CN110156852A - 一种糖基化新甲基橙皮苷二氢查耳酮的制备方法及其应用 - Google Patents
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法及其应用 Download PDFInfo
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- CN110156852A CN110156852A CN201910433383.4A CN201910433383A CN110156852A CN 110156852 A CN110156852 A CN 110156852A CN 201910433383 A CN201910433383 A CN 201910433383A CN 110156852 A CN110156852 A CN 110156852A
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- Prior art keywords
- hesperidin methyl
- new hesperidin
- dihydrochalcone
- methyl dihydrochalcone
- glycosylation
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Abstract
本发明公开提供了一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述方法的具体步骤包括：将原料和糖基供体放入到反应缓冲液中；料液混合均匀后；然后在反应体系加入糖苷酶和糖基转移酶，所述原料为新甲基橙皮苷二氢查耳酮的提取物或转化物及其衍生物。所述方法中所制备的糖基化新甲基橙皮苷二氢查耳酮溶解度增加，提高了利用效率，降低使用成本，改善了前甜和后甜，口感更接近与蔗糖，使其用途范围更为广泛。
Description
技术领域
本发明公开涉及生物工程领域，具体涉及一种糖基化新甲基橙皮苷二氢查耳酮的制备方法及其应用。
背景技术
甜味剂是赋予食品甜味的一类十分重要的食品添加剂，由于它甜度高，且热量低，市场前景非常广阔。随着人们饮食观念的改变，甜味剂替代蔗糖的趋势日益显著。无热量、非营养性高倍甜味剂，是各国科学家研究最多的一个领域，也因此经常被称为功能性高倍甜味剂。
但高倍甜味剂也存在一定的缺陷，如很多产品具有苦涩味和金属味，味道不纯等，比如糖精钠、安赛蜜、甜菊糖等后苦味比较重，单独使用，达到一定用量时后苦味会非常重，使得它们的应用受到限制。寻找能够降低甜味剂后苦味的方法引起了人们广泛的兴趣。
在国内外市场中，甜味剂的作用需求越来越高，对甜味剂的安全性也提出了很高的要求，开发出安全性高，质量稳定，需求量高，天然的甜味剂产品越来越重视。然而在市场上天然的高倍甜味剂的口感效果都不理想。例如：甜菊糖明显的苦味及一定程度的涩味和薄荷醇味，浓度高时会有异味感；甘草甜素甜味时间长，不自然。
人工合成的高倍甜味剂，主要有糖精钠、甜蜜素、安赛蜜、阿斯巴甜、蔗糖素等，具有甜度倍数高、无热量、非龋齿性等特点。但是这些人工合成的甜味剂的安全性，越来越受到质疑，已有大量的报道称糖精钠、甜蜜素等甜味剂在人体内不能很好的代谢，给肾脏造成了巨大的负担。天然甜味剂具有甜度高、安全性高、药食同源等特点，具有很广阔的是商业价值。
新甲基橙皮苷二氢查耳酮(NHDC)是一种天然的甜味剂，自然界存在于多叶棘豆植物中。NHDC具有甜度高(为蔗糖的1000倍以上)，安全、低热等高倍甜味剂的特点。NHDC还可以与多种甜味剂成分协同增甜，及苦味抑制，降低甜味剂用量和成本。在生理活性方面，研究发现NHDC具有降糖，降胆固醇，抗氧化等活性。但是在食品加工中，NHDC的应用仍存在一些局限性，例如：溶解度低，甜味慢，后甜时间过长等问题。
发明内容
本发明公开的目的是提供一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，以达到提高新甲基橙皮苷二氢查耳酮的溶解度的目的。
为实现上述目的，技术方案如下：
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其具体步骤包括：
将原料和糖基供体放入到反应缓冲液中，料液混合均匀后，然后在反应体系加入糖苷酶和糖基转移酶。
所述原料为新甲基橙皮苷二氢查耳酮的提取物或转化物及其衍生物。
所述糖基供体为葡萄糖、UDP-葡萄糖、木糖、UDP-木糖、半乳糖、UDP-半乳糖、赤藓糖、α-环糊精、β-环糊精、淀粉、木聚糖、蔗糖、麦芽糊精、UDP-鼠李糖或鼠李糖，所述糖基供体的浓度为1-50g/L。
所述反应缓冲液为磷酸氢二钠-柠檬酸钠缓冲液，所述磷酸氢二钠-柠檬酸钠缓冲液的质量分数为0.05-1％。
所述原料与反应缓冲液的比例为(1：10)-(1：50)，所述反应缓冲液的pH值为2-8，反应温度为35-75℃，所述反应的时间为1-24h。
所述的糖苷酶为鼠李糖苷酶，糖基转移酶为葡萄糖基转移酶。
所述添加的糖苷酶与糖基转移酶的比例为(10：90)-(90：10)，所述两种酶总量的质量分数为添加原料的10％-50％，所述质量分数进一步优化为10％-30％。
根据上述方法所得糖基化新甲基橙皮苷二氢查耳酮的结构为：
其中：R1＝R2＝Glu、Rha、Xyl或Gal；n＝1-9；m＝1-9。
一种药物组合物，包含上述的糖基化新甲基橙皮苷二氢查耳酮、药学上可接受的盐、载体、赋形剂、稀释剂、媒介物或它们的组合。
所述糖基化新甲基橙皮苷二氢查耳酮在食品、药品、饲料和化妆品上的应用。
所述糖基化新甲基橙皮苷二氢查耳酮在预防和治疗糖尿病、葡萄糖代谢方面的应用。
本公开的有益效果主要体现在：提供了一种糖基化新甲基橙皮苷二氢查耳酮的制备方法及其应用，所述方法中所制备的糖基化新甲基橙皮苷二氢查耳酮溶解度增加，提高了利用效率，降低使用成本，改善了前甜和后甜，口感更接近与蔗糖，使其用途范围更为广泛。
附图说明
图1糖基化新甲基橙皮苷二氢查耳酮的HPLC液相图。
图2糖基化新甲基橙皮苷二氢查耳酮溶解度曲线。
图3小鼠口服葡萄糖耐量实验(OGTT)图。
图4小鼠口服葡萄糖胰岛素糖耐量实验(ITT)。
具体实施方式
以下各步骤仅用以说明本公开的技术方案，而非对其限制；尽管参照前述各步骤对本公开进行了详细的说明，但本领域的普通技术人员应当理解：其依然可以对前述各步骤所记载的技术方案进行修改，或者对其中部分或者全部技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本公开各步骤技术方案的范围。
实施例1
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其具体步骤包括：
以新橙皮苷二氢查耳酮为原料，反应缓冲液为质量分数为0.9％的磷酸氢二钠-柠檬酸钠缓冲液，缓冲液的pH4.9，原料与反应缓冲液的比例为1：25，反应温度55℃，反应时间控制6h；然后在反应体系中鼠李糖苷酶：葡萄糖基转移酶＝15：80，总酶的质量分数为投入新橙皮苷二氢查耳酮的10％，该体系中加入10g/L的葡萄糖。在该反应体系中，糖基化新甲基橙皮苷二氢查耳酮的收率98.2％。HPLC检测结果如图1，从图中可知该反应体系能有效的糖基化新甲基橙皮苷二氢查耳酮，由于多糖基化新甲基橙皮苷二氢查耳酮链接的糖基的数量不同，在HPLC的图中出峰时间会出现一次减小的峰。
实施例2
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其具体步骤包括：
以新橙皮苷二氢查耳酮为原料，反应缓冲液为质量分数为0.1％的磷酸氢二钠-柠檬酸钠缓冲液，反应缓冲液的pH 2，原料与反应缓冲液的比例为1：10，反应温度50℃，反应时间控制4h，然后在反应体系中鼠李糖苷酶：葡萄糖基转移酶＝10：90，总酶的质量分数为投入新橙皮苷二氢查耳酮的15％，该体系中加入5g/L的葡萄糖。在该反应体系中，糖基化新甲基橙皮苷二氢查耳酮的收率80.1％。
实施例3
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其具体步骤包括：
以新橙皮苷二氢查耳酮为原料，反应缓冲液为质量分数为1％的磷酸氢二钠-柠檬酸钠缓冲液，反应缓冲液的pH 8，原料与反应缓冲液的比例为1：50，反应温度60℃，反应时间控制6h，然后在反应体系中鼠李糖苷酶：葡萄糖基转移酶＝90：10，总酶的质量分数为投入新橙皮苷二氢查耳酮的20％，该体系中加入5g/L的鼠李糖。在该反应体系中，糖基化新甲基橙皮苷二氢查耳酮的收率96.8％。
实施例4
一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其具体步骤包括：
以新橙皮苷二氢查耳酮为原料，反应缓冲液为质量分数为0.9％的磷酸氢二钠-柠檬酸钠缓冲液，反应缓冲液的pH 4.5，原料与反应缓冲液的比例为1：20，反应温度60℃，反应时间控制6h，然后在反应体系中鼠李糖苷酶：葡萄糖基转移酶＝10：90，总酶的质量分数为投入新橙皮苷二氢查耳酮的10％，该体系中加入3g/L的UDP-鼠李糖。在该反应体系中，糖基化新甲基橙皮苷二氢查耳酮的收率88.3％。
实施例5糖基化新甲基橙皮苷二氢查耳酮溶解度测定
化合物溶解能力的大小直接影响到药物在溶液体系和细胞体系的应用。本实验利用紫外分光光度法对饱和状态的糖基化新甲基橙皮苷二氢查耳酮的水溶液进行溶解度值的测定。本实验中，配制2.3g/L糖基化新甲基橙皮苷二氢查耳酮(为实施例1所制备)的水溶液，按照一定比例稀释后测吸光度做出标准曲线，对282nm区间的特征峰进行积分作为纵坐标。再测定配制的饱和溶液稀释液的吸光值，通过内标法得到稀释液的浓度，最后计算出饱和溶液浓度。标准曲线图如图1。
根据图2，得到标准曲线方程为y＝5267.2854A–121.95，R2＝0.9909。饱和溶液经100倍稀释后，吸光度积分值为961.2，浓度为5.18g/L，则糖基化新甲基橙皮苷二氢查耳酮的溶解度是562.7g/L。
实施例6糖基化新甲基橙皮苷二氢查耳酮急毒性的测定
在28±1℃的温度，70±5％的湿度条件下，选取7～8周龄，健康的清洁级NIH小鼠20只雌雄各半，体重在20-22g。将饲料和水消毒，试验前和试验的观察期内，均按正常饲料条件饲养。
将实施例1制备的糖基化新甲基橙皮苷二氢查耳酮溶解在0.5％Tween80中，浓度为300mg/mL，将该液体经口给药小鼠，按小鼠体重0.02ml/g为给药剂量。给药后观察1，4，8，12h，以后每12h观察一次。观察死亡情况，每天记录小鼠体重变化以及其他的症状。第10天，以断颈的方式处死小鼠，取各器官进行病理检查。
在第10天，全部小鼠存活，0.02ml/g剂量的糖基化新甲基橙皮苷二氢查耳酮未见毒性反应。小鼠各器官病理检查正常，没有发现病变，10天内小鼠体重未见减轻。因此，说明本公开所制备的的糖基化新甲基橙皮苷二氢查耳酮在口服给药动物时未见毒性。
实施例7糖基化新甲基橙皮苷二氢查耳酮在苦味抑制剂的应用
选择5种苦味物质分别为：甜菊糖苷、柚苷、橙皮苷、咖啡因、人工牛黄，参考食品添加剂中规定的用量和物质本身不同的苦味强度设置以上5种苦味物质最终浓度分别为2000ppm、500ppm、300ppm，1000ppm、3000ppm。
待测糖基化新甲基橙皮苷二氢查耳酮(为实施例1所制备)的浓度分别为400ppm、200ppm、100ppm。
待测苦味抑制剂的配制方法：精确称取0.8g糖基化新甲基橙皮苷二氢查耳酮，用100mL左右的纯净水溶解，定容到1000mL的容量瓶中，配制成400ppm的待测苦味抑制剂溶液，200ppm、100ppm的待测苦味抑制剂溶液直接用400ppm的待测苦味抑制剂溶液稀释制得。
感官评价人员：3男3女，这些人需要对感官评价实验感兴趣，并且能够客观公正的对待感官评价实验，具有良好的语言表达能力及基本的感官辨别能力。
苦味抑制感官实验：将不同浓度的待测苦味抑制剂等体积加入到苦味物质中，让感官评价人员品尝混合后的苦味强度，用纯水做空白对照实验。感官评价人员保持品尝的混合样品溶液在口中连续转动但不吞入，使样品流经舌头的每一部位，一个样品测试完后需要大量清水漱口，两个相邻的样品溶液品尝时需要间隔15min以上保证测试结果的准确度和可靠度结果用数表示，最后计算其平均值，参考表1的评分标准，分值为0-10分。
表1苦味评分标准
| 苦味强度 | 对应分数 |
| 极苦 | 8-10 |
| 很苦 | 6-8 |
| 苦 | 4-6 |
| 较苦 | 2-4 |
| 不苦 | 0-2 |
首先对上述5中苦味物质2000ppm甜菊糖苷、300ppm橙皮苷、500ppm柚苷、1000ppm咖啡因、3000ppm人工牛黄，请感官评价人员进行打分，来作为空白对照的分数，结果如表2。
表2不同苦味物质的苦味评分
| 苦味物质 | 浓度(ppm) | 苦味分数(分) |
| 咖啡因 | 1000 | 8.0 |
| 人工牛黄 | 3000 | 7.6 |
| 柚苷 | 500 | 9.5 |
| 橙皮苷 | 300 | 8.4 |
| 甜菊糖苷 | 2000 | 6.5 |
将配制的不同浓度的糖基化新甲基橙皮苷二氢查耳酮(400ppm、200ppm、100ppm)，分别与2000ppm甜菊糖苷、300ppm橙皮苷、500ppm柚苷、1000ppm咖啡因、3000ppm人工牛黄按相同的体积混合均匀，然后请感官人员品尝打分，评定结果如表3，从表3中可见，5个化合物中，糖基化新甲基橙皮苷二氢查耳酮对上述物质的苦味具有一定的抑制作用，在糖基化新甲基橙皮苷二氢查耳酮400ppm、200ppm、100ppm下对上述物质具有很好的抑制效果，均使苦度下降了两个等级，苦味抑制效果好。
表3糖基化新甲基橙皮苷二氢查耳酮抑制苦味的评定结果
实施例8糖基化新甲基橙皮苷二氢查耳酮对营养性肥胖C57BL/6J小鼠糖脂代谢的影响
1.实验材料
1.1实验动物及条件
C57BL/6J小鼠，雄性，SPF级，4周龄，由中山大学实验动物中心提供。许可证号：SCXK(粤)2009～0004。饲养条件：温度20-25℃，湿度55±1％，12h/12h光照黑暗循环，24h自由饮食饮水。
1.2主要药物和试剂
糖基化新甲基橙皮苷二氢查耳酮为实施例1所制备；辛伐他汀，杭州默沙东制药有限公司；标准饲料和高脂饲料，由广东省动物中心提供；甘油三酯(TG)试剂盒，中生北控生物科技股份有限公司提供；总胆固醇(TC)试剂盒，中生北控生物科技股份有限公司提供；直接高密度脂蛋白胆固醇(HDL-C)测定试剂盒，中生北控生物科技股份有限公司；直接低密度脂蛋白胆固醇(LDL-C)测定试剂盒，中生北控生物科技股份有限公司；游离脂肪酸微量测定试剂盒，普利莱基因技术有限公司；罗康全优越型血糖试纸，瑞士罗氏制药公司提供。
2.实验方法及结果分析
2.1动物的选定、分组及处理
C57BL/6J雄性小鼠，随机选取10只为正常对照组，喂以普通标准饲料(饲料配方：粗蛋白18.5％，粗脂肪4.5％，碳水化合物61％。能量比：粗蛋白21％，粗脂肪11％，碳水化合物68％，总能量3.5Kcal/g)，其余小鼠给予高糖高脂饲料(饲料配方：粗蛋白27％，粗脂肪24％，碳水化合物37％；能量比：蛋白23％，脂肪46％，碳水化合物31％，总能量4.7Kcal/g)。喂养12周后，参考体重大于正常组的平均体重±1.78倍标准差和大于正常体重的20％的标准，选取合格的肥胖小鼠，按照体质量均一的原则分为模型对照组，阳性药辛伐他汀组，糖基化新甲基橙皮苷二氢查耳酮剂量组，每组10只，组间及组内动物分别作标记。正常对照组给予普通饲料，其余各组仍继续给予高糖高脂饲料喂养。实施例1所制备糖基化新甲基橙皮苷二氢查耳酮用蒸馏水配制成1000mg/L，辛伐他汀用蒸馏水配制成100mg/L(现配现用)。
糖基化新甲基橙皮苷二氢查耳酮的给药剂量：按小鼠体重100ml/kg，每天给药1次，连续给药14周。
辛伐他汀药物剂量按小鼠体重0.3ml/kg，每天给药1次，连续给药14周。
模型对照组与正常对照组每天灌服等体积的生理盐水，每天给药1次，连续给药14周。
对给药前和给药后各组小鼠的体重进行检测，以观察不同组小鼠的体重变化。
2.2小鼠口服葡萄糖耐量实验(OGTT)和胰岛素糖耐量实验(ITT)
小鼠口服葡萄糖耐量实验(OGTT)：小鼠禁食12h(不禁水)后，按各药物组相应剂量灌胃给药，糖基化新甲基橙皮苷二氢查耳酮组和模型对照组给予溶剂，每组6只，1h后，各组以2.5mg/kg葡萄糖溶液灌胃，分别于0、30、60、90、120、150、180、210min后取尾静脉血用血糖仪测定血糖值，绘制血糖曲线。结果如图3。
胰岛素糖耐量实验(ITT)：于给药结束前1天，在禁食不禁水的情况下，腹腔注射给予各组小鼠0.75units/kg人胰岛素，于给药前(0min)以及给药后0、30、60、90、120、150、180、210min尾静脉取血，用血糖仪测定血糖值，绘制血糖曲线，如图4所示。
3.结果分析
对各组的小鼠进行体重检测，结果如表4，发现与正常对照组比较，模型组小鼠体重显著增加(P<0.01)。从给药第9周开始，辛伐他汀、糖基化新甲基橙皮苷二氢查耳酮小鼠体重均开始下降，给药结束后辛伐他汀、糖基化新甲基橙皮苷二氢查耳酮组小鼠体重与模型对照组比较均有显著性降低(P<0.01)。根据图3可以看出给药后糖基化新甲基橙皮苷二氢查耳酮组小鼠的血糖始终低于模型对照，根据图4可以看出给药后糖基化新甲基橙皮苷二氢查耳酮组小鼠的血胰岛素的水平上升缓慢，上升幅度降低，且血糖的含量也相应的降低了。因此糖基化新甲基橙皮苷二氢查耳酮能够控制小鼠的血糖水平，有利于体重的减轻，具有减肥的作用。
表4小鼠体重变化
Claims (10)
1.一种糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述方法的具体步骤包括：将原料和糖基供体放入到反应缓冲液中；料液混合均匀后；然后在反应体系加入糖苷酶和糖基转移酶，所述原料为新甲基橙皮苷二氢查耳酮的提取物或转化物及其衍生物。
2.根据权利要求书1所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述糖基供体为葡萄糖、UDP-葡萄糖、木糖、UDP-木糖、半乳糖、UDP-半乳糖、赤藓糖、α-环糊精、β-环糊精、淀粉、木聚糖、蔗糖、麦芽糊精、UDP-鼠李糖或鼠李糖，所述糖基供体的浓度为1-50g/L。
3.根据权利要求书1所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述反应缓冲液为磷酸氢二钠-柠檬酸钠缓冲液，所述磷酸氢二钠-柠檬酸钠缓冲液的质量分数为0.05-1％。
4.根据权利要求书1所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述原料与反应缓冲液的比例为(1：10)-(1：50)，所述反应缓冲液的pH值为2-8，反应温度为35-75℃，所述反应的时间为1-24h。
5.根据权利要求书1所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述的糖苷酶为鼠李糖苷酶，糖基转移酶为葡萄糖基转移酶。
6.根据权利要求书1所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法，其特征在于，所述添加的糖苷酶与糖基转移酶的比例为(10：90)-(90：10)，所述两种酶总量的质量分数为添加原料的10％-50％，所述质量分数进一步优化为10％-30％。
7.一种根据权利要求书1-6任意一项所述的糖基化新甲基橙皮苷二氢查耳酮的制备方法所制备的糖基化新甲基橙皮苷二氢查耳酮，其特征在于，所述糖基化新甲基橙皮苷二氢查耳酮结构为：
其中：R1＝R2＝Glu、Rha、Xyl或Gal；n＝1-9；m＝1-9。
8.一种药物组合物，包含权利要求书7中所述的糖基化新甲基橙皮苷二氢查耳酮、药学上可接受的盐、载体、赋形剂、稀释剂、媒介物或它们的组合。
9.权利要求书7所述的糖基化新甲基橙皮苷二氢查耳酮在食品、药品、饲料和化妆品上的应用。
10.权利要求书7所述的所述糖基化新甲基橙皮苷二氢查耳酮在预防和治疗糖尿病、葡萄糖代谢方面的应用。
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