CN103841837A - 用于制备供人消耗的含番茄红素的油性树脂和番茄红素晶体的有效方法 - Google Patents
用于制备供人消耗的含番茄红素的油性树脂和番茄红素晶体的有效方法 Download PDFInfo
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Abstract
本发明提供一种用于制备供人消耗的含有番茄红素的油性树脂和番茄红素晶体的方法。本发明提供一种用于从含有番茄红素的油性树脂制备番茄红素晶体的有效方法,其中有至少85重量%的番茄红素,包含至少90重量%的反式番茄红素和痕量顺式番茄红素和其他类胡萝卜素。就人消耗而言,具有高含量反式番茄红素的商品级番茄红素晶体产品是理想且适合的,用作抗氧化剂,用于预防肿瘤和黄斑退化性疾病,作为抗氧化剂,和作为食品/饲料着色剂。该方法简单、便利、经济且在商业上可行。
Description
技术领域
本发明涉及用于制备供人消耗的包含番茄红素(lycopene)的油性树脂(oleoresin)和番茄红素晶体的有效方法。更特别地,本发明涉及一种用于制备富含高含量反式番茄红素的番茄红素晶体和番茄油性树脂的方法。该方法包括从番茄果实及其产品制备番茄油性树脂,以及从番茄油性树脂制备番茄红素晶体。高含量反式番茄红素使其适合用作抗氧化剂、人营养补充剂,用于预防肿瘤和心脏相关疾病,以及用作食品/饲料着色剂。
背景技术
番茄红素是一种在红色水果,如番茄和西瓜中发现的类胡萝卜素。类胡萝卜素是可用作人体抗氧化剂的天然色素。抗氧化剂用于减轻自由基的影响,而自由基被认为造成人体细胞损害。
番茄红素是一种多烯烃,具有13个C-C双键的无环开链不饱和类胡萝卜素,其中11个是呈线性排列的共轭双键。两个中间-CH3基团在1、6位,其余的-CH3相对彼此在1、5位。番茄红素的颜色和抗氧化剂的性质是由于共轭双键的延伸系统。
番茄红素得名于番茄的物种分类,番茄(Lycopersicon esculentum)。它是番茄中的主要烃类类胡萝卜素,而其他类胡萝卜素含量较少。番茄果实中的类胡萝卜素的组成为:番茄红素(C40H56),80-90%;α-胡萝卜素(C40H56),0.03%;β-胡萝卜素(C40H56),3-5%;γ-胡萝卜素(C40H56),1-2%,八氢番茄红素(phytoene),(C40H64),5.6-10%;六氢番茄红素(phytofluene),(C40H64),2.5-3%;链孢红素(neurosprene),(C40H64),7-9%;以及叶黄素(C40H58),0.011-1.1%(Gross.J,1987,水果中的色素(Pigments in Fruits),学术出版社(Academic Press),伦敦(London))。
番茄红素因其捕捉过氧自由基的能力而具有抗氧化活性。它存在各种几何异构体,例如:全反式(all-trans)、单顺式(mono-cis)和聚顺式(poly-cis)形式。在自然中,番茄红素以全反式形式存在,且这些键中的七个可以在热、光或某些化学反应的影响下从反式形式向单或聚顺式形式异构化。在新鲜的番茄中,全反式异构体是最主要的异构体,也是热力学上最稳定的形式。在加工或存储期间,番茄红素会经历反式到顺式的异构化。在各种基于番茄的食品中,反式异构体占35-96%,5-顺式异构体占4-27%,9-顺式和15-顺式异构体含量相当低。
番茄红素的顺式异构体的物理和化学性能与它们的全反式对应物明显不同。在顺式异构体中观察到的某些区别是色彩强度降低、熔点较低,消光系数较小和紫光光谱中有助于识别的蓝移,称为顺式峰。因其结构形式,顺式异构体更具有极性,在油和烃类溶剂中更具溶解性,且不易结晶。
在番茄加工过程中,因为在有例如铜、铁等金属离子及氧的存在下曝露在热中,番茄红素也会发生降解。在产品储存期间,番茄红素顺式异构体可以转化成反式异构体,因为在基态顺式异构体不稳定而反式异构体是稳定的。还已知与反式番茄红素相比,番茄红素的顺式异构体更易溶于胆酸胶束,且可优先掺合入乳糜微粒(Boileau等,J.Nutrition.129,1176-1181(1999)。
人体内可能有反式到顺式番茄红素的体内异构化。另一种可能性是顺式异构体比反式形式更具生物可利用性,如以下所报道的,,在消耗热加工番茄产品包含较高量的顺式番茄红素,相比之下,新鲜番茄产品具有大量反式番茄红素(Shi和Maguer,Crit.Rev.Biotechnol.20,293-334(2000))。在82℃由热加工番茄且去除果汁获得的番茄浆粉和番茄浆残渣显示顺式番茄红素构成总番茄红素的约56.8%,其可以用作制备富含顺式番茄红素的番茄油性树脂潜在来源(Wang和Chen.Eu.Fd.Res.Technol-222,347-355(2006))。有证据表明顺式番茄红素比反式番茄红素更具生物可利用性(Un Lu等,Brit.J.Nutr.98,140-146,2007)。
在番茄外皮中番茄红素的超临界二氧化碳萃取显示总番茄红素的回收性良好,且乙醇和丙酮被用作改性剂。通过加入α-生育酚或迷迭香提取物提高番茄红素在溶剂中储存的稳定性(Ollanketo等,Eu.Fd.Res.Technol,212,561-565(2001))。
使用二氧化碳,密度0.9g/ml,从干燥的粉末状番茄外皮超临界流体萃取全反式番茄红素,在萃取物中获得88%全反式番茄红素(Salud Gomez-Prieto等,J Agr.Fd.Chem.51,3-7(2003))。该研究表明萃取压力和SCF二氧化碳密度是助于番茄红素顺式或反式异构体选择性溶解度的决定因素。
在人体血浆中,番茄红素是一种异构体混合物,包含至少60%的总番茄红素顺式异构体(Yang Kun等,番茄红素:它的性能和对人类健康的关系(Lycopene:its properties and relationships to human health);Fd.Rev.International.22,309-333(2006))。在血浆中鉴定到异构体,例如全反式、5-顺式、9-顺式以及13-顺式番茄红素,其中构型稳定性顺序为5-顺式>全反式>9-顺式>13-顺式>15-顺式番茄红素。
但是,在计算模型研究中,游离电位显示,5-顺式番茄红素具有最高抗氧化性能,顺序为5-顺式>9-顺式>7-顺式>13-顺式>15-顺式>全反式番茄红素(Chasse等,J.Mol.struc.(Theochem)571,27-37(2001);cited in Adv.Fd.and Nutr.Res.51,99-164(2006),Rao等)。
在食物系统中大多数对番茄红素的稳定性研究关注降解。在金属离子或氧存在下通过热加工的番茄产品中,番茄红素可能被部分破坏。预期在番茄加工过程中番茄红素可能经历至少两种变化,异构化及氧化。在加工过程中番茄红素异构化可能发生。另一方面,在储存时可能发生从顺式型到反式型的转化(John Shi等,番茄中的番茄红素:受食品加工影响的化学和物理性能(Lycopenein tomatoes:Chemical and physical properties affected by food processing),食品科学和营养学评论(Critical reviews in food science and nutrition),40,1-42,(2000))。
番茄红素起到癌症预防剂的作用。番茄红素是重要的,因为它显示对前列腺癌、肺癌及广义上皮癌提供保护作用(Micozzi等,与降低肿瘤风险相关的挑选的原料和烹饪的食品的番茄红素分析(Carotenoid analysis of selected raw andcooked foods associated with lower risk of cancer),Journal of Natl.CancerInstitute,82,282-28(1990))。发现番茄红素的摄取与其他部位,例如消化道、胰脏及膀胱等的癌症风险降低有关。发现血液番茄红素水平较高的女性消耗较高水平的番茄红素及维他命A,且罹患癌症的机率降低1/3。
消耗从水果及蔬菜所获得的番茄红素能降低罹患心脏疾病的可能性。它可预防低密度脂蛋白、胆固醇的氧化,并降低动脉粥状硬化及冠状心脏疾病的发病风险(Kristenson等,立陶宛人和瑞士人冠状动脉心脏疾病抗氧化剂状态和死亡率:50岁男性的伴随交叉研究(Antioxidant state and mortality from coronaryheart deceases in Lithuanian and Swedish men:Concomitant cross sectional studyof men aged50),Brit.Med.J314,629-633(1997);Kohlmeir等,EURAMIC研究中番茄红素和心肌梗死的风险(Lycopene and Myocardial Infarction risk in theEURAMIC study),American Journal of Epidemiology,146,618-626(1997))。
生物可利用性定义为人体通过吸收可利用的所摄入的营养部分,以供正常生理功能及代谢过程。
食物组成和结构影响番茄红素的生物可利用性,其可能影响番茄红素从番茄组织基质的释放。烹调或精磨食物可通过破坏或软化植物细胞壁及破坏番茄红素-蛋白质复合物而增加生物可利用性。例如烹调的加热过程以及例如剁碎的机械结构破坏,是提高生物可利用性的便利方式,其通过分解所述细胞壁结构、破坏色质体膜及降低细胞完整性因此使得番茄红素更易于使用。发现当番茄加热至100℃1小时,20-30%的总番茄红素由顺式异构体组成(Stahl等,人体中番茄红素的摄取及热加工番茄果汁比未加工番茄果汁几何异构体更多(Uptakeof lycopene and its geometrical isomers is greater from heat processed than fromunprocessed tomato juice in humans),J.Nutrition,122,2162-2166(1992))。
与油一起共摄入,番茄类食品的番茄红素的生物可利用性明显高于新鲜的番茄。需要热处理及油介质将番茄红素萃取入疏油相。假设在玉米油存在下加热番茄果汁1小时会将番茄红素由反式转换成顺式型式,从而增加人体吸收水平。
多种膳食纤维降低生物可利用性。果胶是一种典型的膳食纤维,影响人类膳食类胡萝卜素的吸收。高甲氧基果胶与膳食纤维的血胆固醇过少效应以及引发高粘度条件的低吸收有关。
番茄红素的吸收似乎在低剂量时更有效,且与β-胡萝卜素一起摄取的番茄红素会比单独摄取时吸收更多。在补充高剂量β-胡萝卜素之后可观察到血清中番茄红素水平的显著下降(Jackson,M.J.,微营养素的生物可利用性评价(Theassessment of bio-availability of micro-nutrients);前言(Introduction),EuropeanJournal of Clinical Nutrition,51,S1-S2(1997))。
食品加工会提高番茄红素的可利用性。以下两种方式可提升番茄类食品的番茄红素的生物可利用性:从食物基质中将番茄红素萃取至亲脂相中,以及热加工和机械破坏番茄组织细胞。在脂质介质中番茄红素比新鲜番茄中的生物利用性高。过度烹调也会破坏番茄红素。应寻找最优的加工技术参数从而最大程度破坏基质但尽可能减少番茄红素的破坏(Gartner等,自番茄浆比自新鲜番茄的番茄红素更具生物利用性(Lycopene is more bio-available from tomato pastethan from fresh tomatoes),Amer.Journal of Clinical Nutrition56,116-122(1997);Brown等,单一摄取蔬菜或纯化β-胡萝卜素后正常人的血浆类胡萝卜素(Plasmacarotenoids in normal men after a single ingestion of vegetable or purifiedbeta-carotene),Journal of clinical Nutrition49,1258-1265(1989))。
番茄红素是脂溶性的,其通常用例如氯仿、己烷、丙酮、苯、石油醚或二硫化碳等溶剂进行萃取,但安全的溶剂是优选的。在溶剂萃取可能缓慢且不完全的情况下,利用有效地机械研磨材料来促进完全萃取。脱水物质可以采用水不溶性溶剂萃取。需要在溶剂萃取前湿润脱水物质以获得完全萃取。因为敏感性,萃取是在微光及惰性气氛中完成。为了避免在萃取期间氧化及异构化,可加入如对苯二酚等抗氧化剂以及如氢氧化钙等中和剂。萃取样品应该在黑暗中储存,在氮气气氛下储存在冷冻器中(-20℃)。
萃取之后,皂化是去除不想要的脂质、叶绿素及其他杂质最有效的方法。可以在低温下利用石油醚或丙酮作分步结晶获得产物的进一步纯化和结晶。已经开发出某些快速且有效的方法用于番茄红素分析及鉴定,其是利用微波-溶剂萃取、加压增速溶剂萃取技术,其中由番茄回收的番茄红素为98.0-99.6%,(Sadler等,从复原的番茄浆和粉红葡萄水果原浆中快速萃取β-胡萝卜素和番茄红素(Rapid extraction of beta-carotene and lycopene from reconstituted tomatopaste and pink grape fruit homogenates),Journal of Food Science,55,1460-146(1990);Benthin等,药用植物的加压液体萃取(Pressurized liquid extraction ofmedicinal plants),J.Chrom.,A.831,211-219(1999))。
可以采用物理及化学方法进行番茄及番茄类食品中番茄红素含量的测定。物理方法是根据颜色参数与样品番茄红素浓度的关系。在化学分析中,从番茄组织中萃取番茄红素并定量。
与化学分析方法相比,颜色测量法是方便且较快速的用于评估质量的方法。质量劣化可能是天然色素损失所致。如果能正确估计收获及加工后番茄样品中的番茄红素浓度,用色度计测量色度值是有用的。其对番茄红素浓度预测仍不够正确到足以取代化学萃取方法。
分光光度法:己烷和丙酮用于从番茄组织萃取番茄红素,且在460-470nm测定吸光度。需要纯样品校正曲线。
HPLC法:使用C18固定相的反相HPLC法可以进行维生素原A类胡萝卜素的顺式及反式异构体的部分分离。流动相:乙腈/THF85/15稀释剂IPA/THF80/20+0.5%BHT。流速1.5ml/分钟。运行时间20分钟。
为加工,番茄被清洗、挑选及切片。切片的番茄经过热及冷破坏方法以制备果汁。通常使用螺旋或桨式提取器来获得番茄汁。在制造其他番茄产品例如果浆、果泥、果糊或果酱时,利用蒸汽旋管或真空蒸发器来浓缩番茄汁。对于灌装番茄,干馏切片的或整个番茄。番茄经脱水法以干燥。可能先有降解及掉色,且番茄产品受许多因素影响。番茄红素降解的主因是异构化及氧化。
在番茄中,外果皮有最高的番茄红素及其他类胡萝卜素含量,外壁及小叶内含物(lobular content)有最高的胡萝卜素。番茄外皮含有12毫克番茄红素/100克,而成熟番茄含有3.4毫克番茄红素/100克。番茄外皮中番茄红素浓度高于成熟番茄约3倍。番茄果实的外皮和果皮富含番茄红素。发现多数番茄红素附于番茄不溶纤维部分。
番茄红素的化学及物理性质:熔点—172~175℃;溶解性—可溶于氯仿、己烷、苯、二硫化碳、丙酮、石油醚;敏感性—光、氧、高温、酸、金属离子,例如Cu(II)、Fe(III)催化其氧化。λ最大(反式)-番茄红素,446纳米(E1%-2250)、472纳米(E1%-3450)、505纳米(E1070-3150)。
多种番茄产品在加工时会发生颜色劣化,因为加工时于高温下暴露在空气中造成全部反式番茄红素自然发生异构化及氧化。伴随着暴露在氧气和光中,分化番茄组织的热处理可导致番茄红素的破坏。这些变化主要是由经加工的番茄产品的储放寿命稳定性所需的相对严苛热加工施加的热应力造成。
温度影响番茄红素降解的性质和程度。在50℃番茄红素氧化降解会造成分子裂解,产生产物如丙酮、甲基庚酮、乙酰丙醛或者可能的乙二醛。当在高温下保持长时间,会发生番茄红素损失。加热时间长度是控制番茄红素降解的关键因素。看来除气及高温短期热处理对于保留颜色品质是有益的。
有氧可用是番茄红素氧化破坏的最重要作用因素。当有氧存在下在100℃加热,大于30%的番茄红素会降解,而在二氧化碳存在下损失5%(Cole等,番茄红素稳定性.I.由氧降解(Stability of lycopene.I.Degradation by oxygen),J.ofScience food Agric,8,360-365(1957))。相较于升高的温度,暴露在增强的光中的番茄红素破坏度较小。
在高温、真空下进行番茄切片脱水一段时间。在脱水期间,样品中番茄红素的保留情况一般略有下降。在渗透脱水期间,番茄红素含量保持不变。这可解释为渗透脱水时糖溶液使氧无法接近番茄,且在低操作温度下降低番茄红素的氧化。热处理碎裂番茄组织并增加暴露于氧和光,造成番茄红素的破坏。
脱水番茄样品中总番茄红素及顺式异构体含量(Shi等,番茄脱水时番茄红素降解和异构化(Lycopene degradation and isomerisation in tomatodehydration),Food Res.Intl.32,15-31(1999))
样本 | 总番茄红素 | 番茄红素损失 | 全反式异构体 | 顺式异构体 |
(微克/克干重) | (%) | (%) | (%) | |
新鲜番茄 | 775 | 0 | 100 | 0 |
渗透处理 | 775 | 0 | 100 | 0 |
渗透-真空干燥 | 737 | 2.4 | 93.5 | 6.50 |
真空干燥 | 731 | 3.2 | 89.9 | 10.10 |
风干 | 726 | 3.90 | 84.4 | 16.6 |
在番茄加工中去皮是重要的操作。化学处理包括在氢氧化钠或氯化钙热溶液中碱液去皮。
物理处理包括通过高压或过热蒸汽进行蒸汽去皮。新去皮方法如采用液氮、液态空气或氟氯烷-12深冷急冻,或以红外线作为热源的IR去皮法。碱液去皮期间,热溶液溶解表皮蜡质,穿透表皮,消解胞间层、细胞壁,并引起外皮分离。碱溶液的浓度和使用的温度在8-25℃及60-100℃,取决于品种及果实成熟度。使用蒸汽去皮,番茄暴露在新鲜蒸汽中足够长的时间以松开果皮但不会太长以致于冲洗(flush)软化或被煮熟。化学及蒸汽去皮都会造成番茄果实外果皮层食用部分的较高的损失。Schulte(1965)发现以红外线方法将番茄去皮会产生5.30%的果皮损失,而蒸汽法会有7.50%的果皮损失(W.A.Schulte,化学和物理番茄去皮系统的效能和它们对罐装产品质量的影响(Efficiency of chemicaland physical tomato peeling systems and their effects on canned products quality),Ph.D.Thesis,p.199,1965,Ohio State Univ.USA)。在番茄加工期间的废料主要是种子、果皮组织及外皮残余物。番茄表皮区含有番茄中超过80-90%的总番茄红素。可知大量番茄红素通常作为番茄加工废料被丢弃。在食品工业中这种废料是重要的番茄红素来源。
番茄红素含量的降低和反-顺式异构化导致生物性能降低。
(Schierle等,食品和人血浆中番茄红素的含量和异构比(Content and isomericratio of lycopene in food and human blood plasma).Food chem.59(3),459-465(1996)
生物活性潜力取决于异构化及氧化的程度以及番茄类产品在储存时经加工的稳定性。已有报导说热、光、酸及其它因素会导致异构化。真实评估经加工番茄类食品的品质和健康益处不仅取决于番茄红素含量而且取决于异构物的分布。在番茄产品生产和储存过程中控制番茄红素异构化性能有利于改善产品颜色及品质。
热加工:热处理明显提高顺式异构体的比例。与在水中加热相比,在油中加热番茄类食品对异构化反应有较大的影响。不只是热处理期间和温度,如油或脂质等食品基质组份也会影响番茄红素的异构化反应。
脱水效果:脱水方法显示顺式异构体显著增加以及全反式异构体的同步减少。在渗透处理中主要机制为异构化反应,而风干异构化反应和氧化则是影响总番茄红素含量及生物效能的两个因素。脱水及表面积增加通常会导致稳定性不佳。残留在番茄表层的渗透溶液(含糖)阻止氧气渗透并氧化番茄红素。因此,与其他脱水方法相比,渗透处理可降低番茄红素损失。
番茄红素降解及颜色变化:在较低温度,番茄颜色保持更好。在渗透处理期间,颜色品质保持不变。
番茄红素储存稳定性:降解最重要的因素是储存时有氧可用。小心选择储存条件,通过储存在惰气气氛或真空中,使产品不受如空气的影响,在储存过程中保持初始颜色水平是可能的。
抗氧化剂应用:在食品加工及储存过程中破坏番茄红素的主要原因是氧化。小心施用适量的合适抗氧化剂(乙氧喹、抗坏血酸、酸式焦磷酸钠)可获得有益结果。储存时的低储存温度、少光、低水活性、低湿度也对番茄红素氧化具有有限的影响。
对于食品和药品工业,番茄红素作为天然色素及营养素对生产和品质有双重影响。因为对人类膳食有显著的生理效应,番茄红素被认为是“21世纪的维生素”。
使果实成熟的果实发育过程也可能对例如番茄红素的果实组分有影响。可通过在施肥、收获时间及品种选育(variety selection)上改进技术来提高番茄果实中的番茄红素含量。此目标可能使冬季在温室产生高品质番茄。
食品中番茄红素的生物可利用性不仅受到它的异构体形式,还有以下方面的影响:食品基质、存在所释放番茄红素的胶束化的足量脂质、以及存在腔内干扰因素例如果胶及其他膳食纤维。在番茄类食品工业中番茄红素的降解是非常重要的。应该优化加工技术从而避免番茄红素氧化及异构化。
药品公司及为功能食品开发非常需要自番茄工业化生产番茄红素。现今,在番茄加工的去皮过程中,大量的外皮和外果皮组织通常被当作番茄加工废料而丢弃。某些新技术,例如膜分离技术、超临界流体二氧化碳技术以及溶剂萃取技术正被应用于扩大番茄红素生产规模。符合食品安全规定的高质量番茄红素产品将为食品工业提供潜在利益。高价值番茄红素产品的成功商品化可改善番茄类产品及番茄红素产品在全球市场上的竞争力。
许多研究已经表明食用富有番茄红素的食品对于避免心脏疾病及数种类型的癌症(例如肺、前列腺、子宫颈、消化道和乳房)是有益的。近来的研究正着眼于番茄红素在如黄斑退行性疾病以及血脂氧化等方面的效果。
支持上述发现的研究人员促使人们将番茄红素纳入其通常保健膳食中。番茄红素的优良来源为粉红葡萄柚(pink grapefruit)、番石榴、西瓜及玫瑰果(rosehips),但最常见的且最可能的是番茄。
新鲜番茄是番茄红素最佳来源,但煮熟的番茄产品,例如番茄和披萨酱、番茄汁、番茄汤甚至是番茄沙司是更加浓缩的。例如,一颗新鲜番茄含有3.7毫克番茄红素,而一杯番茄汤则有24.8毫克番茄红素。因为在煮熟形式的番茄产品中是顺式番茄红素,身体可以更容易吸收此种番茄红素。
并非所有人都接受番茄红素的益处。世界健康规范机构尚未认可番茄红素为营养物,但是由于早期研究有前途的结果,健康社群正认真考虑膳食中番茄红素的有益效果。当然,多数健康专家同意富含水果和蔬菜的膳食是健康生活方式的一部分。
美国专利号为5,837,311,Zelkha等(1998)描述一种采用具有δH及δP值的溶剂从番茄浆萃取番茄红素的萃取方法。由此方法获得的油性树脂具有含量为2-10%的番茄红素。然而,作者没有报道纯化步骤。
美国专利号为5,897,866,Bombardelli等(1999)描述一种使用正己烷及氯化溶剂从番茄萃取番茄红素的方法。该方法包括萃取以及之后的柱色谱分离,其是冗长且产业可行性有疑问。没有提及分离的番茄红素晶体的纯度。
Ausich等的美国专利号为5,858,700(1999)报道利用碱和丙二醇的皂化反应从番茄及番茄产品制备番茄红素晶体。由此方法获得90%番茄红素晶体,但未提及异构体形式。
Kawaragi等的美国专利号为5,871,574(1999),教导使用有机溶剂的酶介导萃取及纯化番茄红素。由此方法获得的产物报道有大于10%的番茄红素含量。
Konya等的美国专利号为6,331,652(2001),报道用于制备番茄红素的方法。该方法基本上是化学方法,包括多步反应,然后是柱色谱分离和纯化。
Estrella Decastro Antonio等的EP1201762(2002)报道用于从真菌来源如布拉霉属(blakeslea)、笄霉属(choanephora)或须霉属(phycomyces)制备番茄红素的方法。乙酸乙酯和乙醇及异丙醇用于萃取和纯化,通过该方法获得94%纯度的番茄红素晶体。
Giori等的WO03/079816(2003)已经描述了一种从新鲜番茄提取和纯化番茄红素的方法。压碎新鲜番茄,通过真空蒸馏去除水从而获得番茄浓缩物。该浓缩物经用水饱和乙酸乙酯萃取两次。用水洗涤萃取物并浓缩从而得到具有6%番茄素含量的番茄油性树脂。该浓缩物进一步用水、乙酸乙酯洗涤,还用乙醇(45℃)洗涤,用乙酸乙酯老化和洗涤,从而获得95%纯度的结晶的番茄红素。
Ho等的WO036125(2006)已经描述了一种由番茄浆开始的生物方法。(1)发酵去除糖;(2)酶混合物从而从叶绿体释放色素和植酸,洗涤从而去除重金属,随后灭菌并用丙烷/丁烷气体萃取,获得包含13%番茄红素的番茄提取物。
发明目的
因此,本发明的主要目的在于提供一种用于制备供人耗用的含番茄红素油性树脂和番茄红素晶体的有效方法。
本发明的另一目的在于提供用于获得包含至少85重量%的番茄红素的营养性番茄红素组合物的方法。
另一目的在于提供包含大量反式番茄红素和痕量顺式番茄红素和其他类胡萝卜素的番茄红素晶体。
还有一目的在于从任何含番茄红素的原料,包括番茄废料、番茄外皮、番茄浆和脱水番茄外皮制备油性树脂。
进一步的目的在于利用公认安全溶剂(GRAS溶剂)萃取和纯化番茄红素晶体。
还有另一目的在于获得无残留溶剂杂质的番茄红素晶体。
还有另一目的在于提供一种用于制备含番茄红素油性树脂和番茄红素晶体的方法,其中,该方法是简单、便捷、经济和商业上可行的。
发明概要
本文以下描述本发明的方法,所述方法如实施例所示是说明性的,在任何情况下均不应视为用于限制本发明的范围。
因此,本发明提供一种用于从含番茄红素的油性树脂制备番茄红素晶体的有效方法,所述油性树脂具有至少85重量%的富含反式番茄红素的番茄红素,包括以下步骤:
(a)将无溶剂的含番茄红素油性树脂与脂肪族醇在升高温度下混合;
(b)于搅拌下将水性碱溶液加入至步骤(a)获得的反应混合物中;
(c)将所述反应混合物维持在约40℃至约60℃一段时间,所述时间足以皂化脂质和蜡;
(d)于搅拌下用水稀释步骤(c)获得的反应混合物;
(e)将所述经稀释的反应混合物过滤并收集番茄红素晶体;和
(f)采用脂肪族醇洗涤该晶体,并将该晶体于真空下干燥。
含番茄红素的油性树脂与脂肪族醇的重量体积比例为1:0.5-1:1。
用于制备碱溶液的碱可选自:氢氧化钠、氢氧化钾或它们的混合物,较佳为氢氧化钾。水性碱含有20至45重量%的碱。含醇的含番茄红素的油性树脂的混合物与水性碱的重量比为0.5-1.0。
加入碱后获得的反应混合物在40℃-60℃维持1-3小时从而皂化脂质和蜡。
经皂化的混合物和水的比例为0.5-l。
过滤经稀释的反应混合物及用脂肪族醇清洗后,得到的晶体在40℃在真空下干燥。
所述无溶剂的含番茄红素油性树脂系由包括以下步骤的方法制备:
(a)采用非极性和极性溶剂的混合物从含番茄红素材料萃取番茄红素;
(b)收集胶束并分离含番茄红素的非极性层;
(c)在减压、50-60℃温度下从所述含番茄红素的非极性层去除溶剂,从而获得无溶剂的含番茄红素油性树脂。
本发明方法所使用的含番茄红素油性树脂可由任何含番茄红素的原料制备,较佳为番茄废料、番茄浆、新鲜番茄或番茄粉。本方法中使用的非极性溶剂为己烷,极性溶剂选自:脂肪族醇及酯溶剂。脂肪族醇可选自:甲醇、乙醇、异丙醇及它们的混合物。酯溶剂可为乙酸乙酯。所述的无溶剂含番茄红素的油性树脂具有5-10重量%的番茄红素含量,其中含50-70重量%反式番茄红素。用于制备含番茄红素的油性树脂的非极性与极性溶剂之比,对于湿的含番茄红素原料来说为40:60,对于干燥的含番茄红素原料来说为50:50。
发明详述
根据本发明,从含番茄红素的材料,优选番茄果实和它的产品,在两步方法中获得适于供人消耗的富含反式番茄红素的营养番茄红素组合物,该方法包括:
(1)由含番茄红素的材料制备含番茄红素的油性树脂;和
(2)由含番茄红素的油性树脂制备番茄红素晶体。
本发明的细节如所述。
本文所使用的所有技术和科学术语具有本发明所属领域普通技术人员通常理解的含义,除非本说明书另有定义。
番茄是番茄红素的优良来源。其他来源包括西瓜、粉红葡萄柚及番石榴。有许多可用的工业番茄产品例如番茄酱、番茄浆、脱水番茄粉末以及副产品如带有纤维的番茄外皮和种子。这些产品各自是可用于番茄红素萃取的潜在原料,且可采用湿和干燥的原料进行萃取。
本发明方法中,通过混合含番茄红素的材料与非极性和极性溶剂的混合物来制备含番茄红素的油性树脂。对于湿的含番茄红素材料使用己烷:乙醇(40:60)构成的溶剂混合物,对于干燥的含番茄红素材料使用己烷:乙酸乙酯(50:50)构成的溶剂混合物萃取番茄红素,因为其具有良好的选择性且沸点能使得完全去除产生的萃取物中的残余溶剂。湿的含番茄红素材料与溶剂混合物之比为1:8,对于干燥的含番茄红素材料则为1:4。接触2小时并连续搅拌使得易于萃取及分为二层。红色非极性上层含有番茄红素,而极性下层含有水分。用棉花过滤胶束非极性上层,将含番茄红素的溶剂混合物置于减压和50-60℃的高温度下从而得到具有番茄红素含量为5-10重量%的无溶剂的含番茄红素油性树脂,反式番茄红素在50-70重量%范围内。
进一步将所述含有至少5重量%番茄红素的含番茄红素油性树脂与脂肪族醇混合,在60℃的升高的温度下均质30分钟。将水性碱溶液(45重量%)加入到反应混合物,加热回流一小时从而皂化反应混合物中的脂质和蜡。在搅拌下用去离子水稀释经皂化的反应混合物,以有效分离出番茄红素晶体。过滤稀释的溶液,以温水清洗滤饼以去除碱和其它杂质,接着用脂肪族醇清洗以去除痕量水。移出获得的红色结晶的番茄红素并在真空(30-40℃)下干燥。
可进一步将番茄红素晶体与植物油混合并微粒化从而形成番茄红素油性悬浮物,其包含小于0.1至l微米大小的粒子,以及约1-40重量%的番茄红素。
或者,可将获得的番茄红素晶体与允许的组分及粘结剂组合来形成可分散于水中的番茄红素粉末,具有约1-5重量%番茄红素。
本发明的具体实施方式中,含番茄红素材料较佳为新鲜番茄、番茄废料、番茄浆或番茄粉末。
分析方法包含使用分光光度计以测定总番茄红素含量,以及使用HPLC以测定反式番茄红素含量。使用珀金埃尔默(Perkin Elmer)1700分光光度计在470纳米测定番茄油性树脂或番茄红素晶体的样品溶于己烷的番茄红素含量,及在己烷中使用摩尔消光系数3450来计算番茄红素浓度。使用Ishida等人的HPLC改进方法定量测定油性树脂或番茄红素晶体中的全部全反式番茄红素含量。
本发明的组合物在抵挡心脏疾病及各种不同的肿瘤上是特别有益的。本发明更特别提供一种无法天然获得的富含50-90重量%反式番茄红素的番茄红素组合物。
以下实施例用于例示说明本发阴,因此不应被解读为限制本发明的范围。
实施例1
由湿的番茄外皮制备番茄油性树脂
在搅拌下,采用2400毫升比例为40:60的己烷-乙醇溶剂混合物萃取称重的番茄外皮(300克,0.022重量%番茄红素)2小时。搅拌后,倾析出胶束获得残余物。在搅拌下,采用1800毫升的40:60的己烷-乙醇溶剂混合物在两小时期间萃取残余物两次。如此获得的胶束合并在一起产生两层。上层是含有番茄红素的己烷层,而下层是水性层。然后将上下层分离开,采用棉花过滤并在50-60℃真空干燥浓缩,获得0.52克油性树脂。采用分光光度计分析获得的油性树脂,发现含有10.13%番茄红素。采用HPLC分析反式番茄红素的相对面积百分比为68.43%。
实施例2
由湿的番茄浆制备番茄油性树脂
在搅拌下,采用1500毫升比例为40:60的己烷-乙醇溶剂混合物萃取称重的番茄浆(300克,0.0845重量%番茄红素)2小时。搅拌后,倾析出胶束获得残余物。在搅拌下,采用1800毫升的40:60的己烷-乙醇溶剂混合物在两小时期间萃取残余物两次。如此获得的胶束合并在一起产生两层。上层是含有番茄红素的己烷层,而下层是水性层。然后将上下层分离开,采用棉花过滤并在50-60℃真空蒸发浓缩,获得2.4克油性树脂。采用分光光度计分析获得的油性树脂,发现含有10.30%番茄红素。采用HPLC分析反式番茄红素的相对面积百分比为72.42%。
实施例3
由脱水番茄外皮制备番茄油性树脂
在搅拌下,采用400毫升比例为50:50的己烷-乙酸乙酯溶剂混合物萃取称重的100克粉末状脱水番茄外皮(100克,0.22重量%番茄红素)2小时。搅拌后,倾析出胶束获得残余物。采用相同的溶剂混合物萃取残余物四次。由此获得的胶束合并在一起,经过滤、在50-60℃真空蒸发浓缩,获得2.3克油性树脂。采用分光光度计分析获得的油性树脂,发现含有6.10%番茄红素。采用HPLC分析反式番茄红素的相对面积百分比为62.42%。
实施例4
由番茄油性树脂制备番茄红素晶体
在搅拌下,采用25毫升乙醇在50℃均质称重的番茄油性树脂(25克,6-7重量%番茄红素)30分钟。将水性氢氧化钾溶液(45重量%)加入均质溶液。然后通过在58-62℃加热并连续搅拌1-3小时以皂化混合物。采用200毫升去离子水稀释得到的皂化混合物,在相同温度下搅拌30分钟,在热条件下过滤。然后在58-62℃用水洗涤沉淀物一小时。过滤沉淀物质,用25毫升乙醇洗涤床层(bed)。获得的沉淀物经真空干燥获得1.1克含97重量%番茄红素的番茄红素晶体。HPLC分析反式番茄红素相对面积百分比为95.53%。
实施例5
由番茄油性树脂制备番茄红素晶体
在搅拌下,采用25毫升乙醇在50℃均质称重的番茄油性树脂(25克,7-8重量%番茄红素)30分钟。将水性氢氧化钾溶液(45重量%)加入均质溶液。然后通过在58-62℃加热并连续搅拌1-3小时以皂化混合物。采用200毫升去离子水稀释得到的皂化混合物,在相同温度下搅拌30分钟,在热条件下过滤。然后在58-62℃用水洗涤沉淀物一小时。过滤沉淀物质,用25毫升乙醇洗涤床层。获得的沉淀物经真空干燥获得1.4克含87.8重量%番茄红素的番茄红素晶体。HPLC分析反式番茄红素相对面积百分比为94.45%。
本发明的优点
本方法获得包括至少85重量%番茄红素的营养番茄红素组合物。
由所述方法所获得的番茄红素晶体含有高含量的反式番茄红素以及痕量的顺式番茄红素和其它类胡萝卜素。
由任何含番茄红素的原料制备所述油性树脂,该原料包括番茄废料、番茄外皮、番茄浆及脱水番茄外皮。
使用公认安全的溶剂(GRAS溶剂)完成番茄红素晶体的萃取和纯化。
获得的番茄红素晶体不含任何残留溶剂杂质。
用于制备含番茄红素油性树脂及番茄红素晶体的方法简单、便利、经济且在商业上可行。
就供人消耗而言,生产具有高含量反式番茄红素的商品级番茄红素晶体是理想且适合的,其可作为抗氧化剂以便应用于预防癌症及黄斑退化性疾病,及作为食品/饲料着色剂。
Claims (28)
1.一种制备番茄红素晶体组合物的方法,该组合物具有富含反式番茄红素的至少85重量%的番茄红素,所述方法包括以下步骤:
(a)将无溶剂含番茄红素的油性树脂与脂肪族醇在升高的温度下混合;
(b)在搅拌下将水性碱溶液加入到步骤(a)获得的反应混合物中;
(c)将所述反应混合物维持在约40℃至约60℃的温度下一段时间,所述时间足以皂化脂质和蜡;
(d)在搅拌下用水稀释步骤(c)获得的反应混合物;
(e)过滤所述稀释的反应混合物并收集番茄红素晶体;和
(f)用脂肪族醇清洗所述晶体,并于真空下干燥该晶体。
2.如权利要求1所述的方法,其特征在于,步骤(a)中含番茄红素的油性树脂与脂肪族醇的重量体积比例为1:0.5-1:1。
3.如权利要求1所述的方法,其特征在于,步骤(b)中所述水性碱包含20重量%-45重量%的碱。
4.如权利要求1所述的方法,其特征在于,步骤(b)中所述碱选自:氢氧化钾、氢氧化钠和/或它们的混合物。
5.如权利要求1所述的方法,其特征在于,所述皂化反应混合物维持1-3小时的时间。
6.如权利要求1所述的方法,其特征在于,步骤(b)中含醇的含番茄红素的油性树脂的混合物与水性碱的重量比为0.5-1.0。
7.如权利要求1所述的方法,其特征在于,步骤(d)中反应混合物与水的重量体积比为0.5-1.0。
8.如权利要求1所述的方法,其特征在于,步骤(f)中所述干燥于40℃在真空下进行。
9.如权利要求1所述的方法,其特征在于,所述番茄红素晶体组合物含有至少80重量%的反式番茄红素,其余为顺式番茄红素和其它类胡萝卜素。
10.如权利要求1所述的方法,其特征在于,所述番茄红素晶体组合物含有至少90重量%的反式番茄红素,其余为顺式番茄红素和其它类胡萝卜素。
11.如权利要求1所述的方法,其特征在于,所述番茄红素晶体与植物油混合并被微粒化从而形成番茄红素油性悬浮物,包含小于1微米尺寸的颗粒以及约1-40重量%的番茄红素。
12.如权利要求1所述的方法,其特征在于,所述番茄红素晶体与植物油混合并被微粒化从而形成番茄红素油性悬浮物,包含小于0.1微米尺寸的颗粒以及约1-40重量%的番茄红素。
13.如权利要求1所述的方法,其特征在于,所述番茄红素晶体与允许的组分和粘结剂组合从而形成在水中可分散的番茄红素粉末,具有约1-5重量%的番茄红素。
14.一种制备无溶剂含番茄红素的油性树脂的方法,包括以下步骤:
(a)采用非极性和极性溶剂的混合物从含番茄红素材料萃取番茄红素;
(b)收集胶束并分离含番茄红素的非极性层;
(c)在减压、50-60℃温度下从所述含番茄红素的非极性层去除溶剂,从而获得无溶剂含番茄红素的油性树脂。
15.如权利要求14所述的方法,其特征在于,所述油性树脂由新鲜番茄制得。
16.如权利要求14所述的方法,其特征在于,所述油性树脂由番茄废料制得。
17.如权利要求14所述的方法,其特征在于,所述油性树脂由番茄酱制得。
18.如权利要求14所述的方法,其特征在于,所述油性树脂由脱水的番茄外皮制得。
19.如权利要求14所述的方法,其特征在于,用于从湿番茄制备番茄油性树脂的非极性和极性溶剂之比为40:60。
20.如权利要求14所述的方法,其特征在于,用于从干番茄粉末制备番茄油性树脂的非极性和极性溶剂之比为50:50。
21.如权利要求14所述的方法,其特征在于,所述非极性溶剂为己烷。
22.如权利要求14所述的方法,其特征在于,所述极性溶剂选自:脂肪族醇和酯溶剂。
23.如权利要求1、14和22所述的方法,其特征在于,所述脂肪族醇可选自:甲醇、乙醇、异丙醇和它们的混合物。
24.如权利要求1、2、14和23所述的方法,其特征在于,所述脂肪族醇为乙醇。
25.如权利要求14和22所述的方法,其特征在于,所述酯溶剂为乙酸乙酯。
26.如权利要求14所述的方法,其特征在于,所述油性树脂组合物具有5重量%至lO重量%含量范围的番茄红素。
27.如权利要求14所述的方法,其特征在于,所述含番茄红素材料为番茄油性树脂组合物,包含至少60重量%的反式番茄红素,其余为顺式番茄红素和其他类胡萝卜素。
28.如权利要求14所述的方法,其特征在于,所述含番茄红素材料为番茄油性树脂组合物,包含至少70重量%的反式番茄红素,其余为顺式番茄红素和其他类胡萝卜素。
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WO2019080018A1 (zh) | 2017-10-25 | 2019-05-02 | 晨光生物科技集团股份有限公司 | 一种生产番茄红素原料的预处理方法 |
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JP7189613B2 (ja) * | 2019-02-25 | 2022-12-14 | 学校法人 名城大学 | リコピン含有家禽卵 |
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CN106280542B (zh) * | 2016-08-15 | 2017-11-17 | 晨光生物科技集团股份有限公司 | 一种提高番茄红素油树脂品质的生产方法 |
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JP6047576B2 (ja) | 2016-12-21 |
WO2013041935A1 (en) | 2013-03-28 |
TWI526417B (zh) | 2016-03-21 |
IL231483A0 (en) | 2014-04-30 |
AU2012311207B2 (en) | 2016-07-21 |
EP2757904A1 (en) | 2014-07-30 |
CA2848955A1 (en) | 2013-03-28 |
AU2012311207A1 (en) | 2014-03-27 |
KR20140064950A (ko) | 2014-05-28 |
US20150004236A1 (en) | 2015-01-01 |
US9456994B2 (en) | 2016-10-04 |
JP2014527080A (ja) | 2014-10-09 |
EP2757904B1 (en) | 2017-01-11 |
TW201317204A (zh) | 2013-05-01 |
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