CN107404926A - 用于在水介质中用非离子两亲性化合物作为提取佐剂制备植物来源的基质的提取物的方法 - Google Patents
用于在水介质中用非离子两亲性化合物作为提取佐剂制备植物来源的基质的提取物的方法 Download PDFInfo
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- CN107404926A CN107404926A CN201680013093.9A CN201680013093A CN107404926A CN 107404926 A CN107404926 A CN 107404926A CN 201680013093 A CN201680013093 A CN 201680013093A CN 107404926 A CN107404926 A CN 107404926A
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Abstract
本发明涉及一种用于制备植物来源的基质的提取物,特别是植物的提取物的方法,其涉及借助于水溶液的固液提取,所述水溶液含有至少一种非离子两亲性化合物,优选农业来源的非离子两亲性化合物,所述非离子两亲性化合物的浓度至少等于其最小助溶浓度。
Description
技术领域
本发明的领域涉及一种用于在水介质中用非离子两亲性化合物作为提取辅助物制备植物基质提取物的方法。
背景技术
固液提取是将存在于固体,特别是植物中的物质提取到液体溶剂中的过程。浸渍(macération)、泡制(infusion)和煎煮(décoction)为常规的固液提取方法。
溶剂在工作温度为液体,具有溶解、稀释或提取其他物质的性质,而不会使所述物质化学改性,且其自身不会被改性。它们被大量用于许多其他工业应用(油漆、洗涤剂、涂层、植物检疫产品等),并且常规上是石油化学来源的。
然而,石油储备的减少和对化学品的更严格的管理使得有必要寻找更环境友好的替代方案。
绿色提取是基于提取工艺的发现和设计,所述提取工艺降低能源消耗,并允许使用替代溶剂-农业溶剂(agro-solvant),同时保证安全、高品质的提取物,其可用作药物、化妆品、农产品、精细化工和生物燃料行业的成分(Green extraction of natural products(GNEP2013),(2014),Comptes Rendus Chimie,17,179-180)。在此背景下,现有工艺的改进和新工艺的设计是旨在减少提取步骤的环境影响的许多工作的主题,导致技术(如通过超声波、微波、超临界CO2和快速真空膨胀的提取)的出现和普及。并行地,寻找非石油化学来源的替代的提取溶剂构成了另一条改进的道路。
因此,来源于木材、田间作物(淀粉或糖生产)和油质物种的农业溶剂的市场正在充分扩张,带来萜烯衍生物、醇(乙醇、丁醇、1,3-丙二醇)、糠醛衍生物和甲基酯(FormuleVerte No.8,2011十二月,28–32页)。
水是一种天然溶剂,其被认为是可再生的。然而,其高极性不允许某些感兴趣的亲脂性分子的提取。
因此,需要有用于提取不同极性范围的化合物的新溶剂(越来越广的极性范围,或亲脂性化合物的提取的优化)。
在水溶液中的某些非离子两亲性化合物在足够的浓度时允许溶解亲脂性化合物。
烟酰胺、二甲基异山梨醇、烷基多糖苷和尿素是这些非离子两亲性化合物的示例。已经探索了这些化合物在水介质中作为某些亲脂性分子的溶解辅助物的潜力(SanghviR.,Evans D.,Yalkowsky S.Stacking complexation by nicotinamide:a useful way ofenhancing drug solubility.(2007)336:35-41)。
但是溶解性质不足以允许从植物基质中提取溶质。事实上,在植物提取领域,提取溶剂必须穿透植物基质,破坏膜并将化合物释放到浸渍溶剂中(扩散、解吸附、溶解等现象),并允许基质溶质向包围固体的液体膜扩散,并向溶剂转移(限制步骤)。根据所使用的溶剂,植物细胞膜或多或少地被削弱,这可能允许或可能不允许释放包含在所述细胞内的化合物。
发明内容
本申请人已经指出,以足够的浓度使用的非离子两亲性化合物的水溶液能够从植物基质中提取具有不同极性范围的溶质。
因此,本发明涉及一种用于制备植物基质提取物的方法,其涉及借助于水溶液的固液提取,所述水溶液含有至少一种非离子两亲性化合物,优选农业来源(agrosourcé)的非离子两亲性化合物,所述非离子两亲性化合物的浓度至少等于其最小助溶浓度。
本发明涉及含有极性、中等极性和亲脂性化合物的总提取物或富含感兴趣的亲脂性化合物的提取物的借助于非离子两亲性化合物的水溶液的制备。
在本发明的情况下,术语“亲脂性化合物”是指具有正的正辛醇/水分配系数(也被称为log P或log kow)的化合物。
根据本发明,术语“非离子两亲性化合物(composé amphiphile non ionique)”是指可以以任何比例溶于水的化合物,并且其不具有表面活性剂性质,以避免形成胶束。
这种提取方法是一种替代方案,其能够替代污染性的石油化学有机溶剂如乙酸乙酯、己烷、丙酮等,因为优选的非离子两亲性化合物可以是农业来源的,即,基本上来源于植物生物质。
根据本发明的方法借助于水溶液实施植物基质的提取,所述水溶液含有最小足够浓度,即最小助溶浓度的非离子两亲性化合物,优选农业来源的非离子两亲性化合物。
术语“最小助溶浓度(concentration minimale hydrotropique)”是指一种浓度,在该浓度以上时,这些非离子两亲性化合物开始形成聚集体,即,具有一些物理性质的新的微环境,所述物理性质不同于当化合物被稀释时所观察到的那些,并且不同于胶束行为。这种最小助溶浓度对于每种非离子两亲性化合物是特异性的,并且通常具有摩尔浓度的数量级。其可以通过几种物理化学方法来确定,如通过测量表面张力、电导率或动态和静态光散射来确定(Self-association of nicotinamide in aqueous solution:Light-scattering and vapor pressure osmometry studies(1996)85(8):848-853),或者仅简单地通过建立亲脂性化合物的溶解曲线(溶解的溶质含量相对于非离子两亲性化合物的浓度的函数)来确定。苏丹红(一种易于通过分光光度法测量的亲脂性染料)可以被用作参比。该浓度的值取决于非离子两亲性化合物的性质,而不取决于溶质的性质。其对应于最小浓度,在所述最小浓度以上时溶质的溶解曲线呈指数形式。
根据本发明的另一个特征,含有所述非离子两亲性化合物,优选农业来源的非离子两亲性化合物的水溶液,构成了所使用的唯一提取溶剂。
根据本发明的一个有利的特征,通过在所述水溶液中浸渍植物基质进行固液提取,并在搅拌下保持固液提取,所述水溶液含有至少等于最小助溶浓度的最小浓度的至少一种非离子两亲性化合物。
根据本发明,表述“含有至少等于最小助溶浓度的浓度的至少一种非离子两亲性化合物的水溶液”是指含有大于或等于上面提及的最小助溶浓度(CMH)的浓度的至少一种非离子两亲性化合物的水溶液。还有必要考虑可能存在于植物基质中的水含量,并因此调节非离子两亲性化合物的浓度,以使其能够在根据本发明的方法中令人满意地使用。
根据本发明的另一个特征,所述水溶液中的非离子两亲性化合物的浓度为最小助溶浓度的1至10倍,优选1至6倍,更优选1至2倍,甚至更优选1.4至1.8倍。有利地,在实践中,可以在水溶液中以等于1.5mol/L的浓度使用非离子两亲性化合物。
根据本发明的另一个有利的特征,非离子两亲性化合物以相对于所述溶液的重量以重量计小于60%,优选相对于所述溶液的重量以重量计小于50%,更优选相对于所述溶液的重量以重量计小于40%,甚至更优选相对于所述溶液的重量以重量计小于30%的浓度存在于所述水提取溶液中。将特别地观察到,该浓度阈值隐含地排除了使用乙醇作为用于亲脂性化合物的提取溶剂,乙醇通常以高得多的比例,在约80%的范围内使用。
根据本发明的另一个特征,取决于所使用的提取技术,将所述水溶液加热到20℃至回流的温度,持续几分钟至几小时的一段时间。
根据本发明的另一个特征,植物基质(以千克表示)与所述水溶液(以升表示)之间的比例为1:5至1:50。
根据本发明的另一个特征,通过本领域技术人员熟知的任何其他提取系统(如通过微波或超声波的提取,或逆流提取等)进行固液提取。
根据本发明的一个有利的特征,提取后进行通过过滤或离心的固液分离。
根据本发明的一个有利的特征,所述非离子两亲性化合物,优选农业来源的非离子两亲性化合物,为通式Alk-O-Zp的烷基多糖苷,其中:
·Alk表示具有3至7个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段,和
·Z代表亲水性糖苷基团,如葡萄糖、木糖、阿拉伯糖,和
·1<p<5
根据本发明的一个特别的实施方案,Z表示葡萄糖基团。
根据本发明的另一个特别的实施方案,Z表示木糖基团。
根据本发明的又一个特别的实施方案,Z表示阿拉伯糖基团。
根据本发明的一个特别的实施方案,Alk表示具有7个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段。
根据本发明的另一个特别的实施方案,Alk表示具有6个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段。
根据本发明的又一个特别的实施方案,Alk表示具有5个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段。
根据本发明的又一个特别的实施方案,Alk表示具有4个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段。
根据本发明的另一个特征,农业来源的非离子两亲性化合物为来源于蓖麻属(ricin)的C7脂肪醇和小麦葡萄糖(非转基因(sans OGM))的组合。
根据本发明的一个有利的特征,所述化合物为戊基糖苷,其疏水性戊基片段对应于通过甜菜或马铃薯粉的发酵获得的C5醇,并且其糖苷片段来源于谷物。
根据本发明的一个有利的特征,所述化合物为C4脂肪醇与木糖苷的组合。
在本申请的情况下,缩写APG表示烷基聚葡萄糖苷,缩写APX表示烷基聚木糖苷,两个缩写后任选地跟随着符号Cx,x表示烷基片段的碳原子数。
在本发明的另一个特别的实施方案中,所述非离子两亲性化合物,优选农业来源的非离子两亲性化合物,为二醇,所述二醇选自异戊二醇(3-甲基-1,3-丁二醇)和/或甲基丙二醇,优选异戊二醇。
在本发明的情况下有用的非离子两亲性化合物可以有利地为市售产品Kuraray的Isopentyldiol或Stearinerie Dubois的Dub Diol之一。
本发明还涉及含有至少等于最小助溶浓度的浓度的至少一种非离子两亲性化合物,优选农业来源的非离子两亲性化合物的水溶液作为植物、真菌、地衣、藻类、微藻类培养物或去分化的植物细胞培养物的固液提取溶剂,优选作为唯一的提取溶剂的用途。所述用途涉及与本发明的方法相关的所提及的所有溶剂和植物基质。
根据本发明,术语“植物基质(matrice végétale)”是指植物、真菌、地衣、藻类、微藻类培养物或去分化的植物细胞培养物的全部或部分。
所述植物、真菌、地衣或藻类是干燥的或新鲜的,冷冻的或解冻的,并且是完整的(既不粉碎也不研磨)、粉碎的或研磨的。所述微藻类培养物或去分化的植物细胞培养物是完整的,研磨的,优选新鲜的,但可以被干燥、过滤以回收生物质,并且任选地被预处理,例如通过超声波方法预处理,以释放细胞内的内容物。
术语“植物部分”尤其是指地上部分,如茎、枝、叶子、果实、种子和/或花;和/或地下部分,如根茎、根和/或球茎。
表述“地衣、真菌或藻类部分”是指这些生物体的任何器官,如叶状体(thalles)、子实体、宏观子实体、菌丝体和/或丝状体。
在本发明的一个特别的实施方案中,将使用整个植物(既不粉碎也不研磨)的全部或部分。
在本发明的情况下有用的植物当中,可以特别地提及:灯笼草(Physalisperuviana)的果实、白花酸藤果(Embelia ribes)的果实、香桃木(Myrtus communis)的叶子、胡椒属物种(Piper spp.)的地下部分和叶子、蓝桉树(Eucalyptus globulus)的叶子、山竹(Garcinia mangostana)的果皮、啤酒花(Humulus lupulus)的雌花序、金鸡钠树属物种(Cinchona sp.)的树皮、大荨麻(Urtica dioica)的地上部分、蜡菊属物种(Helichrysumsp.)的地上部分、香荚兰属物种(Vanilla sp.)的果实、姜黄属物种(Curcuma spp.)的根茎、生姜(Zingiber officinale)的根茎、油橄榄(Olea europaea)的果实和叶子。
在本发明的情况下有用的藻类特别地包括蓝藻(algues bleues)或蓝藻(Cyanobactéries),以及真核生物包括裸藻、隐芽植物、粘着植物、灰胞藻,红藻(alguesrouges)或红藻(Rhodophyta),不等鞭毛门(Stramenopiles)尤其包括硅藻和褐藻(alguesbrunes)或褐藻(Phéophycées),和最后的绿藻类特别地包括石莼纲。
在本发明的情况下有用的地衣当中,可以特别地提及:冰岛地衣(Cetrariaislandica)的叶状体、松萝属物种(Usnea spp.)的叶状体、石蕊属物种(Cladonia spp.)的叶状体和肺衣属物种(Lobaria spp.)的叶状体。
在本发明的情况下有用的真菌当中,可以特别地提及:彩绒革盖菌(Coriolusversicolor)、冬虫夏草属物种(Cordyceps spp.)。
在本发明中有用的植物细胞培养物当中,可以特别地提及:含羞草(Mimosapudica)细胞培养物、雷公藤(Tripterygium wilfordii)细胞培养物。
在一定的浓度时,出人意料地,非离子两亲性化合物将能够提取水中的亲脂性化合物。这种最小助溶浓度对于每种非离子两亲性化合物是特异性的,并且可以容易地通过例如苏丹红的溶解的分光光度测定来确定。这种最小助溶浓度通常在摩尔浓度的数量级。
优选地,非离子两亲性化合物为烷基糖苷或烷基多糖苷。
在本发明的情况下有用的非离子两亲性化合物可以有利地为市售原材料SEPICLEAR(Société SEPPIC)和(Société WHEATOLEO)之一。其也可以为木糖单体片段,所述木糖单体片段具有被C4烷氧基取代的异头羟基官能团。
提取条件(持续时间、非离子两亲性化合物的浓度、pH、温度等)可以根据植物/非离子两亲性化合物对子而变化,从而优化提取产率和/或选择性。这种具体的改变是本领域技术人员使用他们在固液提取领域的一般知识的领域。
通常,方法包括干燥的或新鲜的植物基质研磨物在搅拌下,在20℃至回流的温度,在含有至少等于最小助溶浓度的浓度的非离子两亲性化合物的水溶液中的浸渍,以允许提取亲脂性化合物。
根据一个优选的实施方案,除了非离子两亲性化合物的水溶液以外,在提取步骤本身中不使用其他溶剂。以特定的浓度使用的非离子两亲性化合物的水溶液是提取方法中使用的唯一溶剂。
在本发明的一个特别的实施方案中,植物(kg)与溶剂(L)的比例为1:5至1:50。当然,可以将残渣重新提取一次或多次,以将植物提取完全。
可以在常规反应器中进行提取,或者通过本领域技术人员熟知的任何其他提取系统(微波、超声波、逆流提取等)辅助提取。
取决于所使用的提取技术,提取的持续时间可以在几分钟到几个小时之间变化。
提取可以被应用于用非离子两亲性化合物均质化的新鲜的植物基质,同时考虑植物基质的水分含量。
提取后进行通过离心和/或过滤的固液分离。
术语“离心”是指利用卧螺式离心机或任何类型的离心机,根据混合物的组分在密度上的不同,通过使它们经受离心力将它们分离的活动,以获得完全澄清的溶液。
术语“过滤”是指正面或切向过滤,其中可以考虑存在过滤辅助物(如珍珠岩或硅藻等)。这种过滤拦住了最后的固体残留物,目的是获得完全澄清的溶液。其后可以进行膜过滤,所述膜过滤具有根据所要考虑的分子的尺寸定义的截断。其还可以被在树脂或二氧化硅上的过滤替代,或者其在树脂或二氧化硅上的过滤之后进行,以富集感兴趣的化合物,例如通过使用吸附树脂。
在一个特别的实施方案中,固液分离后获得的溶液被按原样保存或被冻干,所述溶液包含感兴趣的分子以及非离子两亲性化合物,所述化合物允许提取物在终产物中更好地溶解。
因此,获得含有宽的极性范围(极性、中等极性、非极性)的化合物的总提取物。
还可以将由此获得的提取物在一定体积的水中稀释,所述水任选地补充有一种或多种选自盐、酸或碱的佐剂,从而使得非离子两亲性化合物的终浓度低于上面定义的足够的浓度。因此,能够通过沉淀和固液分离(如过滤或离心)来回收亲脂性化合物。
因此,获得富含亲脂性化合物的提取物。感兴趣的亲脂性化合物可以为黄酮类、酚酸类、萜烯(单-萜烯、二-萜烯、三萜烯)和甾醇化合物、二芳基庚烷衍生物、木脂素类、香豆素类、醌类、蒽醌类、呫吨酮类、间苯三酚类、环烯醚萜类、倍半萜内酯类、生物碱类、蔗糖酯、极性脂质等。
它们可以特别地为卡瓦内酯类、香桃木醇类(myrtucommulones)、蒽贝素、奎宁及其衍生物、香草醛及其衍生物,α-倒捻子素、黄腐酚、单半乳糖二酰基丙三醇和二半乳糖二酰基丙三醇、山楂酸、熊果酸、迷迭香酸、鼠尾草酚、高良姜素、短叶松素、小豆蔻明、姜黄素类、姜辣素、姜烯酮。
富含亲脂性化合物的总提取物或提取物可以被稀释、浓缩、干燥,或者通过向期望的终产物中加入合适的经批准的防腐剂(如二醇类、或山梨酸、苯甲酸、柠檬酸及其盐等,或酒精(最低15°))来按原样保存。
可以考虑真空干燥、冻干或雾化技术,以制备干燥提取物。获得的提取物可以用或不用基质干燥和/或溶解在液体基质中。
如上面所定义获得的液体、糊剂或干燥提取物可以被按原样用于旨在局部或口服施用的化妆品、药物或食品组合物中。
优势为:
-如果滤液被按原样保存或被冻干,则制备含有宽的极性范围的分子的总提取物,以及非离子两亲性化合物,其允许提取物在终产物中更好地溶解。
-如果通过沉淀纯化亲脂性化合物,则制备富含亲脂性化合物的提取物,所述提取物借助于水提取和农业来源的物质获得,所述农业来源的物质替代了有毒的且基于石油化学的溶剂如己烷、乙酸乙酯或丙酮。
具体实施方式
提供以下实施例用于信息性目的,而非限制。
实施例
实施例1:富集的灯笼草提取物
将100g干燥且研磨的灯笼草果实与700mL 1.5M庚基葡萄糖苷水溶液(SEPICLEARSociété SEPPIC)在40℃搅拌2h。过滤后,将滤液酸化至pH 2,然后用15倍体积的水稀释。离心后,取出沉淀(culot)并干燥。获得富集的提取物,产率为以重量计2.1%。
实施例2:富集的灯笼草提取物
将20g干燥且研磨的灯笼草果实与140mL 0.75M庚基葡萄糖苷水溶液在40℃搅拌2h。过滤后,将滤液用6.6倍体积的水稀释。离心后,取出沉淀并干燥。获得富集的提取物,产率为以重量计0.64%。
实施例3:富集的灯笼草提取物
将20g干燥且研磨的灯笼草果实与140mL 3M庚基葡萄糖苷水溶液在40℃搅拌2h。过滤后,将滤液用22倍体积的水稀释。离心后,取出沉淀并干燥。获得富集的提取物,产率为以重量计0.98%。
由不同的富集的灯笼草提取物获得的结果:
提取物 | 产率 | 蔗糖酯含量 |
根据实施例1 | 2.11% | 19.5% |
根据实施例2 | 0.64% | 16.4% |
根据实施例3 | 0.98% | 16.2% |
乙酸乙酯(1h,回流) | 2.04% | 12.9% |
庚烷(1h,回流) | 1.04% | 3.0% |
在实施例1至3中,用庚基葡萄糖苷水溶液提取灯笼草果实,然后通过稀释使提取物沉淀,产生了富含蔗糖酯的提取物。果实的糖被提取,但在稀释期间被保留在溶液中,并且不会沉淀。所得的提取物的质量优于使用石油化学来源的溶剂(乙酸乙酯、庚烷)获得的提取物。
实施例4:香草提取物
将5kg干燥且研磨的香草豆荚用50L 1.5M庚基葡萄糖苷水溶液在50℃提取3h。加压过滤后,用25L相同的溶液冲洗残渣。将滤液浓缩,从而获得呈红棕色糖浆状溶液形式的香草提取物。
由香草提取物获得的结果:
提取物 | 产率 | 香草醛及衍生物的含量 |
根据实施例4 | 800% | 0.3% |
在庚基葡萄糖苷基质上的这种提取物含有相当大比例的香草醛及衍生物,其同时被预配制,从而有助于将其引入化妆品、营养食品或药物制剂的水相中。
实施例5:富集的山竹(mangoustan)的提取物
将100kg干燥且研磨的山竹的果皮与1000L 1.5M的庚基葡萄糖苷水溶液在40℃搅拌2小时。过滤后,将滤液酸化至pH=2,然后用11倍体积的酸化至pH=2的水稀释。离心后,取出沉淀并干燥。获得富含呫吨酮类的提取物(以α-倒捻子素表示为21.3%),产率为以重量计7.3%。所得的提取物不含单宁。
相比之下,干燥且研磨的山竹的果皮的乙醇回流提取以相同的植物质量/溶剂体积比例得到了具有较低的呫吨酮含量(以α-倒捻子素表示为19.5%)的提取物,但是得到了较高的产率(27%)。所得的提取物含有单宁。
相比之下,干燥且研磨的山竹的果皮的己烷回流提取以相同的植物质量/溶剂体积比例得到了具有较高的呫吨酮含量(以α-倒捻子素表示为89.1%)的提取物,但是得到了较低的产率(以重量计1.2%)。所得的提取物不含单宁。
因此,与乙醇提取相比,用1.5M庚基葡萄糖苷水溶液的提取允许呫吨酮类的选择性提取。其还允许比己烷提取更高的提取产率。
实施例6:富集的卡瓦胡椒(Piper methysticum)提取物
在搅拌下在40℃,将1kg干燥且研磨的卡瓦胡椒的地下部分用700mL的1.5mol/L戊基木糖苷水溶液(APXC5)提取1.5小时。过滤后,将滤液用4倍体积的水稀释。离心后,以6.2%的产率获得对应于富集的卡瓦胡椒的提取物的沉淀。提取物含有3.0%的卡瓦内酯类。
相比之下,干燥且研磨的卡瓦胡椒的地下部分的乙酸乙酯回流提取以相同的植物质量/溶剂体积比例得到了8.2%的产率。提取物含有5.3%的卡瓦内酯类。
相比之下,干燥且研磨的卡瓦胡椒的地下部分的水回流提取以相同的植物质量/溶剂体积比例得到了23.1%的产率。提取物含有0.25%的卡瓦内酯类。
三种提取物具有不同的卡瓦内酯组成:
-用1.5mol/L戊基糖苷水溶液提取获得的提取物具有比乙酸乙酯提取物更高的低极性卡瓦内酯类(甲氧醉椒素、去甲氧基醉椒素、卡瓦胡椒素A、B和C)含量(总卡瓦内酯类44.8%相比于35.3%)。
-相反,用1.5mol/L戊基糖苷水溶液提取获得的提取物具有比乙酸乙酯提取物更低的高极性卡瓦内酯类(麻醉椒苦素、二氢麻醉椒苦素、醉椒素和二氢醉椒素)含量(总卡瓦内酯类55.2%相比于64.7%)。
-通过水提取获得的提取物含有1.66%卡瓦内酯类,并且不含低极性卡瓦内酯类(甲氧醉椒素、去甲氧基醉椒素、卡瓦胡椒素A、B和C)。
因此,用1.5mol/L戊基糖苷水溶液的提取允许以与乙酸乙酯提取相当的总产率选择性提取低极性的卡瓦内酯。
实施例7:明胶胶囊
根据实施例5的山竹的提取物 200mg
淀粉 45mg
硬脂酸镁 2mg
实施例8:霜剂
实施例9:示例性溶解曲线
制备了苏丹红在不同浓度的各种非离子两亲性化合物水溶液中的溶解曲线。在用苏丹红使溶液饱和并过滤后,在稀释后,通过紫外分光光度法在476nm处测量溶解在每种溶液中的苏丹红含量。溶解曲线出现在图1中。y轴代表乘以稀释度的DO值,这些值与浓度成正比(根据Beer-Lambert定律)。
这些曲线能够确定根据本发明的非离子两亲性化合物的最小助溶浓度。
Plantacare(癸基葡萄糖苷)是不合适的,其具有明显的表面活性剂行为(在低浓度时有高溶解度,化合物形成胶束)。通过稀释回收感兴趣的化合物是不可能的。此外,由表面活性剂引起的泡沫形成显著阻碍了过滤。
根据类似的方法(溶解的α-倒捻子素的HPLC测定),用α-倒捻子素获得的曲线的形状与用苏丹红获得的那些相当,表明该值取决于两亲性化合物,而非取决于溶质。
α-倒捻子素在各种浓度的非离子两亲性化合物的水溶液中的溶解曲线出现在图2中。
因此,可以从这些曲线中推断,APXC4具有15-20%的CMH,并且戊基木糖苷具有5-10%的CMH。
异戊二醇的CMH为40至45%。
这些值对于实施提取方法是必要的,例如从山竹的果皮中提取α-倒捻子素:
化合物 | 浓度 | g%植物的提取的α-倒捻子素的g |
APX C4 | 5% | 0.36 |
APX C4 | 25% | 7.87 |
异戊二醇 | 59% | 6.59 |
戊基木糖苷 | 40% | 7.30 |
AcOEt | 100% | 7.49 |
在25%APXC4中,从山竹的果皮中提取的活性物质含量等于通过乙酸乙酯回流提取获得的活性物质含量,而在5%时则不是这样(浓度低于CMH)。
然后,当两亲性化合物的终浓度低于CMH时,可以通过稀释来回收这种活性物质,如下表所示:
通过将戊基木糖苷溶液稀释至15%,少量α-倒捻子素沉淀,浓度保持在CMH以上。在7%戊基木糖苷中,提取的100%的α-倒捻子素沉淀。
实施例10:
-新鲜的橄榄饼的提取
在压榨后,称取10g橄榄果肉研磨物,以回收油(含有76%的水);加入相当量的12gAPXC4(干物质)和水,从而使最终的APXC4浓度为50%(考虑植物的含水量)。在50℃加热3h并过滤,以回收澄清的棕色滤液,产率为87.5%。
平行地,将该相同的橄榄果肉冻干(产率为24.5%),并将其用乙酸乙酯回流提取1h。蒸发溶剂后,获得浑浊的绿色油状物,产率为23.4%干物质和5.7%新鲜物质。
在以下条件下通过CCM评价获得的提取物:
·固定相:用硅胶60涂布的CCM板
·流动相:乙酸乙酯/环己烷(1:1)
·显色剂:硫酸香草醛+加热至120℃
比较在图3中出现的CCM谱,显示出用APXC4的提取物(LX 1872)含有三萜烯类(齐墩果酸和山楂酸),而AcOEt提取物(LX 1874)除了三萜烯类以外还含有甘油三酸酯类。因此,存在感兴趣的分子,而不必将材料干燥并将其用有毒且挥发性的溶剂提取。此外,叶绿素和中性脂质均不被提取。
Claims (18)
1.一种用于制备植物基质提取物,特别是植物提取物的方法,其涉及借助于水溶液的固液提取,所述水溶液含有至少一种非离子两亲性化合物,优选农业来源的非离子两亲性化合物,所述非离子两亲性化合物的浓度至少等于其最小助溶浓度。
2.根据权利要求1所述的方法,其特征在于含有所述非离子两亲性化合物的水溶液构成了所使用的唯一提取溶剂。
3.根据权利要求1至2中任一项所述的方法,其特征在于通过在含有至少一种非离子两亲性化合物的所述水溶液中浸渍植物进行固液提取,并在搅拌下保持固液提取。
4.根据权利要求1至2中任一项所述的方法,其特征在于在微波下、在超声波下或在逆流过程中进行固液提取。
5.根据权利要求4所述的方法,其特征在于所述水溶液中的非离子两亲性化合物的最小助溶浓度为最小助溶浓度的1至10倍,优选1至6倍,更优选1至2倍,甚至更优选1.4至1.8倍。
6.根据权利要求1至5中任一项所述的方法,其特征在于非离子两亲性化合物以相对于所述溶液的重量以重量计小于60%,优选相对于所述溶液的重量以重量计小于50%,更优选相对于所述溶液的重量以重量计小于40%,甚至更优选相对于所述水溶液的重量以重量计小于30%的浓度存在于所述水溶液中。
7.根据权利要求1至6中任一项所述的方法,其特征在于取决于所使用的提取技术,将所述水溶液加热到20℃至回流的温度,持续几分钟至几小时的一段时间。
8.根据权利要求1至7中任一项所述的方法,其特征在于以千克表示的植物与以升表示的所述水溶液之间的比例为1:5至1:50。
9.根据权利要求1至8中任一项所述的方法,其特征在于提取后进行通过过滤或离心的固液分离。
10.根据权利要求1至9中任一项所述的方法,其特征在于所述非离子两亲性化合物为通式Alk-O-Zp的烷基多糖苷,其中:
·Alk表示具有3至7个碳原子的、饱和的或不饱和的、直链或支链疏水性脂肪族烃片段,和
·Z代表亲水性糖苷基团,如葡萄糖、木糖和阿拉伯糖,和
·1<p<5。
11.根据权利要求10所述的方法,其特征在于非离子两亲性化合物为来源于蓖麻属的C7脂肪醇和小麦葡萄糖(非转基因)的组合。
12.根据权利要求10所述的方法,其特征在于所述化合物为戊基糖苷,其疏水性戊基片段对应于通过甜菜或马铃薯粉的发酵获得的C5醇,并且其糖苷片段来源于谷物。
13.根据前述权利要求中任一项所述的方法,其特征在于所使用的植物选自灯笼草Physalis peruviana的果实、白花酸藤果Embelia ribes的果实、香桃木Myrtus communis的叶子、胡椒属物种Piper spp.的地下部分和叶子、蓝桉树Eucalyptus globulus的叶子、山竹Garcinia mangostana的果皮、啤酒花Humulus lupulus的雌花序、金鸡钠树属物种Cinchona sp.的树皮、大荨麻Urtica dioica的地上部分、蜡菊属物种Helichrysum sp.的地上部分、香荚兰属物种Vanilla sp.的果实、姜黄属物种Curcuma spp.的根茎、生姜Zingiber officinale的根茎和油橄榄Olea europaea的果实和叶子。
14.根据权利要求9至13中任一项所述的方法,其特征在于固液分离后获得的溶液被按原样保存或被冻干,所述溶液包含感兴趣的分子以及非离子两亲性化合物,所述非离子两亲性化合物允许提取物在终产物中更好地溶解。
15.根据前述权利要求中任一项所述的方法,其特征在于在获得的提取物中,通过沉淀纯化亲脂性化合物。
16.化妆品和/或药物组合物,其含有通过实施如权利要求1至15中任一项所述的方法获得的富集亲脂性化合物的总植物基质提取物或植物基质提取物。
17.根据权利要求16所述的组合物,其特征在于所述组合物被制备成适合于局部施用的形式。
18.根据权利要求16所述的组合物,其特征在于所述组合物被制备成适合于口服施用的形式。
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WO2013184884A1 (en) * | 2012-06-06 | 2013-12-12 | Basf Corporation | Improved methods for botanical and/or algae extraction |
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US6365601B1 (en) * | 1999-09-16 | 2002-04-02 | Council Of Scientific And Industrial Research | Process for extraction of piperine from piper species |
WO2009077970A1 (en) * | 2007-12-17 | 2009-06-25 | Alma Mater Studiorum-Università Di Bologna | A process to obtain aqueous extracts containing carotenoids and obtained extracts |
WO2013184884A1 (en) * | 2012-06-06 | 2013-12-12 | Basf Corporation | Improved methods for botanical and/or algae extraction |
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CN107405296A (zh) * | 2015-03-18 | 2017-11-28 | 皮埃尔·法布尔皮肤化妆品公司 | 通过用助溶溶液挤出来制备植物性来源的基质的提取物的方法 |
CN107405296B (zh) * | 2015-03-18 | 2020-10-02 | 皮埃尔·法布尔皮肤化妆品公司 | 通过用助溶溶液挤出来制备植物性来源的基质的提取物的方法 |
CN111840170A (zh) * | 2020-08-26 | 2020-10-30 | 浙江千芊凝生物科技有限公司 | 一种玫瑰精华液及其制备方法 |
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EP3270886A1 (fr) | 2018-01-24 |
CA2978505C (fr) | 2023-10-17 |
BR112017017747B1 (pt) | 2021-06-22 |
ES2843640T3 (es) | 2021-07-19 |
US10299502B2 (en) | 2019-05-28 |
JP2018509292A (ja) | 2018-04-05 |
CN107404926B (zh) | 2021-03-16 |
CA2978505A1 (fr) | 2016-09-22 |
BR112017017747A2 (pt) | 2018-04-03 |
EP3270886B1 (fr) | 2020-10-21 |
FR3033702B1 (fr) | 2018-04-20 |
KR20170129132A (ko) | 2017-11-24 |
JP6887954B2 (ja) | 2021-06-16 |
PT3270886T (pt) | 2021-01-21 |
US20170367393A1 (en) | 2017-12-28 |
FR3033702A1 (fr) | 2016-09-23 |
KR102626146B1 (ko) | 2024-01-16 |
WO2016146837A1 (fr) | 2016-09-22 |
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