CN105669788A - 一种从竹笋中提取活性化合物的方法及其应用 - Google Patents
一种从竹笋中提取活性化合物的方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种从竹笋中提取活性化合物的方法,包括将竹笋粉碎,经乙醇水溶液回流提取,浓缩至无乙醇后,得溶液,石油醚脱脂,再依次用乙酸乙酯和正丁醇进行萃取,萃取液浓缩后进行柱层析分离,收集溶液,溶液浓缩干燥后得到样品并进行结构鉴定;本发明制备得到的化合物具有一定的酪氨酸酶抑制活性,能够有效预防和治疗黑色素合成异常导致的人体色素沉着性疾病、黑色素瘤以及其它需要抑制酪氨酸酶活性的病症,可用于制备治疗此类疾病的药物。
Description
技术领域
本发明属于生物技术领域,具体涉及一种从竹笋中提取活性化合物的方法及在制备具有酪氨酸酶抑制活性的抑制剂中的应用。
背景技术
竹笋是禾本科多年生植物竹子的嫩茎,自古被称作“菜中珍品”,在我国食用已有2500多年的历史。竹笋鲜嫩,肉质松脆,味道鲜美,含有高蛋白、低淀粉、低脂肪,还含有糖类及钙、磷、铁、胡萝卜素、VB1、VB2、VC等多种营养物质,其中人体所需的氨基酸含量特别丰富,长期食用竹笋有促进肠道蠕动、帮助消化、预防肠癌和心血管疾病之功效。竹笋的主要功用在食用方面,此外,竹笋还以提取物的形式在食品、饮品、保健(功能)食品、天然药物、以及食品添加剂和化妆品添加剂等领域得到广泛应用。
酪氨酸酶(Tyrosinase)广泛分布于微生物、动植物以及人体中,是目前己知的生物体中参与黑色素(Melanin)合成的关键酶,不仅决定黑素合成的速率,还是黑素细胞分化成熟的特征性标志,与人的衰老、昆虫的伤口愈合与发育、果蔬的褐变等有密切关系。它不但用于色素增加性皮肤病(白癜风、黄褐斑、雀斑、老年斑等)的临床治疗,而且可用于化妆品使肤色增白,还有可能应用于农业生产上作为一种害虫调控剂和食品工业上作为食品添加剂。
到目前为止,受限于有效性、安全性以及成本等因素,只有极少数酪氨酸酶抑制剂被用于商业上。因此,在医药、食品和化妆品领域,目前迫切需要寻找安全和有效的酪氨酸酶抑制剂。而且,由于近年来人们对“组分天然化”和“回归大自然”的呼声越来越高,安全而无毒副作用的天然植物成为该类产品的发展方向,天然的酪氨酸性抑制剂可能是一种替代非天然酪氨酸酶活性抑制剂的先导化合物的良好来源。
发明内容
本发明提供一种从竹笋中提取活性化合物的方法,包含以下步骤:
(1)取竹笋粉碎,用竹笋质量5~10倍的乙醇水溶液回流提取2~3次,每次回流2~3小时,过滤,合并滤液;
(2)将步骤(1)滤液浓缩至无乙醇后,离心分离去沉淀,得溶液;
(3)将步骤(2)溶液用石油醚脱脂,然后依次用乙酸乙酯和正丁醇萃取;
(4)将乙酸乙酯萃取部分浓缩成浸膏,用正相硅胶柱分离,采用体积比30:1~1:1的氯仿-甲醇系统梯度洗脱;
收集体积比20:1的氯仿-甲醇洗脱液,浓缩后采用硅胶柱层析,石油醚-丙酮溶液洗脱,洗脱液浓缩,在浓缩过程中有固体小颗粒析出,用丙酮溶解,加入石油醚进行重结晶,得到化合物对羟基苯甲醛,其中石油醚-丙酮溶液为石油醚和丙酮按体积比8:1混合制得;
收集体积比15:1的氯仿-甲醇洗脱液,浓缩后采用正相硅胶柱层析,石油醚-丙酮溶液梯度洗脱,收集体积比9:1~7:1的石油醚-丙酮洗脱液浓缩制得对羟基苯甲酸甲酯粗品,收集体积比6:1~3:1的石油醚-丙酮洗脱液浓缩制得对羟基亚苄基丙酮粗品,将两个粗品分别经凝胶柱层析,甲醇为洗脱溶剂,分别收集洗脱液浓缩得到对羟基苯甲酸甲酯和对羟基亚苄基丙酮;
收集体积比8:1的氯仿-甲醇洗脱液,浓缩后经反相硅胶柱层析,用体积比为30:70~60:40的甲醇-水溶液梯度洗脱,将体积比为50:50的洗脱液经正相硅胶柱层析,体积比3:1的石油醚-丙酮混合液洗脱,洗脱液结晶,得到化合物对羟基苯甲酸;
(5)将正丁醇萃取部分浓缩成浸膏,水溶解后加入大孔树脂柱吸附,用质量百分比浓度为40~60%的乙醇溶液洗脱,HPLC跟踪分析,收集含2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈成分的洗脱液,浓缩后拌入硅胶,常规干燥,过正相硅胶柱进行柱层析,以体积比5:1~1:1的氯仿-甲醇混合液进行洗脱,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈的粗品,在重结晶溶剂中加热溶解至饱和,置于低温环境下进行重结晶,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈。
可用于本发明的竹子品种原料没有特别限制,可以是不同属的竹子,优选牡竹属的竹笋为主,如龙珠、麻竹、山竹。竹笋可以是竹笋肉也可以是竹笋全株,还可以是竹笋的废弃物如笋头和笋壳等。
所述步骤(1)的乙醇水溶液为质量百分比浓度为50-90%的溶液。
所述步骤(4)中反相硅胶柱填料为RP-18或RP-8,凝胶柱填料为羟丙基葡聚糖凝胶SephadexLH20。
所述步骤(5)中重结晶溶剂为氯仿和甲醇按体积比2:1混合制得的溶液。
从竹笋中提取的具有酪氨酸酶抑制活性的多酚类化合物,包括2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈(Ⅰ)、对羟基亚苄基丙酮(Ⅱ)、对羟基苯甲醛(Ⅲ)、对羟基苯甲酸(Ⅳ)、对羟基苯甲酸甲酯(Ⅴ),化学结构如下:
;
本发明另一目的是将上述化合物应用在制备酪氨酸酶抑制剂中;即在制备预防和治疗黑色素合成异常导致的人体色素沉着性疾病或黑色素瘤药物中的应用。
本发明步骤(5)是现有技术的常规大孔吸附树脂上完成的,大孔吸附树脂用乙醇清洗后还可重复使用,大孔吸附树脂为非极性树脂或弱极性树脂;优选地,树脂为D101大孔树脂。
本发明优点和技术效果:本发明中竹笋原料具有生长量大、生长快、原料易得;单体成分工艺操作简便、重复性好,产品纯度高,适合工业化生产,能够有效预防和治疗黑色素合成异常导致的人体色素沉着性疾病、黑色素瘤以及其它需要抑制酪氨酸酶活性的病症,可用于制备治疗此类疾病的药物。
具体实施方式
下面将结合实施例进一步详细说明本发明的实质内容和有益效果,该实施例仅用于说明本发明而非对本发明的限制。
实施例1:本从竹笋中提取活性化合物的方法,具体操作如下:
(1)取18kg竹笋样品粉碎,用竹笋质量5倍质量百分比浓度80%的乙醇水溶液回流提取3次,每次回流2小时,过滤,合并滤液;
(2)将步骤(1)滤液浓缩至无乙醇后,离心分离去沉淀,得溶液;
(3)将步骤(2)溶液用石油醚脱脂,然后依次用乙酸乙酯和正丁醇萃取;
(4)将乙酸乙酯萃取部分浓缩成浸膏,重75g,用80g硅胶拌样,常规干燥,干法上样,用正相硅胶柱分离,采用体积比30:1~1:1的氯仿-甲醇系统梯度洗脱,收集体积比20:1的氯仿-甲醇洗脱液,浓缩后采用硅胶柱(200~300目硅胶)层析,石油醚-丙酮溶液(体积比8:1)洗脱,洗脱液浓缩,在浓缩过程中有固体小颗粒析出,用丙酮溶解,加入石油醚进行重结晶,得到化合物13.6g对羟基苯甲醛;
收集体积比15:1的氯仿-甲醇洗脱液,浓缩后采用正相硅胶柱层析(填料200-300目),石油醚-丙酮溶液梯度洗脱,收集体积比8:1的石油醚-丙酮洗脱液浓缩制得对羟基苯甲酸甲酯粗品,收集体积比4:1的石油醚-丙酮洗脱液浓缩制得对羟基亚苄基丙酮粗品,将两个粗品分别经凝胶柱层析(凝胶柱填料为羟丙基葡聚糖凝胶SephadexLH20),甲醇为洗脱溶剂,分别收集洗脱液浓缩得到560mg对羟基苯甲酸甲酯和720mg对羟基亚苄基丙酮;
收集体积比8:1的氯仿-甲醇洗脱液,浓缩后经反相硅胶柱层析(反相硅胶柱填料为RP-C18),用体积比为30:70~60:40的甲醇-水溶液梯度洗脱,将体积比为50:50的洗脱液经正相硅胶柱层析,体积比3:1的石油醚-丙酮混合液洗脱,收集洗脱液得到1.6g对羟基苯甲酸粗品,结晶,将粗品加热溶解后置于冰箱中,5℃下结晶,得到化合物对羟基苯甲酸;
(5)将正丁醇萃取部分浓缩成浸膏,水溶解后加入D-101大孔树脂柱吸附,用质量百分比浓度为50%的乙醇溶液洗脱,HPLC跟踪分析,收集含2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈成分的洗脱液,浓缩后拌入硅胶,常规干燥,过正相硅胶柱进行柱层析,以体积比3:1的氯仿-甲醇混合液进行洗脱,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈的粗品,在重结晶溶剂(氯仿和甲醇按体积比2:1混合制得的溶液)中加热溶解至饱和,置于低温环境下进行重结晶,得到13.0g2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈。
上述方法制得的多酚类化合物的核磁共振光谱数据:
2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈:
;
对羟基亚苄基丙酮:13C-NMR(CDCl3,100MHz,δ):198.2(s,C-9),159.0(s,C-4),145.0(d,C-7),130.5(s,C-1),126.4(d,C-2,6),116.2(d,C-3,5),115.3(d,C-8),28.9(q,C-10);1H-NMR(CDCl3,400MHz,δ):7.43(2H,d,J=8.4Hz,H-2,6);6.90(2H,d,J=8.4Hz,H-3,5),7.25(1H,d,J=16.0Hz,H-7Hz),6.59(1H,d,J=16.0Hz,H-8Hz),2.3(3H,s,CH3-10)。
对羟基苯甲醛:13C-NMR(MeOD,100MHz,δ):191.4(d,C-7,),163.2(s,C-7),132.3(d,C-2,6),128.9(s,C-1),115.9(d,C-3,5);1H-NMR(MeOD,400MHz,δ):9.71(s,H-7),7.68(d,J=8.5Hz,H-26)6.85(d,J=8.5Hz,H-3,5)。
对羟基苯甲酸:13C-NMR(MeOD,100MHz,δ):169.4(s,C-7),163.2(s,C-4),133.2(d,C-2,6),122.8(s,C-1),l16.3(d,C-3,5);1HNMR(MeOD,400MHz,δ):7.85(2H,d,J=8.5Hz,H-2,6),6.81(2H,d,J=8.5Hz,H-3,5)。
对羟基苯甲酸甲酯:13C-NMR(CDCl3,100MHz,δ):167.5(s,C-7),161.2(s,C-4),131.8(d,C-2,6),115.2(d,C-3,5),121.6(s,C-1),51.7(q,C-8);1H-NMR(CDCl3,400MHz,δ):7.87(2H,d,J=8.8Hz),6.81(2H,d,J=8.8Hz),3.83(3H,s)。
上述化合物的酪氨酸酶抑制活性的评价实验如下:
实验原理:酪氨酸或者多巴在酪氨酸酶的催化作用下转化为多巴色素,多巴色素在475nm处具有特征吸收,因此,可以通过比色法测定酪氨酸酶的活性。
测定方法:0.5mL含有不同浓度各单体化合物与0.5mL的10μg/mL酪氨酸酶溶液和1.5mL缓冲液充分混匀,置30℃水浴孵育20分钟;然后在每一试管中,加入1.0mL的0.2%左旋多巴(L-DOPA),30℃水浴准确反应5分钟,即刻用分光光度计于475nm处测定多巴色素的吸收峰。
酶活性抑制率=[A空白-(A样品-A背景)]/A空白×100%
A空白:含底物和酶,不加待测样品反应后的吸收值;
A样品:含底物和酶,加入待测样品反应后的吸收值;
A背景:含底物和待测样品,不加酶的吸收值。
实验表明,应用本实施例制备的化合物对酪氨酸酶具有显著的抑制作用,结果见表1,可以应用于美容祛斑等药物和保健品开发,以及果蔬护色保鲜等领域。
表1:5个化合物对酪氨酸酶的抑制活性(mM)
。
实施例2:本从竹笋中提取活性化合物的方法,具体操作如下:
(1)取12kg竹笋样品粉碎,用竹笋质量10倍质量百分比浓度50%的乙醇水溶液回流提取2次,每次回流3小时,过滤,合并滤液;
(2)将步骤(1)滤液浓缩至无乙醇后,离心分离去沉淀,得溶液;
(3)将步骤(2)溶液用石油醚脱脂,然后依次用乙酸乙酯和正丁醇萃取;
(4)将乙酸乙酯萃取部分浓缩成浸膏,重45g,用50g硅胶拌样,常规干燥,干法上样,用正相硅胶柱分离,采用体积比30:1~1:1的氯仿-甲醇系统梯度洗脱,收集体积比20:1的氯仿-甲醇洗脱液,浓缩后采用硅胶柱(300-400目硅胶)层析,石油醚-丙酮溶液(体积比9:1)洗脱,洗脱液浓缩,在浓缩过程中有固体小颗粒析出,用丙酮溶解,加入石油醚进行重结晶,得到化合物7.7g对羟基苯甲醛;
收集体积比15:1的氯仿-甲醇洗脱液,浓缩后采用正相硅胶柱层析(200-300目),石油醚-丙酮溶液梯度洗脱,收集体积比7:1的石油醚-丙酮洗脱液浓缩制得对羟基苯甲酸甲酯粗品,收集体积比3:1的石油醚-丙酮洗脱液浓缩制得对羟基亚苄基丙酮粗品,将两个粗品分别经凝胶柱层析(凝胶柱填料为羟丙基葡聚糖凝胶SephadexLH20),甲醇为洗脱溶剂,分别收集洗脱液浓缩得到370mg对羟基苯甲酸甲酯和440mg对羟基亚苄基丙酮;
收集体积比8:1的氯仿-甲醇洗脱液,浓缩后经反相硅胶柱层析(反相硅胶柱填料为RP-C18),用体积比为30:70~60:40的甲醇-水溶液梯度洗脱,将体积比为50:50的洗脱液经正相硅胶柱层析,体积比3:1的石油醚-丙酮混合液洗脱,收集洗脱液得到0.9g对羟基苯甲酸粗品,结晶,将粗品加热溶解后置于冰箱中,5℃下结晶,得到化合物对羟基苯甲酸;
(5)将正丁醇萃取部分浓缩成浸膏,水溶解后加入D-101大孔树脂柱吸附,用质量百分比浓度为40%的乙醇溶液洗脱,HPLC跟踪分析,收集含2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈成分的洗脱液,浓缩后拌入硅胶,常规干燥,过正相硅胶柱进行柱层析,以体积比5:1的氯仿-甲醇混合液进行洗脱,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈的粗品,在重结晶溶剂(氯仿和甲醇按体积比2:1混合制得的溶液)中加热溶解至饱和,置于低温环境下进行重结晶,得到8.7g2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈。
上述方法制得的多酚类化合物的核磁共振光谱数据同实施例1;
上述化合物酪氨酸酶抑制活性的评价实验方法同实施例1,结果见表2。
表2:5个化合物对酪氨酸酶的抑制活性(mM)
。
实施例3:本从竹笋中提取活性化合物的方法,具体操作如下:
(1)取25kg竹笋样品粉碎,用竹笋质量8倍质量百分比浓度90%的乙醇水溶液回流提取3次,每次回流3小时,过滤,合并滤液;
(2)将步骤(1)滤液浓缩至无乙醇后,离心分离去沉淀,得溶液;
(3)将步骤(2)溶液用石油醚脱脂,然后依次用乙酸乙酯和正丁醇萃取;
(4)将乙酸乙酯萃取部分浓缩成浸膏,重104g,用120g硅胶拌样,常规干燥,干法上样,用正相硅胶柱分离,采用体积比30:1~1:1的氯仿-甲醇系统梯度洗脱,收集体积比20:1的氯仿-甲醇洗脱液,浓缩后采用硅胶柱(100-200目硅胶)层析,石油醚-丙酮溶液(体积比7:1)洗脱,洗脱液浓缩,在浓缩过程中有固体小颗粒析出,用丙酮溶解,加入石油醚进行重结晶,得到化合物17.7g对羟基苯甲醛;
收集体积比15:1的氯仿-甲醇洗脱液,浓缩后采用正相硅胶柱层析(200-300目),石油醚-丙酮溶液梯度洗脱,收集体积比9:1的石油醚-丙酮洗脱液浓缩制得对羟基苯甲酸甲酯粗品,收集体积比6:1的石油醚-丙酮洗脱液浓缩制得对羟基亚苄基丙酮粗品,将两个粗品分别经凝胶柱层析(凝胶柱填料为羟丙基葡聚糖凝胶SephadexLH20),甲醇为洗脱溶剂,分别收集洗脱液浓缩得到740mg对羟基苯甲酸甲酯和870mg对羟基亚苄基丙酮;
收集体积比8:1的氯仿-甲醇洗脱液,浓缩后经反相硅胶柱层析(反相硅胶柱填料为RP-8),用体积比为30:70~60:40的甲醇-水溶液梯度洗脱,将体积比为50:50的洗脱液经正相硅胶柱层析,体积比3:1的石油醚-丙酮混合液洗脱,收集洗脱液得到2.4g对羟基苯甲酸粗品,结晶,将粗品加热溶解后置于冰箱中,5℃下结晶,得到化合物对羟基苯甲酸;
(5)将正丁醇萃取部分浓缩成浸膏,水溶解后加入D-101大孔树脂柱吸附,用质量百分比浓度为40%的乙醇溶液洗脱,HPLC跟踪分析,收集含2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈成分的洗脱液,浓缩后拌入硅胶,常规干燥,过正相硅胶柱进行柱层析,以体积比1:1的氯仿-甲醇混合液进行洗脱,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈的粗品,在重结晶溶剂(氯仿和甲醇按体积比2:1混合制得的溶液)中加热溶解至饱和,置于低温环境下进行重结晶,得到21g2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈。
上述方法制得的多酚类化合物的核磁共振光谱数据同实施例1;
上述化合物酪氨酸酶抑制活性的评价实验方法同实施例1,结果见表3。
表3:5个化合物对酪氨酸酶的抑制活性(mM)
。
Claims (6)
1.一种从竹笋中提取活性化合物的方法,其特征在于,包含以下步骤:
(1)取竹笋粉碎,用竹笋质量5~10倍的乙醇水溶液回流提取2~3次,每次回流2~3小时,过滤,合并滤液;
(2)将步骤(1)滤液浓缩至无乙醇后,离心分离去沉淀,得溶液;
(3)将步骤(2)溶液用石油醚脱脂,然后依次用乙酸乙酯和正丁醇萃取;
(4)将乙酸乙酯萃取部分浓缩成浸膏,用正相硅胶柱分离,采用体积比30:1~1:1的氯仿-甲醇系统梯度洗脱;
收集体积比20:1的氯仿-甲醇洗脱液,浓缩后采用硅胶柱层析,石油醚-丙酮溶液洗脱,洗脱液浓缩,在浓缩过程中有固体小颗粒析出,用丙酮溶解,加入石油醚进行重结晶,得到化合物对羟基苯甲醛,其中石油醚-丙酮溶液为石油醚和丙酮按体积比8:1混合制得;
收集体积比15:1的氯仿-甲醇洗脱液,浓缩后采用正相硅胶柱层析,石油醚-丙酮溶液梯度洗脱,收集体积比9:1~7:1的石油醚-丙酮洗脱液浓缩制得对羟基苯甲酸甲酯粗品,收集体积比6:1~3:1的石油醚-丙酮洗脱液浓缩制得对羟基亚苄基丙酮粗品,将两个粗品分别经凝胶柱层析,甲醇为洗脱溶剂,分别收集洗脱液浓缩得到对羟基苯甲酸甲酯和对羟基亚苄基丙酮;
收集体积比8:1的氯仿-甲醇洗脱液,浓缩后经反相硅胶柱层析,用体积比为30:70~60:40的甲醇-水溶液梯度洗脱,将体积比为50:50的洗脱液经正相硅胶柱层析,体积比3:1的石油醚-丙酮混合液洗脱,洗脱液结晶,得到化合物对羟基苯甲酸;
(5)将正丁醇萃取部分浓缩成浸膏,水溶解后加入大孔树脂柱吸附,用质量百分比浓度为40~60%的乙醇溶液洗脱,HPLC跟踪分析,收集含2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈成分的洗脱液,浓缩后拌入硅胶,常规干燥,过正相硅胶柱进行柱层析,以体积比5:1~1:1的氯仿-甲醇混合液进行洗脱,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈的粗品,在重结晶溶剂中加热溶解至饱和,置于低温环境下进行重结晶,得到2R-β-D-吡喃葡萄糖基-2-对羟基苯乙腈。
2.根据权利要求1中所述的从竹笋中提取活性化合物的方法,其特征在于:步骤(1)的乙醇水溶液为质量百分比浓度为50-90%的溶液。
3.根据权利要求1中所述的从竹笋中提取活性化合物的方法,其特征在于:步骤(4)中反相硅胶柱填料为RP-18或RP-8,凝胶柱填料为羟丙基葡聚糖凝胶SephadexLH20。
4.根据权利要求1中所述的从竹笋中提取活性化合物的方法,其特征在于:步骤(5)中重结晶溶剂为氯仿和甲醇按体积比2:1混合制得的溶液。
5.权利要求1所述从竹笋中提取活性化合物的方法制得的化合物在制备酪氨酸酶抑制剂中的应用。
6.根据权利要求5所述应用,其特征在于:在制备预防和治疗黑色素合成异常导致的人体色素沉着性疾病或黑色素瘤药物中的应用。
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CN112159439B (zh) * | 2020-09-28 | 2023-11-21 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 紫杉氰糖苷类化合物及其制备方法和应用 |
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