CN103239365B - 取自厚叶五味子的木脂素化合物及其获取方法 - Google Patents
取自厚叶五味子的木脂素化合物及其获取方法 Download PDFInfo
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- CN103239365B CN103239365B CN201210028050.1A CN201210028050A CN103239365B CN 103239365 B CN103239365 B CN 103239365B CN 201210028050 A CN201210028050 A CN 201210028050A CN 103239365 B CN103239365 B CN 103239365B
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Abstract
本发明公开皮肤美白用木脂素化合物其盐，以及从厚叶五味子获取木脂素化合或者其盐的方法。
Description
技术领域
本发明涉及具有皮肤美白效果的木脂素化合物及其获取方法。
背景技术
人的肤色取决于制造皮肤表层黑色素的黑素细胞活动性、血管分布、皮肤厚度或者类胡萝卜素和胆红素等是否含色素等多种因素。尤其，在如酪氨酸酶等诸多酶的作用下，从黑素细胞产生的黑色素即黑色素的形成水平是决定肤色的最重要因素之一。
皮肤中的黑色素，具有保护身体不受紫外线伤害的功能，但黑色素过多，也会引起痣、雀斑、点、老年斑等而使肤色变得暗淡，甚至起到促进皮肤老化、诱发皮肤癌等作用。
因此，通常都采用如抗坏血酸、曲酸、熊果苷、对苯二酚或其衍生物等普遍被认为具有皮肤美白效果的物质治疗或减轻黑色素生成过多导致的皮肤色素沉着的问题，但这些物质的皮肤美白效果并不是很完美，反而皮肤刺激性强而使用有限。
发明内容
要解决的技术问题
为解决上述问题，本发明提供具有皮肤美白作用的木脂素化合物及其盐。
此外，本发明还提供从厚叶五味子提取木脂素化合物及其盐的方法。
技术方案
本发明一方面提供皮肤美白效果卓越的木脂素化合物及其盐。
本发明另一方面提供木脂素化合物或者其盐的获取方法，其特征在于，包括：将厚叶五味子用有机溶剂提取的阶段；将上述阶段中取得的厚叶五味子提取物，用溶剂极性指数在1~9之间的溶剂之中，选择一种以上溶剂进行分馏的阶段；以及将上述阶段中取得的溶剂分馏物，重新用溶剂分离而获取木脂素化合物或者其盐的阶段。
有益效果
本发明一方面提供的木脂素化合物或其盐的皮肤美白效果卓越。上述木脂素化合物或其盐可从厚叶五味子中获取。
附图说明
图1是对厚叶五味子提取物馏分实施ESI-MS分析的结果图表。
图2是对厚叶五味子提取物馏分实施1H-NMR分析的结果图表。
图3是对厚叶五味子提取物馏分实施DEPT分析的结果图表。
图4是对厚叶五味子提取物馏分实施13C-NMR分析的结果图表。
图5是显示南五味子属木脂素F（Kadsura lignan F）的抑制黑色素生成效果的实验结果图。
具体实施方式
本说明书中提及的“皮肤”是指覆盖包括人类的动物身体表层的组织，是包括覆盖面孔或身体等在内的身体表层的组织乃至头皮和头发的最广义的概念。本说明书中提及的“提取物”为广泛概念，不管其提取方法、提取溶剂、被提取成分或者提取物的形态如何，只要是萃取天然物成分而获取的物质均包括在内。
本发明的发明人员从厚叶五味子提取物分离出木脂素化合物，再阐明所分离的木脂素化合物具有皮肤美白效果而使本发明得以完成。
本发明另一方面提供皮肤美白用木脂素化合物及其盐，用如下化学式1表示。本发明又另一方面，以下化学式1的木脂素化合物或其盐可抑制黑色素生成而具有卓越的皮肤美白效果。本说明书中，以下化学式F(Kadsuralignan F)1的木脂素化合物还可以用南五味子属木脂素来表达。
[化学式1]
本发明一方面的特点在于，木脂素化合物的盐包括药学上可接受的盐。
本说明书中“药学上可接受的”是意指按通常的医药学剂量（medicinal dosage）服用后，没有发生严重毒性，从而通过政府或者相应管制机构的可用于动物进一步说是可用于人体的批准或者已获相应批准，或者列入药典， 或者被认定为其它普通药典。
本说明书中“药学上可接受的盐”是指药学上允许并具备母体化合物(parentcompound)优选药理活性的本发明一方面上的盐。所述盐包括：（1）由盐酸、氢溴酸、硫磺酸、硝酸、磷酸等无机酸形成；或者由乙酸、丙酸、己酸、环戊丙酸、乙醇酸、丙酮酸、乳酸、丙二酸、琥珀酸、羟基丁二酸、顺丁烯二酸、反丁烯二酸、酒石酸、柠檬酸、苯甲酸、3-羟基苯甲酸、4-羟基苯甲酸、肉桂酸、苯基乙醇酸、甲基磺酸、乙烷磺酸、1、2-乙烷-二磺酸、2-羟基乙烷磺酸、苯磺酸、4-氯苯磺酸、2-萘磺酸、4-甲苯磺酸、樟脑磺酸、4-甲基二环[2,2,2]-oct-2-N-1-羧酸、葡庚糖酸、3-苯基丙酸、三甲基乙酸、丁基乙酸、十二烷基硫酸、葡糖酸、谷氨酸、羟基萘甲酸、水杨酸、硬酯酸或者粘糠酸等形成的酸加成盐(acid addition salt)；或者（2）母体化合物中的酸性质子被置换时形成的盐。
本发明一方面特征在于，包括取自厚叶五味子的木脂素化合或者其盐。本发明的另一方面特征在于，木脂素化合物其盐可以从厚叶五味子提取物分离获取。
本发明一方面的特征在于，厚叶五味子（Kadsura coccinea (Lem. )A. C.Smith）有时也称为“黑老虎”。本发明一方面的特征在于，厚叶五味子提取物包括但不限于厚叶五味子的叶子、茎、根、花、果实或者种子的提取物。
本发明一方面提供：包括上述化学式1中表示的木脂素化合物或者其盐的化妆料、药学以及食品合成物。本发明在另一方面，包含木脂素化合物或者其盐为有效成分的化妆料、药学以及食品合成物的皮肤美白效果卓越，具体地说，可以改善或预防痣、雀斑、点、老年斑及其它皮肤疹斑等皮肤色素沉着。本发明又另一方面涉及的化妆料、药学及食品合成物可以包含：在合成物总重量中所占重量比达0.001~80%，具体地占0.01~50%，更具体地占0.1~10%的木脂素化合物或者其盐。所述重量比是发挥本发明所期待的皮肤美白效果的最适当比例，可以满足合成物的稳定性和安全性，效果与成本比也按所述范围包含为宜。
本发明一方面涉及的化妆料合成物，可以以适用于局部使用的全部剂型提供。例如，溶液、在水相分散乳相获得的乳剂、在油相分散水相获得的乳剂、悬浮液、固体、凝胶、粉末、糊状物、泡沫（foam）或者气雾剂合成物的剂型提供。这种剂型合成物是可以按照该领域通常使用的方法制造。
本发明一方面涉及的化妆料合成物，除上述物质之外，在不影响主要效果的范围内，可优选包含可提升主要效果的其它成分。具体地说，可以包含曲酸、熊果苷或者抗坏血酸衍生物，以提升皮肤美白效果。本发明另一方面涉及的化妆料合成物还可以包含：保湿剂、润肤剂、表面活性剂、紫外线吸收剂、防腐剂、杀菌剂、抗氧化剂、pH调整剂、有机及无机颜料、香料、清凉剂或者止汗剂。所述成分的配比量是在不降低本发明目的和效果的范围内，可以随意选择。比如，占合成物总重量的0.01~5%，具体是0.01~3%。
本发明一方面涉及的药学合成物可以经口、直肠、局部、经皮、静脉、肌肉、腹腔或皮下等渠道投药。
经口投药的剂型可以选择包括但不限于片剂、丸剂、软质及硬质胶襄、颗粒、粉剂、小颗粒、液态、乳油或小丸剂。 这些剂型除有效成分之外，还可以含有稀释剂（例：乳糖、葡萄糖、蔗糖、甘露醇、纤维素或糖胶）、助滑剂（例：硅石、滑石、硬脂酸、聚乙二醇），或者粘结剂（例：硅酸铝镁、淀粉糊、凝胶、黄芪胶、甲基纤维素、羧甲基纤维素钠或聚乙烯吡咯烷酮）。此外，还可以含有崩解剂、吸收剂、着色剂、香味剂或者甜味剂等药剂学上的添加剂。
非经口投药制剂包括但不限于注射剂、点滴剂、乳液、软膏、凝胶、乳霜、悬浮剂、乳剂、坐剂、片剂或喷雾剂（spray）。
本发明一方面涉及的药学合成物的有效成分根据被投药对象的年龄、性别、体重、病理状态及其严重度、投药渠道或者开方人判断有所区别。基于这种因素，其适用量取决于该行业普通技能人员的技能水平。例如一天投药用量可以定为0.1mg/kg~100mg/kg，具体是，可以适用但不限于5 mg/kg/日~50 mg/kg/日。
本发明一方面涉及的食品合成物包括喜欢吃的食品的合成物或者保健食品合成物。
关于上述食品合成物的剂型，没有特殊限制，但可以选用片剂、颗粒剂、粉末剂，或者如饮料等液态、凝胶、块等剂型。各剂型的食品合成物除有效成分之外，可以从该领域通常使用的成分中，根据剂型或者使用目的适当选择配合使用，而且与其它原料配合使用，效果会进一步得到提升。
上述有效成分的投药量取决于该行业普通技术人员的技能水平，例如，一天投药用量，可以定为0.1mg/kg/~5000mg/kg，更具体地可以定为但不限于50 mg/kg~500 mg/kg，而且根据被投药的对象年龄、健康情况和合并症等多种因素而有所不同。
本发明一方面提供木脂素化合物或者其盐的获取方法，包括：用有机溶剂提取厚叶五味子的阶段；从溶剂极性指数在1~9之间的溶剂中，选择其中之一以上溶剂对上述阶段取得的厚叶五味子提取物实施分馏的阶段；以及用溶剂对上述阶段取得的溶剂馏分重新实施分离而获取木脂素化合物或者及盐的阶段。本发明另一方面涉及的木脂素化合物或者其盐的获取方法包括上述化学式1的木脂素化合物或其盐的获取方法。本发明又另一方面涉及的木脂素化合物或者其盐的获取方法包括：皮肤美白用化合物或者其盐的获取方法。
本发明在另一方面，用于提取厚叶五味子的有机溶剂包括但不限于由乙醇、丙酮、己烷、乙醚、醋酸乙酯、丁酮以及氯仿组成的组合之一以上。上述乙醇包括C1~C5的低级乙醇，C1~C5的低级乙醇还包含甲醇、乙醇、异丙醇、n-丙醇、丁醇以及异丁醇组成的组合之一以上。
本发明在另一方面，获取木脂素或者其盐的阶段可以包括：从分馏阶段取得的溶剂馏分中，溶剂极性指数在2~5之间的溶剂馏分，按100:0 ~ 0:100容积比，利用从含有石油醚（petroleum ether）和醋酸乙酯的混合溶剂中的一种以上溶剂进行分离的阶段；以及将在上述阶段取得的分离物中，将用石油醚和醋酸乙酯容积比在10:1 ~ 1:10之间的溶剂分离的分离物，按70:30 ~ 80:20的容积比，用包含乙醇和水的混合溶剂，实施色谱分离的阶段。
本发明另一方面涉及的溶剂分离阶段，在溶剂馏分中可以选择溶剂极性指数在2~5之间，具体是2.5~4.5之间的溶剂馏分。本发明又另一方面涉及的溶剂分离阶段，可以利用硅胶柱实施溶剂分离。本发明的又另一方面，包含石油醚以及醋酸乙酯的混合溶剂可以利用石油醚和醋酸乙酯容积比在100:0 ~ 0:100之间，具体是50:1 ~ 1:50，更具体是20:1 ~1:20的溶剂。
本发明另一方面，色谱法包含高速液相色谱法（HPLC）。本发明又另一面涉及的用于色谱法的溶剂包括乙醇，具体是甲醇和水容积比在10:1 ~ 1:10，具体是10:1 ~ 5:1，更具体是10:1 ~ 4:1之间的溶剂。
下面结合实施例和实验例进一步详细描述本发明的构成和效果。但，这些实施例和实验例仅为提高对本发明的理解水平而提供，并不是对本发明的范畴和范围进行限制。
实施例
获取南五味子属木脂素F
用95%乙醇在70~75℃温度下，将厚叶五味子（30kg）利用两个小时的时间反复提取三次后取得厚叶五味子提取物（2640g）。提取三次时使用的95%乙醇的量分别为150L、150L以及120L。将取得的厚叶五味子提取物在水中溶化之后，从溶剂极性指数（PolarityIndex）在2~9之间的溶剂中，选择其中之一以上溶剂，分别获取各溶剂的馏分。其中极性指数（Polarity Index）在2.5~4.5之间的溶剂馏分，利用硅胶柱再实施分离。分馏溶液是使用容积比在100：0~0：100之间的石油醚（Petroleum ether）和醋酸乙酯（EtOAc）混合溶剂，分馏结果共获取十个分馏物。其中取石油醚和醋酸乙酯的容积比在10：1~4：1之间的溶剂分馏物，用乙醇再结晶以后，对除沉淀物之外的剩余溶液实施过滤浓缩。然后对浓缩的试样实施HPLC（DOS柱，溶剂条件是甲醇：H2O=72:28~79:21）而获取五个馏分，其中对第四个馏分（100mg）实施ESI-MS、1H-NMR、DEPT及13C-NMR分析，再用图1~4标示出其结果，从而确定实施分析的白色粉末形态的馏分就是南五味子属木脂素F（Kadsuralignan F）。具体地说，ESI-MS以及1H-NMR结果如下。
ESI-MS: m/z 421.16 [M+Na]+。
1H-NMR (400MHz, CD3Cl3)δ: 6.42 (1H,s,H-1),4.30 (1H,d,J=6.9Hz,H-6),2.65(1H,m,H-7),2.05 (1H,m,H-8), 4.89 (1H,s,H-9),6.30 (1H,s,H-11),1.05 (6H,d,J=7Hz,C-17,C-18),5.90 (1H,s,H-19), 5.96 (1H,s,H-20),3.76 (3H,s,1-OCH3),3.84(3H,s,14-OCH3); 13C-NMR (100MHz, CD3Cl3)δ: 144.6 (C-1),137.1 (C-2),147.4 (C-3),103.5 (C-4),140.0 (C-5),90.4 (C-6), 37.4(C-7),52.9 (C-8),90.1 (C-9),136.7 (C-10),100.1 (C-11),148.3 (C-12),135.8 (C-13), 142.6 (C-14),119.0 (C-15),118.2(C-16),14.1 (C-17),13.6 (C-18),101.0 (C-19),100.9 (C-20),60.2 (1-OCH3),60.1(14-OCH3)。
实验例
南五味子属木脂素F的皮肤美白效果评估
将大鼠黑素细胞的细胞株melan-a细胞株在RPMI 1640(Gibco BRL, NY, USA)培养基，再添加经10%热处理-钝化的牛血清（FBS, Gibco BRL, NY, USA）、100 mg/mL青霉素钾、100 mg/mL硫酸链霉素（Gibco BRL, NY, USA）以及PMA(Sigma-Aldrich, St Louis,MO, USA)的细胞培养基进行培养。Melan-a细胞培养是在48孔板上，按1.5X104 细胞/孔方式播种以后，在10% CO2、 37℃的细胞培养基培养24小时。然后处理实施例中取得的分别包含0.3 ppm、0.6 ppm、 1.25 ppm、2.5 ppm或5 ppm南五味子属木脂素F的细胞培养基并培养了六天的时间。并使用50ppm熊果苷作为阳性对照组，每三天更换一次包含新南五味子属木脂素F或者熊果苷的细胞培养基。溶剂是使用DMSO在细胞培养基按1/1000比例稀释。培养之后清除培养基，用磷酸缓冲液（Phosphate Buffered Saline, PBS）清洗细胞之后，放入含10%DMSO的1 mol/L NaOH溶液100 ㎕，在60℃下使细胞溶化一个小时。然后利用MolecularDevices公司的酶标仪（SpectraMax 190 ELISA reader, Molecular DevicesCorporation, USA, CA）测定其吸光率而对OD 475值进行评估。然后基于所获得的测定量，利用合成黑色素的标准曲线(Sigma-Aldrich, St Louis, MO, USA)计算各个试样的黑色素量。然后用各试样中测定的蛋白质浓度修正，求出各试样的蛋白质与黑色素量之比，再把获得的数据与无处理对照组进行对比而推定抑制黑色素生成的能力（%）。然后用图5标示出其结果。
如图5所示，南五味子属木脂素F的抑制黑色素生成能力卓越，尤其，5 ppm的南五味子属木脂素F抑制黑色素生成的能力，明显优于已知皮肤美白物质熊果苷50ppm，从而确定，南五味子属木脂素F具有卓越的皮肤美白效果。
下面说明本发明一方面涉及的合成物剂型例，但此剂型仅用以详细说明，并不是对本发明进行限制，除此剂型之外其它多种剂型均可适用。
[剂型例1] 化妆水
利用下表中记录的成分，按照通常使用的方法制造化妆水。
【表1】
| 成分 | 含量(重量%) |
| 南五味子属木脂素F | 2.0 |
| 丙三醇 | 3.0 |
| 丁二醇 | 2.0 |
| 丙二醇 | 2.0 |
| 羟基乙烯基聚合物 | 0.1 |
| PEG 12壬基苯基醚 | 0.2 |
| 聚山梨醇酯80 | 0.4 |
| 乙醇 | 10.0 |
| 三乙醇胺 | 0.1 |
| 防腐剂、色素、香料 | 适量 |
| 纯净水 | 残留量 |
[剂型例2] 乳霜
使用下表中记录的成分，按通常方法制造乳霜。
【表2】
| 成分 | 含量(重量%) |
| 南五味子属木脂素F | 1.0 |
| 聚山梨醇酯60 | 1.5 |
| 山梨糖醇酐倍半异硬脂酸酯 | 0.5 |
| PEG 60硬化蓖麻油 | 2.0 |
| 液状石蜡 | 10.0 |
| 角鲨烷 | 5.0 |
| 辛酸/癸酸甘油三酯 | 5.0 |
| 丙三醇 | 5.0 |
| 丁二醇 | 3.0 |
| 丙二醇 | 3.0 |
| 三乙醇胺 | 0.2 |
| 防腐剂、色素、香料 | 适量 |
| 纯净水 | 残留量 |
[剂型例3] 片剂
取南五味子属木脂素F 100 mg、大豆提取物50mg、葡萄糖100mg、红参提取物50mg、淀粉96mg、硬脂酸镁4mg混合在一起，再添加乙醇形成颗粒之后烘干压制成片剂。
[剂型例4] 保健饮料
南五味子属木脂素 F.................................1000 ㎎
柠檬酸.............................................. 1000 ㎎
低聚糖.............................................. 100 g
牛磺酸.............................................. 1 g
纯净水.............................................. 残留量
按照通常制造饮料的方法，将上述成分混合之后，在85℃左右的温度搅拌加热一个小时，然后过滤所得溶液再实施灭菌。
Claims (3)
1.木脂素化合物或其盐在制备用于抑制皮肤细胞中黑色素的生成的组合物中的用途，其中，所述木脂素化合物由以下化学式1表示:
[化学式1]
2.根据权利要求1所述的用途，其特征在于，木脂素化合物或其盐取自厚叶五味子。
3.根据权利要求1所述的用途，其特征在于，所述组合物为化妆料合成物、药学合成物或食品合成物。
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| 黑老虎及胡桃枝皮的化学成分研究;李贺然;《中国优秀博硕士学位论文数据库（医药卫生科学辑）》;中国学术期刊（光盘版）电子杂志社;20061115(第11期);11页第2段、27-29页表2.1.1 * |
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