL、12.5μg/mL、50μg/mL、100μg/mL、200μg/mL)。
其中,图8-A为寡糖对TNF-α分泌量的影响,纵坐标为TNF-α分泌量pg/mL,横坐标从1-5分别为空白、脂多糖LPS、寡糖终反应浓度12.5μg/mL、6.25μg/mL、3.125μg/mL;
图8-B为寡糖对IL-6分泌量的影响,纵坐标为IL-6分泌量pg/mL,横坐标从1-5分别为空白、脂多糖LPS、寡糖终反应浓度200μg/mL、100μg/mL、50μg/mL。
具体实施方式
为更进一步阐述本发明为达成预定发明目的所采取的技术手段及功效,以下结合附图及较佳实施例,对依据本发明申请的具体实施方式、结构、特征及其功效,详细说明如后。在下述说明中,不同的“一实施例”或“实施例”指的不一定是同一实施例。此外,一个或多个实施例中的特定特征、结构、或特点可由任何合适形式组合。
本发明中的术语“护肤品”指的是可以是护肤水、护肤乳液、护肤面膜、护肤霜等;本发明实施例的护肤品也可以指化妆品。
一种铁皮石斛寡糖,铁皮石斛寡糖含有3-9个糖苷残基,并在非还原端具有葡萄糖残基;含有6个糖苷残基的结构如式(I)所示:
其中,糖苷残基包括半乳糖残基、甘露糖残基和葡萄糖残基;半乳糖残基、甘露糖残基和葡萄糖残基按照摩尔比计为(3~2):(2~1):(2~1),优选为2:1:1。
铁皮石斛寡糖的提取方法,包括以下步骤:
1)制备铁皮石斛粉末:对铁皮石斛茎进行干燥处理后,再将其粉粹过筛,得到铁皮石斛粉末;
优选的,干燥处理的温度为50-60℃;所述干燥处理后的铁皮石斛茎的水分质量含量低于6%;所述过筛的目数为20-40目;
2)制备铁皮石斛水提液:将所述铁皮石斛粉末和水混合后,进行至少一次沸水浴,然后合并水提液,得到铁皮石斛水提液;
优选的,所述铁皮石斛粉末和水按照质量体积比1:(50-80)g/mL混合;进行2-3次沸水浴;每次沸水浴的时间为1-2h;
3)制备铁皮石斛浓缩水提液:将所述铁皮石斛水提液离心后,再减压浓缩,得到铁皮石斛浓缩水提液;
优选的,离心条件为:3000-4000rpm/min,8-12min,室温;减压浓缩条件为:采用旋转蒸发方式,回收乙醇温度为<50℃,压力为0.7Pa-0.9Pa;铁皮石斛浓缩水提液的料液质量体积比为1:(5-10)g/ml;
4)制备复溶液:在所述铁皮石斛浓缩水提液中加乙醇,沉淀,然后离心并弃去上清液;在得到的沉淀中加入水复溶,得到复溶液;
优选的,在所述铁皮石斛浓缩水提液中加入体积浓度为95%的乙醇至混合液的醇浓度以体积百分比计为70%-80%后,进行隔夜沉淀;离心条件为3500-4500rpm,18-22min,室温;所述沉淀和水的重量体积比1:(4-6)g/ml加入水复溶;
5)制备铁皮石斛寡糖水溶液:对所述复溶液除蛋白后,冷冻干燥得铁皮石斛粗多糖;在所述铁皮石斛粗多糖中加水溶解后,再向其中加入纤维素酶进行反应后,灭活并离心,弃去沉淀,得到铁皮石斛寡糖水溶液;
优选的,以Sevage法对所述复溶液除蛋白;冷冻干燥温度为45℃;在所述铁皮石斛粗多糖中加水溶解至4.5-5.5mg/ml;纤维素酶的加入量为所述铁皮石斛粗多糖重量的2%-4%;加入纤维素酶后,进行反应的反应温度为55-65℃、反应时间为2h-4h;通过煮沸25-35min灭活处理;离心条件为3500-4500rpm,15-25min,室温;所述铁皮石斛寡糖水溶液中的寡糖含量大于80%;
6)制备铁皮石斛寡糖:将铁皮石斛寡糖水溶液纯化,得到铁皮石斛寡糖;
优选的,纯化是采用过G75凝胶柱的方式;铁皮石斛寡糖的纯度为99.86%。
一种铁皮石斛寡糖衍生物,为上述的铁皮石斛寡糖的葡萄糖残基与疏水残基反应生成的;疏水残基包括直链或支链C1-C18烷基、C1-C18烷基羧酸、C1-C18烷基胺、C1-C18芳基烷基和C1-C18烷基酰胺中的任意一种,或
包括苯甲酰基、苯乙酰基、苯丙酰基中的任意一种(以苯基取代羟基、甲氧基)。
铁皮石斛寡糖衍生物的制备方法,包括以下步骤:
1)将脂肪酸还原成脂肪醇;
优选的,反应过程为:脂肪酸10mmol、NaBH4 20mmol、AlCl3 40mmol、THF 27ml、MeOH3ml,反应温度为100℃,反应时间为8h,产率为90%;
2)脂肪醇与铁皮石斛寡糖进行糖苷化;
优选的,利用还原得到的脂肪醇与铁皮石斛寡糖进行糖苷化反应,反应过程为:醇糖摩尔比1:(8~10)、催化剂十六烷基溴化铵,反应温度为110~115℃,反应时间为3h,产率为80%。
下面通过具体实施例对本发明进一步详细说明如下:
实施例1:
本实施例主要是从铁皮石斛茎分离纯化出铁皮石斛寡糖,并进一步结构鉴定:
将铁皮石斛新鲜茎切断放置于鼓风干燥箱中55℃干燥,测其水分,水分达到6%以下时,将其粉碎过20-40目筛;取铁皮石斛粉末50克加超纯水2500ml,沸水浴2次,每次2h,合并水提液。之后离心,离心条件:3000-4000rpm,10min,室温25℃,获得铁皮石斛水提液;将铁皮石斛水提液减压浓缩至500ml,得到铁皮石斛浓缩水提液。向铁皮石斛浓缩水提液中加入适量95%乙醇至混合水液醇浓度为70-80%,隔夜沉淀,之后离心,离心条件:4000rpm,20min,室温25℃,弃去上清液,得到沉淀;按沉淀重量1:5(m:v)(g/ml)加入水复溶,得到复溶液。Sevage法对复溶液除蛋白后,冷冻干燥得铁皮石斛粗多糖,取200mg铁皮石斛粗多糖加水溶解至5mg/ml,按铁皮石斛多糖重量的2%-4%投入纤维素酶,混匀,在60℃反应2h-4h后,煮沸30min灭活,离心,离心条件:4000rpm,20min,室温25℃,弃去沉淀;得铁皮石斛寡糖水溶液(铁皮石斛寡糖水液中寡糖含量大于80%)。取适量铁皮石斛寡寡糖水液过G75凝胶柱,得纯化的铁皮石斛寡糖150mg(纯度为99.86%,分子量≈1000)。
采用高效液相色谱对铁皮石斛寡糖的纯度进行了鉴定,结果如图1所示;采用氢谱核磁共振解析和碳13核磁共振解析对铁皮石斛寡糖的结构进行了鉴定,结果如图2所示;同时采用MS质谱分析对铁皮石斛寡糖的结构进行了定量分析,结果如图3所示。
实施例2:
DPPH自由基清除实验
1试剂:
DPPH、水溶性维生素E(Trolox)(Trolox溶解于无水乙醇,浓度为10mM,-20℃保存)、纯水。
2实验方法:
将待测药物与DPPH(终浓度为100M)混合反应,设定3个重复孔,同时设置不含药物的空白对照孔和Trolox阳性对照孔,30℃,1h,酶标仪测定OD值,检测波长为515nm,计算得到抗氧化率。
抗氧化率(%)=(1-实验孔OD515nm/空白孔OD515nm)×100%
3实验结果:
如表1所示。
表1
样品 | 终反应浓度 | 抗氧化率(%) |
Trolox | 25 | 95.668% |
铁皮石斛寡糖 | 4% | 11.335% |
铁皮石斛寡糖 | 8% | 14.346% |
铁皮石斛寡糖 | 11% | 16.213% |
铁皮石斛寡糖 | 15% | 21.155% |
铁皮石斛寡糖 | 20% | 25.217% |
4结论:
依据表1的数据制作了对比更为清晰的图4,从图4和表1可以看出,本实验对铁皮石斛寡糖的DPPH自由基清除能力进行了评价。结果显示,15%-20%浓度下,铁皮石斛寡糖具有一定的抗氧化率(>20%)。
实施例3:
弹性蛋白酶抑制率实验
1试剂:
样品、阳性对照儿茶素、Tris、HCl、猪胰弹性蛋白酶、N-琥珀酰-丙氨酸-丙氨酸-丙氨酸-p-硝基苯胺、DMSO
2实验方法:
(1)配置溶液
样品溶液配制:配置1mg/ml的样品溶液(用纯水或者缓冲液配置,如果不溶于水或缓冲液,则先用DMSO溶解样品,然后再加水或者缓冲液,原则上DMSO的含量不能超过5%)。
阳性对照配置:1mg/ml的儿茶素;
配置缓冲液:Tris-HCl缓冲液0.1M PH=8.0;
称取配置底物溶液:N-琥珀酰-丙氨酸-丙氨酸-丙氨酸-p-硝基苯胺(AAAPVN)溶液(2mM);
配置:猪胰弹性蛋白酶液(0.171U/mL)取28.5μl溶于10ml Tris-HCl缓冲液。
(2)添加溶液到96孔板里50μL样品+50μL猪胰弹性蛋白酶+100μL反应底物。
(3)室温保持5min之后,在420nm处吸光值。
弹性蛋白酶抑制率(%)=(1-样品OD420nm/实验孔OD420nm)×100%
3实验结果:
如表2所示。
表2
样品名称 | 终反应浓度 | 弹性蛋白酶抑制率% |
表儿茶素没食子酸 | 100μg/ml | 68.540% |
铁皮石斛寡糖 | 4% | -2.135% |
铁皮石斛寡糖 | 8% | 3.886% |
铁皮石斛寡糖 | 11% | 8.417% |
铁皮石斛寡糖 | 15% | 9.723% |
铁皮石斛寡糖 | 20% | 15.827% |
4结论:
依据表2的数据制作了对比更为清晰的图5,从图5和表2可以看出,本实验对铁皮石斛寡糖的弹性蛋白酶抑制率进行了评价。结果显示,20%浓度下,铁皮石斛寡糖具有一定的弹性蛋白酶抑制活性(>10%)。
实施例4:
胶原蛋白酶抑制率实验
1.试剂:
蛋白酶缓冲液、蛋白酶、蛋白酶基质、抑制剂(1,10-Phenanthroline)。所有试剂在-20℃保存。
2.实验方法:
(1)溶液配制:
胶原蛋白酶反应混合物如表3所示。
表3
组成 | 含量(%) |
胶原蛋白酶缓冲液 | 60 |
胶原蛋白酶底物 | 40 |
(2)组分设计如下:
①背景空白孔:100μl/孔的蛋白酶缓冲液
②样本孔:100μl,可配置成不同浓度。
③阳性对照孔:10μl蛋白酶+90μl蛋白酶缓冲液
④抑制剂对照孔:10μl蛋白酶+2μl抑制剂+88μl蛋白酶缓冲液如表4所示。
表4
(3)按上述组别加好试剂后,每孔添加100μl胶原蛋白酶反应混合物,避光孵育后再345nm处测量OD值。
孵育时间根据待测样品的活性而定,低活性样品可以孵育1-3h。
胶原蛋白酶抑制率(%)=(OD背景孔-OD样品孔)/(OD背景-OD阳性对照孔)
3.实验结果:
如表5所示。
表5
4结论:
依据表5的数据制作了对比更为清晰的图6,从图6和表5可以看出,本实验对铁皮石斛寡糖的胶原蛋白酶抑制率进行了评价。结果显示,0.4%-4%浓度下,铁皮石斛寡糖具有很强的胶原蛋白酶抑制活性(>50%)。
实施例5:
促进透明质酸分泌实验
1试剂及细胞:
人永生化皮质细胞(Hacat细胞)、人透明质酸Elisa试剂盒、蒸馏水
2实验方法:
96孔板每孔接种100ml细胞悬液,悬液浓度为4×105个/ml。孵育24h后弃去原培养液,用PBS洗涤1-2次后加入含有不同浓度待测药物的无血清培养基,继续孵育24h。设置不含药物的空白对照和TGF-β阳性对照,之后用含有1%PMSF的ripa裂解液裂解细胞,离心后取上清液,按胶原蛋白ELISA试剂盒中提供的方法检测透明质酸的分泌,酶标仪测定OD值,检测波长为450nm。OD值代入标准曲线的回归方程计算得到透明质酸分泌增加率。
3实验结果:
如表6所示。
表6
样品 | 终反应浓度 | 透明质酸分泌量(ng/ml) |
空白对照 | 0.2508 | |
铁皮石斛寡糖 | 4% | 0.2294 |
铁皮石斛寡糖 | 8% | 0.5530 |
铁皮石斛寡糖 | 11% | 0.3691 |
铁皮石斛寡糖 | 15% | 0.4930 |
铁皮石斛寡糖 | 20% | 0.5392 |
4结论:
依据表6的数据制作了对比更为清晰的图7,从图7和表6可以看出,本实验对铁皮石斛寡糖的促透明质酸分泌能力进行了评价。结果显示,8%-20%浓度下,铁皮石斛寡糖具有一定的促透明质酸分泌活性(>0.3ng/ml)。
实施例6:
铁皮石斛寡糖的免疫调节活性评估
1实验细胞与试剂:
RAW264.7细胞、TNF-α,IL-6试剂盒、蒸馏水
2实验方法:
取对数生长RAW264.7细胞经细胞计数后接种于12孔板中。置于培养箱中过夜,弃去细胞上清液,无菌操作下给予不同浓度铁皮石斛寡糖、脂多糖,和基础培养基1640,干预24h后收集上清液,-20℃保存备用。按照ELISA试剂盒的说明书检测TNF-α和IL-6分泌量变化。酶标仪测定OD值,检测波长为450nm。OD值代入标准曲线的回归方程计算得到TNF-α,IL-6分泌增加率。
3实验结果:
如表7所示。
表7
4结论:
依据表7的数据制作了对比更为清晰的图8,从图8和表7可以看出,本实验对铁皮石斛寡糖对RAW264.7细胞免疫调节活性的影响进行了评价。结果显示,在3.125μg/mL浓度下能极显著增加RAW264.7巨噬细胞对TNF-α的分泌与阳性对照LPS相当。在50μg/mL浓度下能极显著增加RAW264.7巨噬细胞对IL-6的分泌与阳性对照LPS相当。
实施例7:脂肪酸的糖苷化
1实验试剂:
铁皮石斛寡糖、脂肪酸、NaBH4、MeOH、金属盐、AlCl3、THF、催化剂等
2实验方法与结果:
1)将C6脂肪酸还原成脂肪醇:脂肪酸10mmol;NaBH4 20mmol;AlCl3 40mmol;THF27ml;MeOH 3ml,反应温度:100℃反应时间:8h产率:90%
2)糖苷化:利用还原得到的脂肪醇与铁皮石斛寡糖进行糖苷化反应:醇糖摩尔比:1:8~10;催化剂十六烷基溴化铵,反应温度:110~115℃反应时间:3h产率:80%
3结果讨论:
反应表明铁皮石斛寡糖具有末端糖苷同样可以与脂肪酸发生糖苷化反应。
实施例8:
本实施例提供一种抗衰老或免疫调节面霜,其中,按照质量百分比计,面霜包括:富含寡糖的铁皮石斛原液0.4-0.6%,硬脂酸7.5-8.5%,C16醇1.5-2.5%,自乳化单甘酯1.5-2.5%,氢化羊毛脂1.5-2.5%,液体石蜡11-13%,甘油6-8%,乳化剂1-2%,防腐剂0.1-0.3%,香精0.1-0.3%,水余量;按常规制作化妆品的方法制得上述配方的面霜。
实施例9:
本实施例提供一种抗衰老或免疫调节乳剂,其中,按照质量百分比计,乳剂包括:富含寡糖的铁皮石斛原液0.4-0.6%,硬脂酸1.3-1.5%,鲸蜡醇0.08-0.12%,2-乙基醇鲸蜡基硬脂酸酯1.7-1.9%,肉豆蔻酸异丙酯0.1-0.3%,2-己基-1-癸醇0.9-1.1%,液体石蜡7-8%,甘油2.5-3.5%,丙二醇7-9%,三乙醇胺0.08-0.12%,羧乙烯基聚合物0.3-0.4%,Arlacel 1651.5-2.5%,防腐剂0.1-0.3%,香精0.1-0.3%,水余量;按常规制作化妆品的方法制得上述配方的乳剂。
实施例10:
本实施例提供一种抗衰老或免疫调节化妆水,其中,按照质量百分比计,化妆水包括:富含寡糖的铁皮石斛原液1-10%,聚丙烯酸钠0.3-0.4%,甘油3.5-4.5%,1,3-丁二醇2-3%,维生素B5 0.4-0.6%,熊果苷0.4-0.6%,EDTA-Na2 0.04-0.06%,去离子水余量;化妆水的制备方法为:将聚丙烯酸钠溶入水中,搅拌,充分溶胀,再加入其余成分,持续搅拌;然后再加入富含寡糖的铁皮石斛原液搅拌后,加去离子水定容,得到化妆水。
较佳的方案为:将聚丙烯酸钠0.35克溶入70ml水中,搅拌,充分溶胀。缓缓加入处方中其余成分,不停搅拌;然后加入本发明的实施例1制备的富含寡糖得铁皮石斛原液10%,搅拌使其混合均匀。去离子水,加至100ml,包装即可。
实施例11:
本实施例提供一种抗衰老或免疫调节修复霜,其中,按照质量百分比计,修复霜包括:甘油5-7%,卡波姆1.4-1.6%,三乙醇胺1.4-1.6%,丙二醇5.5-6.5%,尼伯金乙酯0.15-0.25%,富含寡糖的铁皮石斛原液9-11%,精油0.4-0.6%,去离子水余量;
修复霜的制备方法为:取卡波姆于适量去离子水中,搅匀,静置过夜,使其充分溶胀后,加入甘油,用三乙醇胺调节pH值,使凝胶基质粘稠性增加;另取配方量的富含寡糖的铁皮石斛原液、丙二醇及去离子水,混合均匀,再将卡波姆凝胶加入,加入配方量的精油和尼伯金乙酯,合并搅拌至均匀细腻,加蒸镏水至足量,研磨均匀,得到修复霜。
较佳的方案为:甘油6克,卡波姆1.5克,三乙醇胺1.5克,丙二醇6克,尼伯金乙酯0.2克,本发明的实施例1所得富含寡糖得铁皮石斛原液10%,去离子水适量,加至总重量为100克。制备方法:取卡波姆于适量去离子水中,搅匀,静置过夜,使其充分溶胀后,加入甘油后,用三乙胺调节pH值,使凝胶基质粘稠性增加。另取处方量的丹参酮提取物、丙二醇及去离子水,混合均匀。再将卡波姆凝胶加入,加入0.5%精油,尼伯金乙酯,合并搅拌至均匀细腻,加蒸镏水至足量,研磨均匀,即可。
以上所述,仅是本发明的较佳实施例而已,并非对本发明作任何形式上的限制,依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰,均仍属于本发明技术方案的范围内。
Claims (10)
2.权利要求1所述的一种铁皮石斛寡糖,其特征在于,所述糖苷残基包括半乳糖残基、甘露糖残基和葡萄糖残基;优选的,半乳糖残基、甘露糖残基和葡萄糖残基的摩尔比计为(3~2):(2~1):(2~1),优选为2:1:1。
3.一种铁皮石斛寡糖衍生物,其特征在于,所述铁皮石斛寡糖衍生物为权利要求1或2所述的铁皮石斛寡糖的葡萄糖残基与疏水残基反应生成的;
优选的,所述疏水残基包括直链或支链C1-C18烷基、C1-C18烷基羧酸、C1-C18烷基胺、C1-C18芳基烷基和C1-C18烷基酰胺中的任意一种,或
所述疏水残基包括包括苯甲酰基、苯乙酰基、苯丙酰基中的任意一种。
4.权利要求1或2所述的一种铁皮石斛寡糖在制备抗衰老或免疫调节产品中的应用;优选的,所述产品包括药物、食品、制剂及化妆品;优选的,所述化妆品的类型包括面霜、乳剂、化妆水或修复霜。
5.权利要求3所述的铁皮石斛寡糖衍生物在制备抗衰老或免疫调节产品中的应用;优选的,所述产品包括药物、食品、制剂及化妆品;优选的,所述化妆品的类型包括面霜、乳剂、化妆水或修复霜。
6.权利要求1或2所述的一种铁皮石斛寡糖的提取方法,其特征在于,包括以下步骤:
1)制备铁皮石斛粉末:对铁皮石斛茎进行干燥处理后,再将其粉粹过筛,得到铁皮石斛粉末;
2)制备铁皮石斛水提液:将所述铁皮石斛粉末和水混合后,进行至少一次沸水浴,然后合并水提液,得到铁皮石斛水提液;
3)制备铁皮石斛浓缩水提液:将所述铁皮石斛水提液离心后,再减压浓缩,得到铁皮石斛浓缩水提液;
4)制备复溶液:在所述铁皮石斛浓缩水提液中加乙醇,沉淀,然后离心并弃去上清液;在得到的沉淀中加入水复溶,得到复溶液;
5)制备铁皮石斛寡糖水溶液:对所述复溶液除蛋白后,冷冻干燥得铁皮石斛粗多糖;在所述铁皮石斛粗多糖中加水溶解后,再向其中加入纤维素酶进行反应后,灭活并离心,弃去沉淀,得到铁皮石斛寡糖水溶液;
6)制备铁皮石斛寡糖:将铁皮石斛寡糖水溶液纯化,得到铁皮石斛寡糖。
7.权利要求6所述的一种铁皮石斛寡糖的提取方法,其特征在于,
步骤1)中,优选的,干燥处理的温度为50-60℃;所述干燥处理后的铁皮石斛茎的水分质量含量低于6%;所述过筛的目数为20-40目;
步骤2)中,优选的,所述铁皮石斛粉末和水按照质量体积比1:(50-80)g/mL混合;进行2-3次沸水浴;每次沸水浴的时间为1-2h;
步骤3)中,优选的,离心条件为:3000-4000rpm/min,8-12min,室温;减压浓缩条件为:采用旋转蒸发方式,回收乙醇温度为<50℃,压力为0.7Pa-0.9Pa;铁皮石斛浓缩水提液的料液质量体积比为1:(5-10)g/ml。
8.权利要求7所述的一种铁皮石斛寡糖的提取方法,其特征在于,
步骤4)中,优选的,在所述铁皮石斛浓缩水提液中加入体积浓度为95%的乙醇至混合液的醇浓度以体积百分比计为70%-80%后,进行隔夜沉淀;离心条件为3500-4500rpm,18-22min,室温;所述沉淀和水的重量体积比1:(4-6)g/ml加入水复溶;
步骤5)中,优选的,以Sevage法对所述复溶液除蛋白;冷冻干燥温度为45℃;在所述铁皮石斛粗多糖中加水溶解至4.5-5.5mg/ml;纤维素酶的加入量为所述铁皮石斛粗多糖重量的2%-4%;加入纤维素酶后,进行反应的反应温度为55-65℃、反应时间为2h-4h;通过煮沸25-35min灭活处理;离心条件为3500-4500rpm,15-25min,室温;所述铁皮石斛寡糖水溶液中的寡糖含量大于80%;
步骤6)中,优选的,纯化是采用过G75凝胶柱的方式;铁皮石斛寡糖的纯度为99.86%。
9.权利要求3所述的一种铁皮石斛寡糖衍生物的制备方法,其特征在于,包括以下步骤:
1)将脂肪酸还原成脂肪醇;
2)脂肪醇与铁皮石斛寡糖进行糖苷化。
10.权利要求9所述的一种铁皮石斛寡糖衍生物的制备方法,其特征在于,步骤1)中,反应过程为:将脂肪酸9-11mmol、NaBH4 18-22mmol、AlCl338-42mmol、THF 25-29ml、MeOH 2-4ml混合反应,反应温度为95-105℃,反应时间为7.5-8.5h,产率为88-92%;
步骤2)中,利用还原得到的脂肪醇与铁皮石斛寡糖进行糖苷化反应,反应过程为:醇糖摩尔比1:(8~10),混合后以催化剂十六烷基溴化铵催化,反应温度为110~115℃,反应时间为2.5-3.5h,产率为78-82%。
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114478578A (zh) * | 2021-12-24 | 2022-05-13 | 上海中医药大学 | 测定羧酸酯酶1的特异性生物发光探针底物及其制备方法和应用 |
CN114796245A (zh) * | 2022-04-29 | 2022-07-29 | 上海中医药大学 | 一种石斛寡糖的新用途 |
CN114853824A (zh) * | 2022-04-29 | 2022-08-05 | 上海中医药大学 | 一种石斛寡糖的制备方法 |
WO2022183763A1 (zh) * | 2021-03-05 | 2022-09-09 | 中国科学院昆明植物研究所 | 一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用 |
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---|---|---|---|---|
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101716283A (zh) * | 2009-11-20 | 2010-06-02 | 合肥工业大学 | 铁皮石斛多糖指纹图谱的构建方法 |
CN103113483A (zh) * | 2013-01-24 | 2013-05-22 | 北京航空航天大学 | 一种从铁皮石斛中提取多种活性成分的方法 |
CN108477612A (zh) * | 2018-02-06 | 2018-09-04 | 刘利勇 | 一种包含铁皮石斛纯化提取物的石斛营养粉及制备方法 |
CN109232759A (zh) * | 2018-09-19 | 2019-01-18 | 北京明弘科贸有限责任公司 | 一种石斛小分子多糖提取液的制备工艺及其应用 |
CN109535269A (zh) * | 2018-09-26 | 2019-03-29 | 北京明弘科贸有限责任公司 | 一种石斛小分子多糖提取液的制备工艺及其应用 |
CN110128564A (zh) * | 2019-06-06 | 2019-08-16 | 杭州寿而健健康产品有限公司 | 一种小分子铁皮石斛多糖的提取方法 |
US20200363404A1 (en) * | 2019-05-14 | 2020-11-19 | Hong Kong Baptist University | Chromophore-labeled oligosaccharide markers and methods of use thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107267574B (zh) * | 2017-06-30 | 2020-03-31 | 广东国方医药科技有限公司 | 一种铁皮石斛多糖片段及其提取方法 |
CN109295131B (zh) * | 2017-12-04 | 2021-09-24 | 合肥工业大学 | 一种石斛活性寡糖的受体定位固相酶解制备方法 |
CN108635300A (zh) * | 2018-07-19 | 2018-10-12 | 南京润斛堂生物科技有限公司 | 一种含有小分子石斛多糖的化妆品及制备方法与应用 |
CN113004432B (zh) * | 2021-03-05 | 2022-02-25 | 中国科学院昆明植物研究所 | 一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用 |
-
2021
- 2021-03-05 CN CN202110247117.XA patent/CN113004432B/zh active Active
- 2021-11-09 EP EP21876726.7A patent/EP4082519A4/en active Pending
- 2021-11-09 US US17/788,422 patent/US20230257484A1/en active Pending
- 2021-11-09 KR KR1020227028738A patent/KR20220131532A/ko active Search and Examination
- 2021-11-09 WO PCT/CN2021/129570 patent/WO2022183763A1/zh unknown
- 2021-11-09 JP JP2022523441A patent/JP2023528104A/ja active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101716283A (zh) * | 2009-11-20 | 2010-06-02 | 合肥工业大学 | 铁皮石斛多糖指纹图谱的构建方法 |
CN103113483A (zh) * | 2013-01-24 | 2013-05-22 | 北京航空航天大学 | 一种从铁皮石斛中提取多种活性成分的方法 |
CN108477612A (zh) * | 2018-02-06 | 2018-09-04 | 刘利勇 | 一种包含铁皮石斛纯化提取物的石斛营养粉及制备方法 |
CN109232759A (zh) * | 2018-09-19 | 2019-01-18 | 北京明弘科贸有限责任公司 | 一种石斛小分子多糖提取液的制备工艺及其应用 |
CN109535269A (zh) * | 2018-09-26 | 2019-03-29 | 北京明弘科贸有限责任公司 | 一种石斛小分子多糖提取液的制备工艺及其应用 |
US20200363404A1 (en) * | 2019-05-14 | 2020-11-19 | Hong Kong Baptist University | Chromophore-labeled oligosaccharide markers and methods of use thereof |
CN110128564A (zh) * | 2019-06-06 | 2019-08-16 | 杭州寿而健健康产品有限公司 | 一种小分子铁皮石斛多糖的提取方法 |
Non-Patent Citations (3)
Title |
---|
OFFICINALETAO-BIN HE等: "Structural characterization and immunomodulating activity ofpolysaccharide from Dendrobium officinale", 《INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES》 * |
童微等: "铁皮石斛多糖化学修饰及其对免疫活性的影响", 《食品科学》 * |
薛燕等: "铁皮石斛多糖复合酶法提取工艺及其抗氧化性", 《食品工业科技》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022183763A1 (zh) * | 2021-03-05 | 2022-09-09 | 中国科学院昆明植物研究所 | 一种铁皮石斛寡糖、铁皮石斛寡糖衍生物及其制备方法和应用 |
CN114478578A (zh) * | 2021-12-24 | 2022-05-13 | 上海中医药大学 | 测定羧酸酯酶1的特异性生物发光探针底物及其制备方法和应用 |
CN114478578B (zh) * | 2021-12-24 | 2024-03-29 | 上海中医药大学 | 测定羧酸酯酶1的特异性生物发光探针底物及其制备方法和应用 |
CN114796245A (zh) * | 2022-04-29 | 2022-07-29 | 上海中医药大学 | 一种石斛寡糖的新用途 |
CN114853824A (zh) * | 2022-04-29 | 2022-08-05 | 上海中医药大学 | 一种石斛寡糖的制备方法 |
CN114796245B (zh) * | 2022-04-29 | 2023-11-10 | 上海中医药大学 | 一种石斛寡糖的新用途 |
CN116656758A (zh) * | 2023-06-26 | 2023-08-29 | 上海植纳生物科技有限公司 | 一种石斛寡糖和石斛鲜汁及其制备方法和应用 |
CN116656758B (zh) * | 2023-06-26 | 2024-03-22 | 上海植纳生物科技有限公司 | 一种石斛寡糖和石斛鲜汁及其制备方法和应用 |
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