Dracomolphin A-E, new lignans from Dracocephalum moldavica

Fitoterapia. 2021 Apr:150:104841. doi: 10.1016/j.fitote.2021.104841. Epub 2021 Feb 1.

Abstract

Eight new lignans, dracomolphin A-E (1-8), together with eight known lignans (9-16) were isolated from the aerial part of Dracocephalum moldavica. The structures of the isolated compounds were established based on NMR and HRESIMS data. Dracomolphin A (1-4) was elucidated as a lignan possessed a 5-membered ketal ring formed between C-8' and C-3, C-4. The two stereogenic centers rendered dracomolphin A as a mixture of two diastereomeric pairs of enantiomers (1-4). All of the four isomers were separated successfully by using chiral HPLC and their stereochemical features were determined by CD spectra. Bioactivity screening revealed that compounds 1-4, 6, 7, 12, 15 and 16 were potential Nrf2 transcriptional activators. Dracomolphin E (8) reduced cell viability of lung cancer NCI-H292 cells associated with apoptosis.

Keywords: Circular dichroism; Dracocephalum moldavica; Ketal; Lignans.

MeSH terms

  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • China
  • Humans
  • Lamiaceae / chemistry*
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Components, Aerial / chemistry
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Lignans
  • Phytochemicals