CN103626732B - 一种促凝血补骨脂有效成分及其提取分离方法、应用 - Google Patents
一种促凝血补骨脂有效成分及其提取分离方法、应用 Download PDFInfo
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Abstract
本发明属于中药提取技术领域,具体涉及一种促凝血补骨脂有效成分及其提取分离、应用。该促凝血补骨脂有效成分由补骨脂中提取分离得到,同时,该有效成分可以缩短血浆复钙时间,从而起到促凝血的作用,可应用于制备促凝血药物。
Description
技术领域
本发明属于中药提取技术领域,具体涉及一种促凝血补骨脂有效成分及其提取分离方法、应用。
背景技术
补骨脂PsoraleaeFructus为豆科植物补骨脂PsoraleacorylifoliaLinn.的干燥果实,又名破故纸、黑故子等,为常用中药,味辛、苦、性温,归肾、脾经,具有补肾助阳,纳气平喘,温脾止泻的功效。现代研究表明,补骨脂含黄酮类、香豆素类、脂肪酸类和单萜酚类等多种化学成分,具有抗氧化、降血糖、扩张血管、保肝、抗肿瘤、抗菌、抗病毒、雌激素样和抑制α-葡萄糖苷酶等作用。
补骨脂甲素(bavachin),别名:补骨脂二氢黄酮;分子式:C20H20O4;分子量:324.37;CAS登录号:19879-32-4;本品为一种查尔酮类化合物,其开环生成的查耳酮具有扩张冠脉的作用;能显著提高ALP活性,并能促进骨细胞的增殖和分化的作用,可用于骨质疏松的治疗。另外,补骨脂甲素对猪油有一定的抗氧化作用;能直接抑制sinilan病毒SV40DNA聚合酶的复制;其为补骨脂的主要抑菌活性成分,对苹果腐烂病菌具有很高的抑制活性,其EC50为6.144g/L,EC90为89.631g/L,显示出一定的农用价值。此外,补骨脂甲素有较强的由于毒性所至的抗诱变活性。
大豆苷元(daidzein),别名:大豆甙元、黄豆苷元、大豆素、大豆黄酮;分子式:C15H10O4;分子量:254.24;CAS登录号:486-66-8;本品是一种异黄酮类植物雌激素,呈白色粉状,无毒、无味、不溶于水,在醇、酮类溶剂中有一定的溶解度,极易溶于二甲亚砜中,主要存在于黄豆、鹰嘴豆、小扁豆和蚕豆等豆类中,具有抗氧化、抗动脉粥样硬化、抑制血管平滑肌细胞增殖、抗心律失常、保护急性心肌缺血和脑缺血、弱雌激素样(在内源性雌激素水平低时)与抗雌激素样作用(体内雌激素水平较高时)、免疫调节、抗肿瘤、抑制前列腺增生等作用。另有研究证实可抑制嗜酒大鼠的酒精消耗,显著抑制豚鼠离体胆囊肌条自发性收缩活动,使收缩力降低,紧张性下降,还可对抗乙酰胆碱、组胺引起的离体胆囊肌条收缩运动。目前,大豆苷元主要以口服制剂应用,用于高血压、冠心病、骨质疏松、前列腺癌、乳腺癌、脑血栓、眩晕症、突发性耳聋的辅助治疗,也可用于妇女更年期综合征。
紫云英苷(astragalin),别名:黄芪苷、莰非醇-3-O-葡萄糖苷、山柰酚-3-葡萄糖苷、百蕊草素Ⅱ;分子式:C21H20O11;分子量:448.38;CAS登录号:480-10-4,具有降血压、解痉、利尿、利胆和镇咳剂等作用。
血液为人体重要的物质,临床上各种原因引起的出血较为常见,如不及时有效的制止,致使血液耗损,而造成机体衰弱,甚至危及生命。一些临床症状,如①先天性缺陷症:凝血因子Ⅷ、Ⅸ、Ⅺ先天性缺乏或蛋白分子异常症、凝血因子Ⅶ、Ⅹ、Ⅴ先天性缺乏症或蛋白分子异常症、纤维蛋白原或凝血酶原先天性缺乏症或蛋白分子异常症。②获得性缺乏症:严重肝病使凝血因子合成减少,如重症肝炎、慢性肝炎、肝硬化;维生素K缺乏或利用障碍,如吸收不良综合症、脂肪泻、阻塞性黄疸、广谱抗生素治疗、口服抗凝剂;消耗过多,如原发性或继发性纤溶亢进。③循环抗凝物增加或肝素治疗等均可导致血浆复钙时间延长,使血液不停地流。止血药可通过收缩小动脉及毛细血管,或增强血小板功能,或加速、加强血液凝固过程,或抑制血块溶解过程而产生止血作用。目前临床应用的止血药除少量传统药物如维生素K、氨甲环酸、卡巴克络等,大部分为生化药物如从动物血中提取的凝血酶、从动物器官中提取的抑肽酶,使用这些药品可能会发生过敏、出现血清肌酐一过性增高等不良反应。
目前尚无来自于补骨脂中补骨脂甲素、大豆苷元和紫云英苷对血浆复钙时间影响的报道。
发明内容
本发明的目的在于提供一种促凝血补骨脂有效成分,同时提供一种促凝血补骨脂有效成分的提取分离方法和应用。
为了实现以上目的,本发明采用以下技术方案:
一种促凝血补骨脂有效成分的提取分离方法,包括以下步骤:
1)补骨脂粉碎,用甲醇浸提,浸提液合并、过滤、浓缩得补骨脂甲醇浸膏,补骨脂甲醇浸膏分散于(75-85%v/v)甲醇水溶液中,依次用石油醚、乙酸乙酯、正丁醇萃取,回收溶剂,所得乙酸乙酯萃取物即为乙酸乙酯部位,所得正丁醇萃取物即为正丁醇部位;
2)乙酸乙酯部位进行200~300目硅胶柱色谱,用石油醚-乙酸乙酯梯度洗脱,体积比例为80:1~5:5,以TLC检测合并,各组分反复经硅胶H柱色谱、LC3000型高效液相柱色谱、SephadexLH-20柱色谱和重结晶得到化合物1和化合物2;
3)正丁醇部位经反复硅胶柱色谱,用氯仿-甲醇梯度洗脱,体积比例为100:1~7:3,经LC3000型高效液相柱色谱、SephadexLH-20柱色谱分离得到化合物3。
按照以上提取分离方法得到的促凝血补骨脂有效成分。
促凝血补骨脂有效成分在促凝血方面的应用。
促凝血补骨脂有效成分在制备促凝血药物方面的应用。
所述补骨脂甲醇浸膏的具体制备方法为:补骨脂粉碎后,用甲醇(90%v/v以上)室温浸提2-3次,每次2-4d,浸提液合并、过滤、浓缩得补骨脂甲醇浸膏。
化合物1、2、3分别是补骨脂甲素、大豆苷元和紫云英苷,其结构如下:
。
本发明采用特殊的方法从补骨脂中提取分离出了有效成分,同时,本发明采用体外血浆复钙时间法对有效成分的体外凝血效果进行了考察,结果表明,有效成分可以缩短血浆复钙时间,从而起到促凝血的作用,可应用于制备促凝血药物。
具体实施方式
实施例1
促凝血补骨脂有效成分的提取分离方法:
(1)补骨脂1kg,用甲醇室温冷浸提取3次,每次3d,提取液合并、过滤、浓缩,得甲醇总浸膏;
(2)将甲醇总浸膏分散于80%甲醇水中,依次用石油醚、乙酸乙酯和正丁醇萃取,回收溶剂,得到补骨脂石油醚部位30.3g、乙酸乙酯部位60.2g和正丁醇部位50.6g;
(3)乙酸乙酯部位进行200~300目硅胶柱色谱,用石油醚-乙酸乙酯梯度洗脱(体积比80:1~5:5),以TLC检测合并,得到5个组分,各组分反复经硅胶H柱色谱、LC3000型高效液相柱色谱、SephadexLH-20柱色谱和重结晶得到化合物1和2;
(4)正丁醇部位经反复硅胶柱色谱,氯仿-甲醇梯度洗脱,体积比例为100:1~7:3,经LC3000型高效液相柱色谱、SephadexLH-20柱色谱分离得到化合物3。
运用多种谱学技术鉴定结构如下:
化合物1为补骨脂甲素:无色结晶,mp203~204.5℃;EI-MSm/z325[M+1]+。1H-NMR(CDCl3,400MHz)δ:7.6(1H,s,H-5),7.2(2H,d,J=8.4,H-2′6′),6.8(2H,d,J=8.4,H-3′,5′),3.3(1H,d,J=1.1,H-2),3.15(2H,d,J=7.7,CH2),2.94(1H,dd,J=13.5,16.8,H-3b),2.64(1H,dd,J=2.5,16.7,H-3a),1.65(3H,s,11b-CH3),1.60(3H,s,11a-CH3)。
化合物2为大豆苷元:白色粉末,mp319~321℃;EI-MSm/z254[M]+。1H-NMR(DMSO-d 6 ,400MHz)δ:8.30(1H,s,H-2),7.95(1H,d,J=8.5,H-5),7.35(2H,d,J=8.5,H-2′6′),6.96(1H,dd,J=8.5,2.5,H-6),6.86(1H,d,J=2.5,H-8),6.8(2H,d,J=8.41,H-3′5′);13C-NMR(DMSO-d 6 ,100MHz)δ:174.68(C-4),162.48(C-7),157.41(C-9),157.15(C-4′),152.84(C-2),130.07(C-2′,6′),127.29(C-5),123.46(C-1′),122.52(C-3),116.62(C-10),115.10(C-6),114.92(C-3′,5′),102.08(C-8)。
化合物3为紫云英苷:黄色针状结晶,mp170~172℃;ESI-MSm/z447[M-H]-。1H-NMR(DMSO-d6,400MHz)δ:7.89(2H,d,J=8.5,H-2′6′),7.18(2H,d,J=8.5,H-3′5′),6.82(1H,s,H-8),6.45(1H,s,H-6),4.44(1H,d,J=3.0,H-1′);13C-NMR(DMSO-d6,100MHz)δ:161.4(C-2),137.2(C-3),181.4(C-4),160.1(C-5),106.0(C-6),167.4(C-7),97.4(C-8),166.0(C-9),107.1(C-10),124.3(C-1′),131.5(C-2′,6′),116.1(C-3′5′),164.7(C-4′),101.8,75.4,78.7,74.3,80.1,65.3(3-葡萄糖上的碳信号)。
效果实验:
化合物1、2、3的凝血作用实验。
方法:家兔体外血浆复钙时间
仪器和材料:TGL-16高速离心机(江苏金坛中大仪器厂)、秒表计时器、LRH-150生化培养箱(上海一恒科技有限公司)、注射生理盐水(山东齐都药业有限公司,2012053107)、维生素k1注射液(天津药业集团新郑股份有限公司,1109051)、注射用灯盏花素(湖南恒生制药有限公司,20110202)、38g/L枸橼酸钠溶液(自制)、2.775g/L氯化钙溶液(自制)。
实验动物:獭兔,雄性,体重2.0-2.5kg。
样品溶液的配制:称取实施例1化合物1、化合物2和化合物3各1mg作为样品,分别加入溶剂(乙醇:丙二醇:生理盐水体积比=1:1:3)1mL,混悬,超声至溶解或分散均匀形成溶液,备用。
药品溶液配制:量取一定体积的维生素k1注射液,加入一定体积的溶剂(乙醇:丙二醇:生理盐水体积比=1:1:3),配成维生素k1浓度为1mg/mL溶液;称取注射用灯盏花素各1mg,加入溶剂(乙醇:丙二醇:生理盐水体积比=1:1:3)1mL,混悬,超声至溶解或分散均匀,备用。
取家兔耳缘静脉取血3.6mL,加枸橼酸钠溶液400μL,混匀,1000r/min离心15min,取上清液(下述血浆)备用。样品组加入血浆0.1mL及样品溶液0.1mL,阳性对照组加入血浆0.1mL及药品溶液0.1mL,空白组加入血浆0.1mL及空白溶剂(乙醇:丙二醇:生理盐水体积比=1:1:3)0.1mL。各组于37℃温育1min后分别向每管加入2.775g/LCaCl2溶液0.1mL,计时,直到检测到弥漫性蛋白颗粒时停止计时,维生素K1、灯盏花素对照组重复3次,样品组重复6次,求算术平均值和标准差,即为血浆复钙时间。结果采用平均值和标准差表示,采用SPSS17.0软件单因素方差分析法(One-WayANOVA)进行统计学分析。测定结果详见表1。
表1
注:样品组与空白组相比:△ P<0.05,△△ P<0.01,△△△ P<0.001.
样品组与维生素k1组相比:* P<0.05,** P<0.01,*** P<0.001.
样品组与灯盏花素组相比:# P<0.05,## P<0.01,### P<0.001.
由上表1可以看出,与空白组相比,补骨脂甲素、大豆苷元和紫云英苷能显著性地缩短血浆复钙时间(P<0.001,P<0.001,P<0.01和P<0.05);与维生素k1组相比,补骨脂甲素、大豆苷元和紫云英苷对血浆复钙时间均无显著性差异(P>0.05)。可见,补骨脂甲素、大豆苷元和紫云英苷具有一定的促凝血作用,且与维生素k1作用相似。
Claims (2)
1.一种促凝血补骨脂有效成分的提取分离方法,其特征在于,包括以下步骤:
1)补骨脂粉碎,用甲醇浸提,浸提液合并、过滤、浓缩得补骨脂甲醇浸膏,补骨脂甲醇浸膏分散于甲醇水溶液中,依次用乙酸乙酯、正丁醇萃取,回收溶剂,所得乙酸乙酯萃取物即为乙酸乙酯部位,所得正丁醇萃取物即为正丁醇部位;
2)乙酸乙酯部位进行200~300目硅胶柱色谱,用石油醚-乙酸乙酯梯度洗脱,比例为80:1~5:5,以TLC检测合并,各组分反复经硅胶H柱色谱、LC3000型高效液相柱色谱、SephadexLH-20柱色谱和重结晶得到化合物1和化合物2;
3)正丁醇部位经反复硅胶柱色谱,用氯仿-甲醇梯度洗脱,比例为100:1~7:3,经LC3000型高效液相柱色谱、SephadexLH-20柱色谱分离得到化合物3;化合物1、2、3即为促凝血补骨脂有效成分;
化合物1、2、3分别是补骨脂甲素、大豆苷元和紫云英苷,其结构如下:
。
2.一种权利要求1制备的促凝血补骨脂有效成分在制备促凝血药物方面的应用。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001001996A1 (en) * | 1999-06-29 | 2001-01-11 | University Of Western Australia | Compositions and methods for treating or preventing osteoporosis |
CN101406513A (zh) * | 2008-12-03 | 2009-04-15 | 天津中医药大学 | 补骨脂提取物、含有它的药物组合物及其制备方法和用途 |
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Non-Patent Citations (3)
Title |
---|
Ability of Different Flavonoids To Inhibit the Procoagulant Activity of Adherent Human Monocytes;A. Lale 等;《J. Nat. Prod.》;19960322;第59卷(第3期);273-276 * |
Antibacterial prenylflavone derivatives from Psoralea corylifolia,and their structure–activity relationship study;Sheng Yin 等;《Bioorganic & Medicinal Chemistry》;20040702;第12卷(第16期);4387-4392 * |
补骨脂中新异黄酮成分的分离与结构鉴定;杨彤彤 等;《药学学报》;20060131;第41卷(第01期);76-79 * |
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