Citation: Quan Xu, Ye-Qing Du, Pan-Pan Chen, Yili Sun, Ze-Nan Yang, Hui Zhang, Bencan Tang, Hong Wang, Jia Li, Yue-Wei Guo, Xu-Wen Li. Computation assisted chemical study of photo-induced late-stage skeleton transformation of marine natural products towards new scaffolds with biological functions[J]. Chinese Chemical Letters, ;2025, 36(5): 110141. doi: 10.1016/j.cclet.2024.110141 shu

Computation assisted chemical study of photo-induced late-stage skeleton transformation of marine natural products towards new scaffolds with biological functions

Quan Xu ^{a, d, 1} ,
Ye-Qing Du ^{a, 1} ,
Pan-Pan Chen ^{c, 1} ,
Yili Sun ^{a, b, 1} ,
Ze-Nan Yang ^{a, b, g} ,
Hui Zhang ^a ,
Bencan Tang ^e ,
Hong Wang ^d ,
Jia Li ^{a, b, *,} ,
Yue-Wei Guo ^{b, d, f, *,} ,
Xu-Wen Li ^{a, b, g, *,}

a.
State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
b.
Shandong Laboratory of Yantai Drug Discovery, Bohai rim Advanced Research Institute for Drug Discovery, Yantai 264117, China
c.
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, United States
d.
Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China
e.
Key Laboratory for Carbonaceous Waste Processing and Process Intensification Research of Zhejiang Province, Department of Chemical and Environmental Engineering, The University of Nottingham Ningbo China, Ningbo 315100, China
f.
School of Medicine, Shanghai University, Shanghai 200444, China
g.
University of Chinese Academy of Sciences, Beijing 100049, China

jli@simm.ac.cn

ywguo@simm.ac.cn

xwli@simm.ac.cn

Received Date: 11 April 2024
Revised Date: 16 June 2024
Accepted Date: 19 June 2024
Available Online: 19 June 2024

Figures(7)

A computer-assisted chemical investigation of an intriguing photoreaction of norditerpenoids (3‒7) has been first reported, leading to not only their biomimetic conversion, but also the generation of several new products with uncommon 4,14-dioxabicyclo[10.2.1]pentadecane scaffold (8, 9, 12‒14). In bioassay, compounds 10 and 15 exhibited significant stimulation of GLP-1 secretion. This study has given an insight for the application of computational methods on the late-stage skeleton transformation of complex natural products towards new bioactive compounds.
- Marine natural product,
- Photosynthesis,
- DFT calculation,
- Biomimetic conversion,
- GLP-1
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