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Antifeedant, cytotoxic, and anti-inflammatory neo-clerodane diterpenoids in the peltate glandular trichomes and fresh leaves of Ajuga forrestii
Phytochemistry ( IF 3.2 ) Pub Date : 2021-03-13 , DOI: 10.1016/j.phytochem.2021.112731
Ying Wang , Yan-Chun Liu , Wen-Yuan Li , Kai Guo , Yan Liu , Sheng-Hong Li

The Lamiaceae plant Ajuga forrestii Diels is a traditional Chinese herbal medicine with abundant glandular trichomes (GTs), but their chemistry and biological functions remain uninvestigated. Here, a panel of six highly functionalized neo-clerodane diterpenoids was localized to the peltate GTs of A. forrestii using laser microdissection coupled with HPLC analysis, indicating that the GTs of A. forrestii are an excellent material for the elucidation of the yet unclear biosynthetic pathway of natural neo-clerodane diterpenoids. In addition, four undescribed neo-clerodane diterpenoids with an acyclic C-9 side chain including two pairs of 1:1 mixture of inseparable diastereomers, ajuforrestins D-G, were isolated from the fresh leaves of A. forrestii together with six known compounds. The structures of the undescribed compounds were elucidated by spectroscopic (including 1D and 2D NMR and HR-ESI-MS) analyses. Biological assays indicated that the major GT compound ajugacumbin B and undescribed ajuforrestins D/E showed antifeedant activity against Helicoverpa armigera, suggesting that neo-clerodanes in A. forrestii should be involved in plant defence against insects. Moreover, the abietane diterpenoid ajuforrestin B exhibited significant anti-inflammatory activity on the secretion of interleukin-2 (IL-2) and cytotoxicity against three cancer cell lines, NCI-H1975, HepG2 and MCF-7, suggesting that ajuforrestin B could positively contribute to the therapeutic effects of this traditional Chinese medicine.



中文翻译:

带叶腺毛和新鲜Ajuga forrestii叶片中的拒食,具有细胞毒性和抗炎作用的环丙二烷二萜

唇形科植物Ajuga forrestii Diels是一种传统的中草药,具有丰富的腺毛(GTs),但尚未对其化学和生物学功能进行研究。在这里,使用激光显微切割结合HPLC分析,将一组六种高度功能化的新新环戊烷二萜类化合物定位于forrestii的骨状GTs ,这表明forrestii的GTs是阐明尚不清楚的生物合成的优良材料。天然新新戊二烯二萜的合成途径。此外,四个未描述的与无环C-9侧链包括2双1 -clerodane二萜类化合物:非对映体不可分离的1:1混合物,ajuforrestins DG,从新鲜叶中分离A. forrestii一起具有六个已知的化合物。通过光谱分析(包括1D和2D NMR和HR-ESI-MS)阐明了未描述化合物的结构。生物学分析表明,主要的GT化合物金丝桃素B和未描述的ajuforrestins D / E对棉铃虫表现出拒食活性,表明在A. forrestii中存在新的环戊烷应参与植物抗虫。此外,abinetane二萜类化合物ajuforrestin B对白细胞介素2(IL-2)的分泌具有显着的抗炎活性,并且对三种癌细胞系NCI-H1975,HepG2和MCF-7具有细胞毒性,这表明ajuforrestin B可以发挥积极作用达到这种中药的治疗效果。

更新日期:2021-03-15
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