Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2018-05-09 , DOI: 10.1016/j.bioorg.2018.05.001 Jian-Chao Zhao , Zhi-Lin Luan , Jia-Hao Liang , Zhong-Bin Cheng , Cheng-Peng Sun , Ya-Li Wang , Meng-Yue Zhang , Tian-Yuan Zhang , Yong Wang , Tian-Mei Yang , Ying-Ying Wu , Yi-Xuan Zhang , Xin-Yu Zhao , Xiao-Chi Ma
A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2′-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal diffraction analyses as well as quantum chemical calculation. The abosulte configuration of terpendole A (2) was determined for the first time. Compound 1 displayed the significant agonistic effect on pregnane X receptor (PXR) with EC50 value of 134.91 ± 2.01 nM, and its interaction with PXR was investigated by molecular docking. Meantime, a plausible biosynthetic pathway for compounds 1–3 is also discussed in the present work.
中文翻译:
Drechmerin H,一种新颖的1(2),2(18) -二山高的吲哚二萜从真菌Drechmeria藻。作为人类妊娠X受体的天然激动剂
一种新颖的1(2),2(18) -二开环吲哚二萜, drechmerin H(1),从发酵肉汤中分离Drechmeria藻。连同新的吲哚二萜类化合物2'- Epi萜烯A(3)和已知的类似物萜烯A(2)。它们的结构通过HRESIMS,1D和2D NMR,ECD和X射线单晶衍射分析以及量子化学计算来确定。首次确定了萜烯A(2)的阿糖胞苷构型。化合物1对EC 50对孕烷X受体(PXR)表现出显着的激动作用通过分子对接研究了其值134.91±2.01nM,并且其与PXR的相互作用。同时,在本工作中还讨论了化合物1-3的合理生物合成途径。