CN114917355A - 柚皮苷-壳寡糖偶联物及其制备方法和应用 - Google Patents

柚皮苷-壳寡糖偶联物及其制备方法和应用 Download PDF

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CN114917355A
CN114917355A CN202210692080.6A CN202210692080A CN114917355A CN 114917355 A CN114917355 A CN 114917355A CN 202210692080 A CN202210692080 A CN 202210692080A CN 114917355 A CN114917355 A CN 114917355A
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naringin
conjugate
chitooligosaccharide
chitosan oligosaccharide
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王�华
欧阳祝
黄林华
郭莉
谈安群
周琦
易鑫
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Abstract

本发明提供了一种柚皮苷‑壳寡糖偶联物及其制备方法和应用，按照如下步骤制备：将柚皮苷和壳寡糖分别配制成乙醇溶液，然后混合，搅拌反应完后，蒸去溶剂，真空干燥得到产品。柚皮苷溶解性提高，可应用于抗氧化、抑菌、杀菌方面。为柚皮苷在畜禽饲料领域、生物医疗领域和功能保健食品等领域的开发应用提供新思路。

Description

柚皮苷-壳寡糖偶联物及其制备方法和应用
本申请是申请日2021年3月31日、申请号202110352150.9、发明名称为“柚皮苷-壳寡糖偶联物及其制备方法和应用”的发明专利申请的分案申请。
技术领域
本发明涉及一种柚皮苷-壳寡糖偶联物及其制备方法和应用，属于化合物领域。
背景技术
柚皮苷是由4’,5,7-三羟基二氢黄酮苷元与鼠李糖苷[2-O-(6-脱氧-α-L-甘露聚糖)-β-D-葡萄糖]所构成的化合物，是一种双氢黄酮类化合物。由于A环和B环之间完全没有共轭，所以在282nm有强烈的紫外吸收峰，使柚皮苷显示多种生物学活性和药理作用。其具有抗炎、抗病毒、抗癌、抗突变、抗过敏、抗溃疡、镇痛、降血压活性，能降血胆固醇、减少血栓的形成，改善局部微循环和营养供给，可用于生产防治心脑血管疾病。
柚皮苷广泛存在于柑桔皮渣中，具有作为人类膳食补充剂和畜禽天然抗生素的潜力。但由于其溶解度较低，味道偏苦，很少被直接使用，因此提高柚皮苷的生物利用度显得尤为重要。
发明内容
为了解决上述技术问题，本发明提供了一种柚皮苷-壳寡糖偶联物，以提高其溶解性、生物活性和生物利用度，本发明第二目的在于提供该种柚皮苷-壳寡糖偶联物的制备方法，第三目的在于提供其应用。
为了实现本发明的上述第一目的，本发明提供了一种柚皮苷-壳寡糖偶联物，其结构式为：
Figure BDA0003700420950000011
n＝2-20；其中所述柚皮苷和壳寡糖分别以摩尔比2:1、1:1、1:2、1:3或1:5进行偶联，且所述壳寡糖的分子量为3000或者800-1000。
优选地，所述偶联物对沙门氏菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为40mg/mL。
优选地，所述偶联物对金黄色葡萄球菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为80mg/mL。
优选地，所述偶联物对大肠杆菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为40mg/mL。
进一步优选地，所述偶联物的水溶性比所述柚皮苷的水溶性提高约54.8倍。
为了实现本发明的上述第二目的，本发明提供了所述柚皮苷-壳寡糖偶联物的制备方法，按照如下步骤制备：将所述柚皮苷和壳寡糖分别配制成乙醇溶液，然后混合，搅拌反应完后，经旋转蒸发蒸去溶剂，再真空干燥得到产品。
为了实现本发明的上述第三目的，本发明提供了所述柚皮苷-壳寡糖偶联物在清除自由基或抗氧化上的应用；作为抑菌和/或杀菌药物的应用；在畜禽饲料中的应用；在生物医疗或功能保健食品中的应用。
柚皮苷与壳寡糖、低聚壳寡糖通过氢键或范德华力等非共价键形成稳定偶联物可改善柚皮苷的溶解性，经过高效液相色谱分析偶联物的水溶性，柚皮苷-壳寡糖偶联物在原有柚皮苷的溶解度上提高约54.8倍。
通过ABTS+、DPPH、-OH三种方法测定柚皮苷及偶联物的体外抗氧化活性，偶联物对DPPH自由基清除效果尤为明显，对ABTS+自由基和-OH自由基的清除效果相比柚皮苷而言也有所提升。偶联物对大肠杆菌、金黄色葡萄球菌和鼠伤寒沙门氏菌的抑制效果也大大增强，且偶联物D、偶联物E、偶联物d和偶联物e对致病菌有一定的杀菌效果。这为柚皮苷在畜禽饲料领域、生物医疗领域和功能保健食品等领域的开发应用提供新思路。
附图说明：
图1为柚皮苷、柚皮苷与壳寡糖(分子量3000左右)物质的量比2:1，1:1，1:2，1:3，1:5形成的柚皮苷-壳寡糖偶联物扫描电镜图。
图2为柚皮苷、柚皮苷与低聚寡聚糖(分子量800-1000)物质的量比2:1，1:1，1:2，1:3，1:5柚皮苷-低聚壳寡糖偶联物扫描电镜图。
图3为柚皮苷、壳寡糖、柚皮苷与寡聚糖(分子量3000左右)按照物质的量比2:1，1:1，1:2，1:3，1:5制成的柚皮苷-壳寡糖偶联物傅里叶红外光谱图。
图4为柚皮苷、低聚壳寡糖、柚皮苷与低聚寡聚糖(分子量800-1000)按照物质的量比2:1，1:1，1:2，1:3，1:5制成的柚皮苷-低聚壳寡糖偶联物傅里叶红外光谱图。
图5为柚皮苷、壳寡糖、柚皮苷与寡聚糖(分子量3000左右)按照物质的量比2:1，1:1，1:2，1:3，1:5柚皮苷-壳寡糖偶联物X射线衍射图。
图6为柚皮苷、低聚壳寡糖、柚皮苷与低聚寡聚糖(分子量800-1000)物质的量比2:1，1:1，1:2，1:3，1:5制成的柚皮苷-低聚壳寡糖偶联物X射线衍射图。
图7为柚皮苷、物理混合物、柚皮苷与寡聚糖(分子量3000左右)按照物质的量比2:1，1:1，1:2，1:3，1:5制成的柚皮苷-壳寡糖偶联物溶解度图。
图8为柚皮苷、物理混合物、柚皮苷与低聚寡聚糖(分子量800-1000)物质的量比2:1，1:1，1:2，1:3，1:5柚皮苷-低聚壳寡糖偶联物溶解度图。
图9为柚皮苷、壳寡糖、低聚壳寡糖、偶联物的抗氧化活性。
具体实施方式：
下面结合实施例对本发明作进一步详细说明。
实施例1
以柚皮苷和壳寡糖(分子量3000左右)为原料，分别按摩尔比为2:1、1:1、1:2、1:3、1:5的比例，用95％乙醇分别配制柚皮苷溶液和壳寡糖溶液，将两者混合，涡旋振荡5min。然后在45℃下旋转蒸发挥发去大部分溶剂，于60℃真空干燥12h，粉碎过筛即得柚皮苷-壳寡糖偶联物。得到的偶联物同时分别用偶联物A、偶联物B、偶联物C、偶联物D、偶联物E表示。
以柚皮苷和低聚壳寡糖(分子量800-1000)为原料，按照上述方法，可制得柚皮苷-低聚壳寡糖偶联物。得到的偶联物同时分别用偶联物a、偶联物b、偶联物c、偶联物d、偶联物e表示。
制备后通过场发射扫描电镜、傅里叶红外光谱、X射线衍射仪测定偶联物结构。结果见图，图中Naringin表示柚皮苷。
柚皮苷和偶联物对大肠杆菌、金黄色葡萄球菌、沙门氏菌的最低抑菌浓度和最低杀菌浓度见表1。
表1柚皮苷和偶联物对大肠杆菌、金黄色葡萄球菌、沙门氏菌的最低抑菌浓度和最低杀菌浓度。表中MIC表示最低抑菌浓度，MBC表示最低杀菌浓度。
Figure BDA0003700420950000041
本发明选用分子量近1000和3000的壳寡糖，制备不同比例的柚皮苷-壳寡糖偶联物，通过扫描电子显微镜SEM、傅里叶红外光谱FT-IR、X射线衍射仪XRD分析比较柚皮苷、柚皮苷-壳寡糖和柚皮苷-低聚壳寡糖偶联物的理化性质。结果表明柚皮苷与壳寡糖、低聚壳寡糖通过氢键或范德华力等非共价键形成稳定偶联物。经过高效液相色谱分析偶联物的水溶性，柚皮苷-壳寡糖偶联物在原有柚皮苷的溶解度上提高约54.8倍。通过ABTS+、DPPH、-OH三种方法测定柚皮苷及偶联物的体外抗氧化活性，偶联物对DPPH自由基清除效果尤为明显，对ABTS+自由基和-OH自由基的清除效果相比柚皮苷而言也有所提升，其中偶联物A和偶联物e的抗氧化活性最高。通过抑菌实验分析得偶联物对大肠杆菌、金黄色葡萄球菌和鼠伤寒沙门氏菌的抑制效果也大大增强，且偶联物D、偶联物E、偶联物d和偶联物e对致病菌有一定的杀菌效果，可以达到抗生素土霉素的杀菌效果，是潜在的抑菌剂。总体而言，柚皮苷与壳寡糖在比例为2:1时形成的偶联物，抗氧化活性较好。在比例1:3和1:5时形成的偶联物，柚皮苷溶出率和抑菌活性较好。柚皮苷与低聚壳寡糖在比例1:3和1:5时形成的偶联物，其柚皮苷溶出率、抗氧化和抑菌活性均较好。
以上内容是结合具体的优选实施方式对本发明所作的进一步详细说明，不能认定本发明的具体实施只局限于这些说明，对于本发明所属技术领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干简单推演或替换，都应当视为属于本发明的保护范围。

Claims (10)

1.一种柚皮苷-壳寡糖偶联物，其结构式为：
Figure FDA0003700420940000011
n＝2-20；其中所述柚皮苷和壳寡糖分别以摩尔比2:1、1:1、1:2、1:3或1:5进行偶联，且所述壳寡糖的分子量为3000或者800-1000。
2.权利要求1所述的柚皮苷-壳寡糖偶联物，其特征在于：所述偶联物对沙门氏菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为40mg/mL。
3.权利要求1所述的柚皮苷-壳寡糖偶联物，其特征在于：所述偶联物对金黄色葡萄球菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为80mg/mL。
4.权利要求1所述的柚皮苷-壳寡糖偶联物，其特征在于：所述偶联物对大肠杆菌的最低抑菌浓度为10mg/mL且最低杀菌浓度为40mg/mL。
5.权利要求1-4任一项所述的柚皮苷-壳寡糖偶联物，其特征在于：所述偶联物的水溶性比所述柚皮苷的水溶性提高约54.8倍。
6.权利要求1-5任一项所述的柚皮苷-壳寡糖偶联物的制备方法，其特征在于，按照如下步骤制备：将所述柚皮苷和壳寡糖分别配制成乙醇溶液，然后混合，搅拌反应完后，经旋转蒸发蒸去溶剂，再真空干燥得到产品。
7.权利要求1-5任一项所述的柚皮苷-壳寡糖偶联物在清除自由基或抗氧化上的应用。
8.权利要求1-5任一项所述柚皮苷-壳寡糖偶联物作为抑菌和/或杀菌药物的应用。
9.权利要求1-5任一项所述柚皮苷-壳寡糖偶联物在畜禽饲料中的应用。
10.权利要求1-5任一项所述柚皮苷-壳寡糖偶联物在生物医疗或功能保健食品中的应用。
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