School of Pharmacy, Henan University, Kaifeng 475004, China; Eucommia Ulmoides Cultivation and Utilization of Henan Engineering Laboratory, Kaifeng 475004, China.
School of Pharmacy, Henan University, Kaifeng 475004, China.
Bioorg Chem. 2019 Oct;91:103129. doi: 10.1016/j.bioorg.2019.103129. Epub 2019 Jul 20.
Cyclopianes, featuring a highly rigid 6/5/5/5-fused tetracyclic framework, are structurally unique and biologically significant and belong to a rarely reported diterpenoid family. Chemical investigation of an EtOAc extract of a deep-sea-derived Penicillium sp. led to the isolation of three new cyclopiane diterpenes, namely, conidiogenols C-D (1-2) and conidiogenone L (3). The structures were determined by extensive analyses of the spectroscopic data in association with ECD calculations and chemical conversion for configurational assignments. Compound 1 represents the second example of cyclopianes bearing a hydroxyl group at C-13. Compound 2, the third example of conidiogenols, possesses a distinct α-oriented 1-hydroxy group relative to other analogues. The bioassay study demonstrated that compounds 2 and 4-6 exhibited moderate inhibitory effects against five esophageal cancer cell lines with IC values ranging from 25 to 55 μM. The cytotoxicities of all compounds toward esophageal cancer cell lines were evaluated for the first time.
Cyclopianes，具有高度刚性的 6/5/5/5 稠合四环骨架，结构独特，具有重要的生物学意义，属于报道较少的二萜烯家族。对深海来源的青霉属 Penicillium sp. 的 EtOAc 提取物进行化学研究，分离得到三种新的环番二萜烯，即 conidiogenols C-D（1-2）和 conidiogenone L（3）。通过对光谱数据的广泛分析以及ECD 计算和构型归属的化学转化，确定了结构。化合物 1 是第二个在 C-13 位带有羟基的环番。化合物 2 是第三个 conidiogenols，与其他类似物相比，具有独特的α-取向 1-羟基。生物测定研究表明，化合物 2 和 4-6 对五种食管癌细胞系表现出中等抑制作用，IC 值范围为 25-55μM。这是首次评估所有化合物对食管癌细胞系的细胞毒性。
