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引用本文:   迟绍明, 杨松霖, 晋文, 杨惠文, 王宇飞, 雷泽, 朱洪友, 赵焱. 花旗松素、槲皮素和桑色素与丙二胺桥联β-环糊精的包合作用及抗氧化活性. 分析化学, 2020, 48(2): 215-223. doi:  10.19756/j.issn.0253-3820.191554 [复制]

Citation:   CHI Shao-Ming , YANG Song-Lin , JIN Wen , YANG Hui-Wen , WANG Yu-Fei , LEI Ze , ZHU Hong-You , ZHAO Yan . Inclusion and Antioxidant Properties of Taxifolin, Quercetin and Morin Hydrate with Diaminopropane Bridged Bis(β-cyclodextrin)s. Chinese Journal of Analytical Chemistry, 2020, 48(2): 215-223. doi: 10.19756/j.issn.0253-3820.191554 [复制]

花旗松素、槲皮素和桑色素与丙二胺桥联β-环糊精的包合作用及抗氧化活性

收稿日期: 2019-09-16

基金项目: 本文系国家自然科学基金项目(Nos.21362046,21062030)和"扬帆计划"引进创新创业团队专项资助项目(No.201312S09)资助

Inclusion and Antioxidant Properties of Taxifolin, Quercetin and Morin Hydrate with Diaminopropane Bridged Bis(β-cyclodextrin)s

Received Date:  2019-09-16

Fund Project:  This work was supported by the National Natural Science Foundation of China (Nos.21362046, 21062030) and the Yangfan Innovative and Entepreneurial Research Team Project (No. 201312S09).

黄酮类化合物花旗松素(TFL)、槲皮素(QCT)和桑色素(MH)具有抗氧化、抗炎、抗过敏、抗肿瘤等多种生物活性,但这些化合物水溶性差,口服利用率低,影响其药效的发挥。桥联β-环糊精(bis(β-CD) s)可通过两个环糊精空腔对客体分子的协同键合,增强环糊精对药物分子的键合能力,从而显著改善药物分子的水溶性。本研究考察了TFL、QCT和MH在溶液和固相中与丙二胺桥联β-环糊精(H2)的包合行为。通过紫外-可见吸收光光谱(UV-Vis)、一维核磁共振氢谱(1H NMR)、二维核磁共振氢谱(2D NMR)、扫描电子显微镜(SEM)、X射线衍射(XRD)、傅里叶变换红外光谱(FT-IR)等对3种包合物(TFL/H2、QCT/H2和MH/H2)进行表征。结果表明,3种黄酮类化合物的A环和C环分别从环糊精的小口端包结到H2的两个空腔中,形成1∶1夹心式的包结模式。3种包合物的稳定常数(KS)大小顺序为KMH/H2 > KTFL/H2 > KQCT/H2。主-客体的尺寸、形状匹配关系和氢键相互作用力,是影响包合物稳定的重要因素。形成包合物后,TFL、QCT和MH在水中的溶解度分别提高了130.2、180.4和210.1倍。此外,1,1-二苯基-2-三硝基苯肼(DPPH)自由基清除法抗氧化活性实验结果表明,包合物TFL/H2、MH/H2的抗氧化活性显著增强了游离药物的活性。本研究为高水溶性、较好抗氧化活性的黄酮类化合物药物的开发提供了重要参考。

关键词:   花旗松素, 槲皮素, 桑色素, 丙二胺桥联β-环糊精, 协同键合, 水溶性, 抗氧化活性
Key words:   Taxifolin, Quercetin, Morin hydrate, Diaminopropane bridged bis(β-cyclodextrin)s, Cooperative bonding, Water solubility, Antioxidant activity
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目录

花旗松素、槲皮素和桑色素与丙二胺桥联β-环糊精的包合作用及抗氧化活性

迟绍明, 杨松霖, 晋文, 杨惠文, 王宇飞, 雷泽, 朱洪友, 赵焱

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