CN102559797A - 一种白藜芦醇多聚体的制备方法 - Google Patents
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- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 235000021283 resveratrol Nutrition 0.000 title claims abstract description 24
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Abstract
一种白藜芦醇多聚体的制备方法，以白藜芦醇为原料，包括茶多酚氧化酶的提取和氧化反应以及分离、浓缩各单元过程，其特征在于：所述的氧化反应是向质量百分浓度4-8％的白藜芦醇溶液中加入酶活力≥10U/L的茶多酚氧化酶，使茶多酚氧化酶质量百分浓度≥5％，于35-55℃下搅拌反应25-135min。本方法原料易得，工艺简单，产物得率≥50％，纯度≥85％。本多聚体主要为二聚体、三聚体和四聚体。
Description
一、技术领域
本发明涉及一种植物生物活性物质的制备方法，具体地说是一种白藜芦醇多聚体的制备方法。
二、背景技术
白藜芦醇(Resveratrol，简称Res)，化学名为3，4’，5-三羟基二苯乙烯(3，4’，5-trihydrolystilbene)，为无色针状晶体，熔点256-257℃，升华温度261℃。易溶于乙醚、氯仿、甲醇、丙酮等。是植物体内一种天然的二苯乙烯类多酚物质，在自然界中多以单体及糖苷形式存在，一般有四种异构形式：顺反式白藜芦醇和顺反式白藜芦醇，其中反式异构体的生物活性强于顺式异构体，在紫外线照射下反式异构体能够转化为顺式异构体。
白藜芦醇氧化后形成的低聚物(包括二聚体、三聚体等)统称viniferins，它们是植物在恶劣环境中或遭到病原体侵染时所分泌的植物抗毒素。在体外可通过化学和酶氧化白藜芦醇而得到，如用自由基DPPH处理，得到一种白藜芦醇二聚体(δ-viniferin)，用FeCl3处理，得到得到一个同质异构的二聚体(ε-viniferin)；还可以被灰霉菌纯化的漆酶、山葵的过氧化物酶、大豆的酯氧合酶催化形成二聚体，如下式所示：
白藜芦醇的不同聚合物对霜霉病菌均具有不同杀伤力，也具有更强的保护心血管和抗癌的潜在活性。另有研究表明，viniferins等茋类化合物对阿尔茨海默症的尽淀粉质纤维也有体外抑制作用。
白藜芦醇聚合物viniferins的体外合成方法可以分为生物合成和化学合成两类。已见报道的生物合成主要包含以下四种途径：(1)使用真菌产生的类似漆酶的茋合物氧化酶，将白藜芦醇氧化成聚合物δ-viniferin。(2)分别用嗜热甲烷八叠球菌和绒毛栓菌产生的漆酶与白藜芦醇作用，催化合成了δ-viniferin，反应24h后产量可分别达到31％和18％。(3)经辣根过氧化物酶处理后，白藜芦醇亦可被催化脱氢生成δ-viniferin。(4)利用大豆脂肪氧化酶也可氧化白藜芦醇合成δ-viniferin。化学合成法：有研究采用DPPH处理白藜芦醇，得到了二聚体δ-viniferin，产量达18％。
三、发明内容
本发明旨在提供一种产物收率和纯度都较高的酶氧化法制备白藜芦醇低聚体的方法，所要解决的技术问题是遴选酶氧化法所需的氧化酶。
本发明选择的氧化酶是普遍存在于茶叶中的茶多酚氧化酶。
本发明的技术方案是以白藜芦醇为原料，包括茶多酚氧化酶的提取和氧化反应以及分离、浓缩各单元过程，与现有技术的区别是所述的氧化反应是向质量百分浓度4-8％的白藜芦醇溶液中加入酶活力≥10U/L的茶多酚氧化酶，使茶多酚氧化酶质量百分浓度≥5％，于25-55℃下搅拌反应25-135min，反应结束后用丙酮萃取，丙酮相减压浓缩至干得到白藜芦醇低聚体viniferins。
茶多酚氧化酶是这样制备的：用绿茶鲜叶，超低温冻干粉碎茶叶后，加30％丙酮水溶液溶解，弃去沉淀，上清液低温加入过量丙酮，低温离心，沉淀为茶叶多酚氧化酶。
酶活力是这样测定的：以藜芦醇为底物，3mL反应混合液中，含50mmol/L乙酸钠缓冲液(pH＝4.5)2.4mL，1mmol/L底物和0.6mL粗酶液(提取液经10000r/min离心10min后取上清液作为粗酶液)，30℃水浴保温反应30min，于465nm处测定吸光度(465nm处藜芦醇摩尔消光系数ξ465＝1.21×104L·mol-1·cm-1)，以100℃灭活的酶反应混合液为对照。酶活定义为每分钟内催化氧化1μmol藜芦醇的酶量为1个酶活单位(U/L)。
本方法原料易得，工艺简单，产物得率≥50％，纯度≥85％(高效液相检测)。液相色谱分析表明本低聚体主要为二聚体、三聚体和四聚体。如图2所示。
四、附图说明
图1是液质联用图谱中的液相色谱，出峰时间11.64分钟是白藜芦醇低聚体的特征峰。
图2液相谱图中特征峰所含各物质的分子量数据，即质谱分子离子峰，样品中所含m/z分别为453.1、499.1、680.2和907.2的物质依次是白藜芦醇二聚体、三聚体和四聚体。
图3是合成产物(白藜芦醇低聚体)液相色谱图，产物纯度达90％。
五、具体实施方式
取质量百分浓度5％的白藜芦醇溶液1000mL，加入酶活力为10U/L的茶多酚氧化酶100g，于40℃搅拌反应30min，反应结束后用丙酮萃取两次，合并丙酮相，减压蒸馏回收丙酮，得到白藜芦醇低聚体27.5克，得率55％，纯度90％。
高效液相色谱检测条件：波长为310nm，流速为1mL/min，
流动相为乙睛∶水(25∶75)，采用C18柱(4.6X150mm)。
质谱检测条件：ESI(一)电喷雾离子源(负离子模式)，干燥气的温度为350℃，干燥气的流速为8L/min，雾心气压力为40ps。
Claims (1)
1.一种白藜芦醇多聚体的制备方法，以白藜芦醇为原料，包括茶多酚氧化酶的提取和氧化反应以及分离、浓缩各单元过程，其特征在于：所述的氧化反应是向质量百分浓度4-8％的白藜芦醇溶液中加入酶活力≥10U/L的茶多酚氧化酶，使茶多酚氧化酶质量百分浓度≥5％，于35-55℃下搅拌反应25-135min。
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| CN110590881A (zh) * | 2019-09-23 | 2019-12-20 | 中国科学院西北高原生物研究所 | 马蔺子种仁中的新低聚茋类化合物及其提取方法和用途 |
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Application publication date: 20120711 |