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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (12): 2114-2120. 上一篇    下一篇

研究论文

具有生物活性的紫檀芪和3-甲氧基紫檀芪及其糖苷类化合物的合成

汪钢强，陈玉玲，韩明松，孙亮，汪秋安*   

  1. (湖南大学化学化工学院 化学生物传感与计量学国家重点实验室 长沙 410082)
  • 收稿日期:2011-05-12 修回日期:2011-07-09 发布日期:2011-09-02
  • 通讯作者: 汪秋安 E-mail:wangqiuan@yahoo.com

Synthesis and Biological Activity of Pterostilbene and 3-Methoxy Pterostilbene and Their Glucosides Derivatives

WANG Gang-Qiang, CHEN Yu-Ling, HAN Ming-Song, SUN Liang, WANG Qiu-An   

  1. (State Key Laboratory of Bio-chemical Sensing and Chemometrics, College of Chemistry and Chemical Engineer-ing, Hunan University, Changsha 410082)
  • Received:2011-05-12 Revised:2011-07-09 Published:2011-09-02

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1546

被引次数

17 | 2

以3,5-二羟基苯甲酸、对羟基苯甲醛或香草醛为原料, 以Wittig-Horner反应为关键步骤, 合成了天然产物紫檀芪(1)和3-甲氧基紫檀芪(2). 以稀碱NaOH水溶液作缩合剂, 四丁基溴化铵(TBAB)为相转移催化剂, 使1和2在氯仿-水体系中分别与糖基供体α-溴代乙酰葡萄糖、乳糖和麦芽糖进行糖苷化反应, 合成了一系列未见文献报道的紫檀芪和3-甲氧基紫檀芪的糖苷类化合物3～10. 所合成化合物的结构已由核磁共振谱、红外光谱和质谱所证实. 并用MTT蛋白染色法对紫檀芪(1)和3-甲氧基紫檀芪(2)进行了体外抗肿瘤细胞生物活性测试, 发现其对HL-60(白血病细胞)、SMMC-7721(肝癌细胞)和SK-BR-3(乳腺癌细胞)三种肿瘤细胞均具有较好的细胞毒活性.

关键词: 紫檀芪, 3-甲氧基紫檀芪, 合成, 糖苷化反应, 生物活性

Natural products pterostilbene (1) and 3-methoxy pterostilbene (2) were synthesized using 3,5-dihydroxybenzoic acid, hydroxybenzaldehyde or vanillin as the starting material. Wittig-Horner reaction is the key step of the synthetic route. Eight novel pterostilbene and 3-methoxy pterostil-bene-4-O-β-D-glycosides 3～10 were synthesized form 1 and 2 with corresponding α-acetylglycosyl bromicdes by glycosidation and deacetylation reaction. The synthetic procedure of glycosidation was modified by using dilute NaOH (aq.) in a solvent mixture of CHCl3/H2O and Bu4N＋Br－ (TBAB) as a phase transfer catalyst. The structures of all compounds synthesized were determined by MS, 1H NMR and IR techniques. 1 and 2 were evaluated for biological activity against four human cancer cell lines by the standard MTT method, and the results showed that they exhibited potent cytotoxicity against HL-60, SMMC-7721, and SK-BR-3 cancer cell lines.

Key words: pterostilbene, 3-methoxy pterostilbene, synthesis, glycosidation reaction, biological activity

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