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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.
Highlights
The genus Psephellus Cass., belonging to the Asteraceae family, tribe Cynareae, includes approximately 80 species
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
Ethnopharmacological relevance of Psephellus species and accumulation of antitumor compounds in genera Centaurea, Arctium, Cirsium, and Psephellus belonging to tribe Cynareae initiated the present phytochemical investigation that resulted in the isolation and structural elucidation of 12 secondary metabolites
Summary
The genus Psephellus Cass., belonging to the Asteraceae family, tribe Cynareae, includes approximately 80 species. River Area, and Upper Fırat Area of the country [1,2,3] Psephellus species such as P. appendicigerus, P. erzincani, and P. karduchorum have been used in traditional medicine as wound healing agents and in the treatment of abscesses [4,5,6,7]. Human isolated flavonoids and scopoletin evaluated for their Human gynecological malignant cell lines isolated from cervical (SiHa, HeLa) and female (MDA-MB-231) were utilized with regard to previous investigations where they were found to be breast cancers (MDA-MB-231). 19-deoxychlorojanerin (2), aguerin B (4), cynaropicrin (5), and eleganin (6) were shown to have chlorojanerineffects (1), 19-deoxychlorojanerin aguerin (5),and and6-methoxyluteolin eleganin (6) were noteworthy on all of the tested cell(2), lines, whileBapigenin, jaceosidine, shown to have noteworthy effects on all of the tested cell lines, while apigenin, jaceosidine, and 6were moderately active on HeLa cells.
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