Lanicepines A and B, Sesquiterpenes with Amino Acid-Derived Substituents from the Flowering Aerial Parts of Saussurea laniceps .
Naonobu TanakaYuki YoshinoFusako NakanoShin-Ichiro KurimotoKazuyoshi KawazoeDaisuke TsujiKohji ItohShun-Lin LiHan-Dong SunYoshihisa TakaishiYoshiki KashiwadaPublished in: Journal of natural products (2022)
Two new guaianolide sesquiterpenes, lanicepines A ( 1 ) and B ( 2 ), possessing unusual amino acid-derived substituents at C-13, were isolated from the flowering aerial parts of Saussurea laniceps , a traditional herbal medicine also known as "snow lotus". The structures of 1 and 2 were elucidated based on spectroscopic analysis including applications of the modified Mosher's method and Marfey's method as well as ECD calculations. Lanicepine A ( 1 ) contains a dihydropyridinone moiety with a carbamoyl and a hydroxymethyl group. This substituent was considered to consist of asparagine and a C 4 unit. In contrast, lanicepine B ( 2 ) has a substituent that seems to be derived from l-proline and a C 4 unit. Lanicepines A ( 1 ) and B ( 2 ) and two related known sesquiterpenes isolated from the same plant material, 11β,13-dihydrodesacylcynaropicrin ( 3 ) and 11β,13-dihydrodesacylcynaropicrin 8- O -β-d-glucoside ( 4 ), demonstrated inhibitory activity against IL-1β production from LPS-stimulated microglial cells.
Keyphrases
- amino acid
- inflammatory response
- induced apoptosis
- cell cycle arrest
- arabidopsis thaliana
- molecular docking
- magnetic resonance
- lipopolysaccharide induced
- high resolution
- density functional theory
- neuropathic pain
- anti inflammatory
- endoplasmic reticulum stress
- cell death
- oxidative stress
- spinal cord injury
- magnetic resonance imaging
- signaling pathway
- computed tomography
- spinal cord
- drug induced
- data analysis