Nešić Milica D, Nešić Milan S, Raca Irena Lj, Bukleski Miha, Radulović Niko S
Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia.
Department of Biology and Ecology, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia.
Plants (Basel). 2025 May 10;14(10):1432. doi: 10.3390/plants14101432.
(Apiaceae) includes multiple infraspecific taxa with longstanding taxonomic ambiguities, often resulting from incomplete morphological and chemical characterizations. Herein, diethyl ether extracts were analyzed from four Balkan populations that were tentatively identified as subsp. (. ) and subsp. (. ). Comprehensive chromatography and spectroscopic techniques (GC-MS and 1D/2D NMR) enabled the isolation of several newly identified aliphatic polyunsaturated esters, including compounds bearing uncommon conjugated tetraene and triyne backbones. These novel structures differ from canonical falcarinol derivatives by lacking the usual 3-hydroxylation, suggesting a divergent branch in the crepenynate pathway. The chemical profiles of each sample correlated closely with leaf morphology and infraspecific designations: for example, the Galičica Mt. population of featured a unique newly detected heptadecadientriyne, while the populations from Šar Planina and Suva Planina displayed distinct polyunsaturated repertoires. Extracts from likewise contained stereoisomeric compounds that highlight metabolic divergence. Collectively, these findings demonstrate significant chemotypic variation within the complex and provide the first account of less-polar secondary metabolites, including newly discovered polyunsaturated metabolites. Future research integrating molecular markers and bioactivity assays may elucidate how these specialized metabolites contribute to both the taxonomy and pharmacological potential of these understudied taxa.
伞形科包含多个种下分类单元，长期存在分类学上的模糊性，这往往是由于形态学和化学特征描述不完整所致。在此，对来自巴尔干半岛四个种群的乙醚提取物进行了分析，这些种群初步鉴定为亚种（。）和亚种（。）。综合色谱和光谱技术（气相色谱 - 质谱联用和一维/二维核磁共振）能够分离出几种新鉴定的脂肪族多不饱和酯，包括具有罕见共轭四烯和三炔主链的化合物。这些新结构与典型的镰叶芹醇衍生物不同，缺乏常见的3 - 羟基化，表明在 crepenynate 途径中有一个不同的分支。每个样品的化学图谱与叶片形态和种下分类密切相关：例如，加利契察山的种群具有一种独特的新检测到的十七碳五烯三炔，而沙尔普拉尼纳山和苏瓦普拉尼纳山的种群则显示出不同的多不饱和化合物库。同样，的提取物含有突出代谢差异的立体异构体化合物。总体而言，这些发现表明在该复合体中存在显著的化学型变异，并首次报道了极性较小的次生代谢产物，包括新发现的多不饱和代谢产物。未来整合分子标记和生物活性测定的研究可能会阐明这些特殊代谢产物如何对这些研究较少的分类单元的分类学和药理学潜力做出贡献。
