Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland.
Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516, Zielona Góra, Poland.
Sci Rep. 2021 Feb 19;11(1):4262. doi: 10.1038/s41598-021-83736-6.
The synthesis of phytol-derived γ-butyrolactones as well as their evaluation for deterrent activity towards peach-potato aphid Myzus persicae and antiproliferative activity against four selected cancer cell lines are reported. Products were obtained in good yields (19-96%) and their structures were fully characterized by spectroscopic data (NMR, HRMS). Four synthesized δ-halo-γ-lactones (4-7) are new and have not been previously described in the literature. In the choice test phytol (1) appeared deterrent to M. persicae, whereas modifications of its structure did not cause the avoidance of the treated leaves by the aphids. In contrast, aphids were attracted to the leaves treated with the new trans-δ-chloro-γ-lactone (6). Electrical Penetration Graph (EPG) technique applied to explore the aphid probing and feeding activity revealed that neither phytol nor lactone 6 affected aphid probing and the consumption of phloem sap, which means that both phytol and the lactone 6 might have acted as postingestive modifiers of aphid behavior. The results of in vitro antitumor assays showed that obtained phytol derivatives exhibit cytotoxic activity against studied cancer cell lines (leukemia, lung and colon carcinoma and its doxorubicin resistant subline). Halolactones 4-6 were identified as the compounds, which arrest cell cycle of leukemia cells mainly in G2/M and S phases.
本文报道了植物醇衍生的γ-丁内酯的合成及其对桃蚜 Myzus persicae 的驱避活性和对四种选定癌细胞系的抗增殖活性的评价。产物产率高（19-96%），其结构通过光谱数据（NMR、HRMS）得到充分表征。四种合成的δ-卤代-γ-内酰胺（4-7）是新的，以前没有在文献中描述过。在选择试验中，植物醇（1）对桃蚜有驱避作用，而其结构的修饰并没有导致蚜虫避开处理过的叶片。相比之下，蚜虫被用新的反式-δ-氯-γ-内酰胺（6）处理过的叶片所吸引。电穿透图（EPG）技术用于探索蚜虫的探测和取食活动，结果表明，植物醇和内酯 6 都不影响蚜虫的探测和韧皮部汁液的消耗，这意味着植物醇和内酯 6 可能都作为蚜虫行为的后消化调节剂。体外抗肿瘤试验结果表明，所得到的植物醇衍生物对研究的癌细胞系（白血病、肺癌和结肠癌及其阿霉素耐药亚系）具有细胞毒性活性。卤代内酯 4-6 被鉴定为主要将白血病细胞的细胞周期阻滞在 G2/M 和 S 期的化合物。
