Shaaban Mohamed, Issa Marwa Y, Ghani Mohamed A, Hamed Abdelaaty, Abdelwahab Ahmed B
a Institute of Organic and Biomolecular Chemistry , University of Göttingen , Göttingen , Germany.
b Chemistry of Natural Compounds Department, Pharmaceutical Industries Research Division , National Research Centre , Dokki-Cairo , Egypt.
Nat Prod Res. 2019 Jan;33(1):24-33. doi: 10.1080/14786419.2018.1431631. Epub 2018 Feb 2.
During our continual searching programme for novel bioactive metabolites from Sarcophyton trocheliophorum, collected from Red Sea, we describe herein the isolation and structural elucidation of further two new pyrane-based cembranoid diterpenes: 9-hydroxy-7,8-dehydro-sarcotrocheliol (1) and 8,9-expoy-sarcotrocheliol acetate (2), along with the well-known sarcotrocheliol acetate (3), (+)-sarcophine (4), (+)-sarcophytoxide (5) and (-)-sarcophytoxide (6). The chemical structures of compounds 1 and 2 were determined on the basis of 1D and 2D NMR (H, C, H-H COSY, HMQC, HMBC and NOE), mass spectra (ESI and HR-ESIMS) and by comparison with related structures. The antimicrobial activities of the reported compounds 1-6 were investigated. According to the molecular docking study of compounds 1-6 using 3D structure of α,β tubulin in complex with taxol (PDB code 1JFF) and epothilone A (PDB code 1TVK), sarcophine (4) displayed the highest affinity towards both crystal structures, followed by 5 and 6, meanwhile pyrane-based cembranoid diterpenes (1-3) showed less affinity.
在我们从红海采集的肉芝软珊瑚中持续寻找新型生物活性代谢产物的研究项目中，本文描述了另外两种新的基于吡喃的西松烷型二萜类化合物的分离和结构解析：9-羟基-7,8-脱氢肉芝软珊瑚醇（1）和8,9-环氧肉芝软珊瑚醇乙酸酯（2），以及已知的肉芝软珊瑚醇乙酸酯（3）、（+）-肉芝碱（4）、（+）-肉芝氧化酮（5）和（-）-肉芝氧化酮（6）。化合物1和2的化学结构是基于一维和二维核磁共振（氢谱、碳谱、氢-氢化学位移相关谱、异核多量子相干谱、异核多键相关谱和核Overhauser效应谱）、质谱（电喷雾电离质谱和高分辨电喷雾电离质谱）并与相关结构进行比较确定的。对所报道的化合物1-6的抗菌活性进行了研究。根据使用与紫杉醇（PDB代码1JFF）和埃坡霉素A（PDB代码1TVK）复合的α,β微管蛋白的三维结构对化合物1-6进行的分子对接研究，肉芝碱（4）对两种晶体结构均表现出最高亲和力，其次是5和6，同时基于吡喃的西松烷型二萜类化合物（1-3）显示出较低的亲和力。
