Anti-inflammatory Eudesmane Sesquiterpenoids from Artemisia hedinii

Abstract

Fourteen new eudesmane sesquiterpenoids (1, 3–5, 7–16) and seven known analogues were isolated from the whole plant of Artemisia hedinii. Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data, and their absolute configurations were confirmed by X-ray diffraction experiments and TDDFT ECD calculation. Compounds 1–15 were identified as eudesmane acids, which represent a kind of lactone ring-opening eudesmane-type sesquiterpenes with an acetoxyl or a hydroxy group attached to C-9. Compounds 1 and 2, 5 and 6, and 7 and 8 are three pairs of epimers isomerized at C-3, C-5, and C-11, respectively. Compounds 1–9, 11–13, 15–19, and 21 could influence the proinflammatory phenotype of the M1 macrophage. Among them, compounds 5, 8, 9, 12, 16, and 19 consistently exhibited anti-inflammatory effects, as evidenced by downregulating classic pro-inflammatory cytokines TNF-α, IL-12, IL-6, and IFN-γ in LPS-induced primary bone marrow derived M1 macrophages.

New Compounds from Plants: A Perspective View

“…Another abietane diterpene compound was reported and named mutabilol, the compound was obtained from the leaves of Plectranthus mutabilis Codd (Lamiaceae) [82]. The chemical structure of mutabilol (37) shows two carbonyls in its non-aromatic cyclic structure.…”

Neuroprotective Properties of Eudesmin on a Cellular Model of Amyloid-β Peptide Toxicity

“…This benzofuran can preserve synaptic structure and function, illustrated by experiments where 10 -6 M of fomannoxin can induce a reversion or protection against A␤ soluble oligomers and disrupts their aggregation [36]. Lignans isolated from conifers species have been recently studied and shown to exhibit similar anti-inflammatory, antihypertensive, and antioxidant properties [37][38][39][40]. Additionally, these privileged natural scaffolds have been studied as potential phytohormones for, among others, the treatment or prevention of cancer and neuroprotective properties [38].…”

Sesquiterpenoids from Stem Bark of Chisocheton lasiocarpus and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell

“…Sesquiterpenoid has properties as an oil but not infrequently as a crystalline (Ludwiczuk et al, 2017). Sesquiterpenoids have wide range of biological activities such as cytotoxic activities (Naini et al, 2022), anti-inflammatory (Wang et al, 2021), antibacterial and antifungal (Perveen et al, 2020), and antimalarial (Shen et al, 2020). The existence of sesquiterpenoid can be found in plants, especially in higher plants (Connolly & Hill, 1991).…”