CN110194754A - 一种蹄叶橐吾脂溶性提取物及其制备方法和用途 - Google Patents
一种蹄叶橐吾脂溶性提取物及其制备方法和用途 Download PDFInfo
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- CN110194754A CN110194754A CN201910354465.XA CN201910354465A CN110194754A CN 110194754 A CN110194754 A CN 110194754A CN 201910354465 A CN201910354465 A CN 201910354465A CN 110194754 A CN110194754 A CN 110194754A
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- Medicines Containing Plant Substances (AREA)
Abstract
本发明公开了一种蹄叶橐吾脂溶性提取物及其制备方法和用途。所述提取物的活性单体成分包括蜂斗菜内酯A，鹿蹄橐吾醛和木犀草素，其具有抑制肿瘤细胞SH‑SY5Y及MCF‑7增殖作用，还具有一定的清除DPPH自由基的作用，提供了抗氧化、延缓衰老、提高机体免疫力、预防癌症等的医药或保健品用途，还可用于天然抗氧化剂的用途，还提供了肥胖症以及肥胖引起的的高血脂、高血压、糖尿病、脂肪肝、冠心病、睡眠呼吸暂停综合症等疾病的药物以及与上述疾病有关的医药和保健品用用途。
Description
技术领域
本发明属于药用植物提取技术领域，具体涉及一种蹄叶橐吾脂溶性提取物及其制备方法和用途。
背景技术
蹄叶橐吾(Ligularia fischeri)为菊科(Compositae)橐吾属多年生草本植物，又名马蹄叶、肾叶橐吾等。该植物在中国分布广泛，近些年来在韩国也多有报道。该植物根及根茎多有用药记载，名为山紫菀，其嫩叶在我国东北及韩国等地也多有食用报道。其具有散寒润肺、化痰止咳、理气活血等功效，用于治疗肺痈咳嗽、跌打损伤、关节脓肿等症。蹄叶橐吾中主要活性成分为倍半萜类、绿原酸类、肽类成分等，现代药理研究显示其提取物具有抗炎、抑菌、抗肿瘤、抗氧化等活性。
虽然蹄叶橐吾记载有各种药效及功能，但尚未有研究其确切活性物质和功能的报道。蹄叶橐吾提取物具有很大的医药用途意义，该提取物的市场空间广阔，发展潜力巨大。
发明内容
本发明的目的在于提供一种从蹄叶橐吾花及花茎部位提取其脂溶性成分的制备方法。
本发明的目的还在于提供上述提取物作为抗氧化剂及在制备用于延缓衰老、提高机体免疫力、预防癌症的药物或保健品中的应用。
本发明的目的还在于提供上述提取物在制备用于预防和治疗肥胖症以及由肥胖引起的高血脂、高血压、糖尿病、脂肪肝、冠心病、睡眠呼吸暂停综合症的药物中的应用
一种蹄叶橐吾脂溶性提取物，所述提取物的活性单体成分包括：
所述提取物中活性单体成分的质量分数≥20％。
上述蹄叶橐吾脂溶性提取物的制备方法，按照如下步骤进行：
(1)取干燥粉碎的蹄叶橐吾的花及花茎部位，加入20-90％乙醇水溶液作为提取溶剂，料液比为1:5～1:20(质量体积比，单位g/ml)，采用热回流提取法或组织破碎提取法提取，提取次数2～4次，合并提取液，按10:1-20:1的比例浓缩，放置4-12小时；
(2)将步骤(1)制备的浓缩液抽滤，其滤液经乙酸乙酯萃取后分取乙酸乙酯层，或经90-110目柱用硅胶拌样后用石油醚、乙酸乙酯依次抽提，收集乙酸乙酯溶液部，将乙酸乙酯溶剂除去，并干燥得暗黄色固体物；
(3)将步骤(2)中暗黄色固体物经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1-1:1，依次洗脱，收得组份A、组份B、组份C。
对步骤(3)中组份A经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为30:1-20:1-10:1，依次洗脱，硅胶TLC法检测收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚、乙酸乙酯及其混合溶剂，获得白色结晶状固体蜂斗菜内酯A(Bakkenolide A)。
对步骤(3)中组份B经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1，依次洗脱，硅胶TLC法检测收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚、乙酸乙酯及其混合溶剂，获得灰白色固体鹿蹄橐吾醛(Liguhodgsonal)。
对步骤(3)中组份C经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为10:1-5:1-1:1，依次洗脱，硅胶TLC法鉴定，收集合并相同流份，浓缩得黄色固体，对该固体经葡聚糖凝胶柱Sephadex LH-20，洗脱溶剂采用甲醇，硅胶TLC法检测收集合并相同流份，浓缩干后，得黄色粉末状固体物木犀草素。
所述乙醇水溶液为75％乙醇水溶液。
本发明的有益效果：本发明成功从蹄叶橐吾中制备脂溶性提取物，得到蜂斗菜内酯A，鹿蹄橐吾醛和木犀草素，具有抑制肿瘤细胞SH-SY5Y及MCF增殖作用，还具有一定的清除DPPH自由基的作用，提供了抗氧化、延缓衰老、提高机体免疫力、预防癌症等的医药或保健品用途，还可用于天然抗氧化剂的用途，还提供了肥胖症以及肥胖引起的的高血脂、高血压、糖尿病、脂肪肝、冠心病、睡眠呼吸暂停综合症等疾病的药物以及与上述疾病有关的医药和保健品用用途。
具体实施方式
下面结合具体实施例对本发明做进一步说明。
实施例1蹄叶橐吾脂溶性提取物的制备
取干燥粉碎的采自贵州山区的蹄叶橐吾花部50g，加入75％乙醇水溶液作为提取溶剂，料液比为1:10(质量体积比，单位g/ml)，采用组织破碎提取法提取，提取时间为10s，过滤，药渣再同法提取一次，过滤，合并两次滤液，按15:1的比例浓缩，放置12小时，抽滤，其滤液经乙酸乙酯萃取后分取乙酸乙酯层，将乙酸乙酯溶剂除去，并干燥得暗黄色固体物1.5g，即为蹄叶橐吾脂溶性提取物。
实施例2蹄叶橐吾脂溶性提取物的制备
取干燥粉碎的采自贵州山区的蹄叶橐吾花部50g，加入60％乙醇水溶液作为提取溶剂，料液比为1:15(质量体积比，单位g/ml)，采用热回流提取法提取，提取时间1h，过滤，药渣再同法提取一次，过滤，合并两次滤液，按10:1的比例浓缩，放置6小时，抽滤，其滤液经100目柱用硅胶拌样后用石油醚、乙酸乙酯依次抽提，收集乙酸乙酯溶液部，将乙酸乙酯溶剂除去，并干燥得暗黄色固体物1.7g，即为蹄叶橐吾脂溶性提取物。
实施例3单体化合物的制备
取干燥粉碎的采自贵州山区的蹄叶橐吾花及花茎部650g(每次取80-100g，分7次进行)，加入75％乙醇水溶液作为提取溶剂，料液比为1:10(质量体积比，单位g/ml)，采用组织破碎提取法提取，提取时间为10s，过滤，药渣再同法提取一次，过滤，合并两次滤液，按16:1的比例浓缩，放置4小时，抽滤，其滤液经乙酸乙酯萃取后分取乙酸乙酯层，将乙酸乙酯溶剂除去，并干燥得暗黄色固体物23g，即为蹄叶橐吾脂溶性提取物。取20g提取物，经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1-1:1，依次洗脱，收得组份A(10g)、组份B(3g)、组份C(3.5g)。
对组份A经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为30:1-20:1-10:1，依次洗脱，硅胶TLC法检测收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚-乙酸乙酯混合溶剂，获得白色结晶状固体3g，经硅胶TLC法鉴定为单一成分，该成分经核磁共振法(1H-NMR、13C-NMR)鉴定为Bakkenolide A(化合物1)。化合物(1)的1H NMR(500MHz，CDCl3)：δ5.10(1H，brs)，5.02(1H，brs)，4.76(2H，tq，J＝2.1，15.0Hz)，2.28(1H，m)，2.08(1H，t，J＝13.0Hz)1.97(1H，q，J＝13.0，6.7Hz，overlapped)，1.96(2H，s)，0.99(3H，s)，1.53(2H，m)，1.47(2H，m)，1.23(2H，m)，0.84(3H，d，J＝6.8Hz)；13C-NMR(CDCl3)：δ16.57，19.37，21.22，23.56，31.11，34.12，42.59，44.25，46.41，48.79，50.09，70.59，105.99，150.58，183.06。
对组份B经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1，依次洗脱，硅胶TLC法检测收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚、乙酸乙酯及其混合溶剂，获得灰白色固体130mg，经硅胶TLC法鉴定为单一成分该成分经核磁共振法(1H-NMR、13C-NMR)鉴定为Liguhodgsonal(化合物2)。化合物(2)的1H-NMR(300MHz，)：δ10.21(1H，s，CHO)，8.45(1H，s，OH)，7.14(1H，d，J＝2.7Hz)，6.86(1H，d，J＝2.7Hz)，3.42(1H，dd，J＝17.4，4.9Hz)，2.83(1H，m，overlapped)，2.79(1H，m，overlapped)，2.31(1H，m)，1.94(1H，m)，1.81(3H，s，CH3)，1.60(1H，m)；13C-NMR(CD3COCD3)：δ21.00，28.17，30.64，31.74，42.52，109.79，117.20，122.10，130.71，136.17，140.34，150.39，156.17，193.18。
对组份C经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为10:1-5:1-1:1，依次洗脱，硅胶TLC法鉴定，收集合并相同流份，浓缩得黄色固体，对该固体经葡聚糖凝胶柱Sephadex LH-20，洗脱溶剂采用甲醇，硅胶TLC法检测收集合并相同流份，浓缩干后，得黄色粉末状固体物300mg，经硅胶TLC法鉴定为单一成分，该成分经核磁共振法(1H-NMR、13C-NMR)鉴定为木犀草素(化合物3)。化合物(3)的1H-NMR(300MHz，DMSO-d6)：δ12.97(1H，s，5-OH)，10.81(1H，s，OH)，9.89(1H，s，OH)，9.39(1H，s，OH)，7.40(1H，dd，J＝2.2，8.1Hz，overlapped)，7.39(1H，brs，overlapped)，6.88(1H，d，J＝8.1Hz)，6.66(1H，s)，6.43(1H，d，J＝2.0Hz)，6.18(1H，d，2.0Hz)；13C-NMR：δ182.11，164.57，164.35，161.94，157.74，150.15，146.19，121.96，119.44，116.47，113.83，104.16，103.33，99.28，94.28。
实施例4对肿瘤细胞的增殖抑制活性试验
取人神经母细胞瘤SH-SY5Y、乳腺癌细胞MCF-7置于含10％胎牛血清的高糖培养基DMEM中培养，以5×103个/孔加入96孔板中，每孔100μL，在37℃含5％CO2的培养箱中培养12小时贴壁后吸弃原培养基。然后空白组中仅加入DMEM培养基；对照组加入DNEM培养基不加药物，实验组分别加入含实施例1制备的蹄叶橐吾脂溶性提取物(提取物I)0.01-100μg/mL、各单体化合物12.5-100μM待测药物的DMEM培养基；继续培养48h，吸去上清液，加入DMEM培养基后再加入5mg/mL的MTT试剂，继续培养4h，吸去上清液，加入150μL DMSO，震荡10min，利用酶标仪在570nm下测定吸光度值(A值)，并根据吸光度值计算细胞增殖抑制情况，每个药物浓度设6个复孔。实验组的药物为实施例3的提取物I和单体化合物及阳性对照药顺铂。细胞增殖抑制率(％)＝(A对照-A实验)/(A对照-A空白)×100％。结果见表1和表2。
表1化合物1-3、提取物I对细胞SH-SY5Y的增殖抑制率(％)
注：提取物I*的浓度单位是μg/mL，其他药物浓度单位是μM。
表2化合物1-3、提取物I对细胞MCF-7的增殖抑制率(％)
注：提取物I*的浓度单位是μg/mL，其他药物浓度单位是μM。
实施例5清除DPPH自由基试验
将化合物2、3及提取物I精确称量，依次配置成浓度为1.56、3.12、6.25、12.5、25.0、50.0μg/mL的50％乙醇溶液，分别取1mL各浓度的50％乙醇样品溶液，加入2mL 0.1mMDPPH 50％乙醇溶液，充分混匀，室温下避光反应30min，测其在525nm处吸光值。以1mL 50％乙醇代替样品做空白。以维生素C(Vc)作为阳性对照药。用下式计算化合物对DPPH自由基清除能力：(％)＝(A0-A1)/A0×100，其中A0为空白吸光值，A1为样品吸光值。计算得Vc对DPPH自由基半数清除率IC50为1.46μg/mL，提取物I及化合物2、3的IC50分别为：15.2、7.3及2.3μg/mL。DPPH自由基清除试验结果表示，蹄叶橐吾提取物具有一定的清除自由基的作用。可用于抗氧化、抗衰老、提高机体免疫力、预防癌症等医药、保健、食品工业等用途。
Claims (7)
1.一种蹄叶橐吾脂溶性提取物，其特征在于，所述提取物的活性单体成分包括：
2.根据权利要求1所述蹄叶橐吾脂溶性提取物，其特征在于，所述提取物中活性单体成分的质量分数≥20％。
3.权利要求1所述蹄叶橐吾脂溶性提取物的制备方法，其特征在于，按照如下步骤进行：
(1)取干燥粉碎的蹄叶橐吾的花及花茎部位，加入20-90％乙醇水溶液作为提取溶剂，料液比为1:5～1:20(质量体积比，单位g/ml)，采用热回流提取法或组织破碎提取法提取，提取次数2～4次，合并提取液，按10:1-20:1的比例浓缩，放置4-12小时；
(2)将步骤(1)制备的浓缩液抽滤，其滤液经乙酸乙酯萃取后分取乙酸乙酯层，或经100-200目柱用硅胶拌样后用石油醚、乙酸乙酯依次抽提，收集乙酸乙酯溶液部，将乙酸乙酯溶剂除去，并干燥得暗黄色固体物；
(3)将步骤(2)中暗黄色固体物经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1-1:1，依次洗脱，收得组份A、组份B、组份C。
4.根据权利要求3所述蹄叶橐吾脂溶性提取物的制备方法，其特征在于，对步骤(3)中组份A经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为30:1-20:1-10:1，依次洗脱，硅胶TLC法检测，收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚、乙酸乙酯及其混合溶剂，获得白色结晶状固体蜂斗菜内酯A。
5.根据权利要求3所述蹄叶橐吾脂溶性提取物的制备方法，其特征在于，对步骤(3)中组份B经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为20:1-10:1-5:1，依次洗脱，硅胶TLC法检测，收集合并相同流份，浓缩得浅黄色固体，对该固体采用溶剂法进行结晶、重结晶，结晶用溶剂为石油醚、乙酸乙酯及其混合溶剂，获得灰白色固体鹿蹄橐吾醛。
6.根据权利要求3所述蹄叶橐吾脂溶性提取物的制备方法，其特征在于，对步骤(3)中组份C经硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂，体积比为10:1-5:1-1:1，依次洗脱，硅胶TLC法鉴定，收集合并相同流份，浓缩得黄色固体，对该固体经葡聚糖凝胶柱SephadexLH-20，洗脱溶剂采用甲醇，硅胶TLC法检测收集合并相同流份，浓缩干后，得黄色粉末状固体物木犀草素。
7.根据权利要求1所述蹄叶橐吾脂溶性提取物的制备方法，其特征在于，所述乙醇水溶液最优为75％乙醇水溶液。
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| CN112089725A (zh) * | 2020-10-28 | 2020-12-18 | 武汉大学 | 川紫菀多糖在制备治疗和/或预防肝病药物中的应用 |
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