Highly Oxygenated Sesquiterpene Lactones fromCousinia aitchisoniiand their Cytotoxic Properties: Rhaserolide Induces Apoptosis in Human T Lymphocyte (Jurkat) Cells via the Activation of c-Junn-terminal Kinase Phosphorylation

Abstract

Infrared-guided chromatographic fractionation of sesquiterpene lactones from the extracts of Cousinia aitchisonii and Cousinia concolor led to the isolation of five pure compounds. A new sesquiterpene lactone, namely, aitchisonolide, and two known sesquiterpene lactones (desoxyjanerin and rhaserolide) were isolated from C. aitchisonii and two known lignans (arctiin and arctigenin) from C. concolor. The structures of these compounds were elucidated by one-dimensional and two-dimensional nuclear magnetic resonance techniques, as well as high-resolution mass spectrometry. The purified and characterized compounds were subjected to cytotoxicity assay. The sesquiterpene lactones desoxyjanerin and rhaserolide showed significant cytotoxic activities against five different cancer cell lines and the normal human embryonic kidney cell line. Rhaserolide was chosen to evaluate the possible mechanism of action. Western blot analysis revealed that rhaserolide could induce apoptosis in Jurkat cells via the activation of c-Jun n-terminal kinase phosphorylation.

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

“…Compounds 1 – 6 , the isolated flavonoids and scopoletin were evaluated for their antiproliferative activities using the MTT assay. Human gynecological malignant cell lines isolated from cervical (SiHa, HeLa) and female breast cancers (MDA-MB-231) were utilized with regard to previous investigations where they were found to be sensitive against metabolites of Cynareae plants [11,20,21,22,23]. In the present assay, chlorojanerin ( 1 ), 19-deoxychlorojanerin ( 2 ), aguerin B ( 4 ), cynaropicrin ( 5 ), and 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.…”

Characterization of Secondary Metabolites in Two Cousinia species

“…According to Iranshahy et al sesquiterpene compounds namely desoxyjanerin and raserolit obtained from the dichloromethane extract of C. aitchisonii were subjected cytotoxic screening on five different cell lines. As a result, both compounds showed significant cytotoxic effect on breast cancer MCF-7 cell line (IC50 = 4.5 μg / mL and 4.6 μg / mL, respectively) [10]. In another study MMP inhibitor effect of C. shulabadensis Attar & Ghahr.…”

“…[2], oxygenated bisabolene derivatives from C. canescens DC., phenolic and triterpenic compounds from C. adenostica Bornm., C. aitchisonii Boiss. [5,[9][10][11][12] and fatty acids from C. aurea C.Winkl., C. seversovii Regel, C. umbrosa Bunge. [13,14].…”

7-Isopenthenyloxycoumarin, Arctigenin, and Hesperidin Modify Myeloid Cell Leukemia Type-1 (Mcl-1) Gene Expression by Hormesis in K562 Cell Line

“…The genus comprises of 210 species in Iran from which 172 species are endemic to the country. 10 Arctigenin (Arg; Figure 1A ) is a bioactive lignin isolated from Cousinia concolor . 10 Moreover, it has been isolated from Bardanae fructus , Arctium lappa , Saussurea medusa , Torreya nucifera , and Ipomea cairica .…”

“… 10 Arctigenin (Arg; Figure 1A ) is a bioactive lignin isolated from Cousinia concolor . 10 Moreover, it has been isolated from Bardanae fructus , Arctium lappa , Saussurea medusa , Torreya nucifera , and Ipomea cairica . 11 Arctigenin has different pharmacological effects including anticancer.…”