Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Zeylleucapenoids A-D, Highly Oxygenated Diterpenoids with Anti-inflammatory Activity from Leucas zeylanica

Version 1 : Received: 4 May 2023 / Approved: 9 May 2023 / Online: 9 May 2023 (12:09:17 CEST)

A peer-reviewed article of this Preprint also exists.

Zhao, T.; Zhang, X.; Nong, X.-H.; Zhou, X.-M.; Chai, R.-R.; Li, X.-B.; Chen, G.-Y. Zeylleucapenoids A–D, Highly Oxygenated Diterpenoids with Anti-Inflammatory Activity from Leucas zeylanica (L.) R. Br.. Molecules 2023, 28, 4472. Zhao, T.; Zhang, X.; Nong, X.-H.; Zhou, X.-M.; Chai, R.-R.; Li, X.-B.; Chen, G.-Y. Zeylleucapenoids A–D, Highly Oxygenated Diterpenoids with Anti-Inflammatory Activity from Leucas zeylanica (L.) R. Br.. Molecules 2023, 28, 4472.

Abstract

Four previously undescribed highly oxygenated diterpenoids (1–4), zeylleucapenoids A–D, characterized by halimane and labdane skeletons, were isolated from the aerial parts of Leucas zeylanica. Their structures were elucidated primarily by NMR experiments. The absolute configuration of 1 was established by theoretical ECD calculations and X-ray crystallographic analysis, whereas those for 24 were assigned by theoretical ORD calculations. Zeylleucapenoid D (4), with an IC50 value of 38.45 μM in RAW264.7 macrophages and nontoxic activity for zebrafish embryo, and obviously inhibited pro-inflammatory cytokines TNF-α and IL-6 in a dose-dependent manner. Compound 4 inhibited of the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, molecular docking analysis indicated the possible mechanism of action for 4 may be bind to targets by hydrogen- and hydrophobic- bond interactions.

Keywords

Leucas zeylanica; Highly oxygenated; Diterpenoids; Anti-inflammatory activity; Molecular docking; Zebrafish model

Subject

Chemistry and Materials Science, Organic Chemistry

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