Three new prenyloxy chromanones from aerial parts of Hypericum aucheri

Fitoterapia. 2019 Nov:139:104421. doi: 10.1016/j.fitote.2019.104421. Epub 2019 Nov 13.

Abstract

Three new prenyloxy chromanone derivatives, aucherine A-C (6, 7 and 9) as well as six known prenylated phloroglucinols (1-5 and 8) were isolated from the aerial parts of Hypericum aucheri Jaub. Et Spach. The structures of the isolated compounds were established by means of spectral techniques (HRESIMS, 1D and 2D NMR). The new compounds were tested on а panel of human tumor cell line using MTT assay. All tested compounds exerted moderate cytotoxicity with IC50 values ranging from 19.6 to 57.8 μM. The influence of the new compounds on some key signaling molecules (procaspase-9 and Bcl-xL), implicated in the regulation of programmed cell death was assessed by Western blot analysis.

Keywords: Aucherines; Bcl-xL; Chromanones; Cytotoxicity; Hypericum aucheri; Procaspase-9.

MeSH terms

  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis
  • Bulgaria
  • Caspase 9 / metabolism
  • Cell Line, Tumor
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Humans
  • Hypericum / chemistry*
  • Molecular Structure
  • Phloroglucinol / isolation & purification
  • Phloroglucinol / pharmacology
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Components, Aerial / chemistry
  • Prenylation
  • bcl-X Protein / metabolism

Substances

  • Antineoplastic Agents, Phytogenic
  • BCL2L1 protein, human
  • Chromones
  • Phytochemicals
  • bcl-X Protein
  • Phloroglucinol
  • CASP9 protein, human
  • Caspase 9