Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
Laboratory of Marine Drugs and Biological Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266003, China.
Mar Drugs. 2022 Oct 20;20(10):649. doi: 10.3390/md20100649.
Natural products have various and complicated structures, which is still a challenge for elucidating these compounds, especially for those lacking two-dimensional nuclear magnetic resonance (2D NMR) correlations mainly caused by high C/H ratios or proton-deficient and multiple heteroatoms through the conventional structural analytical methods. We reported a novel module-assembly calculation method named Dooerafa, which included constructing the meta-structures by a grafting method based on the crucial and the limited 2D NMR correlations, ring-contraction strategy based on mechanic force field and quantum chemical theory, and self-assemble calculation in Python programming for shaping up the structural candidates along with DFT-GIAO calculation. This new method, verified by a known alkaloid spiroreticulatine with the structure determined by X-ray diffraction, was performed for the structural elucidation of aaptourinamine isolated from marine sponge , showing us a brand new scaffold of imidazo [4,5,1-ij]pyrrolo [3,2-f]quinolin-7(8H)-one, which has a biosynthetic relationship with the bioactive and structurally unique aaptamine alkaloid.
天然产物具有多样而复杂的结构，这仍然是阐明这些化合物的一个挑战，特别是对于那些由于高 C/H 比或质子缺乏和多个杂原子而缺乏二维核磁共振（2D NMR）相关性的化合物，通过传统的结构分析方法。我们报道了一种名为 Dooerafa 的新型模块组装计算方法，该方法包括通过基于关键和有限的 2D NMR 相关性的嫁接方法构建元结构、基于力学力场和量子化学理论的环收缩策略，以及用于塑造结构候选物的 Python 编程中的自组装计算，以及 DFT-GIAO 计算。该新方法通过 X 射线衍射确定结构的已知生物碱螺环雷廷验证，用于海洋海绵分离的 aaptourinamine 的结构阐明，为我们展示了一个咪唑 [4,5,1-ij]吡咯 [3,2-f]喹啉-7(8H)-one 的全新支架，它与具有生物活性和结构独特的 aaptamine 生物碱具有生物合成关系。
