Dipartimento di Agraria, Università degli Studi di Napoli Federico II, Portici, Naples, Italy.
Faculty of Pharmacy, University of Nottingham, Nottingham, United Kingdom.
Planta Med. 2021 Oct;87(12-13):1018-1024. doi: 10.1055/a-1479-2866. Epub 2021 Apr 27.
is one of the oldest spurges described and used in folk medicine. It is characterized by blue-grey stems similar to myrtle, and it is spread in the Mediterranean region, Asia, and the USA. Chemical analysis of collected in Turkey afforded the isolation of 4 diterpenes based on the so-called myrsinane skeleton being tetraesters of the tetracyclic diterpene alcohol myrsinol. In this study, the phytochemical analysis of this species collected in Italy has been undertaken to afford the isolation of a new atisane diterpene, named myrsatisane, 3 ingenol derivatives, along with the 4 tetraester derivatives previously found. A triterpene compound based on the euphane skeleton has also been isolated. Structural elucidation of the new myrsatisane was based on spectroscopic techniques, including HR-MS and 1- and 2-dimensional NMR experiments. Its relative configuration was determined by NOE correlations, while absolute stereochemistry was obtained by quantum-mechanical DFT studies. While diterpenes with the atisane skeleton are relatively common in species, this is the first report of an atisane diterpene from . All the isolated terpenes were tested for anti-inflammatory activity on J774A.1 macrophages stimulated with lipopolysaccharide by evaluation of nitrite and pro-inflammatory cytokine Il-1 levels. Among tested compounds, the 3 ingenol diterpenes exhibited a dose-dependent (0.001 - 3 µM) significant activity, thus showing their potential as anti-inflammatory drug candidates.
是最古老的大戟属植物之一，在民间医学中被描述和使用。它的特点是类似于桃金娘的蓝灰色茎，分布在地中海地区、亚洲和美国。对在土耳其收集的进行的化学分析提供了基于所谓的 myrsinane 骨架的 4 种二萜的分离，这些二萜是四环二萜醇 myrsinol 的四酯。在这项研究中，对在意大利收集的进行了植物化学分析，以获得一种新的 atisane 二萜，命名为 myrsatisane，以及以前发现的 3 种 ingenol 衍生物和 4 种四酯衍生物。还分离出一种基于 euphane 骨架的三萜化合物。新的 myrsatisane 的结构阐明基于包括高分辨质谱和 1-和 2 维 NMR 实验在内的光谱技术。其相对构型通过 NOE 相关确定，而绝对立体化学通过量子力学 DFT 研究获得。虽然具有 atisane 骨架的二萜在 中相对常见，但这是首次从 中报道 atisane 二萜。所有分离出的萜类化合物都在 LPS 刺激的 J774A.1 巨噬细胞上进行了抗炎活性测试，通过评估亚硝酸盐和促炎细胞因子 Il-1 水平来评估。在所测试的化合物中，3 种 ingenol 二萜具有剂量依赖性（0.001 - 3 μM）显著活性，因此显示出作为抗炎药物候选物的潜力。
