Absolute structure assignment of an iridoid-monoterpenoid indole alkaloid hybrid from Dipsacus asper

Fitoterapia. 2019 Jun:135:99-106. doi: 10.1016/j.fitote.2019.04.015. Epub 2019 Apr 30.

Abstract

Iridoid-monoterpenoid indole alkaloid hybrids (IMIAHs) represent a rare class of natural products reported from only several plants of Rubiaceae and Dipsacaceae families, while their structural assignments remain a very challenging work due to complexity and flexibility. In the current study, a new IMIAH (1) was isolated from the roots of Dipsacus asper and its structure with absolute configuration was unambiguously established by a combination of spectroscopic analyses, chemical degradation and ECD calculation. A new oleanane-type triterpenoid saponin (2) and 15 known co-metabolites were also obtained and structurally characterized. Our biological evaluations showed that compound 2 exhibited moderate inhibition against acetylcholine esterase (AChE) with an IC50 value of 15.8 ± 0.56 μM, and compound 15 displayed potent cytotoxicity selectively against human A549 and H157 lung cancer cells with IC50 values of 6.94 ± 0.24 and 9.06 ± 0.12 μM, respectively.

Keywords: AChE inhibition; Calculated ECD; Cytotoxicity; Dipsacus asper; Glucoindole alkaloid; Iridoid glucoside.

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dipsacaceae / chemistry
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Humans
  • Iridoids / chemistry
  • Iridoids / isolation & purification
  • Iridoids / pharmacology*
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Plant Roots / chemistry
  • Secologanin Tryptamine Alkaloids / chemistry
  • Secologanin Tryptamine Alkaloids / isolation & purification
  • Secologanin Tryptamine Alkaloids / pharmacology*

Substances

  • Glucosides
  • Iridoids
  • Secologanin Tryptamine Alkaloids
  • oleanane
  • Oleanolic Acid