Zeylleucapenoids A-H, Halimane-type and Labdane-type Diterpenoids with
Anti-inflammatory Activity from Leucas zeylanica
Abstract
Eight new diterpenoids (1-8) characterized as halimane-type and
labdane-type skeletons, and four known (9-12) compounds, were isolated
from Leucas zeylanica. Their structures were determined by comprehensive
spectroscopic analysis, X-ray crystal diffraction and computational
calculations. Compounds 1 and 2 represent structurally unique
6/6/6-fused tricyclic halimane-type diterpenoids. Compounds 8 and 12
exhibit nontoxic effects for zebrafish embryo, while they display
efficient reduction against NO production in a dose-dependent manner and
strongly suppress the secretion of LPS-induced TNF-α and IL-6 cytokines
in RAW264.7 macrophages. In addition, marked reductions of iNOS and
COX-2 in protein were observed. Molecular docking analysis indicated
that both 8 and 12 have high affinities with the target amino acid
residues on protein-binding sites, which may be a possible mechanism
contributing to the anti-inflammatory potential of these molecules.