Issue 13, 2024

Biswulfenioidins A–E, dioxygen-bridged abietane-type diterpenoid dimers with anti-Zika virus potential from Orthosiphon wulfenioides

Abstract

Five novel abietane-type diterpenoid dimers (ADDs), biswulfenioidins A–E (1–5), one known bisditerpenoid (6), and two possible precursors (7 and 8) were isolated from O. wulfenioides. Their structures were determined and characterized by X-ray diffraction, quantum chemical calculations, and extensive spectroscopic methods. Compounds 1–4 were unprecedented 6-O-12′ and 7-O-11′ angular fused dioxygen-bridged ADDs, while 5 and 6 were rare 6-O-7′ and 7-O-6′ parallel fused. Putative biosynthetic pathways of 1–6 were proposed. Interestingly, possible precursors 7 and 8 showed high cytotoxic effects, while dimerized diterpenoids 1–6 exhibited negligible cytotoxicity against Vero cells. Compounds 5 and 6 showed potent activity against Zika virus (ZIKV) superior to the positive drug ribavirin. Western blot and immunofluorescence experiments exhibited that 5 interfered with the replication of the ZIKV by inhibiting the expression of the ZIKV envelope (E) and NS5 protein.

Graphical abstract: Biswulfenioidins A–E, dioxygen-bridged abietane-type diterpenoid dimers with anti-Zika virus potential from Orthosiphon wulfenioides

Supplementary files

Article information

Article type
Research Article
Submitted
06 Apr 2024
Accepted
10 May 2024
First published
16 May 2024

Org. Chem. Front., 2024,11, 3614-3623

Biswulfenioidins A–E, dioxygen-bridged abietane-type diterpenoid dimers with anti-Zika virus potential from Orthosiphon wulfenioides

W. Tu, Y. Huang, Y. Kong, B. Li, B. Wang, T. Dong, W. Chen, M. A. Zeb, X. Li, M. Liu, C. Zheng and W. Xiao, Org. Chem. Front., 2024, 11, 3614 DOI: 10.1039/D4QO00619D

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