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Labdane-Type Diterpenes from the Aerial Parts of Rydingia persica: Their Absolute Configurations and Protective Effects on LPS-Induced Inflammation in Keratinocytes.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-08-11 , DOI: 10.1021/acs.jnatprod.0c00360 Mostafa Alilou 1, 2 , Stefania Marzocco 3 , David Hofer 1 , Shara Francesca Rapa 3 , Rahman Asadpour 4 , Stefan Schwaiger 1 , Jakob Troppmair 2 , Hermann Stuppner 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-08-11 , DOI: 10.1021/acs.jnatprod.0c00360 Mostafa Alilou 1, 2 , Stefania Marzocco 3 , David Hofer 1 , Shara Francesca Rapa 3 , Rahman Asadpour 4 , Stefan Schwaiger 1 , Jakob Troppmair 2 , Hermann Stuppner 1
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Phytochemical investigations of an extract of the aerial parts of Rydingia persica led to the isolation of 14 labdane-type diterpenoids, of which compounds 1–5, 8, and 12–14 turned out to be new natural products, while the remaining compounds were isolated for the first time from the genus Rydingia. Their structures were elucidated using 1D- and 2D-NMR and mass spectrometry, and their absolute configurations were determined by quantum chemical calculation methods. Furthermore, DP4+ NMR chemical shift probability calculations were performed for compounds 12–14, in order to elucidate the orientation of the ambiguous chiral center at C-15, prior to absolute configuration determination. The methanol extract of the aerial parts of R. persica along with subfractions obtained and selected isolated compounds were evaluated for their effects on inflammation-related factors such as nitrotyrosine formation, IL-6 release, and TNF-α release, along with tight-junction proteins claudin-1 and occludin expression in LPS-stimulated HaCaT cells. Occludin and claudin-1 are tight-junction proteins, which play a pivotal role in wound repair mechanisms. Overall, the subfractions and compounds isolated showed moderate to high activity, indicating that labdane-type diterpenoids contribute to the anti-inflammatory and wound-healing activity of R. persica.
中文翻译：
Rydingia persica 地上部分的 Labdane 型二萜：其绝对构型和对 LPS 诱导的角质形成细胞炎症的保护作用。
对Rydingia persica地上部分提取物进行植物化学研究，分离出14种Labdane型二萜类化合物，其中化合物1 – 5 、 8和12 – 14被证明是新的天然产物，而其余化合物均被分离出来首次来自Rydingia属。使用一维和二维核磁共振和质谱阐明了它们的结构，并通过量子化学计算方法确定了它们的绝对构型。此外，对化合物12 – 14进行了 DP4+ NMR 化学位移概率计算，以便在确定绝对构型之前阐明 C-15 处模糊手性中心的方向。评估了桃花地上部分的甲醇提取物以及获得的亚组分和选定的分离化合物对炎症相关因子（例如硝基酪氨酸形成、IL-6 释放和 TNF-α 释放以及紧密连接）的影响。 LPS 刺激的 HaCaT 细胞中蛋白质claudin-1和occludin的表达。 Occludin 和 Claudin-1 是紧密连接蛋白，在伤口修复机制中发挥着关键作用。总体而言，分离的亚组分和化合物显示出中等到高的活性，表明拉丹丹型二萜类化合物有助于桃树的抗炎和伤口愈合活性。
更新日期：2020-08-28
中文翻译：
Rydingia persica 地上部分的 Labdane 型二萜：其绝对构型和对 LPS 诱导的角质形成细胞炎症的保护作用。
对Rydingia persica地上部分提取物进行植物化学研究，分离出14种Labdane型二萜类化合物，其中化合物1 – 5 、 8和12 – 14被证明是新的天然产物，而其余化合物均被分离出来首次来自Rydingia属。使用一维和二维核磁共振和质谱阐明了它们的结构，并通过量子化学计算方法确定了它们的绝对构型。此外，对化合物12 – 14进行了 DP4+ NMR 化学位移概率计算，以便在确定绝对构型之前阐明 C-15 处模糊手性中心的方向。评估了桃花地上部分的甲醇提取物以及获得的亚组分和选定的分离化合物对炎症相关因子（例如硝基酪氨酸形成、IL-6 释放和 TNF-α 释放以及紧密连接）的影响。 LPS 刺激的 HaCaT 细胞中蛋白质claudin-1和occludin的表达。 Occludin 和 Claudin-1 是紧密连接蛋白，在伤口修复机制中发挥着关键作用。总体而言，分离的亚组分和化合物显示出中等到高的活性，表明拉丹丹型二萜类化合物有助于桃树的抗炎和伤口愈合活性。
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