CN113667033A - 肉桂均一多糖及其降血糖用途 - Google Patents
肉桂均一多糖及其降血糖用途 Download PDFInfo
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- CN113667033A CN113667033A CN202111065664.2A CN202111065664A CN113667033A CN 113667033 A CN113667033 A CN 113667033A CN 202111065664 A CN202111065664 A CN 202111065664A CN 113667033 A CN113667033 A CN 113667033A
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- homopolysaccharide
- glucosidase
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- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
本发明属于天然产物开发领域,涉及提供天然产物中具有降血糖作用的活性成分,具体涉及肉桂中的天然均一多糖及其在制备天然降血糖药物中的用途;本发明从肉桂中分离得到一个均一多糖CNP2,对α‑淀粉酶抑制作用的IC50值为253μg/mL,对α‑葡萄糖苷酶抑制作用的IC50值为155μg/mL。本发明的肉桂中的天然均一多糖可进一步作为活性成分,制备天然降血糖药物。
Description
技术领域
本发明属于天然产物开发领域,涉及多糖,具体涉及肉桂中的天然均一多糖,及其在降血糖方面的用途。
背景技术
高血糖会引起血管内皮功能紊乱,导致功能及结构性的血管狭窄、阻塞,组织器官缺血、缺氧、损害;还会刺激多种细胞合成和分泌单核细胞趋化(粘附)因子,从而促进细胞与血管内皮及细胞间的粘附,加重炎症发展及血栓形成,甚至还会诱发各种糖尿病并发症,如酮症酸中毒、慢性肾衰竭、足部溃疡和眼睛失明等。目前我国高血糖人数日益增多,并且有明显的年轻化、低龄化与基层化的趋势。临床上,最常用的是胰岛素注射或化学药物治疗,但都因其具有较大的副作用而限制了长期用药。因此,成分明确、结构明确及安全高效的天然降血糖活性物具有诱人的市场前景和开发价值。
肉桂(Cinnamomum cassia Presl)是中国特有的樟科樟属树种,主要分布在我国的广西、广东和云南等地。肉桂的化学成分包括挥发油、黄酮类化合物、倍半萜、二萜及糖苷类化合物、多糖类化合物和其他物质。研究表明肉桂具有抗氧化、抗菌、抗肿瘤、抗溃疡、降血脂、加强消化功能以及镇痛的作用。多个文献提示肉桂水提物中的非挥发性成分如多糖,具有降血糖活性。研究表明,肉桂水提取物中的活性成分能够通过激活胰岛素受体、增加糖原合成酶的活性等多种机制发挥降血糖作用。此外,研究发现肉桂水提取物还可以通过抑制消化道碳水化合物的消化、调控肝糖原异生、调节转运蛋白等途径协同发挥降血糖作用。中国专利文献CN 110940746A、CN106397624A公布了肉桂多糖的制备方法及其测定方法,主要研究对象为肉桂粗多糖。中国专利文献CN 112891394A肉桂提取物在制备降血糖药物中的应用,主要研究对象为肉桂提取物。我们结合离子交换层析和凝胶柱层析从肉桂水提物中分离制备出具备降血糖活性的均一多糖,迄今为止尚未发现有关该均一多糖的分离制备及其降血糖活性的文献报道。
发明内容
本发明目的是提供天然产物中具有降血糖的活性成分,具体涉及肉桂中的天然均一多糖及其制备天然降血糖药物的用途;尤其涉及肉桂均一多糖CNP2及其制备方法和在制备天然降血糖药物中的用途。
本发明对肉桂的水提物进行分离得到一个均一的多糖,命名为CNP2,经体外实验证实,所述的肉桂均一多糖具有显著的降血糖活性,且与阿卡波糖的活性相当,可进一步开发制备天然降血糖药物。
本发明中,所述的肉桂是樟科植物肉桂Cinnamomum cassia Presl的干燥皮或枝叶或任意组合。
本发明所述的肉桂均一多糖CNP2具有如下结构特征:
CNP2为主要由葡萄糖(Glc)组成的均一多糖;分子量1166g/mol;聚合物分散指数为1.334;糖含量为98.55%;CNP连接方式主要为→4)Glu(1→,Glu(1→和→6)Glu(1→。
本发明所述的肉桂均一多糖CNP2通过下述方法制备:
肉桂Cinnamomum cassia Presl的干燥皮或枝叶或任意组合,粉碎,加水煎煮两次,第一次3h,第二次2h,滤过,滤液合并,滤液浓缩至稠膏状,冷冻干燥,得到肉桂水提物;将肉桂水提物以水复溶,加入Sevage试剂,水提物溶液与Sevage试剂的体积比为4∶1,混合振荡20min,然后离心,保留上层清液,重复上述步骤4次,合并上层清液,浓缩,得到肉桂粗多糖浓缩液;将肉桂粗多糖浓缩液借助DEAE纤维素DE-52离子交换树脂进行初步分离,依次用蒸馏水、0.2、0.4、0.8、1.2、2.0mol/L的氯化钠进行梯度洗脱,流速为0.8mL/min,收集各流份,根据糖显色反应和紫外检测的结果合并相同流分,浓缩得2个次级组分:CP1和CP2。
将CP2浓缩液借助丙烯葡聚糖凝胶S-300层析柱(1.2×70cm)进一步分离,用氯化钠水溶液洗脱,流速为0.4mL/min,4.5mL/管收集,收集各流份,苯酚硫酸法检测,根据糖显色反应和紫外检测的结果合并相同流分,浓缩,冷冻干燥,得到1个次级组分:CNP2。
经体外试验证实,CNP2对α-淀粉酶和α-葡萄糖苷酶具有明显的抑制作用,即有明显的降血糖活性。
CNP2对α-淀粉酶抑制作用的IC50值为253μg/mL,对α-淀粉酶抑制率的最高值达到58%;CNP2对α-葡萄糖苷酶抑制作用的IC50值为155μg/mL,对α-葡萄糖苷酶抑制率的最高值达到68%。
本发明所提供的肉桂均一多糖CNP2,可与药学上可接受的载体混合,用于制备有助于降血糖的食品添加剂,用于制备有助于降血糖的保健品、药物。
本发明肉桂均一多糖CNP2可以作为活性部位与其它天然提取物/有效部位或相关化学合成药物与药学上可接受的赋型剂或辅料一起用于制备药物组合物,该药物组合物可采用制剂学的常规方法制备成各种剂型,如胶囊、片剂、丸剂、口服液、颗粒剂、酊剂、缓释剂等。
本发明的制备方法为条件温和、高效、环保的柱层析方式,该方法简单易行,具有很强的推广应用价值。
附图说明
图1为本发明实例1中离子交换层析和凝胶柱层析曲线。其中,a:肉桂粗多糖的离子交换层析曲线;b:CP2的凝胶柱层析曲线。
图2为本发明实例2中CNP2的GPC色谱图。
图3为本发明实例2中PMP衍生化产物的液相色谱图。其中,a:单糖对照品的PMP衍生化产物,b:CNP2的PMP衍生化产物,1.甘露糖,2.半乳糖,3.葡萄糖,4.木糖,5.岩藻糖。
图4为本发明实例3和实例4中CNP2的体外降血糖活性图。
具体实施方式
实例1、本发明肉桂均一多糖CNP的分离制备
取肉桂的干燥皮或枝叶或任意组合1Kg,粉碎,加水煎煮两次,第一次3h,第二次2h,滤过,滤液合并,滤液浓缩至稠膏状,冷冻干燥,得到肉桂水提物;将3.2g肉桂水提物以160mL水复溶,加入Sevage试剂,水提物溶液与Sevage试剂的体积比为4∶1,混合振荡20min,然后离心,保留上层清液,重复上述步骤4次,合并上层清液,浓缩,得到72mg/mL的肉桂粗多糖浓缩液;取1.5mL肉桂粗多糖浓缩液,借助DEAE纤维素DE-52离子交换树脂进行初步分离,依次用蒸馏水、0.2、0.4、0.8、1.2、2.0mol/L的氯化钠进行梯度洗脱,流速为0.8mL/min,9mL/管收集,收集各流份,根据糖显色反应和紫外检测的结果合并相同流分,浓缩,得2个次级组分:CP1和CP2。
取500μL CP2浓缩液(96mg/mL),用丙烯葡聚糖凝胶S-300层析柱(1.2×70cm)进一步分离,用0.2mol/L的氯化钠水溶液洗脱,流速为0.4mL/min,4.5mL/管收集,收集各流份,苯酚硫酸法检测,根据糖显色反应和紫外检测的结果合并相同流分,浓缩,冷冻干燥,得到1个均一组分CNP2(9.7mg)。
实例2、本发明肉桂均一多糖CNP2的结构表征。
(1)分子质量测定
采用凝胶排渗透色谱法(GPC)对CNP2的重均分子量进行测定。色谱条件:流速为1mL/min,柱温30℃,进样量50μL,运行时间30min,示差折光检测器,以标准葡聚糖的保留时间和分子质量各取自然对数绘制标准曲线,计算纯化多糖的分子质量。
CNP2重均分子量(Mw)为1026g/mol,数均分子量(Mn)为824g/mol,Z均分子量(Mz)为1851g/mol,聚合物分散指数(PDI)为1.245。
(2)总糖含量测定
苯酚-硫酸法测定CNP的总糖含量为98.55%。
(3)糖组成分析
取甘露糖、半乳糖、葡萄糖、木糖、岩藻糖用蒸馏水配置成1mg/mL的混合对照品,取混合对照品400μL,加0.5mol/L PMP甲醇溶液450μL,0.3mol/L氢氧化钠450μL,涡旋混合,70℃水浴30min,放冷至室温,加入0.3mol/L盐酸450μL,涡旋混合,加0.1mol/L乙酸铵溶液稀释至2mL,加1mL氯仿,充分震荡,静置分层,除去下层氯仿,用氯仿同法处理3次,用10000转/min的离心,取上清,进行色谱检测。色谱柱条件为柱温箱为35℃,流速为1mL/min,紫外检测波长为245nm,进样量为5μL,流动相A为0.02mol/LKH2PO4缓冲溶液,B为乙腈,洗脱条件为0min(15%B),10min(20%B),50min(25%B),60min(20%B),70min(15%B)。
取4mg CNP2置于10mL的离心管中,加入1mL盐酸溶液(6mol/L),在70℃水浴中加热30min,冷却,加氢氧化钠(200g/L)至中性,加水至刻度(4mL)的位置,混匀,过滤,继续取滤液。参照上述对照品的PMP衍生方法进行衍生化。
CNP2是主要由葡萄糖组成的多糖。
(4)糖链结构分析
取5mg CNP2溶于1.5mL DMSO中,超声处理30min,待样品溶解后,加入60mg研磨成粉末的氢氧化钠,超声30min,之后向样品中加入450μL的碘甲烷,超声30min,再加入450μL碘甲烷,超声30min,加水5mL终止甲基化,然后用等体积的氯仿萃取一次,之后用等量的水进行洗涤5次,最后用氮气吹干留下的氯仿溶剂,吹干之后向其中加入1mL的甲醇,继续氮吹,重复三次,加入1.25mL 6mol/L盐酸溶液70℃下反应30min,冷却、旋转蒸发至干燥,旋蒸温度为45℃,然后再加入1mL甲醇,旋转蒸发至干燥,即可完成甲基化。向甲基化产物中加入2mL新配置的25mg/mL的硼氢化钠室温反应2h,期间震荡数次,逐滴加入乙酸中和,pH试纸检验,加入0.1mL甲醇,旋转蒸发至干燥,即可完成还原。向还原产物中加入12mL新配置的吡啶/乙酸酐(1∶1),100℃下反应1h,冷却至室温,旋转蒸发至干燥,然后加入甲醇4mL(每次2mL,重复两次),旋转蒸发至干燥,最后加入2mL二氯甲烷取出液体,离心,进行GC-MS分析。
将谱库数据与CNP数据进行匹配,发现CNP的连接方式主要为→4)Glu(1→,Glu(1→和→6)Glu(1→。
实例3、本发明肉桂均一多糖CNP2的α-淀粉酶抑制作用。
α-淀粉酶能够特异性地水解淀粉,因此α-淀粉酶抑制剂是国内外开发的一类新型口服抗糖尿病药物。当α-淀粉酶的活性受到抑制后,淀粉的水解产物(还原糖)相应减少,利用3,5-二硝基水杨酸与还原糖反应,产物显示出红棕色,在540nm处有强吸收,呈现的颜色越浅,即吸光度越低,表明CNP2的抑制作用越强。向0.25mL不同浓度的CNP2溶液(0.01、0.02、0.05、0.10、0.15、0.20、0.25、0.30、0.50、1.00、1.50和2.00g/L)中分别加入0.25mLα-淀粉酶稀释液,37℃孵育15min,再加入0.5mL 2%的可溶性淀粉溶液,37℃反应5min后加入1.0mL DNS试剂,沸水浴5min,冰浴5min,使用蒸馏水定容至10mL,在540nm处使用酶标仪进行吸光度的测定。以单蒸水作为空白对照,以阿卡波糖作为阳性对照,测定值为每份样品三次平行试验后的平均值,计算CNP2的α-淀粉酶抑制率。
在0.01-2g/L的浓度范围内,随质量浓度增加,CNP2对α-淀粉酶抑制活性的上升速度稍慢于阿卡波糖。CNP2对α-淀粉酶抑制作用的IC50值为253μg/mL,对α-淀粉酶抑制率的最高值达到58%。
实例4、本发明肉桂均一多糖CNP2的α-葡萄糖苷酶抑制作用。
α-葡萄糖苷酶能够特异性地水解葡萄糖。以对硝基苯-β-D-葡萄糖醛酸(PNPG)作为底物,当α-葡萄糖苷酶的活性受到抑制后,水解产物相应减少,产物在405nm处有强吸收,吸光度越低,表明CNP2的抑制作用越强。向0.06mL不同浓度的CNP2溶液(0.01、0.02、0.05、0.10、0.15、0.20、0.25、0.30、0.50、1.00、1.50和2.00g/L)中分别加入0.05mL α-葡萄糖苷酶稀释液,37℃孵育10min,再加入0.05mL 5.0mmol/L的PNPG溶液,37℃反应20min后加入0.16mL 0.2mol/L的Na2CO3溶液,在405nm处使用酶标仪进行吸光度的测定。以蒸馏水作为空白对照,以阿卡波糖作为阳性对照,测定值为每份样品三次平行试验后的平均值,计算CNP2的α-葡萄糖苷酶抑制率。
在0.01-2.00g/L的浓度范围内,阿卡波糖和CNP2均是随着浓度的增加,对α-葡萄糖苷酶的抑制作用逐渐增加,CNP2虽然在低浓度下,对α-葡萄糖苷酶的抑制作用不及阿卡波糖,但是在高浓度时对α-葡萄糖苷酶的抑制作用与阿卡波糖相当。CNP2对α-葡萄糖苷酶抑制作用的IC50值为155μg/mL,对α-葡萄糖苷酶抑制率的最高值达到68%。因此,CNP2是一种较强的α-葡萄糖苷酶抑制剂,并显示明显的剂量依赖性。
Claims (5)
1.肉桂均一多糖在制备天然降血糖药物中的用途:所述的肉桂均一多糖为CNP2;
其中,CNP2的结构特征为:CNP2主要由葡萄糖组成的均一多糖,分子量1166g/mol,聚合物分散指数为1.334,糖含量为98.55%,CNP中单糖的连接方式主要为→4)Glu(1→,Glu(1→和→6)Glu(1→。
2.按权利要求1所述的用途,其特征在于,所述的肉桂均一多糖CNP2对α-淀粉酶和α-葡萄糖苷酶具有显著的抑制作用。
3.按权利要求2所述的用途,其特征在于,所述的肉桂均一多糖CNP2对α-淀粉酶抑制作用IC50值为253μg/mL,对α-淀粉酶抑制率的最高值达到58%。
4.按权利要求2所述的用途,其特征在于,所述的肉桂均一多糖CNP2对α-葡萄糖苷酶抑制作用IC50值为155μg/mL,对α-葡萄糖苷酶抑制率的最高值达到68%。
5.如上任一权利要求所述肉桂均一多糖CNP2在制备有助于降血糖的药物或食品添加剂或保健品中的应用。
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VOLNEI BRITO DE SOUZA等: "Functional properties and encapsulation of a proanthocyanidin-rich cinnamon extract (Cinnamomum zeylanicum) by complex coacervation using gelatin and different polysaccharides", 《FOOD HYDROCOLLOIDS》 * |
VOLNEI BRITO DE SOUZA等: "Functional properties and encapsulation of a proanthocyanidin-rich cinnamon extract (Cinnamomum zeylanicum) by complex coacervation using gelatin and different polysaccharides", 《FOOD HYDROCOLLOIDS》, vol. 77, 7 October 2017 (2017-10-07), pages 297 - 306 * |
于峰等: "肉桂多糖对四氧嘧啶致实验性糖尿病小鼠降糖作用的研究", 《食品与药品》 * |
于峰等: "肉桂多糖对四氧嘧啶致实验性糖尿病小鼠降糖作用的研究", 《食品与药品》, vol. 11, no. 11, 10 November 2009 (2009-11-10), pages 1 - 3 * |
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