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2020 , Vol. 40 >Issue 6: 1578 - 1587

DOI: https://doi.org/10.6023/cjoc202001016

研究论文

山竹醇新类似物的合成及其抗肿瘤活性研究

  • 周汇源 ,
  • 吴堰霖 ,
  • 黄典红 ,
  • 张铭婷 ,
  • 陈欢明 ,
  • 钱明成 ,
  • 赵帅 ,
  • 张辛燕 ,
  • 陈新
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  • a 常州大学制药与生命科学学院 江苏常州 213164;
    b 首都医科大学附属北京口腔医院 口腔医学研究所 北京 100050

收稿日期: 2020-01-09

  修回日期: 2020-03-09

  网络出版日期: 2020-04-10

基金资助

国家自然科学基（Nos.21272029，81772868）资助项目.

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Synthesis and Anti-tumor Activity of Novel Garcinol Analogs

  • Zhou Huiyuan ,
  • Wu Yanlin ,
  • Huang Dianhong ,
  • Zhang Mingting ,
  • Chen Huanming ,
  • Qian Mingcheng ,
  • Zhao Shuai ,
  • Zhang Xinyan ,
  • Chen Xin
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  • a School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou, Jiangsu 213164;
    b Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050

Received date: 2020-01-09

  Revised date: 2020-03-09

  Online published: 2020-04-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21272029, 81772868).

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摘要

山竹醇具有广泛的生物学活性，例如抗炎、抗肿瘤、抗氧化、诱导细胞凋亡等.通过对山竹醇进行结构修饰，研究其侧链基团对山竹醇活性的影响，以期提高其抗肿瘤活性.以乙酰丙酮为原料，经过Michael加成、Knoevenagel缩合等多步反应，合成了三个未见文献报道的山竹醇类似物，并用噻唑蓝（MTT）法对其进行生物活性研究，分析其构效关系.结果表明，合成的三种新类似物对口腔鳞癌细胞的抑制活性均低于山竹醇，由此可知，C4位置的异戊烯基和C8位置的烯丙基对山竹醇的生物活性起关键作用.

关键词： 山竹醇; 结构修饰; Michael加成; 抗肿瘤

本文引用格式

周汇源 , 吴堰霖 , 黄典红 , 张铭婷 , 陈欢明 , 钱明成 , 赵帅 , 张辛燕 , 陈新 . 山竹醇新类似物的合成及其抗肿瘤活性研究[J]. 有机化学, 2020 , 40(6) : 1578 -1587 . DOI: 10.6023/cjoc202001016

Abstract

Garcinol possesses a wide range of biological activities, such as anti-inflammation, anti-tumors, anti-oxidation, induction of apoptosis and so on. In this paper, the modification of the side chains in garcinol was carried out to enhance its anti-tumor activity. Employing acetylacetone as starting material, three new analogs of garcinol were prepared by means of Michael addition, Knoevenagel condensation, and so on. Furthemore, their biological activity was assessed by methyl thiazolyl tetrazolium (MTT) method and the structure-activity relationship was analyzed. The results showed that the inhibitory activities of the three new analogs on oral squamous cell carcinoma were moderately lower than that of garcinol. Hence, the isoprenyl group at the C4 position and the allylic group at the C8 position might play vital roles for the biological activity of garcinol.

Key words： garcinol; structural modification; Michael addition; anti-tumor

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