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.
Chem Biodivers. 2021 Jul;18(7):e2100285. doi: 10.1002/cbdv.202100285. Epub 2021 Jun 8.
Herein n-, iso- and anteiso-series of very-long-chained (VLC) alkanes (C -C ), fatty acid benzyl esters (FABEs; C -C ), and 2-alkanones (C -C ) were identified in the wax of Primula veris L. and P. acaulis (L.) L. (Primulaceae). For the very first time in a sample of natural origin, the presence of iso- and anteiso-VLC FABEs and 2-alkanones was unequivocally confirmed by synthetic work, derivatization, and NMR. It should be noted that the studied species produced unusually high amounts of branched wax constituents (e. g., >50 % of 2-alkanones were branched isomers). The domination of iso-isomers, probably biosynthesized from leucine-derived starters, is a unique feature in the Plant Kingdom. The plant organ distribution of these VLC compounds in P. acaulis samples (different habitats and phenological phases) pointed to their possible ecological value. This was supported by a eutectic behavior of binary blends of FABEs and alkanes, as well as by high UV-C absorption by FABEs.
本文首次在Primula veris L. 和 P. acaulis（L.）L.（报春花科）蜡中鉴定出 n-、iso-和 anteiso-系列超长链（VLC）烷烃（C -C ）、脂肪酸苄酯（FABE；C -C ）和 2-烷酮（C -C ）。通过合成工作、衍生化和 NMR，首次在天然来源的样品中明确证实了 iso-和 anteiso-VLC FABE 和 2-烷酮的存在。值得注意的是，所研究的物种产生了异常高含量的支化蜡成分（例如，>50%的 2-烷酮是支化异构体）。可能由亮氨酸衍生引发剂生物合成的 iso-异构体的主导地位是植物界的一个独特特征。在 P. acaulis 样品（不同生境和物候阶段）中这些 VLC 化合物的植物器官分布指向了它们可能的生态价值。这得到了 FABE 和烷烃二元混合物的共晶行为以及 FABE 对 UV-C 的高吸收的支持。
