CN109111420B - 一种低聚原花青素的制备方法 - Google Patents
一种低聚原花青素的制备方法 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A—HUMAN NECESSITIES
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- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及天然植物提取加工技术领域,具体是一种低聚原花青素的制备方法,包括提取、浓缩、纯化、再浓缩、水溶、降聚、喷雾干燥得到低聚原花青素;本发明所选用的原料为天然物料,可用于食品加工和化妆品,所选用的提取溶剂和洗脱溶剂均为酒精,且操作简单,制备的低聚原花青素具有很强的抗氧化性。
Description
技术领域
本发明涉及天然植物提取加工技术领域,具体来说是一种低聚原花青素的制备方法。
技术背景
原花青素是一类黄烷醇单体及其聚合体的多酚化合物,也称缩合单宁。原花青素是一种天然生物活性物质,广泛分布于自然界中,具有调节免疫与抗炎、护肝降脂、保护肠道损伤]、防治动脉粥样硬化、抗紫外线、保护视神经、抗氧化等药理学活性,在食品、保健品、药品和化妆品等领域有较多应用。
原花青素是数量不同的儿茶素或/和表儿茶素聚合而成的多聚体,通常来说5个或5个以上的单体聚合而成的原花青素称为高聚原花青素,2-4个单体聚合而成的原花青素称为低聚原花青素,而通常情况下,低聚原花青素较高聚原花青素更活泼,抗氧化性更强,因此低聚原花青素需求更加广泛。
在天然植物提取的原花青素中,大都为高聚原花青素,因为高聚原花青素分子量大,其抗氧化性并未得到更好的体现,价值并未发挥出来。
中国专利201711424727.2克服了葡萄籽种皮中原花青素难以溶出及其提取物中原花青素聚合度高的难题,采用黑曲霉为菌种发酵葡萄籽,利用黑曲霉产生的纤维素酶、果胶酶等酶类降解葡萄籽种皮利于原花青素的溶出,采用不同体积分数的乙醇作为解吸液洗脱大孔吸附树脂,将原花青素分级,然后进行部分酸解,以利于增加提取物中原花青素低聚体的含量。所得的提取物中低聚原花青素含量≥98%,其平均聚合度在2.5~3.0之间,在体内易吸收,抗氧化活性强。该专利存在以下缺点:酸能够导致原花青素机构中C—C键的裂解,但需要间苯三酚作为亲核物质,才能生成低聚物,另外酸催化高聚原花青素降聚反应速率较慢,需要的混合酸的量多,且需要的反应时间长;而本申请采用碱和双氧水降聚,原花青素在一定碱浓度下可以进行降聚,加入双氧水后加剧原花青素结构中C—C键的裂解,裂解速率加快,且不需要间苯三酚作为亲核物质,产率高。
中国专利201711040011.2公开了荔枝皮原花青素的提取工艺,包括以下步骤:1)将荔枝皮捣碎,加入乙醇溶液提取,得到乙醇提取液;2)将乙醇提取液过滤,将滤液回收乙醇,得到浸膏;3)向浸膏中加入体积浓度为50~70%乙醇溶液调节荔枝皮浓度至0.3~0.5mg/ml,搅拌溶解,上XAD-7大孔树脂,先用蒸馏水洗柱,再用体积浓度为70~90%的乙醇溶液洗脱,分别收集流出液和乙醇洗脱液;4)将流出液上AB-8+树脂,先用蒸馏水洗柱,再用体积浓度为40~50%的乙醇溶液洗脱,收集乙醇洗脱液;5)将两次乙醇洗脱液合并,过滤,滤液浓缩,冷冻干燥,即为荔枝皮原花青素。该专利存在以下缺点:未采用降聚,原花青素聚合度较高,分子量较高,不易被人体和人体微生物吸收,且抗氧化能力较弱。大量使用乙醇,增加回收成本。
中国专利200410016355.6涉及一种低聚体原花青素和这种低聚体原花青素的生产工艺,以及这种低聚体原花青素在食品、保健品、饲料添加剂和兽药中的应用。所述的低聚体原花青素为2~4聚体,并以缩合单宁为原料,以浓度为20~60%的双氧水或氯酸钾为氧化剂进行氧化降解,得黄色至棕黄色半透明液体,再经过分离纯化制得。本发明所述的低聚体原花青素具有较强的抗氧化功能和抗菌功能,作为抗氧化剂应用于食品中口感涩性消失,对消化道淀粉酶活性无不良影响;应用于饲料添加剂中可以有效地降低禽类动物对球虫病的感染率和死亡率,并且在鸡日粮中添加低聚体原花青素能显著降低蛋中胆固醇的含量。该专利存在以下缺点:双氧水浓度高,且加入双氧水的量大,容易氧化刚刚产生的低聚原花青素,低聚原花青素得率低。采用大量的水,高温提取原料中,增加生产成本,且水提低聚原花青素得率低,很难得到高纯度原花青素。
发明内容
本发明的目的在于提供一种低聚原花青素的制备方法,该方法能够快速得到抗氧化性强的低聚原花青素。
为实现上述目的,本发明采用的技术方案是:一种低聚原花青素的制备方法,它包括以下步骤:
(1)提取:将富含原花青素的原料与溶剂充分混合进行提取,过滤得到提取液;
(2)浓缩:将步骤(1)所得的提取液进行真空浓缩,得到原花青素的浓缩液;
(3)纯化:将步骤(2)所得的浓缩液进行大孔吸附树脂吸附,得到含有原花青素的洗脱液;
(4)再浓缩与水溶:将步骤(3)所得洗脱液进行真空浓缩,得到纯度较高的原花青素浓缩液,并在浓缩液中加入水进行调整原花青素浓度得到原花青素水溶液;
(5)降聚:将步骤(4)得到的原花青素水溶液用碱调节pH值8-9,加入降聚促进剂进行降聚,得到低聚原花青素溶液。 pH值过低,解聚效率低,需要加入氧化剂的量大,容易氧化刚刚产生的低聚原花青素,低聚原花青素得率降低; pH值过高,过多的碱容易破坏原花青素的结构,造成得率低;
(6)干燥:将步骤(5)得到的低聚原花青素溶液进行喷雾干燥,得到低聚原花青素产品。
本发明较好的技术方案是:所述的步骤(1)中所用的富含原花青素的原料为葡萄籽、松树皮、油茶籽壳、板栗壳、菜籽外皮、芝麻外皮、花生红衣、蔓越橘果皮等一种或几种混合,粉碎过20-80目筛。
本发明较好的技术方案是:所述的步骤(1)中所用的溶剂为20%-39%的乙醇水溶液,原料与溶剂比为1:5-12(g/mL),提取时间30min-120min,提取温度40℃-59℃ 。
本发明较好的技术方案是:所述的步骤(1)中提取过程可以增加超声波或者微波辅助提取。
本发明较好的技术方案是:所述的步骤(2)中浓缩至浓缩液中乙醇含量为未检出。
本发明较好的技术方案是:所述的步骤(3)中大孔吸附树脂选自HPD-100、D101等中的一种或多种。
本发明较好的技术方案是:所述的步骤(3)中大孔树脂吸附上柱流速为1.5-3BV/h,上样液体积5-7BV,静置吸附时间0.5-2h,水洗液流速2-3BV/h,洗脱溶剂为20%-39%酒精水溶液,洗脱流速2-3BV/h,洗脱剂用量3-5BV。
本发明较好的技术方案是:所述的步骤(4)中浓缩液无酒精气味,用水调整溶液中原花青素浓度为5-10mg/mL。
本发明较好的技术方案是:所述的步骤(5)中碱为碳酸钠、碳酸氢钠、氢氧化钠水溶液,浓度为0.5~10%。
本发明较好的技术方案是:所述的步骤(5)中降聚促进剂为20-30%双氧水,添加量为原花青素水溶液质量3%-5%(w/w)。
本发明较好的技术方案是:所述的步骤(5)中降聚温度为60~70℃,降聚时间为20min~40min。
本发明的有益效果在于:
(1)所选用的原料为天然物料,并提供综合利用的方向。
(2)所选用的提取溶剂和洗脱溶剂均为食品级酒精,且操作简单。
(3)制备强抗氧化性的低聚原花青素,可用于食品加工和化妆品,需求更为广泛。
(4)所得花青素的纯度95%以上,聚合度2.5%以下,以及收率95%以上,单体含量10%以上。
具体实施方式
下面将结合实例对本发明的实施方案进行详细描述,但是本领域技术人员将会理解,下列实施例仅用于说明本发明,而不应视为限定本发明的范围。
实施例1
取200克粉碎葡萄籽,加入1000mL39%乙醇溶液,在50℃下提取90分钟,过滤后浓缩提取液得到浓缩液,浓缩至浓缩液中乙醇含量为未检出;将浓缩液上HPD-100大孔吸附树脂,上柱流速3BV/h,上样流速5BV/h,先用蒸馏水洗柱,水洗流速3BV/h,静置吸附时间1小时,用39%酒精水溶液作为洗脱液,洗脱流速3BV/h,洗脱剂用量3BV,收集酒精洗脱液。将酒精洗脱液浓缩至无酒精气味,再用水调节原花青素浓度5mg/mL,用碳酸钠溶液将原花青素溶液pH调至9.0,加入原花青素溶液质量5%的19%双氧水,在60℃下降聚30min,将降聚后的原花青素溶液进行喷雾干燥得到低聚原花青素粉末。
实施例2
取200克粉碎松树皮,加入1400mL30%乙醇溶液,在59℃下提取60分钟,过滤后浓缩提取液得到浓缩液,将浓缩液上HPD-100大孔吸附树脂,上柱流速3BV/h,上样流速5BV/h,先用蒸馏水洗柱,水洗流速2BV/h,静置吸附时间2小时,用20%酒精水溶液作为洗脱液,洗脱流速3BV/h,洗脱剂用量5BV,收集酒精洗脱液。将酒精洗脱液浓缩至无酒精气味,再用水调节原花青素浓度8mg/mL,用碳酸氢钠溶液将原花青素溶液pH调至8.0,加入原花青素溶液质量3%的19%双氧水,在70℃下降聚20min,将降聚后的原花青素溶液进行喷雾干燥得到低聚原花青素粉末。
实施例3
取200克粉碎茶籽壳,加入1600mL30%乙醇溶液,在40℃下提取120分钟,过滤后浓缩提取液得到浓缩液,将浓缩液上D101大孔吸附树脂,上柱流速3BV/h,上样流速5BV/h,先用蒸馏水洗柱,水洗流速3BV/h,静置吸附时间0.5小时,用30%酒精水溶液作为洗脱液,洗脱流速3BV/h,洗脱剂用量4.5BV,收集酒精洗脱液。将酒精洗脱液浓缩至无酒精气味,再用水调节原花青素浓度10mg/mL,用氢氧化钠溶液将原花青素溶液pH调至8.5,加入原花青素溶液质量3.5%的19%双氧水,在60℃下降聚40min,将降聚后的原花青素溶液进行喷雾干燥得到低聚原花青素粉末。
实施例4
取200克粉碎花生红衣,加入1800mL25%乙醇溶液,在50℃下提取60分钟,过滤后浓缩提取液得到浓缩液,将浓缩液上D101大孔吸附树脂,上柱流速3BV/h,上样流速7BV/h,先用蒸馏水洗柱,水洗流速3BV/h,静置吸附时间1.5小时,用30%酒精水溶液作为洗脱液,洗脱流速3BV/h,洗脱剂用量4BV,收集酒精洗脱液。将酒精洗脱液浓缩至无酒精气味,再用水调节原花青素浓度10mg/mL,用氢氧化钠溶液将原花青素溶液pH调至9.0,加入原花青素溶液质量3%的19%双氧水,在65℃下降聚20min,将降聚后的原花青素溶液进行喷雾干燥得到低聚原花青素粉末。
实施例5
取200克粉碎芝麻外皮,加入2400mL20%乙醇溶液,在59℃下提取30分钟,过滤后浓缩提取液得到浓缩液,将浓缩液上大孔吸附树脂,上柱流速3BV/h,上样流速7BV/h,先用蒸馏水洗柱,水洗流速3BV/h,静置吸附时间1.5小时,用30%酒精水溶液作为洗脱液,洗脱流速3BV/h,洗脱剂用量4BV,收集酒精洗脱液。将酒精洗脱液浓缩至无酒精气味,再用水调节原花青素浓度10mg/mL,用氢氧化钠溶液将原花青素溶液pH调至9.0,加入原花青素溶液质量3%的19%双氧水,在65℃下降聚30min,将降聚后的原花青素溶液进行喷雾干燥得到低聚原花青素粉末。
对比例1
取200克粉碎茶籽壳,加入1000克的水,在90℃下加热50分钟,过滤去除残渣,残渣再用以上同样的提取条件重复2次。收集滤液,浓缩至相对密度为1.275缩合单宁提取物;在缩合单宁提取物中加入2000克50%含量的双氧水,用氢氧化钠调pH至6,加热至40℃降解30分钟。降解完成后,继续加热搅拌,并加入1500克的水补充,挥发干净双氧水,浓缩至1000克,干燥获得金黄或棕黄色产品低聚原花青素。
表1 实施例产品的质量检测指标
表1中,原花青素纯度/%=溶液原花青素含量/溶液干物质重量×100%;得率/%=降聚后原花青素含量/降聚前原花青素含量×100%。
由表1结果可知,实施例1~5降聚前后相比,降聚后原花青素产品的平均聚合度明显小于降聚前的原花青素,且得率和纯度高。
其中表1测定方法如下:
1.原花青素含量测定
原花青素含量测定参照《保健食品检验与评价技术规范》,中华人民共和国卫生部,二ΟΟ三年二月,保健食品功效成分及卫生指标检验规范 第二部分 检验方法十二。
2.平均聚合度的测定
材料:儿茶素标准品(HPLC≥98%),香草醛(分析纯),乙酸(分析纯),盐酸(分析纯)。
方法:称取5mg儿茶素标准品,用乙酸定容到50mL容量瓶中,得到浓度为0.032umol/mL的儿茶素标准溶液,并用乙酸制备成浓度分别为0.0032umol/mL、0.0064umol/mL、0.0096umol/mL、0.0128umol/mL、0.0160umol/mL的儿茶素标准系列溶液。分别移取1mL上述标准系列溶液,添加到装有4%盐酸和1%香草醛的冰醋酸溶液5mL的10mL外表包有锡箔的试管中,加盖摇匀,20℃反应10min,以乙酸作为空白对照,在500nm波长处测定吸光度。按照上述比色条件,测定吸光度并绘制标准曲线。
称取8mg原花青素产品,加入到5mL甲醇中,并用乙酸定容到100mL容量瓶中,超声促溶,并稀释至浓度为40ug/mL的原花青素产品溶液。移取1mL配好的原花青素样品溶液,按照上述比色条件,测定样品溶液的吸光度,将其代入标准曲线计算得到原花青素产品的原花青素物质的量浓度,然后结合测定方法1得到原花青素产品的含量,经计算可得出产物的分子量,进而得到原花青素产品的聚合度。
3.单体含量测定
材料:儿茶素标准品(HPLC≥98%),表儿茶素标准品(HPLC≥98%),没食子酸标准品(HPLC≥98%),表儿茶素没食子酸酯标准品(HPLC≥98%)。
方法:精密称取儿茶素、表儿茶素、没食子酸、表儿茶素没食子酸酯标准品适量,用甲醇分别配制标准溶液,浓度在10~100ug/mL之间。分别精密取10uL注入色谱仪。色谱条件为:色谱柱:Inertsil HPLC色谱柱RP C18(250×4.6mm),检测波长:280nm,流速:1.0mL/min,色谱进样体积:10uL。流动相A:1%乙酸,流动相B:100%乙腈,洗脱梯度为0~5min内B相到10%,5~10minB相由10%到17%,10~17minB相由17%到35%,17~39minB相为35%,39~45minB相由35%到50%,45~55minB相由50%到10%,57名min程序停止。以峰面积积分值对单体进样浓度进行回归,求得标准曲线。
准确称取原花青素产品,用甲醇溶解,配制成1mg/mL的原花青素溶液。进样前用0.22um膜过滤溶液,进样体积为10uL,按照以上色谱条件进行检测并计算各单体峰面积积分值,并利用上述标准曲线求得各单体含量,各单体含量的加和为原花青素产品单体含量。
Claims (7)
1.一种低聚原花青素的制备方法,依次包括如下步骤:
(1)提取:将富含原花青素的原料与溶剂充分混合进行提取,过滤得到提取液;
(2)浓缩:将步骤(1)所得的提取液进行真空浓缩,得到原花青素的浓缩液;
(3)纯化:将步骤(2)所得的浓缩液进行大孔吸附树脂吸附,得到含有原花青素的洗脱液;
(4)再浓缩与水溶:将步骤(3)所得洗脱液进行真空浓缩,得到纯度较高的原花青素浓缩液,并在浓缩液中加入水进行调整原花青素浓度得到原花青素水溶液;
(5)降聚:将步骤(4)得到的原花青素水溶液用碱调节pH值8-9,加入降聚促进剂进行降聚,得到低聚原花青素溶液;
(6)干燥:将步骤(5)得到的低聚原花青素溶液进行喷雾干燥,得到低聚原花青素产品;
步骤(5)中降聚促进剂为10-19%双氧水,添加量为原花青素水溶液质量3-5%;
所述的步骤(1)中所用的富含原花青素的原料为葡萄籽、松树皮、油茶籽壳、板栗壳、菜籽外皮、芝麻外皮、花生红衣、蔓越橘果皮中的一种或几种混合,粉碎过20-80目筛;
所述的步骤(1)中所用的溶剂为重量百分比浓度为20-39%的乙醇水溶液,原料与溶剂比为1g:5-12mL,提取时间30-120min,提取温度40-59℃。
2.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(1)中提取过程增加超声波和微波辅助提取。
3.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(3)中大孔吸附树脂选用HPD-100或D101中的一种。
4.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(3)中大孔树脂吸附上柱流速为1.5-3BV/h,上样液体积5-7BV,静置吸附时间0.5-2h,水洗液流速2-3BV/h,洗脱溶剂为浓度为20%-39%的酒精水溶液,洗脱流速2-3BV/h,洗脱剂用量3-5BV。
5.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(4)中浓缩液无酒精气味,用水调整溶液中原花青素浓度为5-10mg/mL。
6.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(5)中碱为碳酸钠、碳酸氢钠、氢氧化钠的水溶液。
7.根据权利要求1所述低聚原花青素的制备方法,其特征在于:所述的步骤(5)中降聚温度为60-70℃,降聚时间为20-40min。
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