CN112516621A - 一种高含量花椒黄酮的制备方法 - Google Patents
一种高含量花椒黄酮的制备方法 Download PDFInfo
- Publication number
- CN112516621A CN112516621A CN202011275942.2A CN202011275942A CN112516621A CN 112516621 A CN112516621 A CN 112516621A CN 202011275942 A CN202011275942 A CN 202011275942A CN 112516621 A CN112516621 A CN 112516621A
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- CN
- China
- Prior art keywords
- flavone
- pepper
- extracting
- prickly ash
- chinese prickly
- Prior art date
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Classifications
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Abstract
本发明涉及一种高含量花椒黄酮的制备方法。包括以下步骤：原料经溶剂提取浓缩到一定比例后得到花椒黄酮晶体，花椒黄酮晶体通过分离后继续脱溶后得到产品，含溶剂料液通过浓缩后得到含花椒麻素的花椒油树脂。该工艺便于操作，可进行工业化生产，该方法可使花椒黄酮的纯度可达85％以上，花椒麻度萃取得率可达95％以上。
Description
技术领域
本发明属于植物活性成分提取领域，涉及椒渣综合利用的工业生产方法，特别涉及一种同时获得高纯度黄酮类成分和花椒油树脂的制备方法。
背景技术
花椒(Zanthoxylumbungeanum Maxim)为芸香科(Rutaceae)花椒属(ZanthoxylumL)植物,主要分布于东亚与北美,广泛分布于我国。花椒作为传统中药材,收录于《中国药典》,其药用历史悠久,有温中止痛,杀虫止痒。用于脘腹冷痛,呕吐泄泻,虫积腹痛,；外治湿疹,阴痒。
花椒属植物中含有酰胺类成分，且其酰胺大多为链状不饱和脂肪酰胺，其中以山椒素类为代表，是花椒麻味的主要来源。酰胺物质具有杀虫、祛风除湿、镇痛、麻醉、抑菌、兴奋等作用。
黄酮类化合物是植物中常见的一类生物活性成分。黄酮类化合物是植物的次级代谢产物，成分复杂、种类繁多，在食品中可作为甜味剂、食用、抗氧化剂及功能性食品添加剂。有研究表明，花椒中总黄酮含量约为20％，花椒种植的地区、花椒的品种、采收的时间等对花椒黄酮的成分与含量影响较大。花椒中黄酮类化合物主要有槲皮素、金丝桃苷、芦丁和阿福豆苷，具有抗氧化、抗癌、降血糖、降血脂、抗衰老等药理功效。花椒黄酮提取物对超氧阴离子自由基(O2-·)，羟基自由基(·OH)和亚硝酸盐均有一定的清除效果，且与提取物浓度有关，能抑制黄嘌呤氧化酶，可用于痛风的临床治疗。经大孔树脂纯化浓缩后的花椒黄酮提取物的抗氧化活性明显增高。花椒黄酮类化合物红色素在体外试验中表现出明显的抗氧化活性。
目前，在工业生产中，对花椒的提取主要集中在提取花椒油、提取花椒麻味成分等方面，花椒经过萃取后，剩余的花椒渣一般做饲料等进行使用，含有的有效成分未进行再利用。
现有技术中也存在许多花椒黄酮提取、纯化方法，例如，吴亮亮等人考察了花椒黄酮的提取工艺，优化提取溶剂、提取温度等工艺参数(吴亮亮，等花椒总黄酮提取技术研究及黄酮成分分析，食品研究与开发，2011年2月，第32卷第2期)；张曦等人采用超声协同树脂吸附分离法提取花椒总黄酮(张曦，等花椒总黄酮的提取工艺条件研究，应用化工，2012年1月，第41卷第1期)；但是上述提取工艺只停留在粗提取阶段，纯化工艺主要集中在实验室研究阶段，实验室常用的有硅胶柱色谱法、大孔树脂吸附法等，在放大生产过程中存在树脂处理难度大、成本高、产量小、周期长等问题。
目前，结晶工艺有用在花椒其他成分的提取中，例如CN104030937A中将花椒油树脂经提取、结晶后获得了不饱和酰胺类成分；CN106866455A以花椒油树脂为原料，经乙醚、甲醇、石油醚依次提取后，于低温环境冷冻结晶，获得花椒麻味物质。但是，通过提取、结晶获得花椒黄酮的技术未见报道。
鉴于上述情况，为了对上述原料进行综合利用，并提供一种适用于工业化生产、成本低的花椒渣综合利用提取制备方法。该方法既得到了花椒黄酮和花椒油树脂两种产品，又能够对花椒渣进行利用，极大的降低了花椒麻素和黄酮资源的浪费。
发明内容
本发明的目的是提供一种花椒渣综合利用的提取制备方法。所述花椒渣为花椒原料经过超临界萃取后所得的副产物，其中花椒麻度为0.3％以下，花椒黄酮含量在3％-8％。该花椒渣通过本发明的方法处理后得到的花椒黄酮经紫外检测，纯度≥50％，同时得到花椒油树脂中花椒麻度萃取得率≥90％。在一些优选的实施方式中，所述黄酮含量在80％以上，花椒麻度萃取得率≥95％。
本发明提供了一种新的花椒渣的加工方法，该方法包括以下步骤：
步骤1：以花椒渣为原料，经过溶剂提取、浓缩，得到浓缩液；
步骤2：在步骤1得到的浓缩液中加入溶剂，进行结晶，分离得到花椒黄酮和浓缩母液；
步骤3：将步骤2中分离花椒黄酮后的的母液进行浓缩得到花椒油树脂。
本发明技术方案的进一步改进在于：步骤1所述的提取溶剂为有机溶剂；进一步优选甲醇、乙醇或丙酮的含水溶液中的一种，浓度为75％-95％；更进一步优选85％-95％的丙酮水溶液。该提取溶剂的加入量为1-6倍，优选2-5倍，进一步优选3倍或4倍。
步骤1中所述提取温度为20-60℃，优选30-50℃，进一步优选40-45℃；提取时间为20min-4h，优选30min-2h，进一步优选40-60min；提取次数为1-6遍，优选提取2-5遍，进一步优选提取4遍。
步骤1中所述浓缩优选浓缩至有机溶剂含量为35％以下，优选25％以下，进一步优选20％以下；或浓缩至固含量为25-35％。
本发明技术方案的进一步改进在于：步骤2中结晶过程，结晶剂主要为正己烷；加入结晶剂后，通过缓慢搅拌，结晶。结晶剂的加入量为0.5-3倍量，优选1-1.5倍量，进一步优选1倍量。
步骤2中结晶温度为4-25℃，优选10-25℃，进一步优选20-23℃。
此外，本发明技术方案还可选择在结晶后进行脱味工艺，脱味工艺为现有技术中常规的脱味工艺，例如真空干燥脱溶等。
本发明优选的技术方案为：
步骤1：以花椒渣为原料，经过85％-95％的甲醇、乙醇或丙酮提取后浓缩至固含量至25-35％；
步骤2：在步骤1得到的浓缩液中加入正己烷后，通过搅拌结晶，分离，得到花椒黄酮和浓缩母液；
步骤3：将步骤2中分离花椒黄酮后的母液进行浓缩得到花椒油树脂。
本发明优选的另一技术方案为：
步骤1：以花椒渣为原料，经过85％-95％的丙酮提取，提取温度为30-50℃，并重复提取2-6遍，提取后浓缩至固含量至25-35％；
步骤2：在步骤1得到的浓缩液中加入0.5-3倍量正己烷后，缓慢搅拌，在10-25℃条件结晶，分离，得到花椒黄酮和浓缩母液；
步骤3：将步骤2中分离花椒黄酮后的母液进行浓缩得到花椒油树脂。
本发明优选的另一技术方案为：
步骤1：以花椒渣为原料，经过85％-95％的丙酮提取，提取温度为30-50℃，并重复提取2-6遍，提取后浓缩至固含量至25-35％，；
步骤2：在步骤1得到的浓缩液中加入0.5-3倍量正己烷后，缓慢搅拌，在10-25℃条件结晶，分离，得到花椒黄酮和浓缩母液，对所得花椒黄酮进行脱味处理；
步骤3：将步骤2中分离花椒黄酮后的母液进行浓缩得到花椒油树脂，对所得花椒油树脂进行脱味处理。
本发明所制备的花椒黄酮和花椒油树脂适用于食品添加剂、饲料添加剂、作为制备药品和化妆品和制备食品添加剂产品的组分。
本发明的有益效果在于：本发明的方法能够提高花椒的利用率，对花椒渣内黄酮和残留的花椒麻素进行提取，并有效进行了分离，花椒黄酮的纯度可达85％以上，花椒麻度得率在95％以上，提高花椒渣的利用率，方法操作相对简单，易于实现规模化生产。
具体实施方式
下面通过具体的实施方案叙述本发明方法。另外，实施方案应理解为说明性的，而非限制本发明的范围，本发明的实质和范围仅由权利要求书所限定。
花椒黄酮的检测使用紫外分光光度计检测，按芦丁标曲法计算总黄酮含量。花椒麻度使用常规测定花椒麻度的高效液相色谱法检测。
实施例1
花椒渣使用85％丙酮萃取，1：4(重量：体积)比例，45℃，每次萃取1h，萃4遍，在60℃下浓缩，浓缩至丙酮含量为25％以下时，在20℃下，加入1倍体积的正己烷搅拌结晶，分离，对上层在60℃下进行浓缩，80℃脱味30min，得到花椒麻素。下层结晶层80℃脱味30min，得到花椒黄酮。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量88.79％，花椒麻度得率97.12％。
实施例2
花椒渣使用90％丙酮萃取，1：3(重量：体积)比例，40℃，每次萃取40min，萃5遍，在60℃下浓缩，浓缩至丙酮含量为25％以下时，在23℃下，加入1倍体积的正己烷搅拌结晶，分离，对上层在60℃下进行浓缩，80℃脱味30min，得到花椒麻素。下层结晶层80℃脱味30min，得到花椒黄酮。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量88.96％，花椒麻度得率96.12％。
实施例3
花椒渣使用75％乙醇萃取，1：5(重量：体积)比例，56℃，每次萃取1h，萃4遍，在70℃下浓缩，浓缩至乙醇含量为10％以下时，在20℃下，加入0.8倍体积正己烷搅拌结晶，分离，对上层在70℃下进行浓缩，80℃脱味30min，得到花椒麻素。下层结晶层85℃脱味40min，得到花椒黄酮。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量86.79％，花椒麻度得率96.46％。
实施例4
花椒渣使用85％甲醇醇萃取，1：3(重量：体积)比例，43℃，每次萃取50min，萃3遍，在40℃下浓缩，浓缩至甲醇含量为20％以下时，在25℃下，加入1.5倍体积的正己烷搅拌结晶，分离，对上层在40℃下进行浓缩，80℃脱味30min，得到花椒麻素。下层结晶层90℃脱味30min，得到花椒黄酮。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量85.03％，花椒麻度得率92.14％。
对比例1
花椒渣使用60％丙酮萃取，1：4(重量：体积)比例，45℃，每次萃取1h，萃4遍，在60℃下浓缩，浓缩至丙酮含量为25％时，降温搅拌结晶，过滤，得到花椒黄酮，并80℃脱味30min。对滤液加入2倍体积的正己烷，混合精制分层，对上层进行60℃下浓缩，80℃脱味30min，得到花椒麻素。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量82.45％，花椒麻度得率95.12％。
对比例2：
对花椒渣使用70％乙醇萃取，1：5(重量：体积)比例，56℃，一次1h，萃4次。70℃下浓缩至料液比1：1(重量：体积)时，离心，上层澄清液加水稀释到3倍原料量待上柱。
待上柱料液用LX-8大孔树脂柱吸附，吸附流速1BV；吸附完毕后，使用3BV水除杂，使用2BV的75％乙醇解析收集，解析液70℃下浓缩，80℃脱味30min，之后得到的产品为粉状固体。
通过上述花椒渣的萃取方法，得到花椒黄酮紫外含量82.94％。
对比例3：
花椒渣使用丙酮萃取，1：4(重量：体积)比例，45℃，每次萃取1h，萃4遍，60℃下浓缩，80℃脱味30min。
通过上述花椒渣的萃取方法，得到花椒麻度得率为95.16％。
通过上述对比实验可以看出，改变提取溶剂浓度、纯化工艺或省去结晶步骤等均会对最终产品中黄酮含量及花椒麻素的得率产生影响，本申请通过提取纯化工艺及参数的选择获得黄酮含量及花椒麻素含量均较高的产品，具有极好的技术效果。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。
Claims (9)
1.一种高含量花椒黄酮的制备方法，其特征在于包括以下工艺步骤：
步骤1：以花椒渣为原料，经过溶剂提取、浓缩，得到浓缩液；
步骤2：在步骤1得到的浓缩液通过加入溶剂，进行结晶，分离得到花椒黄酮和浓缩母液；
步骤3：将步骤2中分离花椒黄酮后的母液进行浓缩得到花椒油树脂。
2.根据权利要求1所述制备方法，其特征在于：步骤1所述的花椒渣材料为花椒经过提取后的植物材料。
3.根据权利要求1-2任一项所述制备方法，其特征在于：步骤1所述的提取溶剂为甲醇、乙醇或丙酮的含水溶液中的一种，溶液浓度为75％-95％。
4.根据权利要求3所述制备方法，其特征在于：所述提取溶剂为85％-95％的丙酮水溶液。
5.根据权利要求1-4任一项所述制备方法制备获得的花椒黄酮。
6.根据权利要求5所述的花椒黄酮，其特征在于：其中黄酮含量≥85％。
7.根据权利要求1-4任一项所述制备方法制备获得的花椒油树脂。
8.根据权利要求7所述的花椒油树脂，其特征在于：该花椒油树脂中花椒麻度的得率≥95％。
9.权利要求5-8任一项所述花椒黄酮或花椒油树脂作为食品、饲料、药物制品和化妆品的功能性添加剂的应用。
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000000002A (ko) * | 1998-09-26 | 2000-01-15 | 조봉관 | 쑥엑스제 조제방법 및 전자 쑥뜸기 |
| CN102040577A (zh) * | 2010-09-27 | 2011-05-04 | 南京泽朗医药科技有限公司 | 一种黄秋葵黄酮的提纯方法 |
| CN102614308A (zh) * | 2012-04-13 | 2012-08-01 | 中国农业大学 | 一种亚临界水萃取辣椒渣中生物活性物质的方法 |
| US20160367612A1 (en) * | 2014-02-10 | 2016-12-22 | Dr. Willmar Schwabe Gmbh & Co., Kg | Improved method for producing ginko extracts |
| CN109259018A (zh) * | 2018-10-24 | 2019-01-25 | 中国科学院兰州化学物理研究所 | 一种花椒叶中具有保健功能的总黄酮提取物的制备方法及用途 |
| CN109453253A (zh) * | 2018-12-28 | 2019-03-12 | 四川大学 | 一种从花椒油加工副产物中提取黄酮类抗氧化剂的方法 |
| CN110746331A (zh) * | 2019-10-22 | 2020-02-04 | 晨光生物科技集团股份有限公司 | 一种从万寿菊中提取叶黄素和槲皮万寿菊素的工业化方法 |
-
2020
- 2020-11-16 CN CN202011275942.2A patent/CN112516621A/zh active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000000002A (ko) * | 1998-09-26 | 2000-01-15 | 조봉관 | 쑥엑스제 조제방법 및 전자 쑥뜸기 |
| CN102040577A (zh) * | 2010-09-27 | 2011-05-04 | 南京泽朗医药科技有限公司 | 一种黄秋葵黄酮的提纯方法 |
| CN102614308A (zh) * | 2012-04-13 | 2012-08-01 | 中国农业大学 | 一种亚临界水萃取辣椒渣中生物活性物质的方法 |
| US20160367612A1 (en) * | 2014-02-10 | 2016-12-22 | Dr. Willmar Schwabe Gmbh & Co., Kg | Improved method for producing ginko extracts |
| CN109259018A (zh) * | 2018-10-24 | 2019-01-25 | 中国科学院兰州化学物理研究所 | 一种花椒叶中具有保健功能的总黄酮提取物的制备方法及用途 |
| CN109453253A (zh) * | 2018-12-28 | 2019-03-12 | 四川大学 | 一种从花椒油加工副产物中提取黄酮类抗氧化剂的方法 |
| CN110746331A (zh) * | 2019-10-22 | 2020-02-04 | 晨光生物科技集团股份有限公司 | 一种从万寿菊中提取叶黄素和槲皮万寿菊素的工业化方法 |
Non-Patent Citations (1)
| Title |
|---|
| 卫强: "《植物茎叶化学成分的提取分离及活性研究》", 31 December 2018, 安徽大学出版社 * |
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