CN1733719A - 一种从植物油树脂中分离提纯高含量叶黄素晶体的方法 - Google Patents
一种从植物油树脂中分离提纯高含量叶黄素晶体的方法 Download PDFInfo
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Abstract
本发明提供了一种从植物油树脂中分离、提纯食用高级高含量叶黄素晶体的方法,该方法除了使用食用级醇类以外,没有其它有机溶剂。本发明方法简便,皂解后的混合液用酸中和后,水溶性杂质和脂溶性油类分别可用热水和醇洗除,能提高产品纯度的,终产品含量和收率分别可达90%和80%。本发明方法宜于工业化生产。
Description
技术领域:
本发明属于植物化学技术领域。具体涉及一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法。
背景技术:
类胡萝卜素是自然界中广泛存在的一类黄色到红色的物质。在不同的水果和蔬菜中,存在着不同种类的类胡萝卜素,如胡萝卜中β-胡萝卜素,万寿菊花中叶黄素,草莓中玉米黄质,番茄中番茄红素,辣椒类植物中辣椒红色素和辣椒色素的含量都较高。而在一些深色水果和蔬菜、蛋黄、一些鱼类甲壳、鸟类、海藻和细菌中存在较多的类胡萝卜素,其中叶黄素类的含量也较高。
近年来的一些动物和人体试验表明了类胡萝卜素的有益功效。总体上类胡萝卜素可能分为两个亚类,即极性相对较强一点的叶黄素类或含氧类胡萝卜素类,如叶黄素、玉米黄质、虾青素等,以及非极性的碳氢类胡萝卜素类,比如β-胡萝卜素、番茄红素等。这两个亚类的类胡萝卜素中都包含着至少九个共轭双键,这些共轭双键不仅赋予了类胡萝卜素的颜色特征,也使其在疾病防治中具有较强的抗氧化功能,它们能阻止或预防像癌症、动脉硬化、白内障、色斑退化及其它类疾病。而且由于类胡萝卜素的清除高效活性氧自由基及防止自由基产生的能力,它们能限制自由基的氧化破坏作用。
在类胡萝卜素中,由于其潜在的预防色斑退化疾病(ARMD)的能力,叶黄素和玉米黄质越来越引起科学家和公众的关注。叶黄素和玉米黄质是唯一存在于人类视网膜中斑点区域的类胡萝卜素,而此区域与人的视觉敏锐性密切相关(Bone etal.Invest.Ophthamal.Vis.Sci.34:2033-2040,1993).经常食用富含叶黄素和玉米黄质的水果和蔬菜能使患老年色斑退化疾病的风险减少43%(Seddon etal.J.Am.Med.Assoc.272:1413-1420,1994),而且,目前这些化合物在预防老年色斑退化疾病上的代谢途径也已经明了。美国食品和药品监督管理局对叶黄素和玉米黄质的评价是“一般认为安全”(GARS)。因此,这些类胡萝卜素类能单独或与其它物质一起作为营养补充剂和食品着色剂使用,也可应用于临床预防老年色斑退化和癌症等。
由于化学合成叶黄素类涉及到多步反应,费时费力,成本很高。比较经济且易于大规模生产而得到大量叶黄素晶体的方法是从天然资源中提取、分离和纯化得到。
许多蔬菜和水果,比如菠菜、椰菜、甘蓝和玉米等,含有较多的叶黄素,但万寿菊花和金盏花是叶黄素最丰富来源,当然,这些植物中还存在其它类类胡萝卜素。植物中的叶黄素类往往是与一些C12-C18长链脂肪酸如肉豆蔻酸、油酸、亚油酸和棕榈酸等酯化形成单酯或双酯的形式存在。
一般使用有机溶剂从植物,优先从万寿菊花、金盏花和其它深绿色蔬菜中提取叶黄素酯,而且这些有机溶剂本身又比较容易分离出去。万寿菊花珠粒提取物(万寿菊油树酯)是一种很好的叶黄素酯来源,并且其中其它类类胡萝卜素的含量相对不高。在碱性条件下水解后,叶黄素晶体就游离出来,将皂解得到的脂肪酸盐洗掉后,叶黄素晶体可进一步得到纯化。
目前有一些专利和文献报道了从万寿菊珠粒中大规模分离叶黄素晶体的方法。这些文献一般是得到较纯的叶黄素晶体形式,并采用多个分离步骤。
U.S.Pat.No.5,382,714提出在较低的温度下通过水洗皂解后的万寿菊油树脂,并在混合溶剂中低温下结晶,从而分离和提纯叶黄素。但此纯化过程不仅费时,而且使用含氯有机溶剂,得到的产品不适于食品和药物上使用。
U.S.Pat.No.5,648,564说明了一种分离叶黄素结晶的方法,先在万寿菊油树脂的丙二醇溶液中皂解叶黄素二酯,再重结晶。这个过程也有一些缺点:首先,由于丙二醇的粘度较大,在皂化及随后的处理过程中要求温度较高,整个体系在70℃以上的温度要保持10小时左右,这对叶黄素的稳定性显然不利,叶黄素的顺反异构体也会发生变化,而且,随后的分离过程如离心或过滤也比较困难;其次,叶黄素的收率较低,只有59%左右,产品中叶黄素的含量也不高。
U.S.Pat.No.6,262,284中描述了用四氢呋喃同时从万寿菊干花中提取和皂解类胡萝卜素,在此过程中要用大量的有机溶剂,这些溶剂对叶黄素的稳定性不利,有可能会导致产品由于过氧化而引起的降解。
U.S.Pat.No.6.329,557揭示了一种从万寿菊油树脂中工业化规模提取叶黄素结晶的方法。这个过程的缺点是使用大量的有机溶剂正己烷、酮类等,这些溶剂不适于在食品中使用。
U.S.Pat.No.6,380,442报道了一种从植物中分离类胡萝卜素的方法,该方法生产过程中要用大量的水(至少为原料量30倍以上),而且操作比较困难,不宜工业生产。
U.S.Pat.No.6,743,953使用几种有机溶剂从万寿菊油树脂中分离和纯化叶黄素类。此过程中用异丙醇、乙酸乙酯、正己烷、丙酮和甲醇等多种有机溶剂,操作繁杂,有机溶剂消耗大,收率低。因此此方法也不适于工业化生产。
总之,以上这些专利描述的方法有以下几个缺点:1)生产过程中使用到一些有机溶剂,这些溶剂比较困难或者不可能完全去除,导致产品叶黄素结晶不适于人类食用;2)由于使用到的有机溶剂粘度较大,分离和纯化过程中的操作比较困难,为了得到高含量的晶体,需要多次的结晶过程,不适于工业化生产;3)叶黄素的收率较低,由于过程中涉及到多个步骤,导致产品收率低,只有50%左右。
发明内容:
本发明所要解决的技术问题在于克服上述不足之处,研究设计一种适于工业化规模生产高纯度叶黄素和玉米黄质的方法。
本发明提供了一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法。
本发明涉及到一种方便并易于工业化生产的从含叶黄素二酯的植物油树脂中提取叶黄素晶体的方法。
本发明的方法先将植物油树脂中类胡萝卜素酯与食品级醇类形成均一溶液,在碱性环境下水解3-5小时,水解温度为40至85℃,皂化后的反应液再用酸水中和;通过离心或过滤方法得到生成的结晶;用去离子水和醇类的混合溶液多次洗去结晶中的杂质;将得到的结晶用无水乙醇重结晶后干燥得到了产品。
本发明方法得到的产品可供人类食用,叶黄素含量在90%以上,其中全反式叶黄素至少占90%,其余的为玉米黄质、少量的顺式叶黄素和其它类胡萝卜素类。
本发明方法涉及自然资源的原料,如万寿菊花、椰菜、甘蓝、菠菜和玉米。在这些原料中,万寿菊提取物中叶黄素类含量相对较高,是优先的原料。
下面对本发明进行具体描述:
在本发明方法中,通过正己烷萃取到的食用级万寿菊油树脂作为分离全反式叶黄素含量较高的产品的起始原料。基于品种、种植条件、收割时期及提取方法的不同,此油树脂含5-30%的叶黄素脂和少量其它类胡萝卜素如全反式玉米黄质,α-和β-隐黄质以及β-胡萝卜素等。
在本发明的方法中,一般在40到85℃范围内,食用级万寿菊油树脂溶解于食品级醇类中形成均一的溶液,一份重量的油树脂溶解于0.1-2.0倍体积的溶剂中。通过搅拌,叶黄素酯及其它物质如蜡、树脂、其它类胡萝卜素和色素等溶解或分散于此溶剂中形成一种均一的溶液。
向上述均匀分散的油树脂溶液中缓慢滴加碱溶液(如NaOH或KOH)开始皂化,所需碱的量为油树脂中叶黄素酯质量的1.0-3.0倍,混合溶液在40-85℃下搅拌3-5小时直至反应完全,皂解是否完全可通过薄层色谱来监控。在皂解完成后,叶黄素、玉米黄质及其它类胡萝卜素类游离出来,同时油树脂中的脂肪酸如肉豆蔻酸、棕榈酸、硬脂酸等与钠或钾离子分别形成钠皂或钾皂。
用水溶性的酸溶液将混合反应液pH值调至1.0-7.0,优选调到5.0-6.5,所用到的酸可为有机酸如柠檬酸、琥珀酸或醋酸,无机酸如盐酸、硫酸、磷酸等,酸的浓度为10-40%(w/w)之间,中和反应是在40-85℃下反应10-30分钟左右后完成的。
中和后的反应液降温至60℃,缓慢搅拌情况下加入足量的去离子水与醇的混合液,优选去离子水与乙醇的混合液,使溶液中溶质的浓度降低至10-50%(v/v).其中加入的去离子水和醇的量分别为油树脂量的1-4倍和1-2倍。去离子水与植物油树脂原料的用量比例为2∶1-10∶1,醇与植物油原料的用量比例为0.5∶1-2∶1。稀释后的混合液升温至50-70℃,缓慢搅拌并保持1-2小时直至叶黄素和其它类胡萝卜素形成颗粒状结晶。
通过传统的分离过程如离心、过滤、压滤等将上述结晶分离出来,在分离结晶之前,为了进一步减少结晶的浓度以使随后的分离操作过程易于进行,可用一定量的热水稀释溶液。经过分离操作后,脂肪酸、盐、皂、水溶性叶绿素和黄酮等杂质转移到母液中,叶黄素和玉米黄质等结晶留在滤饼中。
进一步的纯化过程包括:将结晶过滤物用过量的60-80℃的热水和乙醇混合物淋洗直至洗出液近乎无色,一般2-3次的淋洗就足够了。为了使最终产品易于干燥,干燥之前结晶用无水乙醇淋洗一次。结晶可用适当的方法如真空干燥、旋转真空干燥、冷冻干燥等进行烘干直到其干燥失重小于5%.
在本发明的方法中,最终产品的纯度和收率不仅取决于皂解过程中溶剂的加入量和稀释过程中醇类的加入量,而且还取决于结晶的时间。溶剂的比例太大,会使溶液中叶黄素酯类的浓度变稀,从而不利于皂解完全,减少产品的收率,降低结晶含量;而溶剂比例过少,会使溶液的粘度较大,不利于反应及随后的分离操作。分离前的稀释过程中醇类加入过多,会降低产品的收率,加入过少,又会增大操作难度。沉淀结晶的时间也不能过短,否则会使收率降低。
通过紫外-可见光分光光度分析和HPLC分析得知最终产品含85-95%类胡萝卜素类,其中包括90-95%全反式叶黄素,0.1-1.0%其几何异构体,2.0-7.0%全反式玉米黄质及少于1.0%的其它类胡萝卜素。这些微量的其它类类胡萝卜素完全不用担心有害,因为其本身也是膳食来源,并且发现人体血清中相对于叶黄素,它们的浓度要高得多。
由于生产过程中,除了食用级醇类外没有用其它有机溶剂,生产的最终结晶产品中不存在毒性有机溶剂残留和其它有毒化合物,可适于人类食用。
本发明的优点为:①生产过程中用的有机溶剂除了食用级醇类外没有其它有机溶剂,产品可安全地作为营养补充剂和食品着色剂使用;②由于方法中使用到的溶剂为水和低级醇类,它们粘度较低,则分离操作过程相对比较容易;③皂解后的混合液用酸中和后,水溶性杂质和脂溶性油类分别可用热水和醇类洗除,对产品纯度的提高比较有利;④终产品的含量和收率可分别达到90%和80%,有明显提高,成本低。因而,本发明方法适于大规模商业化生产。
实施例
实施例1
1000g万寿菊油树脂(总叶黄素含量16.3%)与1000mL乙醇混合,升温至75℃,搅拌直至形成一种均一流动的溶液,边搅拌边缓慢滴加375ml45%NaOH溶液,滴加时间为60分钟,在此温度下皂解反应4小时。
反应液降温到60℃,用25%醋酸水溶液将其pH调到6-7,搅拌10分钟后,加入2000mL去离子水和400mL乙醇,稀释过程中溶液温度保持在65℃,慢速搅拌30分钟。用离心方法分离所得到的结晶,此分离过程比较容易,10分钟内操作完成。收集到的结晶用75℃热水洗2-3次直至洗出液几乎无色,最后用无水乙醇淋洗,再在40℃下进行真空干燥直至其干燥失重小于5%。
最后得到150.4g成品,其中含95.6%总类胡萝卜素(用紫外-可见光光度仪分析),这些类胡萝卜素中含91.4%全反式叶黄素,4.8%全反式玉米黄质(用HPLC分析),其余的为微量其它类类胡萝卜素。总叶黄素收率为85%。
产品中不含有毒的有机溶剂,适合于以营养补充剂和食品添加剂的形式使用。此结晶的应用形式可为油悬液(与植物油混合乳化)、珠粒(通过喷雾冷凝得到的微胶囊)、干粉(通过喷雾干燥得到的微胶囊)等。
实施例2
采用与实施例1相同的原料,用相同的处理方法,只是对皂解完成后的溶液不进行中和处理,而是直接向反应液中加入65℃的2000mL去离子水和400mL乙醇的混合液,慢速搅拌30分钟后,用与实施例1中相同的离心机分离结晶,操作要困难得多,此步操作过程要花30分钟以上。随后的处理过程和检测方法与实施例1相同。
最终产品叶黄素总收率为82%。
实施例3
1Kg万寿菊油树脂(总叶黄素含量为14.5%)同2000mL乙醇混合,升温至60℃,搅拌形成均一流动体系,再向其中滴加500mL45%KOH水溶液,升温至75℃,皂化反应4小时。皂化反应完成后,溶液温度降至60℃,用25%盐酸水溶液中和使混合物pH为6.0-6.5左右,搅拌半小时后,用2000mL去离子水和800mL乙醇的混合液稀释反应液,保持温度在65℃左右,慢速搅拌0.5小时,可以看到叶黄素晶体的产生,使用实施例1中相同的离心机来分离固体物,此晶体也比较易于分离,离心过程用时15分钟左右。
将收集到的滤饼用75℃热水洗2-3次,直至母液几乎无色,最后一次用无水乙醇淋洗后,40℃下真空干燥产品直至其干燥失重小于5%。
最后得到104.5g产品,其类胡萝卜素含量为75.4%(用紫外-可见光光度仪分析),其中全反式叶黄素为90.8%,全反式玉米黄质有6.2%(用HPLC分析),其余为少量的其它类胡萝卜素。总叶黄素收率为54.3%。
Claims (6)
1、一种从植物油树脂中分离,提纯食用级高含量叶黄素晶体的方法,其特征在于该方法包括下列步骤:
(1)含叶黄素二酯的植物油树脂与0.1-2.0倍体积的醇溶剂混合形成溶液,在碱性条件下,40-85℃对该混合液进行皂解3-5小时;
(2)反应结束后,将反应液冷却至60℃,用酸调节至pH为1.0-7.0在40-85℃反应10-30分钟;
(3)以植物油树脂原料重量2-10倍的去离子水和0.5-2倍的醇混合溶剂稀释步骤(2)的反应液,升温至50-75℃,缓慢搅拌0.5-2.0小时,析出叶黄素晶体;
(4)过滤步骤3的结晶液,分离得到叶黄素晶体,用60-85℃热水漂洗结晶2-3次,直至洗出的母液近乎无色,再用无水乙醇淋洗,最后以真空干燥或冷冻干燥方法除去溶剂,使最终的干燥失重小于5%,得到高含量叶黄素结晶。
2、根据权利要求1所述的一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法,其特征在于其中所述的含叶黄素酯的植物油树脂为从万寿菊、金盏花、菠菜、椰菜、或甘蓝植物中提取的植物油树脂。
3、根据权利要求1所述的一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法,其特征在于其中所述步骤(1)的碱为NaOH或KOH,碱的用量为植物油树脂中叶黄素二酯重量的1.0-3.0倍。
4、根据权利要求1所述的一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法,其特征在于其中所述步骤(2)中的酸为磷酸、硫酸、盐酸、醋酸、柠檬酸或琥珀酸及其它有机酸或无机酸,酸的浓度为10-40%重量百分浓度。
5、根据权利要求1所述的一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法,其特征在于其中所述步骤(1和(3)中的醇为甲醇、乙醇、异丙醇或丙醇。
6、根据权利要求1所述的一种从植物油树脂中分离、提纯食用级高含量叶黄素晶体的方法,其特征在于其中所述步骤(3)中的去离子水与植物油树脂原料的用量比例为2∶1-10∶1,醇与植物油树脂原料的用量比例为0.5∶1-2∶1。
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