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

被引:18
作者
Tastan, Pelin [1 ]
Hajdu, Zsuzsanna [2 ]
Kusz, Norbert [2 ]
Zupko, Istvan [3 ,4 ]
Sinka, Izabella [3 ]
Kivcak, Bijen [1 ]
Hohmann, Judit [2 ,4 ]
机构
[1] Ege Univ, Fac Pharm, Dept Pharmacognosy, TR-35040 Bornova, Turkey
[2] Univ Szeged, Inst Pharmacognosy, Interdisciplinary Excellence Ctr, H-6720 Szeged, Hungary
[3] Univ Szeged, Inst Pharmacodynam & Biopharm, Interdisciplinary Excellence Ctr, H-6720 Szeged, Hungary
[4] Univ Szeged, Interdisciplinary Ctr Nat Prod, H-6720 Szeged, Hungary
来源
MOLECULES | 2019年 / 24卷 / 17期
关键词
Psephellus pyrrhoblepharus; Asteraceae; sesquiterpene lactones; chlorojanerin; 19-deoxychlorojanerin; gynecological cancer cells; antiproliferative activity; BIOACTIVITY-GUIDED ISOLATION; SUBTRIBE CENTAUREINAE; ASTERACEAE; PLANTS;
D O I
10.3390/molecules24173165
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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-beta-D-glucoside and 3(Z)-hexenyl-1-O-beta-D-glucoside; and the coumarin scopoletin. The structures were established by the interpretation of their ESI-MS and 1D and 2D NMR data including H-1-NMR, JMOD, H-1, H-1-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 mu M, respectively, against the triple negative breast cancer model MDA-MB-231 cells.
引用
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页数:9
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