CN108138212A - 利用酶法从人参的皂甙中选择性地制备k化合物和y化合物的方法 - Google Patents
利用酶法从人参的皂甙中选择性地制备k化合物和y化合物的方法 Download PDFInfo
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- CN108138212A CN108138212A CN201680062066.0A CN201680062066A CN108138212A CN 108138212 A CN108138212 A CN 108138212A CN 201680062066 A CN201680062066 A CN 201680062066A CN 108138212 A CN108138212 A CN 108138212A
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- ginseng
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Abstract
本发明涉及从人参的皂甙中选择性地制备原本微量存在于人参中的K化合物和Y化合物的方法,具体地说涉及利用特定的酶对从人参中获得的皂甙进行处理,通过转换上述皂甙的结构,从而获得目标化合物,即,能够高收率地获得K化合物和Y化合物的方法。
Description
技术领域
本发明涉及从人参的皂甙中选择性地制备原本微量存在于人参中的K化合物和Y化合物的方法,具体地说涉及利用特定的酶对从人参中获得的皂甙进行处理,通过转换上述皂甙的结构,从而获得目标化合物,即,能够高收率地获得K化合物和Y化合物的方法。
背景技术
人参皂甙具有与其他植物中发现的皂甙所不同的特异的化学结构,因而其药理学性能独特,因人参(ginseng)配糖体(glycoside)的含义还被称为“人参皂苷(ginsenoside)”。人参皂甙的具体种类有:含有人参皂苷Rb1、Rb2、Rc、Rd、K化合物和Mc化合物和O化合物等的人参二醇系和含有人参皂苷Re、Rf、Rg1、Rg3、Rg5、Rh1和Rh2等的人参三醇系,这些人参皂甙表现出不同的效能。
[反应式1]
如上述反应式1所示,尤其是人参二醇系皂甙的人参皂苷Rb1、Rb2和Rc等通过微生物的代谢能够转换为其他人参皂甙,因此一直以来就有利用酶从人参皂甙向其它种类的特定人参皂甙转换的方法。
然而,利用现有酶的转换反应中,由于酶对底物的非特异性大,使得相对于使用的皂甙底物来说需要使用大量的酶,并且所需的人参皂甙的收率极低。
获得现有人参皂甙的方法不是仅仅转换成所需的特定人参皂甙,而是通过对转换成的多种人参皂甙进行提取等方式后,对得到的物质进行精制从而分离出所需的人参皂甙的技术性解决方案。
然而,这种现有方式为了获得纯净的特定人参皂甙,精制过程需要消耗额外的费用、时间等,导致人参皂甙的售价只能提高,限制了与其相关产品中人参皂甙的大量使用。
尤其是K化合物,属于由人参皂甙转换成化合物的过程中最后生成的化合物,因而需要使中间代谢体全部反应所需的各种酶,另外,由于反应中间代谢产物的生成,又降低了代谢体与酶之间的反应性能。不仅如此,由于中间代谢体之间的反应液内的凝结现象,导致收率降低问题的发生。
现有技术文献
专利文献
1、韩国公开专利第10-2014-0107865号(2010年10月06日公开)
发明内容
技术问题
通过现有方法获得特定人参皂甙不仅费用高,而且难以大量得到所需的人参皂甙。因而,需要一种能够大量生产目标人参皂苷的同时,还能降低费用的制备方法。
因此,本发明的目的在于提供一种高收率地获得所需的特定人参皂甙的同时,操作简单的皂甙转换方法。
解决问题的技术方案
为了实现上述目的,本发明提供了一种利用酶对人参的皂甙进行转换,从而高收率地制备K化合物和Y化合物的方法,该方法中的酶为由从曲霉属中分离出的果胶酶、柚苷酶、纤维素酶和半纤维素酶组成的群中选择的一种以上;以及由从木霉属中分离出的果胶酶和纤维素酶组成的群中选择的一种以上。
发明效果
根据本发明,通过利用人参皂甙转换的方法,容易高收率地获得所需的人参皂甙。
附图说明
图1为通过硅胶柱色谱法对人参皂甙转换反应后生成的K化合物和Y化合物的确认结果示意图。
具体实施方式
本发明涉及利用酶法选择性制备K化合物(化学式1)和Y化合物(化学式2)的方法。
在本发明的方法中,由于使用了来源于微生物的酶,因而能够有效地促使由人参的皂甙,具体为人参的人参二醇系皂甙,更具体为人参皂苷Rb1、Rb2、Rc、Rd或它们的化合物向所需的人参皂甙的转换,从而能够高收率地获得K化合物和Y化合物。
具体来讲,本发明中使用的酶优选为从曲霉属的微生物和木霉属(Trichoderma)的微生物中获得的酶,曲霉属的微生物优选为从由黑曲霉菌(Aspergillus niger)、棘孢曲霉菌(Aspergillus aculeatus)、琉球曲霉菌(Aspergillus luchuensis)和米曲霉菌(Aspergillus oryzae)组成的群中选择的一种以上的曲霉属的微生物,木霉属(Trichoderma)的微生物优选为从由侵占木霉菌(Trichoderma aggressivum)、哈茨木霉菌(Trichoderma harzianum)、里氏木霉菌(Trichoderma reesei)和绿色木霉菌(richodermaviride)组成的群中选择的一种以上的木霉属的微生物,最优选为从棘孢曲霉菌和里氏木霉菌中获得的酶。
另外,本发明中使用的酶为从上述微生物中分离出的柚苷酶、半纤维素酶、β-葡聚糖酶、乳酸酶、纤维素酶、β-半乳糖苷酶、果胶酶,优选为果胶酶、柚苷酶、半纤维素酶或纤维素酶。
大部分相同种类的酶尽管起到同样作用,但根据酶来源微生物的种的不同,具体地酶在底物中的作用部位不同,会出现底物特异性的差异。因此,本发明中最优选同时使用由从棘孢曲霉中获得的果胶酶、柚苷酶、纤维素酶和半纤维素酶组成的群中选择的一种以上;以及,由从里氏木霉菌中获得的果胶酶、纤维素酶、或它们的混合物组成的群中选择的一种以上。
本发明中,将人参皂甙以0.01~20重量%的量溶于溶剂后,使用上述酶通过酶法将皂甙转换为所需的人参皂甙。此时,优选使用不降低酶活性的溶剂,例如可以使用水或缓冲溶液等的水性溶剂、或者水或缓冲溶液等的水性溶剂和有机溶剂的混合液。此时,具体使用的缓冲溶液可以为乙酸、柠檬酸盐、磷酸或柠檬酸盐-磷酸等,有机溶剂可以为乙腈、二氧六环、二甲基亚砜、甲醇、乙醇、1-丙醇或2-丙醇等。优选地,使用溶剂的pH范围为2.5~7.5,优选为3~6,更优选为3.5~5.5。
本发明的方法中,相对于使用的底物的用量,优选地,使用的酶的添加总量为1~500重量%,进一步优选为10~400重量%,更进一步优选为10~200重量%。
反应温度为酶不发生失活的温度,温度的维持范围优选为30~60℃,进一步优选为35~60℃,更进一步优选为40~55℃。
另外,同样地,反应时间若在酶保持活性的期间内则对其没有特别的限定,优选地,搅拌反应1~120小时,优选为1~96小时,进一步优选为24~96小时,更进一步优选为24~72小时。
酶反应的进行方式可以为:2种酶同时加入到底物中或者加入一种酶先进行反应后投加剩余的酶的顺序方式进行。
之后在沸腾水浴中使用加热等的公知方法使酶失活,从而获得大量含有K化合物和Y化合物的反应液。
发明的具体实施方式
以下,通过具体实施例对本发明进行详细说明。但是,以下实施例并不用于限定本发明的范围。
[参考例1]制备人参精制皂甙
将2kg的红参、白参、新鲜人参、参须或它们的人参叶、人参花、人参果实放入20L的乙醇中,回流提取3次后,在15℃沉降6天。之后,通过滤布过滤和离心分离法分离出残渣和滤液,将分离出的滤液经减压浓缩得到的浓缩液悬浮于水中,采用1L乙醚提取5次来去除色素,将水层采用lL的1-丁醇提取3次。将由此获得的所有的1-丁醇层采用5%KOH处理后,用蒸馏水洗涤,之后,减压浓缩获得1-丁醇浓缩液,将其溶于少量的甲醇中,然后加入大量的乙酸乙酯,通过将生成的沉降物干燥,获得40~80g的人参精制皂甙(含有人参皂苷Rb1、Rb2、Rc、Rd、Re、Rg1、Rf等)。
[实施例1]通过酶反应制备K化合物和Y化合物
将10g上述参考例1中的人参精制皂甙(含有人参皂苷Rb1、Rb2、Rc、Rd、Re、Rg1、Rf等)溶解于1L水中。
然后向上述混合液中同时添加从棘孢曲霉中分离出的果胶酶和从里氏木霉菌中分离出的果胶酶,此时,以相对于各自底物的100重量%添加上述酶,在30℃反应72小时。通过薄层色谱法周期性地确认底物是否完全耗尽,在沸腾水浴中加热10分钟使酶失活,终止反应。最后,向反应液按1:1的比例(相对于反应液的体积比)加入乙酸乙酯,提取3次、浓缩后,通过硅胶柱色谱法(氯仿:甲醇=9:1)分离出人K化合物和Y化合物(图1)。
10g人参皂甙中存在:2.66g人参皂苷Rb1、0.73g人参皂苷Rb2、1.23g人参皂苷Rc和0.38g人参皂苷Rd。从人参皂苷Rb1、人参皂苷Rc和人参皂苷Rd转换的K化合物的收率为95%以上,从人参皂苷Rb2转换的Y化合物的收率为95%以上。
Claims (9)
1.一种利用酶法从人参的皂甙中制备K化合物和Y化合物的方法,其特征在于,该方法利用由从曲霉属中分离出的果胶酶、柚苷酶、纤维素酶和半纤维素酶组成的群中选择的一种以上的酶;以及由从木霉属中分离出的果胶酶和纤维素酶组成的群中选择的一种以上的酶来转换人参的皂甙,从而制备K化合物(化学式1)和Y化合物(化学式2),
[化学式1]
[化学式2]
2.根据权利要求1所述的方法,其特征在于,所述方法包括:
1)将作为底物的人参的皂甙溶解于水性溶剂或水性溶剂与有机溶剂的混合液中,将由从曲霉属中分离出的果胶酶、柚苷酶、纤维素酶和半纤维素酶组成的群中选择一种以上的酶;以及由从木霉属的微生物中分离出的果胶酶和纤维素酶组成的群中选择的一种以上的酶添加到混合液中,在加热状态的水浴中搅拌反应的阶段;
2)所述底物完全耗尽时,使酶失活,终止反应的阶段;
3)向反应液中添加乙酸乙酯提取后浓缩,分离K化合物和Y化合物的阶段。
3.根据权利要求2所述的方法,其特征在于,所述人参的皂甙为从人参皂苷Rb1、Rb2、Rc、Rd或它们的混合物中选择的一种以上。
4.根据权利要求2所述的方法,其特征在于,所述曲霉属的微生物为由黑曲霉(Aspergillus niger)、棘孢曲霉(Aspergillus aculeatus)、琉球曲霉(Aspergillusluchuensis)、米曲霉(Aspergillus oryzae)组成的群中选择的一种以上,
所述木霉属的微生物为由侵占木霉菌(Trichoderma aggressivum)、哈茨木霉菌(Trichoderma harzianum)、里氏木霉菌(Trichoderma reesei)和绿色木霉菌(richodermaviride)组成的群中选择的一种以上。
5.根据权利要求2所述的方法,其特征在于,同时或依次添加由从所述曲霉属中分离出的果胶酶、柚苷酶、纤维素酶和半纤维素酶组成的群中选择的一种以上的酶;以及由从木霉属中分离出的果胶酶和纤维素酶组成的群中选择的一种以上的酶。
6.根据权利要求2所述的方法,其特征在于,相对于底物的量,所述酶的总量为10~400重量%。
7.根据权利要求2所述的方法,其特征在于,所述酶的反应温度为35~60℃。
8.根据权利要求2所述的方法,其特征在于,所述酶的反应时间为24~96小时。
9.根据权利要求2所述的方法,其特征在于,所述溶剂的pH范围为3~5.5。
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