Targeted Isolation of Dolabellane Diterpenoids from the Soft Coral Clavularia viridis Using Molecular Networking

Xin Dong; Jingshuai Wu; Hongli Jia; Shan Cen; Wei Cheng; Wenhan Lin

doi:10.1021/acsomega.3c02429

Targeted Isolation of Dolabellane Diterpenoids from the Soft Coral Clavularia viridis Using Molecular Networking

ACS Omega. 2023 May 26;8(23):21254-21264. doi: 10.1021/acsomega.3c02429. eCollection 2023 Jun 13.

Authors

Xin Dong¹, Jingshuai Wu¹, Hongli Jia¹, Shan Cen², Wei Cheng¹, Wenhan Lin¹

Affiliations

¹ State Key Laboratory of Natural and Biomimetic Drugs, Ningbo Institute of Marine Medicine, Peking University, Beijing 100191, P.R. China.
² Key Laboratory of Antiviral Drug Research, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P.R. China.

Abstract

LC-MS/MS-based molecular networking annotation coupled ¹H NMR detection allowed the depiction of the soft coral Clavularia viridis to produce a profile of dolabellane-type diterpenoids. Chromatographic separation of the EtOAc fraction resulted in the isolation of 12 undescribed dolabellane-type diterpenoids, namely, clavirolides J-U (1-12). Their structures were characterized by the extensive analysis of the spectroscopic data, including the calculated ECD and X-ray diffraction for the configurational assignments. Clavirolides J-K are characterized by a 1,11- and 5,9-fused tricyclic tetradecane scaffold fused with a α,β-unsaturated-δ-lactone, and clavirolide L possesses a 1,11- and 3,5-fused tricyclic tetradecane scaffold, which extend the dolabellane-type scaffolds. Clavirolides L and G showed significant inhibition against HIV-1 without RT enzyme inhibition, providing additional non-nucleosides with different mechanisms from efavirenz.