CN105829275A - 一种黄腐酚的制备方法 - Google Patents
一种黄腐酚的制备方法 Download PDFInfo
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- CN105829275A CN105829275A CN201480054359.5A CN201480054359A CN105829275A CN 105829275 A CN105829275 A CN 105829275A CN 201480054359 A CN201480054359 A CN 201480054359A CN 105829275 A CN105829275 A CN 105829275A
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- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 title claims abstract description 85
- FUSADYLVRMROPL-UHFFFAOYSA-N demethylxanthohumol Natural products CC(C)=CCC1=C(O)C=C(O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C1O FUSADYLVRMROPL-UHFFFAOYSA-N 0.000 title claims abstract description 84
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 title claims abstract description 84
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Abstract
本发明提供了一种制备黄腐酚的方法,其中,将一种含黄腐酚的提取物与水混合,过渡金属盐溶液添加到所获得的混合物中,然后将得到的黄腐酚沉淀收集,干燥,得到高于90%纯度的黄腐酚。
Description
本发明提供一种从萃取后的废啤酒花、啤酒花植物颗粒或啤酒花中提取高纯度的黄腐酚的方法。所获得的黄腐酚的纯度高,可直接应用于膳食补充剂,饮料及作为治疗产品原料。
黄腐酚(Xn)或((E)-1-[2,4-二羟基-6-甲氧基-3-(3-甲基丁-2-烯基)-苯基]-3-(4-羟基苯基)-丙-2-烯-1-酮)((E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)-phenyl]-3-(4-hydroxyphenyl)-prop-2-en-1-one)是异戊二烯化查耳酮类的天然产物,它主要来源于啤酒花(HumulusLupus(hop))的雌花序。它仅微量存在于啤酒中。该化合物包含α,β不饱和羰基连接的两个苯环:
该分子中存在游离羟基,很容易异构化成一种黄酮生物合成的中间体——黄烷酮。相对于啤酒花的其他成分,黄腐酚更亲脂,因其结构中存在异戊二烯取代基。应当注意的是,在活的生物系统中,异戊二烯化的(法尼基或香叶基香叶基)结构单元能够促进许多细胞内分子附着于细胞膜中,这决定了其相应的活性。同理,在黄腐酚中,这种结构单元显著调节了该化合物的生物活性,更重要的是,影响了它的物理化学特性和亚细胞分布。
体外和体内研究还显示,黄腐酚通过许多机理减少了炎症和氧化过程。其中一个很重要的过程是:消除氧自由基及其活性形式(RTF),抑制环氧合酶(COXI和COXII)的活性,减少前列腺素,NO,TNFα,NFkB的产生和中和膜磷脂(membranephospholipide)的过氧化。
黄腐酚的抗氧化和抗炎活性与其分子中的羟基和异戊烯基取代基相关。α,β-不饱和羰基基团也很重要。该基团参与生物学上重要的亲核试剂的迈克加成反应,例如:蛋白质的L-半胱氨酸和其它含巯基的分子,所获得的共价加成物使得与黄腐酚结合的各种分子丧失生物活性。
黄腐酚的广谱活性可能来自其与重要的生物分子的结合能力。最典型的案例为黄腐酚对聚合酶α合成酶,拓扑异构酶I,碱性磷酸酶,芳香酶,二酰基甘油酰基转移酶,MAPK信号通路蛋白,FAK激酶,Akt和STAT或NF-kB转录因子的影响。XN诱导的所述蛋白质的活性的降低引起细胞多效性,如肿瘤细胞的增殖,细胞循环,粘附和迁移干扰。
值得注意的还有涉及神经保护属性的信息。在MCAO引起的局灶性脑缺血大鼠模型中,即体内局灶性脑缺血模型中,黄腐酚显著减少脑缺血性坏死区。因此黄腐酚也被认为减小了由β淀粉样肽(Aβ)引起的神经毒性作用。已知Aβ介导是自由基机理,这也是阿尔茨海默氏病的主要成因之一,其机理是通过增加自由基的产生和神经细胞脂质过氧化,导致它们的细胞凋亡。
另外,除了对受体的作用,黄腐酚的活性的机制还和其对脂质膜的选择活性相关。黄腐酚与模型脂膜的互动机制的研究显示,主要作用在于其对细胞膜的动力学及膜结构的重大修改。即使极低浓度的黄腐酚也能强烈作用于脂质膜的亲水片段,引起双层膜的厚度的变化。已知新烟碱类,由于疏水性高,能很容易地穿透脂膜,黄腐酚与脂膜的相互作用能显著降低新烟碱类的穿透性,这解释了除了其对尼古丁受体的阻断作用外的强大的活性。
就其化学结构而言,黄腐酚为多酚结构,然而,与多酚不同的是,其几乎不溶于热水,但易溶于醇类或醇类和水的混合溶剂中。
提取后的啤酒花是黄腐酚的良好来源,包括酿造业和啤酒生产业产生的酒花浸膏的废料。提取后的废啤酒花中包含的黄腐酚估计高达1%,具体取决于啤酒花植物的种属。
现有技术中,黄腐酚的制备技术众多。专利DE19939350A1公开了一种富含黄腐酚的啤酒花提取物的制备方法,所述专利中,使用水和乙醇的混合溶剂为提取溶剂。所得的提取物含5-15%的黄腐酚。
专利EP1424385B1公开了一种以压缩的CO2为溶剂从含黄腐酚生料中提取黄腐酚的方法,该方法需要高于500bar的压力及高于60℃的温度。
中国专利CN101440029公开了一种从啤酒花植物及含黄腐酚的产品中提取黄腐酚的方法。该方法使用有机溶剂辅以超声波萃取,之后与硅藻土混合,过滤,以水和甲醇混合溶剂洗出,浓缩,沉淀及干燥,得到86%纯度的的黄腐酚。
专利EP2187899B1公开了从啤酒花植物中制备高黄腐酚含量的组合物的方法,该方法中将一种盐加入含有黄腐酚的溶液中,所述盐的浓度控制在0.05-0.5M之间,随后调整溶液pH值至10.5-12.0之间,过滤所获得的沉淀,酸化滤液至pH为7-8,以获得40-95%纯度的黄腐酚沉淀。
专利US11/790365公开了一种高(60-90%)的黄腐酚含量的粉末的制备方法,所述方法包括通过碱性溶液产生一个富集黄腐酚提取物的悬浊液,分离不溶性产物,通过酸中和溶解的黄腐酚使之沉淀,分离沉淀出的产物。
专利CN101433592公开了使用各种吸附树脂制备高纯度黄腐酚的方法。
综上所述,通过对现有技术的分析显示,有必要开发一种简单,廉价的制备高纯度的黄腐酚的方法。
解决该问题的方法是发展一种从萃取后的废啤酒花,啤酒花类植物颗粒或啤酒花中制备黄腐酚的新方法。
因此,本发明提供一种制备黄腐酚的方法,其中:
a)将一种含黄腐酚的提取物和水混合;
b)将一种过渡金属的盐溶液加入到所得到的混合物中;
c)收集所得黄腐酚沉淀,干燥后得到纯度大于90%黄腐酚。
优选地,步骤b中,所述盐的浓度为0.001-10摩尔/升;更优选地,所述盐的浓度为0.001-0.05摩尔/升或大于5摩尔/升.
优选地,所述步骤b中,在加入盐后还包含:
b1)碱化溶液到pH值大于7;
b2)滤出第一批沉淀,将滤液酸化至pH值低于7;
b3)酸化后的滤液浓缩,得到的黄腐酚的沉淀。
优选地,所述步骤b1中,溶液碱化至pH值在7.5-10.5之间或高于12。
优选地,含黄腐酚的提取物是通过以一种可与水混溶的有机溶剂提取啤酒花废渣、啤酒花、啤酒花植物颗粒或以上的混合物得到的,所述溶剂用量为每公斤原料使用0.1-10升溶剂。
优选地,所述可与水混溶的溶剂选自酮或醇或其混合物。更优选地,所述溶剂选自丙酮、甲醇、乙醇、丙醇或以上的混合物。
优选地,所述提取的温度为5-65℃.
优选地,所述含黄腐酚的提取物和水的比例为每升提取物使用0.1-5升水,更优选地,所述含黄腐酚的提取物和水的比例为每升提取物使用1-3升水。
优选地,步骤b)中,所述过渡金属盐浓度为0.01-0.05M。
优选地,所述过渡金属盐为Cu(II)盐或Zn(II)盐。
优选地,所述过渡金属盐为氯盐,硝酸盐或硫酸盐。
更优选地,所述过渡金属盐为CuCl2,CuSO4,ZnCl2或ZnSO4。
使用本方法得到的黄腐酚纯度至少高于90%,通常高于95%,本方法不需使用复杂的色谱系统或硅胶负载。
本发明方法所得黄腐酚纯度使用HPLC测定。参数如下:SUPELCOSILLC-PAH色谱柱,15厘米×4.6毫米,5微米粒径;柱温:20℃;A相为95%乙腈0.3%HCOOH;B相为2%乙腈0.3%HCOOH;流速:2毫升/分钟;进样量:20微升;检测波长:370和290纳米。
以下结合具体实施例,进一步阐述本发明。
实施例1
250克萃取后的废啤酒花(post-extractionspenthops)倒入丙酮(0.75升),机械搅拌1小时,经滤纸过滤析出物,得到的滤液(0.65升)加入水(1.3L),每升溶液加入300毫升浓度为10克/升的氯化铜溶液(最终浓度控制在0.022M),加入氯化铜后,溶液的pH值稳定至约4.5。实际上,加入氯化铜后,立即出现沉淀物,绿色的残余草酮和叶绿素的结块从黄色溶液中分离出来,该溶液中存在黄腐酚。一小时后,加入NaOH将pH值提高至约10以沉淀过量的铜,在容器的底部可观察到了泥样沉淀和铜的氢氧化物沉淀。以滤纸滤去沉淀物,得到的滤液用HCl酸化至pH6,在旋转蒸发仪上浓缩,得到黄腐酚的结晶。将其滤出后在烘箱中干燥(50-60℃的温度),得到206毫克97.8%HPLC纯度的黄腐酚的结晶。所述提取方法的产率是黄腐酚在废啤酒花中的总含量的82%。
实施例2
以类似实施例1的步骤获得黄腐酚,不同点在于加入氯化铜后,滤去沉淀出的绿色污泥,滤液在旋转蒸发仪上浓缩,析出90.8%HPLC纯度的黄腐酮。
实施例3
以类似实施例1的步骤获得黄腐酚,不同点在于加入的是10克/升的硫酸锌溶液代替了氯化铜。加入锌盐溶液后,溶液的pH值稳定在6左右,观察到沉淀。一小时后,加入NaOH,溶液pH值提升至约10。一小时后,容器的底部观察到进一步地沉淀。经滤纸滤去沉淀物。滤液用HCl酸化至pH6,经旋转蒸发仪浓缩后得到黄腐酚的结晶,将其滤出后在烘箱中干燥(50-60℃的温度),得到97.8%HPLC纯度的黄腐酚的结晶。所述提取方法的产率是黄腐酚在废啤酒花中的总含量的79%。
实施例4
250克萃取后的废啤酒花倒入0.75升甲醇,机械搅拌1小时,经滤纸过滤析出物,得到的滤液以体积比1:2倒入水中(1份滤液比2份水)。所得溶液每升加入300毫升浓度为10克/升的氯化铜溶液,盐的最终浓度控制在0.022M。1h后,出现沉淀物,其为分离于黄色溶液的绿色的物质结块。加入NaOH将pH值提高至约10,一小时后,在容器的底部可观察到了泥样绿色沉淀。以滤纸滤去沉淀物,得到的滤液用HCl酸化至pH6,在旋转蒸发仪上除去剩余的溶剂,得到黄腐酚的结晶的悬浊液。将其经滤纸滤出后在烘箱中干燥(55℃的温度),得到196毫克95.8%HPLC纯度的黄腐酚的结晶。所述提取方法的产率是黄腐酚在废啤酒花中的总含量的78%。
实施例5
以类似实施例1的步骤获得黄腐酚,除了加入氯化铜(II)外,还加入了浓度为10g/l的Cu(II)的硫酸盐(CuSO4),得到94.8%HPLC纯度的黄腐酮。
实施例6
以类似实施例1的步骤获得黄腐酚,不同点在于使用高浓度的氯化铜(II)溶液,浓度范围为0.022-0.044M。得到的黄腐酮纯度为96.3–97.8%。
实施例7
以类似实施例1的步骤获得黄腐酚,不同点在于第一步滤液与水的体积比为1:1,氯化铜溶液浓度为0.022M。得到的黄腐酮纯度为96.8%。
实施例8
以类似实施例1的步骤获得黄腐酚,不同点在于以2-丙醇取代丙酮,氯化铜溶液浓度为0.022M,得到93.8%纯度的黄腐酚。
对比例1
250克萃取后的废啤酒花倒入丙酮(0.75升),机械搅拌1小时,经滤纸过滤析出物,滤液浓缩得到32.8%纯度的黄腐酚。
对比例2
250克萃取后的废啤酒花倒入丙酮(0.75升),机械搅拌1小时,经滤纸过滤析出物。得到的滤液(0.65升)倒入水(1.3升)中,每升滤液加入300毫升浓度为30克/升的氯化钠溶液。然后,加入NaOH将pH值提高至约12,以滤纸滤去沉淀物,得到的滤液用HCl酸化至pH5,在旋转蒸发仪上浓缩,得到黄腐酚的结晶。将其滤出后在烘箱中干燥(50-60℃的温度),得到84.8%HPLC纯度的黄腐酚的结晶。
对比例3
以类似对比例2的方法得到黄腐酚,不同点在于没有使用NaCl,只是碱化pH值到12,得到的黄腐酚纯度为58%。
基于上述实施例,可确知,本发明可通过一个非常简单和廉价的方法获得高纯度的黄腐酚。对本领域技术人员来说,显而易见的是,通过本发明的方法获得的黄腐酚可以以已知的方法来进一步纯化。
Claims (15)
1.一种制备黄腐酚的方法,其特征在于:
a)将一种含黄腐酚的提取物和水混合;
b)将一种过渡金属的盐溶液加入到所得到的混合物中;
c)收集所得黄腐酚沉淀,干燥后得到纯度大于90%黄腐酚。
2.如权利要求1所述的方法,其特征在于,步骤b中,所述盐在混合物中的浓度为0.001-10摩尔/升。
3.如权利要求2所述的方法,其特征在于,步骤b中,所述盐在混合物中的浓度为0.001-0.05摩尔/升。
4.如权利要求1-3中任意一项所述的方法,其特征在于,所述步骤b中,加入盐溶液后还包含:
b1)碱化溶液到pH值大于7;
b2)滤出第一批沉淀,将滤液酸化至pH值低于7;
b3)酸化后的滤液浓缩,得到的黄腐酚的沉淀。
5.如权利要求4所述的方法,其特征在于,所述步骤b1中,溶液碱化至pH值在7.5-10.5之间。
6.如权利要求1-5中任意一项所述的方法,其特征在于,含黄腐酚的提取物是通过以一种能与水混溶的有机溶剂提取萃取后的废啤酒花、啤酒花、啤酒花植物颗粒或其以上混合物得到的,所述溶剂用量为每公斤原料使用0.1-10升溶剂。
7.如权利要求6所述的方法,其特征在于,所述能与水混溶的有机溶剂选自酮或醇或其混合物。
8.如权利要求7所述的方法,其特征在于,所述能与水混溶的有机溶剂选自丙酮、甲醇、乙醇、丙醇或其中一种或多种的混合物。
9.如权利要求1-8任意一项所述的方法,其特征在于,所述提取的温度为5-65℃。
10.如权利要求1-9任意一项所述的方法,其特征在于,所述含黄腐酚的提取物和水的比例为每升提取物使用0.1-5升水。
11.如权利要求10述的方法,其特征在于,所述含黄腐酚的提取物和水的比例为每升提取物使用1-3升水。
12.如权利要求1-11任意一项所述的方法,其特征在于,步骤b)中,所述过渡金属盐的浓度为0.01-0.05摩尔/升。
13.如权利要求1-12任意一项所述的方法,其特征在于,所述过渡金属盐为Cu(II)盐或Zn(II)盐。
14.如权利要求1-12中任意一项所述的方法,其特征在于,所述过渡金属盐为氯盐,硝酸盐或硫酸盐。
15.如权利要求1-14中任意一项所述的方法,其特征在于,所述过渡金属盐为CuCl2,CuSO4,ZnCl2或ZnSO4。
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