CN106632199A - 一种从铁皮石斛中提取抗酪氨酸酶活性物质的方法 - Google Patents
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Abstract
本发明公开了一种从铁皮石斛中提取抗酪氨酸酶活性物质的方法,属于化学提取领域。本发明从铁皮石斛叶片中提取的具有较强抗酪氨酸酶活性的含有两种多酚类化合物的有效部位,所述两种多酚类化合物是草大戟素、桑辛素M。能够有效抑制酪氨酸酶的活性。本发明进一步拓宽了铁皮石斛的应用领域。
Description
技术领域
本发明涉及一种从铁皮石斛中提取抗酪氨酸酶活性物质的方法,属于化学提取领域。
背景技术
铁皮石斛Dendrobium officinale是兰科石斛属多年生附生草本植物,主要分布于西南和江南各省。我国的石斛属植物有76种,其中有33个种作为商品石斛的原植物被收购。铁皮石斛是《中华人民共和国药典》中被收载的5种石斛属植物之一。
分析表明,铁皮石斛的茎的黏性物质主要是水溶性的多糖,铁皮石斛的水溶性多糖为一类免疫增强剂,对提高小鼠外周白细胞和促进淋巴细胞产生移动因子具有明显的作用。铁皮石斛是含有鼓槌菲(chrysotoxene)和毛兰素(erianin)两种抗癌物质的5个种之一。药理研究表明,这两个菲类化合物具有对肝癌和艾氏腹水癌细胞抑制活性。目前对铁皮石斛的开发研究主要集中在铁皮石斛以及提取根茎中的多糖,铁皮石斛叶片的开发还不多。
发明内容
本发明的目的首先在于提供一种具有抗酪氨酸酶活性的有效部位,是从铁皮石斛叶片中提取的具有较强抗酪氨酸酶活性的含有两种多酚类化合物的有效部位,所述两种多酚类化合物是草大戟素、桑辛素M。
本发明的另外一个目的是提供所述具抗酪氨酸酶活性的有效部位的制备方法,通过以下步骤实现:
(1)取二年生萌条的新鲜铁皮石斛叶片,粉碎后,于30℃,用3倍质量的75%乙醇浸没超声提取2次以上,每次1小时,超声功率200W,提取液合并后,用乙酸乙酯萃取,乙酸乙酯与提取液的体积比为3:1,乙酸乙酯相经过减压浓缩得到干燥物;
(2)干燥物用95%乙醇溶解,过滤;
(3)步骤(2)所得过滤液与大孔树脂D101混合拌样,减压浓缩至干;其中,大孔树脂D101的用量与步骤(1)所得干燥物的质量比例为2:1;
(4)将步骤(3)所得混合物上D101大孔树脂,分别用6倍柱体积量的15%、30%、40%浓度的乙醇洗脱;
(5)收集步骤(4)30%乙醇洗脱的洗脱液,浓缩得干燥样品,干燥样品进一步用硅胶柱层析分离,先后分别用20倍柱体积的体积比20:1的二氯甲烷-甲醇和体积比30:1的甲醇-水洗脱,先后分别得到草大戟素、桑辛素M。
本发明的另外一个目的是提供所述的具有酪氨酸酶抑制活性的有效部位在制备抗果蔬酶促褐变抑制剂、化妆品美白剂、预防和治疗黑色素异常导致的人体色素沉着性疾病、黑色素瘤以及其他需要抑制酪氨酸酶活性的病症的药物中的应用。
本发明的两种从铁皮石斛中提取的具有酪氨酸酶抑制活性的多酚类化合物可以作为活性成分,制备成制剂。所述的剂型包括固体粉末、水溶液、醇溶液、乳液、面膜、巴布剂、注射液、滴注液、粉针剂、颗粒剂、片剂、冲剂、散剂、口服液、糖衣剂、薄膜衣片剂、肠溶衣片剂、胶囊剂、口含剂、丸剂、膏剂、丹剂、喷雾剂、滴丸剂、口崩剂、微丸等。
本发明对于铁皮石斛的叶片进行了开发利用,从中分离得到两种具有酪氨酸酶抑制活性的有效部位。有效部位在50、30、10μg/mL三个浓度下,对酪氨酸酶的抑制率分别为37.1%、22.5%、14.3%;而阳性对照曲酸对酪氨酸酶的抑制率分别为24.7%、14.2%、9.3%。可见,本发明提供的铁皮石斛提取物可在开发抗果蔬酶促褐变抑制剂、化妆品美白剂、预防和治疗黑色素异常导致的人体色素沉着性疾病、黑色素瘤的药物中,发挥应用价值。
附图说明
图1草大戟素的结构式
图2桑辛素M的结构式
具体实施方式
高效液相检测条件:
仪器:Waters 1525液相色谱仪配以紫外检测器(2487)。
色谱柱:Alltima C18(250×4.6mm,5μm)。
流动相:A相:含0.1%甲酸的去离子水;B相:甲醇。线性洗脱梯度:0min,10%B;20min,30%B;30min,50%B;40min,70%B;50min,100%B。流速:1.0mL/min,检测波长:280nm。
实施例1有效部位的提取
(1)取1kg二年生萌条的新鲜铁皮石斛叶片,粉碎后,于30℃,用3倍质量的75%乙醇浸没超声提取2次以上,每次1小时,超声功率200W,提取液合并后,用乙酸乙酯萃取,乙酸乙酯与提取液的体积比为3:1,乙酸乙酯相经过减压浓缩得到干燥物;
(2)干燥物用95%乙醇溶解,过滤;
(3)步骤(2)所得过滤液与大孔树脂D101混合拌样,减压浓缩至干;其中,大孔树脂D101的用量与步骤(1)所得干燥物的质量比例为2:1;
(4)将步骤(3)所得混合物上D101大孔树脂,分别用6倍柱体积量的15%、30%、40%浓度的乙醇洗脱;
(5)收集步骤(4)30%乙醇洗脱的洗脱液,浓缩得干燥样品,干燥样品进一步用硅胶柱层析分离,先后分别用20倍柱体积的体积比20:1的二氯甲烷-甲醇和体积比30:1的甲醇-水洗脱,先后分别得到草大戟素、桑辛素M。每一千克铁皮石斛叶片可提取得到10.7mg草大戟素、127mg桑辛素M。
草大戟素的核磁共振光谱数据如下:
1H NMR(Acetone-d6,400MHz)δ:12.210(1H,OH-5),9.019(2H,OH),7.290(1H,d,J=8.4Hz,H-6'),6.465(1H,d,J=2.4Hz,H-2'),6.415(1H,dd,J=8.4,2.4Hz,H-5'),5.955(1H,d,J=2.0Hz,H-8),5.936(1H,d,J=2.0Hz,H-6),5.692(1H,dd,J=13.2,2.8Hz,H-2),3.163(1H,dd,J=17.2,13.2Hz,H-3),2.703(1H,dd,J=17.2,2.8Hz,H-3);13C NMR(Acetone-d6,100MHz)δ:197.8(C=O,C-4),167.6(C,C-7),165.3(C,C-5),164.9(C,C-9),159.7(C,C-2'),156.5(C,C-4'),129.0(CH,C-6'),117.3(C,C-1'),107.9(CH,C-5'),103.6(CH,C-3'),103.1(C,C-10),96.8(CH,C-6),95.9(CH,C-8),75.4(CH,C-2),42.7(CH2,C-3)。ESI-MS:m/z[M-H]-287.1(C15H11O6)。结构解析表明该化合物为草大戟素。
桑辛素M的核磁共振光谱数据如下:
1H NMR(Acetone-d6,400MHz)δ:8.60(3H,br s,OH),7.40(1H,d,J=8.4Hz,H-4),7.20(1H,s,H-3),6.99(1H,d,J=2.0Hz,H-7),6.86(2H,d,J=2.0Hz,H-2',6'),6.81(1H,dd,J=8.4,2.0Hz,H-5),6.37(1H,t,J=2.0Hz,H-4');13C NMR(Acetone-d6,100MHz)δ:159.83(C,C-3',5'),156.78(C,C-7a),156.71(C,C-2),155.58(C,C-6),133.47(C,C-1'),100.8(CH,C-3),122.65(C,C-3a),122.09(CH,C-4),113.31(CH,C-5),98.51(CH,C-3),103.92(CH,C-2',6'),103.61(CH,C-7),102.42(CH,C-4')。ESI-MS:m/z 241.0[M-H]-(C14H9O4)。结构解析表明该化合物为桑辛素M。
实施例2有效部位抑制酪氨酸酶活性的能力
将有效部位溶于DMSO,先配成1mg/mL溶液,然后分别稀释到50、30、10μg/mL。以曲酸为阳性对照,曲酸溶液也分别配成浓度为50、30、10、10μg/mL的溶液。将有效部位、曲酸溶液各30μL,加到用970μL的磷酸盐缓冲溶液中,再添加0.1mg/mL的酪氨酸1mL,然后加入1mL由磷酸盐缓冲溶液配成的200U/mL的酪氨酸酶。在37℃下孵育20min,于492nm处测定吸光值。
酶活性抑制率=[(A2-A1)-(B2-B1)]/(A2-A1)×100%
A1为0min时候未加抑制剂的吸收值;A2为20min后未加抑制剂的吸收值;
B1为0min时候加抑制剂的吸收值;B2为20min后加了抑制剂的吸收值。
有效部位在50、30、10μg/mL三个浓度下,对酪氨酸酶的抑制率分别为37.1%、22.5%、14.3%;阳性对照曲酸对酪氨酸酶的抑制率分别为24.7%、14.2%、9.3%。
虽然本发明已以较佳实施例公开如上,但其并非用以限定本发明,任何熟悉此技术的人,在不脱离本发明的精神和范围内,都可做各种的改动与修饰,因此本发明的保护范围应该以权利要求书所界定的为准。
Claims (7)
1.一种制备具有抗酪氨酸酶活性的有效部位的方法,其特征在于,包括以下步骤:
(1)取二年生萌条的新鲜铁皮石斛叶片,粉碎后,于30℃,用3倍质量的75%乙醇浸没超声提取2次以上,每次1小时,超声功率200W,提取液合并后,用乙酸乙酯萃取,乙酸乙酯与提取液的体积比为3:1,乙酸乙酯相经过减压浓缩得到干燥物;
(2)干燥物用95%乙醇溶解,过滤;
(3)步骤(2)所得过滤液与大孔树脂D101混合拌样,减压浓缩至干;其中,大孔树脂D101的用量与步骤(1)所得干燥物的质量比例为2:1;
(4)将步骤(3)所得混合物上D101大孔树脂,分别用6倍柱体积量的15%、30%、40%浓度的乙醇洗脱;
(5)收集步骤(4)30%乙醇洗脱的洗脱液,浓缩得干燥样品,干燥样品进一步用硅胶柱层析分离,先后分别用20倍柱体积的体积比20:1的二氯甲烷-甲醇和体积比30:1的甲醇-水洗脱,先后分别得到草大戟素、桑辛素M。
2.根据权利要求1所述方法制备得到的具有抗酪氨酸酶活性的有效部位。
3.一种化妆品美白剂,其特征在于,含有权利要求2所述的具有酪氨酸酶抑制活性的有效部位。
4.一种果蔬褐变抑制剂,其特征在于,含有权利要求2所述的具有酪氨酸酶抑制活性的有效部位。
5.一种预防和治疗黑色素异常导致的疾病的药物,其特征在于,含有权利要求2所述的具有酪氨酸酶抑制活性的有效部位;所述疾病包括人体色素沉着性疾病、黑色素瘤。
6.根据权利要求5所述一种预防和治疗黑色素异常导致的疾病的药物,其特征在于,所述药物的剂型包括固体粉末、水溶液、醇溶液、乳液、面膜、巴布剂、注射液、滴注液、粉针剂、颗粒剂、片剂、冲剂、散剂、口服液、糖衣剂、薄膜衣片剂、肠溶衣片剂、胶囊剂、口含剂、丸剂、膏剂、丹剂、喷雾剂、滴丸剂、口崩剂、微丸。
7.铁皮石斛在制备酪氨酸酶抑制剂中的应用。
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CN109044939A (zh) * | 2018-11-01 | 2018-12-21 | 广西南宁元敬本草堂生物科技有限公司 | 一种保湿祛斑美白面膜的制备方法 |
CN111304274A (zh) * | 2020-02-25 | 2020-06-19 | 西南交通大学 | 丙酮酸羧化酶作为毛兰素靶点蛋白的应用 |
CN111494284A (zh) * | 2020-06-01 | 2020-08-07 | 中国科学院昆明植物研究所 | 一种特殊方法炮制的铁皮石斛提取物及其在护肤品中的应用 |
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CN103211732A (zh) * | 2013-04-28 | 2013-07-24 | 江南大学 | 一种具酪氨酸酶抑制活性的混合物的制备方法及其应用 |
CN106008172A (zh) * | 2016-05-18 | 2016-10-12 | 江南大学 | 桑枝中具酪氨酸酶抑制作用有效部位制备方法及其应用 |
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CN103211732A (zh) * | 2013-04-28 | 2013-07-24 | 江南大学 | 一种具酪氨酸酶抑制活性的混合物的制备方法及其应用 |
CN106008172A (zh) * | 2016-05-18 | 2016-10-12 | 江南大学 | 桑枝中具酪氨酸酶抑制作用有效部位制备方法及其应用 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109044939A (zh) * | 2018-11-01 | 2018-12-21 | 广西南宁元敬本草堂生物科技有限公司 | 一种保湿祛斑美白面膜的制备方法 |
CN111304274A (zh) * | 2020-02-25 | 2020-06-19 | 西南交通大学 | 丙酮酸羧化酶作为毛兰素靶点蛋白的应用 |
CN111304274B (zh) * | 2020-02-25 | 2023-01-03 | 西南交通大学 | 丙酮酸羧化酶作为毛兰素靶点蛋白的应用 |
CN111494284A (zh) * | 2020-06-01 | 2020-08-07 | 中国科学院昆明植物研究所 | 一种特殊方法炮制的铁皮石斛提取物及其在护肤品中的应用 |
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