Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia freyniana

Abstract

Two new disesquiterpenoids (1 and 2) and 11 new (3-13) and 10 known (14-23) sesquiterpenoids were isolated from the whole plants of Artemisia freyniana. Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data. The absolute configurations of the new isolates (1-13) were assigned based on single-crystal X-ray diffraction data and comparison of the experimental and calculated ECD data. The eremophilane derivatives 8 and 9 possess an unprecedented 2-isopropyl-3,7,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1 H-indene scaffold, and a putative biosynthetic pathway for these compounds is proposed. Compounds 4, 5, and 9 exhibited inhibitory effects against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophage cells with IC values of 10.8, 12.6, and 11.7 μM, respectively.

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

“…Eremophilane sesquiterpenes, consisting of three isoprenes, possess the identical decalin framework with the eudesmanes and probably belong to a small group of sesquiterpenes. , Eremophilane sesquiterpenoids widely existed in numerous medicinal plants, especially in the Asteraceae family. − Subsequently, the metabolites of eremophilanes produced by theendophytic and marine fungi have increased remarkably, with some exhibiting multiple bioactivities including antifungal, anti-inflammatory, antivirus, antibacterial, and insecticidal activities. − Owing to the structural diversiform and unique biological activities of eremophilane sesquiterpenes, extensive phytochemical and biological investigations have been carried out by numerous scientists. − Consequently, further studies toward the development of novel and medicinally valuable sesquiterpenoids are essential.…”

Cacalol Acetate, a Sesquiterpene from Psacalium decompositum, Exerts an Anti-inflammatory Effect through LPS/NF-KB Signaling in Raw 264.7 Macrophages

“…It is noteworthy that CA might not have an effect only on macrophages. It could also have an effect on other important cells that participate in the inflammatory process, such as endothelial cells, in which NF-kB regulates the expression of adhesion molecules, as well as the generation of NO, among other functions, which future studies could corroborate. , It is also important to mention that CA could be working as a prodrug. This compound, when interacting with the culture medium or when administered directly into the mouse ear, could be reacting with sterases that are present, transforming these into cacalol .…”

Callicarpins, Two Classes of Rearranged ent-Clerodane Diterpenoids from Callicarpa Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis

“…Biosynthetically, the combination of an oxidation and aldol reaction is a common pathway for generating new fused carbocyclic skeletons in natural products. − In our analysis of putative biosynthetic pathways to the 7/6- and 5/6-fused carbocyclic skeletons, known compound 8 was rationally considered as their precursor. First, the oxidation of 8 led to A-ring cleavage and afforded intermediate i with a ketocarbonyl and a formyl group (Scheme ).…”