CN101795586A - 作为强生物和化学抗氧剂应用在食品及食用油中的油棕酚类和类黄酮 - Google Patents
作为强生物和化学抗氧剂应用在食品及食用油中的油棕酚类和类黄酮 Download PDFInfo
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Abstract
本发明涉及油棕酚类作为天然抗氧剂和食品防腐剂的应用，具体地说，本发明涉及来自植物材料的抗氧剂化合物，其中，所述抗氧剂化合物为酚类，包括但不限于提取自棕榈油榨油副产品的酚酸和类黄酮。
Description
技术领域
本发明涉及包括但不限于酚酸和类黄酮的油棕酚类作为天然抗氧剂和食物防腐剂的应用，还涉及一种在具有亲水性和亲脂性的非离子物质中制备用于食品和食用油的油棕乳液的方法。
背景技术
抗氧剂是存在于人体或食物中的、与可氧化底物的浓度相比具有较低浓度并能显著延缓或防止底物氧化的物质。抗氧剂的作用在于，通过抑制和延缓氧化以延长食品的保质期并减少浪费和营养损失。在食品中，抗氧剂或作为内源组分或被添加到其中，通过控制氧化及其有害产物改善产品质量。抗氧剂保护食品免受氧化的机理是，通过提供电子或氢原子，或灭活金属离子和纯态氧来清除自由基。理想的食品级抗氧剂要安全，不会影响色泽、气味或味道，在低浓度下有效，易于整合到食物中，在苛刻的加工条件下不失活，在成品中稳定，并且成本低廉。当抗氧剂通常加入食品中以保持稳定并防止异味时，人们也对其作为治疗剂的潜力表现出了相当的兴趣。因此，抗氧剂同时吸引了食品科学家和健康专家的兴趣。
除了在人体内，在食用油及食品行业中脂质过氧化也是问题。氧自由基，尤其是氢氧自由基的过量产生可影响脂质细胞膜生成脂质过氧化物和活性氧，而这些脂质过氧化物和活性氧不仅与加速老化相关，还与一系列疾病有关。油脂在加热和贮存时会经历氧化变质，抗氧剂被加入其中通过延缓氧化产物的发展延长油脂的保质期。应用最为广泛的抗氧剂或氧化抑制剂是叔丁基氢醌(TBHQ)、丁基大茴香醚(BHA)和二丁基羟基甲苯(BHT)，然而，越来越多的迹象表明了其高健康风险，很多国家现在已限制使用这些合成抗氧剂。通常天然抗氧剂为消费者所喜爱，也更容易获得法规批准。理想的抗氧剂应来自天然源，在较小浓度下有效，且不对油的气味、浊度及色泽产生影响。食物中的脂氧化影响其营养品质、健康、安全、色泽、气味和质地。过去，批准合成抗氧剂在食物中的使用已证实是一种抑制氧化和延长保质期的经济有效的方法。然而，越来越多的消费者关注食物中化学品的使用，因此源自天然食物原料的非合成抗氧剂很快引起了食品生产者的注意。
食品中的天然氧化抑制剂一般都来自于植物材料，其活性成也就是，酚类、类黄酮和多酚类，包括生育酚，是次生植物代谢产物，最初衍生于苯丙氨酸，在某些情况在植物中衍生于酪氨酸。一些常见植物酚类抗氧剂包括类黄酮化合物、肉桂酸衍生物、香豆素和生育酚。虽然已从植物源中提取得到迷迭香提取物和芝麻酚等并用于商业生产，现仍有不少研究在鉴定新的天然抗氧剂。
抗氧剂可根据其作用方式分类。故抗氧剂可分为自由基终止剂、金属离子螯合剂或在封闭系统中与氧发生反应的除氧剂。主抗氧剂与高能脂自由基反应，以将其转化为热动力学上更为稳定的产物，副抗氧剂通过分解氢过氧化物延缓链起始反应的速率。酚类抗氧剂属于自由基终止剂的范畴。
在利用油棕(Elaeis guineensis)果实提取粗棕榈油的过程中，产生了大量体积的液体废料，并随后作为棕榈油榨油废液(POME)丢弃。油棕果实含有大量的酚类化合物，其中大部分水溶性成分最终留在POME中。本发明涉及一种提取自POME的用于食品和食用油的抗氧剂的油棕酚类混合物。为了使水溶性的油棕酚类溶于油/脂系统，用表面活性剂预处理油棕酚类提取物形成乳液。
发明内容
本发明涉及源自植物材料的抗氧剂化合物，其中，所述抗氧剂化合物包括提取自棕榈油榨油副产品的酚类。
本发明进一步涉及利用植物材料生产抗氧剂化合物的方法，其中，所述方法包括以下步骤：
a)从由棕榈油榨油水合副产品得到的植物材料中提取抗氧剂化合物；
b)将所述油棕酚类提取物溶解于溶解媒介中，如乙醇水溶液，并将形成的溶液与表面活性剂混合生成由表面活性剂和所述油棕酚类提取物组成的抗氧剂混合物；
c)不使用其它溶剂，将所述油棕酚类提取物预溶解于丙二醇中。
本发明还涉及通过将水溶性油棕酚类溶于水，并将形成的溶液混合到包含卵磷脂的油混合溶液中，从而将水溶性油棕酚类溶于油的方法：
其中，当加入水合油棕酚类溶液后搅拌包含卵磷脂的油，形成反相胶束；
其中所述水溶性的油棕酚类因此通过反相胶束溶解在油里。
本发明的详细描述
提取自棕榈油水合副产品的油棕酚类(参考-从POME提取油棕酚类的专利)既是水溶性的，也是脂溶性的。这些化合物可以制成用于非水溶性底物(如油脂)的有效抗氧剂，如通过在同时具备水溶性和脂溶性的非离子底物(如表面活性剂)中形成乳液或糊状物。本发明涉及利用从棕榈油榨油液体副产品中得到的水溶性油棕酚类提取物制备油溶性抗氧剂。棕榈油液体副产品即通常所说的棕榈油榨油废液(POME)。这些化合物可以制成用于非水溶性底物(如油脂)的有效抗氧剂，例如，在通过在同时具备水溶性和脂溶性的非离子底物(如表面活性剂)中形成乳液或糊状物。通过溶解包含油棕酚类的提取物到溶解媒介(如乙醇水溶液)中，并将该溶液与表面活性剂混合，用于食用油和食品的由表面活性剂和油棕酚类提取物组成的抗氧剂混合物就产生了。包含油棕酚类和类黄酮的油溶性提取物也可以通过不使用其它溶剂，将所述油棕酚类和类黄酮直接预溶解于丙二醇中制备。
将水溶性油棕酚类溶于油中的另一个方法是，通过溶解水溶性油棕酚类于水中，并将形成的溶液与包含卵磷脂的油溶液混合来完成。存在于油里的卵磷脂量约为总重的0.1～0.5％。所述油选自下列一组物质：植物油、动物油/脂、食用油或它们的混合物。当加入水合油棕酚类溶液后搅拌包含卵磷脂的油，将形成反相胶束，水溶性油棕酚类因此通过反相胶束溶于油中。
具体实施方式
实施例1
1g油棕酚类溶解于12.5ml含有6ml水的乙醇，将上述溶液加入到12g吐温80中，混合物变得均一。
实施例2
0.5841g油棕酚类提取物与6.5g丙二醇混合并加热促进提取物在丙二醇中的溶解。
实施例3
按照实施例1和实施例2制备的油棕酚类混合物在稳定精棕榈油(RPOo)中的应用
用于实验的精棕榈油(RPOo)的游离脂肪酸含量为0.23％，碘值为57.1，过氧化值为15meq/kg，诱导时间为18小时。过氧化值(PV)是一种评价油氧化到何种程度的标准测试，而在110℃下利用酸败仪(Rancimat apparatus)测量的诱导时间是一种已被人们接受的确定抗氧剂相对强度的方法。
实施例1的1.39g油棕酚类混合物加入到55g置于玻璃样品瓶中的精棕榈油，搅拌后混合物变得均一。
实施例2的1.38g油棕酚类混合物加入到55g置于玻璃样品瓶中的精棕榈油，搅拌后混合物变得均一。
55g精棕榈油的空白对照用于比较。
所有样品在70℃烘箱中存放5周，在存放期结束时，利用酸败仪测量过氧化值和以小时为单位的诱导时间。
表1中的结果表明在70℃存放5周后，与空白对照相比，实施例1和实施例2的所述油棕酚类混合物能够延缓精棕榈油的氧化。
表1：精棕榈油于70℃存放5周后的PV值和诱导时间
PV(meq/kg) 诱导时间(h)
对照 88 0
RPOo+实施例1的混合物 51 1
RPOo+实施例2的混合物 65 3
表1清楚地显示了，当加入到RPOo中后，本发明的实施例1和2的油棕酚类混合物延缓了油的氧化变质。
实施例4
将2.5g大豆卵磷脂搅拌加入到500g精棕榈油(RPOo)，待卵磷脂在RPOo中变得均一后，将0.25ml的50％(w/w)的油棕酚类溶液加入到油中并搅拌至反相胶束均一形成。
实施例5
按照实施例4制备的油棕酚类混合物与商用抗氧剂的抗氧效力的比较
本实施例所用精棕榈油(RPOo)与实施例4中一样，其游离脂肪酸含量为0.07％，碘值为56，过氧化值为1.2meq/kg，诱导时间为25小时。
过氧化值(PV)是评价油氧化到何种程度的标准测试。诱导期是氧化急剧加速前的时间长度，单位为小时。诱导期也称为OSI(氧化稳定指数)，定义为氧化速率发生最大改变的点。本实施例中将测试用油置于110℃直至达到诱导期从而确定OSI。本实施例采用氧化稳定性测定仪(Oxidative StabilityInstrument)，因为它运行一次可分析24个样品，而在实施例3中使用的酸败仪运行一次只能测试6个样品。
将按照实施例4制备的450g含有250mg/kg油棕酚类的RPOo转移至500ml棕色玻璃瓶中并且不盖紧瓶盖。制备各含有1000mg/kg迷迭香提取物(购自
Inc)、175mg/kg的BHA(丁基大茴香醚)和75mg/kg的BHT(二丁基羟基甲苯)的RPOo，450g每种抗氧剂加强的RPOo贮存于不盖紧瓶盖的500ml棕色玻璃瓶中。BHA和BHT在RPOo中的量按照油脂CODEX标准19-1981所允的最大水平选择。450g不含任何添加剂的RPOo用作空白对照。
在样品老化前、中、后对样品操作时，所有样品存放于不盖紧瓶盖的500ml棕色玻璃瓶以使曝光最少。油加速老化的烘箱存放测试(AOCS操作规程建议Cg 5-97)用于黑暗中排除光氧化的情况下将被测试油在60℃烘箱中老化/存放以测量被测试油的稳定性。虽然取样时优选在不同的存放容器中各取一部分，但是因为总取样量很小，不会显著影响质量体积比，本实施例中每次取样均取自同一容器。为了保证烘箱到样品热转移的均一性，在每隔一周取样时会系统地改变样品瓶在烘箱中的位置。
表2和表3的结果表明，在60℃存放3周后，与空白对照相比，实施例4的油棕酚类混合物能够延缓RPOo的氧化。表2和表3还表明了，与商用迷迭香、BHA和BHT的效力相比，油棕酚类混合物具有作为抗氧剂稳定油脂的效力。
表2：不同抗氧剂加强的精棕榈油在60℃黑暗中存放3周(21天)的PV变化
| 样品 | 存放前 | 7天后 | 14天后 | 21天后 |
| 对照 | 1.2 | 9.4 | 19.7 | 29.3 |
| RPOo+250mg/kg油棕酚类 | 1.1 | 2.4 | 3.7 | 6.9 |
| RPOo+1000mg/kg迷迭香提取物 | 1.1 | 5.0 | 6.2 | 9.3 |
| RPOo+175mg/kg的BHA | 1.5 | 7.3 | 16.4 | 27.9 |
| RPOo+75mg/kg的BHT | 1.2 | 7.4 | 9.1 | 16.1 |
表3：不同抗氧剂加强的精棕榈油在60℃黑暗中存放3周(21天)的诱导时间的变化
| 样品 | 存放前 | 7天后 | 14天后 | 21天后 |
| 对照 | 25 | 23 | 18 | 13 |
| RPOo+250mg/kg油棕酚类 | 26 | 26 | 25 | 23 |
| RPOo+1000mg/kg迷迭香提取物 | 31 | 30 | 27 | 24 |
| RPOo+175mg/kg的BHA | 27 | 24 | 20 | 18 |
| 样品 | 存放前 | 7天后 | 14天后 | 21天后 |
| RPOo+75mg/kg的BHT | 28 | 26 | 24 | 21 |
虽然本发明结合较优实施方式和实施例在此进行了说明，对本领域的技术人员来说显而易见地是，在不背离由未决的权利要求所限定的本发明的范围的前提下，可以做出一系列的修改和改变。
Claims (10)
1.一种由植物材料得到的抗氧剂化合物，其特征在于，所述抗氧剂化合物为酚类，所述酚类包括但不限于提取自棕榈油榨油副产品的酚酸和类黄酮。
2.根据权利要求1所述的抗氧剂化合物，其特征在于，所述化合物防止食品中油脂的变质。
3.根据权利要求2所述的抗氧剂化合物，其特征在于，所述食品包括油基食品和水基食品。
4.一种从植物材料生产抗氧剂化合物的方法，其特征在于，所述方法包括以下步骤：
d)从由棕榈油榨油水合副产品得到的植物材料中提取抗氧剂化合物；
e)将所述油棕酚类提取物溶解于溶解媒介中，如乙醇水溶液，并将形成的溶液与表面活性剂混合生成由表面活性剂和所述油棕酚类提取物组成的抗氧剂混合物；
f)不使用其它溶剂，将所述油棕酚类提取物预溶解于丙二醇中。
5.根据权利要求4所述的方法，其特征在于，所述步骤b)中的溶解步骤为将水溶性油棕酚类溶于水，并将形成的溶液混合到包含卵磷脂的油混合溶液中。
6.根据权利要求4所述的方法，其特征在于，所述乳液包括油棕酚类与表面活性剂或溶解媒介。
7.一种通过将水溶性油棕酚类溶于水，并将形成的溶液混合到包含卵磷脂的油混合溶液中，从而将水溶性油棕酚类溶于油的方法其特征在于：
当加入油棕酚类溶液后对所述包含卵膦脂的油进行搅拌时，形成反相胶束；
所述水溶性的油棕酚类因此通过反相胶束溶解在油里。
8.根据权利要求7所述的方法，其特征在于，所述存在于油中的卵磷脂的量约为总重的0.1～0.5％。
9.根据权利要求7所述的方法，其特征在于，所述油选自下列一组物质：植物油、动物油/脂、食用油或它们的混合物。
10.一种在油脂和含脂肪类食品中具有抗氧活性的油棕酚类混合物，其特征在于，包含必需量的油棕酚类，所述油棕酚类混合到：
a.非离子表面活性剂，所述混合物通过将油棕酚类和类黄酮提取物溶解于液体媒介中的表面活性剂中制备；
b.丙二醇。
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| MY158598A (en) | 2009-01-29 | 2016-10-31 | Malaysian Palm Oil Board | Composition comprising oil palm phenolics for use in providing neuroprotective effects and cognitive-enhancement |
| MY161839A (en) | 2009-05-18 | 2017-05-15 | Malaysian Palm Oil Board | A composition for use in the prevention and treatment of cardiovascular diseases |
| MY173655A (en) | 2009-06-09 | 2020-02-14 | Malaysian Palm Oil Board | Composition and method for improving vascular health |
| MY161468A (en) * | 2010-09-22 | 2017-04-14 | Malaysian Palm Oil Board | Extraction of crude palm oil and phenolic compounds from oil palm fruitlets |
| WO2014189357A1 (en) | 2013-05-21 | 2014-11-27 | Sime Darby Malaysia Berhad | A process for extracting phenolic compound |
| US20160278416A1 (en) * | 2015-03-24 | 2016-09-29 | Malaysian Palm Oil Board (Mpob) | Methods for producing water soluble oil palm leaf powder and concentrate |
| CN114424789B (zh) * | 2021-12-20 | 2023-08-01 | 暨南大学 | 基于纳米反胶束体系的抗氧化食用油及其制备方法 |
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| US4839187A (en) * | 1984-06-14 | 1989-06-13 | Nestec Sa | Antioxidant compositions |
| KR910004884B1 (ko) * | 1989-02-01 | 1991-07-15 | 한국식품개발연구원 | 유지류의 산화억제방법 |
| US5084293A (en) * | 1990-06-26 | 1992-01-28 | Kalamazoo Holdings, Inc. | Activated ascorbic acid antioxidant compositions and carotenoids, fats, and foods stabilized therewith |
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| MY169539A (en) | 2019-04-22 |
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