Lanicepines A and B, Sesquiterpenes with Amino Acid-Derived Substituents from the Flowering Aerial Parts of Saussurea laniceps

J Nat Prod. 2022 Apr 22;85(4):1180-1185. doi: 10.1021/acs.jnatprod.1c01069. Epub 2022 Feb 18.

Abstract

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 C4 unit. In contrast, lanicepine B (2) has a substituent that seems to be derived from l-proline and a C4 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / analysis
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Saussurea* / chemistry
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes, Guaiane / chemistry

Substances

  • Amino Acids
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane