Costunosides A-C: cytotoxic sesquiterpene lactones from the rhizomes of Aucklandia costus Falc

Nat Prod Res. 2024 Dec;38(23):4113-4124. doi: 10.1080/14786419.2023.2275743. Epub 2023 Nov 6.

Abstract

Three new eudesmane type rare sesquiterpene lactone galactosides, costunosides A-C (1-3) were isolated from the rhizomes of Aucklandia costus along with ten known compounds (4-13). Costunosides A-C (1-3) are the first example of naturally eudesmane glycosides containing a β-galactopyranoside moiety. The structure and relative configurations of these compounds were established by comprehensive analysis of MS and, in particular 1D/2D NMR spectroscopic data. The isolated compounds were tested against a panel of human cancer cell lines, where compounds 3, 6 and 7 have shown promising cytotoxic activity against PC-3, HCT-116 and A549 cell lines with IC50 values in the range of 3.4 µM to 9.3 µM, respectively. Costunosides A-C (1-3) were also screened for inhibition assay of acetyl-cholinesterase (AChE), and butyrylcholinesterase (BChE) and found inactive at a concentration of 10 µM.

Keywords: AChE; Aucklandia costus; BChE; cytotoxic; sesquiterpenes.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Cell Line, Tumor
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Humans
  • Lactones* / chemistry
  • Lactones* / isolation & purification
  • Lactones* / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rhizome* / chemistry
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification
  • Sesquiterpenes* / pharmacology
  • Sesquiterpenes, Eudesmane / chemistry
  • Sesquiterpenes, Eudesmane / isolation & purification
  • Sesquiterpenes, Eudesmane / pharmacology

Substances

  • Lactones
  • Sesquiterpenes
  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes, Eudesmane
  • Cholinesterase Inhibitors