新型花色苷衍生物oxovitisin A制备条件优化及其体外抑制癌细胞增殖活性

doi:10.7506/spkx1002-6630-201616001

食品科学

• 工艺技术 • 下一篇

新型花色苷衍生物oxovitisin A制备条件优化及其体外抑制癌细胞增殖活性

吴闹，王静祎，张倩，郭莹，李书艺，何毅，祝振洲，何静仁

武汉轻工大学食品科学与工程学院，湖北武汉 430023

出版日期:2016-08-25 发布日期:2016-08-30
通讯作者: 何静仁
基金资助:
国家自然科学基金面上项目（31371727）；国际科技合作与交流专项（2014DFG32310）；
湖北省自然科学基金项目（2014CFB891）；湖北省科技支撑计划项目（2015BHE015）

Optimized Preparation of New Anthocyanin Derivative Oxovitisin A and Its Antiproliferation Effect on Cancer Cells in vitro

WU Nao, WANG Jingyi, ZHANG Qian, GUO Ying, LI Shuyi, HE Yi, ZHU Zhenzhou, HE Jingren

College of Food Science and Engineering, Wuhan Polytechnic University, Wuhan 430023, China

Online:2016-08-25 Published:2016-08-30
Contact: HE Jingren

摘要/Abstract

摘要：

以植物花色苷为原料，通过羧基吡喃花色苷形成及微氧化两步反应法制备出具有非氧鎓离子结构和内酯型吡喃环结构的吡喃酮型花色苷衍生物（oxovitisin A），进行了反应温度、pH值、反应介质乙醇体积分数和反应时间影响oxovitisin A生成量的单因素试验，正交试验优化得到oxovitisin A的最佳制备条件。高效液相色谱监测反应过程，高效液相色谱-二极管阵列检测-串联离子阱多级质谱法对反应产物进行定量和定性分析。利用“罗丹明B蛋白染色法”考察了oxovitisin A以及不同结构的吡喃花色苷衍生物（羧基吡喃花色苷、甲基吡喃花色苷）、前体花色苷（锦葵花色苷）的体外抗癌细胞增殖活性。结果表明：以1.0 mg/mL的羧基吡喃花色苷为原料，oxovitisin A的最佳制备条件是pH 3.6、反应温度45 ℃、乙醇体积分数20%、反应时间21 d，各因素对oxovitisin A得率影响的大小次序为pH值＞反应温度＞反应时间＞乙醇体积分数。高效液相色谱-串联质谱结合多级质谱裂解分析表明，反应的主要产物是oxovitisin A，反应第21天得率为26.59%。抗癌细胞活性实验结果表明，oxovitisin A能显著抑制人肠癌细胞（Caco-2）和人乳腺癌细胞（MCF-7）细胞增殖，IC50分别为（238.8±24.6）、（85.7±9）μg/mL，抑制作用明显强于羧基吡喃花色苷和甲基吡喃花色苷。

关键词: 花色苷衍生物, oxovitisin A, 正交试验, 高效液相色谱-串联质谱法, 抗肿瘤活性

Abstract:

A novel polyphenolic compound, named oxovitisin, with unique lactone pyranone ring and non-oxonium
structures was prepared. In this study, oxovitisin A was synthesized by two-step reactions in micro-oxygenation system
by using carboxypyranoanthocyanins (vitisin A) as a precursor, which was formed from pyruvic acid and anthocyanins.
The preparation conditions of oxovitisin A, namely temperature, pH, ethanol and reaction time, were optimized using
combination of single factor and orthogonal array experiments. High performance liquid chromatography-with diodearray
detection (HPLC-DAD) was used to monitor the reaction process and the main adduct was qualitatively and
quantitatively analyzed by HPLC-DAD combined with electron ionization tandem mass spectrometry (HPLC-DAD-EIMS/
MS). The sulforhodamine B (SRB) assay was employed to evaluate the anti-tumor effects of oxovitisin A, vitisin A,
methyl-pyranoanthocyanin and malvidin-3-O-glucoside against Caco-2 and MCF-7 cells in vitro. The results showed that
the optimal preparation conditions were found to be reaction at 45 ℃ for 21 d with 20% ethanol acidified to pH 3.6 using
1.0 mg/mL of vitisin A. The effects of four important variables on oxovitisin A yield followed the decreasing order: pH >
reaction temperature > reaction duration > ethanol concentration. The main reaction product was confirmed by HPLCMS/
MS to be oxovitisin A with a yield of 26.59% after 21 d. The SRB assay showed that oxovitisin A displayed obvious
inhibitory effect on the proliferation of Caco-2 and MCF-7 cells with an IC50 value of (238.8 ± 24.6) and (85.7 ± 9) μg/mL,
respectively, obviously stronger than that of vitisin A and methyl-pyranoanthocyanin.

Key words: anthocyanin derivatives, oxovitisin A, orthogonal array experiment, HPLC-MS/MS, anti-tumor effect

中图分类号:

吴闹，王静祎，张倩，郭莹，李书艺，何毅，祝振洲，何静仁. 新型花色苷衍生物oxovitisin A制备条件优化及其体外抑制癌细胞增殖活性[J]. 食品科学, doi: 10.7506/spkx1002-6630-201616001.

WU Nao, WANG Jingyi, ZHANG Qian, GUO Ying, LI Shuyi, HE Yi, ZHU Zhenzhou, HE Jingren. Optimized Preparation of New Anthocyanin Derivative Oxovitisin A and Its Antiproliferation Effect on Cancer Cells in vitro[J]. FOOD SCIENCE, doi: 10.7506/spkx1002-6630-201616001.

[1]	刘文静，黄彪，傅建炜，韦航，黄财标. 超高效液相色谱-串联质谱法同时测定陈年老茶中16 种真菌毒素残留[J]. 食品科学, 2021, 42(2): 299-305.
[2]	王可利，叶泰，徐斐，曹慧，袁敏，于劲松，阴凤琴，吴秀秀. UPLC-MS/MS法测定黄酒中8 种生物胺[J]. 食品科学, 2021, 42(16): 281-285.
[3]	颜伟华，周莹，郭浩炜，王笑笑. UPLC-MS/MS快速筛查豆芽中27 种植物生长调节剂和抗生素类药物[J]. 食品科学, 2021, 42(12): 302-308.
[4]	张艳侠，赵慧男，孙珊珊，徐向军，郑文静，薛霞，王明栋，刘艳明，祝建华. 通过式SPE-UPLC-MS/MS测定植物油中的9 种酚类抗氧化剂[J]. 食品科学, 2021, 42(10): 322-329.
[5]	薛宏坤, 谭佳琪, 刘成海, 刘钗. 超声-闪式联合法制备蓝莓花色苷提取物及其体内外抗肿瘤活性评价[J]. 食品科学, 2020, 41(6): 259-269.
[6]	刘丽丽，刘玉垠，王杰，赵小娜，鲁周民. 枇杷功能成分及生物活性研究进展[J]. 食品科学, 2020, 41(5): 306-314.
[7]	彭丹，刘亚丽，李林青，毕艳兰. 正交试验设计优化近红外检测牛乳中蛋白质的建模条件[J]. 食品科学, 2020, 41(4): 256-261.
[8]	龚蕾，韩智，程慧，刘杰，彭青枝. 谷物及其制品中脱氧雪腐镰刀菌烯醇及其衍生物的检测及污染规律分析[J]. 食品科学, 2020, 41(4): 307-312.
[9]	曹雪琴，杨飞，陈国通，毛琼玲，李芳，杨中. 超高效液相色谱-串联质谱法同时测定水果中10 种保鲜剂残留量[J]. 食品科学, 2020, 41(4): 319-324.
[10]	章豪，吴银良，张宜文，陈国，江潇潇. PRIME HLB固相萃取-超高效液相色谱-串联质谱法测定蜂产品中10 种头孢类药物的残留量[J]. 食品科学, 2020, 41(22): 330-336.
[11]	黄子彧，林莹莹，宋思家，任发政，郭慧媛,. 清除蜡样芽孢杆菌生物被膜的CIP程序优化[J]. 食品科学, 2020, 41(14): 138-145.
[12]	马俊美，王敬，孙文毅，蒋杰，李强，范素芳. 超高效液相色谱-串联质谱法测定保健食品中90 种那非类药物[J]. 食品科学, 2020, 41(14): 307-313.
[13]	牛瑜琦，马晓斐，李挥，张敬轩，高文惠. QuEChERS-超高效液相色谱-串联质谱法快速测定辣椒红色素中9 种非食用色素[J]. 食品科学, 2020, 41(10): 311-316.
[14]	彭真汾，叶清华，王威，谢倩，陈清西. 普通橄榄和清橄榄果实游离氨基酸差异成分与谷氨酰胺代谢[J]. 食品科学, 2019, 40(4): 229-236.
[15]	任南，赵文涛，陈超，吴彦超，张颖颖，李莹莹，郭文萍，范维，王守伟. 固相萃取联合超高效液相色谱-串联质谱法测定畜肉中3 种儿茶酚胺类物质[J]. 食品科学, 2019, 40(24): 300-305.

新型花色苷衍生物oxovitisin A制备条件优化及其体外抑制癌细胞增殖活性

Optimized Preparation of New Anthocyanin Derivative Oxovitisin A and Its Antiproliferation Effect on Cancer Cells in vitro

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价