CN107496490B - 一种淫羊藿红景天制剂及其制备方法 - Google Patents
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Abstract
公开了一种从植物提取糖苷类物质方法,以及包含淫羊藿提取物和红景天提取物的组合物,所述提取物与一般的提取混合物相比,具有特别良好的抗炎效果。所述组合物可以用于制备可增强人体免疫功能、防辐射和抗炎的药品、保健品或饮品。
Description
技术领域
本发明涉及提取技术领域,特别涉及使用多级柱层析分离从淫羊藿提取糖苷类物质方法,以及涉及包含淫羊藿提取物和红景天衍生物的组合物。
背景技术
淫羊藿是我国的传统补益中药,最初记载于《神农本草经》上,其具有补肾壮阳,强健筋骨,祛除风湿的疗效。淫羊藿药材为小檗科植物淫羊藿的干燥叶,现行药典收录的共有箭叶淫羊藿、柔毛淫羊藿和朝鲜淫羊藿等品种更。淫羊藿具有补肾阳、强筋骨、祛风湿之功效。淫羊藿苷为其单体成分之一,具有改善心血管***、调节内分泌、增强免疫力、性激素样等作用,同时在抗肿瘤、抗肝毒等方面也有着积极的治疗作用。
现代药理研究表明,淫羊藿能增加心脑血管血流量,促进造血功能、免疫功能及骨代谢,具有抗衰老、抗肿瘤等功效。
近些年研究发现,淫羊藿中的苷类物质、黄酮类物质和多糖类物质等单体物质,在改善血管内皮细胞功能尤优于传统炮制淫羊藿中药,然而它们的分离提取存在很大困难。
CN101264120B公开了一种淫羊藿黄酮醇苷饮片,由淫羊藿有效部位提取物制成,淫羊藿苷含量为10-20%wt,淫羊藿次苷II含量为2-5%wt,总黄酮含量为40-60%wt,总黄酮包括淫羊藿次苷II、新朝藿苷1、朝藿定K、淫羊藿苷、朝藿苷I、朝藿苷丙、朝藿苷A、新朝藿苷2和金丝桃苷,淫羊藿黄酮醇苷饮片的制备方法包括:称取粉碎后的朝鲜淫羊藿地上部分,用乙醇水溶液回流提取;提取液过滤、合并后减压浓缩,再用乙醇水溶液稀释,静置后离心,上 Diaion-HP20树脂柱,以乙醇水溶液梯度洗脱,收集60-70%v乙醇水溶液洗脱液,减压浓缩至膏状,干燥后粉碎,得淫羊藿黄酮醇苷饮片。
CN101843629A公开了淫羊藿苷和含有淫羊藿苷的淫羊藿黄酮的新用途,具体涉及所述提取物在制备用于治疗、预防、减轻和/或缓解与神经***髓鞘病损有关的疾病和/或病症的药物中的用途,或者在制备用于减轻髓鞘脱失和/或促进髓鞘修复的药物中的用途。
CN104711300A公开了一种淫羊藿素的制备方法,该方法包括将淫羊藿提取物在果胶酶的作用下进行酶解反应,得到淫羊藿素,优选地,所述的果胶酶包含聚半乳糖醛酸酶和***呋喃糖苷酶。
CN101933550A公开了含有淫羊藿的冲剂,该冲剂由淫羊藿,咖啡粉,冬虫夏草或蛹虫草构成,各物料的重量百分比如下:淫羊藿和冬虫夏草或蛹虫草之和占2-99%,咖啡粉1-98%,或者淫羊藿1-95%,冬虫夏草或蛹虫草1-96%,咖啡粉1-98%。
CN104171175A公开了一种淫羊藿茶,其按照下列方法制备而成:a、采集挑选:每年春季采集淫羊藿嫩叶,挑出杂物及老叶;b、杀青:在160℃~200℃杀青1-3分钟;c、揉搓:将杀青后的淫羊藿嫩叶进行揉搓,揉至成条;d、炒干:将揉至成条的淫羊藿嫩叶在130℃-90℃进行炒干,首先经高温130℃炒制,炒至半干时逐渐下调温度至110℃,经炒制再逐渐下调温度至90℃,直至炒干为止。
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CN104688795A公开了一种由淫羊藿制备总黄酮的方法,该方法包括以下步骤:a.首先将淫羊藿干叶通过乙醇溶液进行提取,得到提取液;b.将步骤a 得到的提取液用大孔树脂柱吸附,接着依次用水和乙醇洗脱所述的大孔树脂柱,收集最后一次乙醇洗脱液;c.将步骤b得到的洗脱液干燥,得到所述的总黄酮。
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CN101804156A公开了复方红景天提取物的制备工艺及抗疲劳作用,其将红景天20g-30g、黄精20g-30g、五味子10g-20g、淫羊藿10g-20g、大枣3g-5g,粗粉加入8-10倍量的水浸泡4h-6h后,100℃加热提取,再超声1h-1.5h,温度为30℃,功率为80W,然后用纱布过滤,滤渣再分别用6倍量与4倍量水重复以上步骤各一次,合并三次滤液,真空干燥,加入人参三醇型皂苷0.5g-1g,得复方红景天提取物。
“淫羊藿提取工艺研究”,陈洛怡等,中国现代应用药学,2000(s1):12-14,研究淫羊藿提取工艺,其中以淫羊藿甙含量作为检测指标,选用L9(3~4)正交试验表安排试验,结果表明水煎法与醇提法提取效果相近,淫羊藿采用水煎法,工艺简便,成本低,提取效率高,是较理想的生产工艺。
由上述现有技术可知,在现有技术中尚存在多种缺陷,现有技术中的淫羊藿提取物实际上为多种物质的混合物,其中包含黄酮类成分,十余种藿苷、藿次苷,多种糖苷,木脂素、生物碱和多糖,麦芽酚,沙立苷,槲皮素,淫羊藿苷A,粗毛淫羊藿苷,脱水淫羊藿素,异戊烯山萘酚,银杏双黄酮,异银杏双黄酮,去甲银杏双黄酮,淫羊藿定A,金丝桃苷,还含有一定量的挥发油、棕桐酸、硬脂酸、油酸、亚麻酸。这些物质中,药效成分参差不齐,甚至一些组分药效偏低,从而不仅导致整体药效较低,并且由于一些低效成分反而会影响高药效成分性能的发挥。此外,现有技术中还存在的问题是,虽然有将淫羊藿提取物和红景天提取物混合制备复合制剂的报导,但是通常都是将两种含有复杂成分的提取物混合,不仅效果差,而且协同作用也较差。本领域需要一种高效的淫羊藿和红景天提取物及其制备方法。
发明内容
为同时解决现有技术中存在的上述技术问题,本发明提供了一种从淫羊藿提取糖苷类物质方法,所述糖苷类物质与提取物中的其它成分相比具有相对较高的药理活性,特别是提高免疫力和抗炎功效。另外,还提供了包含淫羊藿提取物和红景天提取物的组合物,通过二者的复配协同作用,能够提高综合药理活性。为此,本发明提供了以下技术方案。
在本发明的一方面,提供了一种从植物提取糖苷类物质方法,该方法使用多级柱层析分离。
优选地,其中所述植物为淫羊藿。
优选地,在所述多级柱层析分离中,第一级柱层析采用反相硅胶柱。
最优选地,所述提取和分离得到的糖苷类物质为下式(I)所示的化合物:
研究表明,该糖苷类化合物与一般黄酮类化合物例如淫羊藿苷A和B相比,其具有更广泛的生物活性,如抗骨质疏松症、雄激素、抗炎和抗癌作用。因此,本申请将该化合物作为目标提取化合物。
就本发明而言,特别优选地,所述式(I)所示的化合物可通过下面方法制得,该方法包括以下步骤:
(1)在室温下用MeOH(优选3×6L,每次浸泡时间为约20h)提取淫羊藿草药粉(优选1.18kg),将合并的提取物减压蒸发得到棕色残余物(162.5g) 即甲醇提取液;
(2)利用反相硅胶柱(例如RP-18硅胶柱),首先使用MeOH-H2O混合溶液对所述残余物进行梯度洗脱,来进行柱色谱分离,优选的洗脱步骤为0:1(1L), 1:9(1L),2:8(1L),3:7(1L),4:6(1L),5:5(2L),6:4(2L),7:3(1L), 1:0(2L),然后使用丙酮(2L),依次得到10个洗脱组分,记为洗脱组份A-J;
(3)将洗脱组分B(例如6.5g)在硅胶柱(优选60cm×5cm)上进行色谱分离,使用CHCl3-MeOH-H2O混合溶液进行梯度洗脱(洗脱梯度优选为20:1:0 (1L),10:1:0(2L),30:8:1(2L)和15:6:1(2.5L)),得到4个洗脱组份,记为洗脱组分B1-B4;
(4)将洗脱组分B2(例如300.2mg)用MeOH-H2O(1:1)在Sephadex LH-20 (优选100cm×3cm)上分离,得到7个次洗脱组分,记为洗脱组分B2.1-B2.7;
(5)将洗脱组分B2.6(例如95.0mg)通过硅胶CC柱(优选80cm×2.5cm),洗脱液为EtOAc-CHCl3-MeOH-H2O(16:8:3:1),将洗脱液减压浓缩至干,得到淡黄色粉末(例如6.1mg),即为式(I)所示化合物。
经HPLC分析,提取物中式(I)所示化合物的纯度为99.7%。经1HNMR 和质谱分析,其与CAS中记载的经表征的已知化合物一致。正离子模式ESI-MS 显示分子离子峰出现在m/z 667([M+Na]+)和1311([2M+Na]+)。IR(KBr):3423, 2940,1660,1605,1512,1450。1HNMR中,在δ(H)7.88(d,J=8.6,H-C(2’,6’))和 7.11(d,J=8.6,H-C(3’,5’))出现的A2B2耦合***显示了B环中对位取代基的存在;在δ(H)6.72(d,J=10.0,H-C(1”),5.68(d,J=10.0,H-C(2”),2.14(s,Me(4”))和 1.45(s,Me(5”))出现的系列氢原子信号显示存在γ,γ-二甲基色烯环。
实验发现,要想分离获得高纯度的式(I)所示化合物或提取物是极其困难的,其中导致难以获得高纯度化合物的一个重要原因是提取过程中蛋白的干扰,另外,一些低效价多糖也是比较难分离的杂质。本申请人通过上述5级柱层析分离,首次获得了极高纯度的式(I)所示化合物。所述5级分离***之间具有密切的层级和配合关系,其设置选择和顺序非常关键。
当然,本领域技术人员可以意识到,其它洗脱组分也可以用来获得其它有价值的物质而不是全部废弃掉。
在本发明的另一方面,提供了一种包含淫羊藿提取物和红景天提取物的组合物,所述淫羊藿提取物为根据上述方法获得的糖苷类物质,优选为(I)所示化合物。还可以在该组合物中加入雪莲提取物、枸杞提取物或其它具有所需药理活性的提取物。
优选地,所述糖苷类物质的纯度大于99.0wt%。更优选地,所述糖苷类物质的纯度大于99.2wt%。最优选地,所述糖苷类物质的纯度大于99.7wt%。
所述红景天提取物优选为红景天苷。红景天苷可以采取本领域的常规方法进行提取。更优选,所述红景天提取物为改性的红景天提取物,最优选地,所述红景天提取物为通过对红景天苷改性获得的下式(II)或(III)所示的化合物:
与一般天然苷类物质相比,式(II)或(III)所示的化合物对正常小鼠的免疫调节作用更明显,由于吸电子基团Cl和F的引入,增强了其清除自由基的能力,可显著增加小鼠特异的抗体分泌细胞数,以50mg/(kg·d)剂量即可增强迟发型超敏反应强度,另外还表现出对异型小鼠的混合淋巴细胞反应及巨噬细胞的吞噬功能,并且在一定程度上可以降低白细胞介素的活性,表明其二者是一种很有前途的免疫调节剂。
具有结构式(II)~(III)的物质可以通过如下方法合成:在反应容器中加入MCM-22分子筛作为选择性催化剂,然后加入氯仿溶剂,再将天然红景天苷与氯代或氟代的乙酰氯(即酰化剂)以1:1~1.3的摩尔比加入到反应溶剂中(天然红景天苷与氯代或氟代的乙酰氯优选均以氯仿溶液形式加入),反应温度为 20-30℃,反应时间为10-30min,分离和干燥即可获得所述化合物。该方法具有收率高、杂质少的优点。尤其是由于MCM-22分子筛的择形作用,可显著降低副反应的发生。
在本发明的另一方面,提供了所述组合物的用途,其用于制备可增强人体免疫功能的药品、保健品或饮品。
优选地,所述药品为复方中药制剂。优选地,所述组合物用于制备口服胶囊、冲剂等。所述保健品包括口腔用品例如咀嚼片或含片。
在本发明的一个优选实施方式中,所述复方中药制剂中,淫羊藿提取物和红景天衍生物的重量比为1:20-20:1。当加入雪莲提取物时,雪莲提取物与淫羊藿提取物的重量比为1:10-1:20。这样的组合物具有特别良好的抗炎、增强免疫力和/或防辐射的功效。
附图说明
图1是根据本申请实施例1的化合物的1HNMR解析图;
图2是根据本申请实施例1的化合物对PTP1B的抑制曲线图。
具体实施方式
实施例1:式(I)所示化合物的提取
采用下面操作提取式(I)所示化合物:(1)在室温下用MeOH(3×6L,每次浸泡时间为约20h)提取淫羊藿草药粉(1.18kg,原料购自吉林省通化市金厂镇),将合并的提取物减压蒸发得到棕色残余物(162.5g)即甲醇提取液;(2) 利用RP-18反相硅胶柱,首先使用MeOH-H2O混合溶液对所述残余物进行梯度洗脱,来进行柱色谱分离,洗脱步骤为0:1(1L),1:9(1L),2:8(1L),3:7(1L), 4:6(1L),5:5(2L),6:4(2L),7:3(1L),1:0(2L),然后使用丙酮(2L),依次得到10个洗脱组分,记为洗脱组份A-J;(3)将6.5g洗脱组分B在硅胶柱 (60cm×5cm)上进行色谱分离,使用用CHCl3-MeOH-H2O混合溶液进行梯度洗脱(洗脱梯度为20:1:0(1L),10:1:0(2L),30:8:1(2L)和15:6:1(2.5L)),得到4个洗脱组份,记为洗脱组分B1-B4;(4)将300.2mg洗脱组分B2用 MeOH-H2O(1:1)在Sephadex LH-20(100cm×3cm)上分离,得到7个次洗脱组分,记为洗脱组分B2.1-B2.7;(5)将95.0mg洗脱组分B2.6通过硅胶CC柱 (80cm×2.5cm),洗脱液为EtOAc-CHCl3-MeOH-H2O(16:8:3:1),将洗脱液减压浓缩至干,得到6.1mg淡黄色粉末,即为式(I)所示化合物。
实施例2:式(I)所示化合物抑制蛋白酪氨酸磷酸酶1B(PTP1B)和α- 葡萄糖苷酶的能力。具体抑制能力如下表1所示:
表1:式(I)所示化合物抑制蛋白酪氨酸磷酸酶1B(PTP1B)和α-葡萄糖苷酶的能力
在该测试中,乌索酸和阿卡波糖用作阳性对照品。测试方法按照标准方法以微量法进行,具体是:本体系反应总体积100μL,PTP1B底物p-NPP溶解于缓冲液(50mmol·L- 1HEPES pH值7.3,100mmol·L-1NaCl,0.1%BSA,1mmol·L-1 DTT)中,pNPP反应终浓度为5mmol·L-1,提取物由DMSO溶解,取酶液0.5~1μL,由250μL PBS缓冲液稀释并充分混匀,取稀释好的酶液160μL加至96孔板,再加入DMSO(提取物溶剂)1μL,柔和混匀,同时将PTP1B与提取物加入96 孔板室温孵育5min后加入35mmol·L-1p-NPP 20μL,37℃避光反应30min,0.5mol·L-1氢氧化钠终止反应,酶标仪在波长405nm处读取吸光度(A)值,按照标准公式计算相应半数抑制浓度(IC50)值;同时还制作所述化合物对PTP1B的抑制曲线(参见图2)。
实施例3:包含淫羊藿提取物和红景天提取物的胶囊的制造
包含实施例1的淫羊藿提取物和红景天提取物的胶囊制造方法,其中所述红景天提取物为式(II)所示化合物,淫羊藿提取物和红景天衍生物的重量比为 5:1,每个胶囊含有0.1g内容物。
实施例4:测试实施例3的胶囊对小鼠耳廓肿胀的抗炎作用
取昆明小鼠40只,体重150-220g,雌雄各半,随机分为5组,即模型组,常规提取物胶囊组(0.08g·kg-1,对照组,其中淫羊藿提取物按照CN101264120B 中记载的方法获得,其余与实施例3相同),实施例3胶囊组(0.08g·kg-1),每天灌胃给药1次,连续4d,在末次给药后30min,每只小鼠右耳廓两面涂二甲苯 20μL,造成小鼠耳廓肿胀模型,以左耳作对照,20min后脱颈椎处死小鼠,沿耳廓基线剪下两耳,用直径6mm打孔器分别在左右耳对称部位打下圆形耳片,精密称重,以其差值作为炎性肿胀度(mg),并计算肿胀抑制率。
肿胀抑制率=(模型组肿胀度-给药组肿胀度)/模型组肿胀度×100%
与模型组小鼠耳肿胀度比较,实施例3的复方胶囊组与对照胶囊组各剂量组相比对二甲苯引起的小鼠耳肿胀的抑制作用有显著性差异,表明提示复方雪莲胶囊能减轻二甲苯致小鼠耳廓肿胀度,有一定的抗炎作用,见下表2:
表2:复方胶囊对二甲苯致小鼠耳廓肿胀的影响
组别 | 剂量/g·kg-1 | 肿胀度/mg | 抑制率/% |
模型组 | - | 8.55±1.22 | - |
实施例3 | 0.08 | 4.01±0.92 | 53.10% |
对照组 | 0.08 | 5.96±1.23 | 30.29% |
由上面实施例清楚地可以看出,本发明的淫羊藿提取物对PTP1B)和α-葡萄糖苷酶具有良好的抑制作用,并且相对于现有技术中的提取物(即粗提取物,多种成分的混合物)相比,有明显更好的抗炎效果。
本书面描述使用实例来公开本发明,包括最佳模式,且还使本领域技术人员能够制造和使用本发明。本发明的可授予专利的范围由权利要求书限定,且可以包括本领域技术人员想到的其它实例。如果这种其它实例具有不异于权利要求书的字面语言的结构元素,或者如果这种其它实例包括与权利要求书的字面语言无实质性差异的等效结构元素,则这种其它实例旨在处于权利要求书的范围之内。在不会造成不一致的程度下,通过参考将本文中参考的所有引用之处并入本文中。
Claims (5)
1.一种从淫羊藿提取糖苷类物质方法,该方法使用多级柱层析分离,所述提取和分离得到的糖苷类物质为下式(I)所示的化合物:
该方法包括以下步骤:
(1)在室温下用MeOH提取淫羊藿草药粉,将合并的提取物减压蒸发得到棕色残余物即甲醇提取液;
(2)利用反相硅胶柱,首先使用MeOH-H2O混合溶液对所述残余物进行梯度洗脱,来进行柱色谱分离,洗脱步骤为0:1共1L,1:9共1L,2:8共1L,3:7共1L,4:6共1L,5:5共2L,6:4共2L,7:3共1L,1:0共2L,然后使用丙酮2L,依次得到10个洗脱组分,记为洗脱组份A-J;
(3)将洗脱组分B在硅胶柱上进行色谱分离,使用CHCl3-MeOH-H2O混合溶液进行梯度洗脱,洗脱梯度为20:1:0共1L,10:1:0共2L,30:8:1共2L和15:6:1共2.5L,得到4个洗脱组份,记为洗脱组分B1-B4;
(4)将洗脱组分B2用1:1的MeOH-H2O在Sephadex LH-20上分离,得到7个次洗脱组分,记为洗脱组分B2.1-B2.7;
(5)将洗脱组分B2.6通过硅胶CC柱,洗脱液为16:8:3:1的EtOAc-CHCl3-MeOH-H2O,将洗脱液减压浓缩至干,得到淡黄色粉末,即为式(I)所示化合物。
2.一种包含淫羊藿提取物和红景天提取物的组合物,所述淫羊藿提取物为根据权利要求1所述的方法获得的糖苷类物质,所述红景天提取物为下式(II)所示的化合物:
3.根据权利要求2所述的组合物,其中所述糖苷类物质的纯度大于99.0wt%。
4.根据权利要求3所述的组合物,其中所述糖苷类物质的纯度大于99.2wt%。
5.根据权利要求4所述的组合物,其中所述糖苷类物质的纯度大于99.7wt%。
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