Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines

Pelin Tastan, Zsuzsanna Hajdú, Norbert Kúsz, I. Zupkó, Izabella Sinka, Bijen Kivcak, J. Hohmann

Research output: Contribution to journalArticle

Abstract

Multistep chromatographic separations of the chloroform extract of the Turkish endemic plant Psephellus pyrrhoblepharus (Boiss.) Wagenitz (syn. Centaurea pyrrhoblephara Boiss.) resulted in the isolation of six guaianolid-type sesquiterpenes, chlorojanerin (1), 19-deoxychlorojanerin (2), 15-hydroxyjanerin (3), aguerin B (4), cynaropicrin (5), eleganin (6); three flavonoids, apigenin, 6-methoxyluteolin and jaceosidine; two glycosides, benzyl-1-O-β-d-glucoside and 3(Z)-hexenyl-1-O-β-d-glucoside; and the coumarin scopoletin. The structures were established by the interpretation of their ESI-MS and 1D and 2D NMR data including 1H-NMR, JMOD, 1H,1H-COSY, HSQC, HMBC, and NOESY experiments. All compounds were isolated for the first time from P. pyrrhoblepharus. Compounds 1–6, the isolated flavonoids and scopoletin were evaluated for their antiproliferative activities on human gynecological cancer cell lines (SiHa, HeLa, and MDA-MB-231 cells) using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Chlorojanerin (1), 19-deoxychlorojanerin (2), aguerin B (4), cynaropicrin (5), eleganin (6) were shown to have noteworthy effects on all of the tested cell lines, while apigenin, jaceosidine, and 6-methoxyluteolin were moderately active on HeLa cells. The highest activities were demonstrated by the chlorine-containing derivatives chlorojanerin (1) and 19-deoxychlorojanerin (2) with IC50 values of 2.21 and 2.88 µM, respectively, against the triple negative breast cancer model MDA-MB-231 cells.

Original languageEnglish
Article number3165
JournalMolecules
Volume24
Issue number17
DOIs
Publication statusPublished - Aug 30 2019

Fingerprint

glucosides
Asteraceae
Sesquiterpenes
Lactones
Scopoletin
cultured cells
Flavonoids
Human Activities
multiple docking adapters
Apigenin
cancer
Cells
Glucosides
Cell Line
Centaurea
cells
Nuclear magnetic resonance
Triple Negative Breast Neoplasms
Neoplasms
nuclear magnetic resonance

Keywords

  • 19-deoxychlorojanerin
  • Antiproliferative activity
  • Asteraceae
  • Chlorojanerin
  • Gynecological cancer cells
  • Psephellus pyrrhoblepharus
  • Sesquiterpene lactones

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines. / Tastan, Pelin; Hajdú, Zsuzsanna; Kúsz, Norbert; Zupkó, I.; Sinka, Izabella; Kivcak, Bijen; Hohmann, J.

In: Molecules, Vol. 24, No. 17, 3165, 30.08.2019.

Research output: Contribution to journalArticle

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