Thymol derivatives with antibacterial and cytotoxic activity from the aerial parts of Ageratina adenophora
2021
Zhang, Mei | Ouyang, Jin-Kui | Xu, Qiao-Lin | Liu, Shao-Bo | Qian, Tao | Dong, Li-Mei | Tan, Jian-Wen
Three new thymol derivatives, 7-formyl-9-isobutyryloxy-8-hydroxythymol (1), 7,9-di-isobutyryloxy-8,10-dehydrothymol (2) and 2α-methoxyl-3β-methyl-6-methylol-2,3-dihydrobenzofuran (3), along with five known ones (4–8), were isolated from the aerial parts of the invasive plant Ageratina adenophora. Their structures were elucidated by extensive spectroscopic analysis and they were all isolated from the aerial part of A. adenophora for the first time. These compounds, except 8, selectively showed in vitro antimicrobial activity against three Gram-(+) and two Gram-(−) bacterial strains. In particular, compounds 1 and 5 showed notable in vitro antimicrobial activity against all five bacterial strains with IC₅₀ values ranging from 3.9 to 15.6 μg mL⁻¹, as compared to reference compound kanamycin sulfate with a MIC value 1.9–3.9 μg mL⁻¹. Compounds 1 and 5 were further revealed to show in vitro cytotoxic activity against three tested human tumor (MCF-7, NCI-H460 and HeLa) cell lines, with IC₅₀ values ranging from 7.45 to 28.63 μM. Compounds 7 and 8 selectively showed slight but detectable in vitro cytotoxicity toward MCF-7 and NCI-H460 cell lines, with IC₅₀ values 44.65–83.19 μM. No cytotoxic effects were detected in the bioassay of the other four thymol derivatives. The present results provide new data to support that the aerial parts of A. adenophora are a rich source of bioactive chemicals valuable in medicinal applications.
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