Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, Budapest 1117, Hungary; Department of Pharmacognosy, Semmelweis University, Üllői út 26, Budapest 1085, Hungary.
Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre utca 7, Budapest 1092, Hungary.
Fitoterapia. 2018 Jun;127:413-419. doi: 10.1016/j.fitote.2018.04.007. Epub 2018 Apr 11.
While analyzing the fruit composition of nine European Cirsium species representing three sections (i.e., Cephalonoplos, Chamaeleon and Eriolepis), four lignans, three neolignans and three sesquineolignans were determined and used as chemotaxonomic markers. Among them, desmethyl balanophonin and desmethyl picrasmalignan were determined for the first time in the plant kingdom, as the main metabolites of the Chamaeleon section. Prebalanophonin and prepicrasmalignan, identified so far exclusively in C. eriophorum, were also confirmed in C. boujartii and C. vulgare, highlighting the chemotaxonomic significance of these compounds in the Eriolepis section. The antiproliferative assay of the compounds isolated from their optimum sources, confirmed a dose-dependent inhibitory effect of the structures bearing the 4',7-epoxy moiety (balanophonin, picrasmalignan, desmethyl balanophonin, desmethyl picrasmalignan) against SW480 colon cancer cells, while those bearing the 4',7-dihydroxy motif (prebalanophonin, prepicrasmalignan) were inactive.
在分析代表三个节（即 Cephalonoplos、Chamaeleon 和 Eriolepis）的九个欧洲蓟属物种的果实成分时，确定了四种木脂素、三种新木脂素和三种倍半木脂素，并将其用作化学分类学标记。其中，desmethyl balanophonin 和 desmethyl picrasmalignan 是首次在植物界中被确定为 Chamaeleon 节的主要代谢物。Prebalanophonin 和 prepicrasmalignan 迄今为止仅在 C. eriophorum 中被鉴定，也在 C. boujartii 和 C. vulgare 中得到证实，突出了这些化合物在 Eriolepis 节中的化学分类学意义。从最佳来源分离出的化合物的抗增殖测定证实了具有 4',7-环氧部分（bala nophonin、picrasmalignan、desmethyl balanophonin、desmethyl picrasmalignan）的结构对 SW480 结肠癌细胞具有剂量依赖性的抑制作用，而具有 4',7-二羟基基序的结构（prebalanophonin、prepicrasmalignan）则没有活性。
