Zhan Zha-Jun, Tian Ting, Xu Yi-Lian, Yu Hang-Fei, Zhang Cai-Xue, Zhang Zhi-Dong, Tang Qi-Yong, Shan Wei-Guang, Ying You-Min
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, P. R. China.
Institute of Microbiology, Xinjiang Academy of Agricultural Sciences/Xinjiang Laboratory of Special Environmental Microbiology, Urumqi, 830091, P. R. China.
Chem Biodivers. 2019 Aug;16(8):e1900299. doi: 10.1002/cbdv.201900299. Epub 2019 Jul 9.
The biotransformation of huperzine B (hupB), one of the characteristic bioactive constituents of the medicinal plant Huperzia serrata, by a fungal endophyte of the host plant was studied. One new compound, 8α,15α-epoxyhuperzine B (1), along with two known oxygenated hupB analogs, 16-hydroxyhuperzine B (2) and carinatumin B (3), was isolated and identified. The structures of all the isolates were deduced by spectroscopic methods including NMR, MS, IR, and UV spectra. The known compounds 2 and 3 were obtained from a microbial source for the first time. To the best of our knowledge, it is the first report on the microbial transformation of hupB and would facilitate further structural modification of hupB by chemo-enzymatic method. In the LPS-induced neuro-inflammation injury assay, 8α,15α-epoxyhuperzine B (1) exhibited moderate neuroprotective activity by increasing the viability of U251 cell lines with an EC of 40.1 nm.
对药用植物蛇足石杉的特征性生物活性成分之一石杉碱乙（hupB）被宿主植物的一种真菌内生菌进行生物转化的过程进行了研究。分离并鉴定出了一个新化合物8α,15α-环氧石杉碱乙（1），以及两个已知的氧化型石杉碱乙类似物，16-羟基石杉碱乙（2）和龙骨石杉碱乙（3）。所有分离物的结构均通过包括核磁共振（NMR）、质谱（MS）、红外光谱（IR）和紫外光谱（UV）在内的光谱方法推导得出。已知化合物2和3首次从微生物来源获得。据我们所知，这是关于石杉碱乙微生物转化的首次报道，将有助于通过化学酶法对石杉碱乙进行进一步的结构修饰。在脂多糖（LPS）诱导的神经炎症损伤试验中，8α,15α-环氧石杉碱乙（1）通过提高U251细胞系的活力表现出中等程度的神经保护活性，其半数有效浓度（EC）为40.1 nm。
