Oxygenated C17 polyacetylene metabolites from Algerian Eryngium tricuspidatum L. roots: Structure and biological activity

Abstract

The secondary metabolite pattern of Eryngium tricuspidatum has been found to be dominated by C 17 acetylene oxylipins, according to the chemistry reported in the literature for the genus Eryngium. Two new oxylipins, 11acetoxy-falcarindiol (4) and 1,2-dihydro-11-acetoxy-falcarindiol (5) have been isolated, along with main related polyacetylenes 1-3 and the already known monoterpene aldehydes 6-10, from the petroleum ether extract of roots. The structure and the absolute configuration of compounds 4 and 5 have been determined by spectroscopic methods as well as by comparison with related known compounds. Polyacetylenes 1-4 inhibited significantly the in vitro growth of a series of cancer cell lines, ranging from 0.3 to 29 μM, whereas 5 was inactive.

Therapeutic Potential of Plant Oxylipins

“…(3S)-16,17-Didehydrofalcarinol (32) has been shown to inhibit colon cancer cell proliferation [126]. C17 acetylenic oxylipins from Eryngium tricuspidatum, including two rare oxylipins, 11-acetoxy-falcarindiol (37) and 1,2-dihydro-11-acetoxy-falcarindiol (36), inhibited all cancer cell lines tested in vitro at concentrations ranging from 0.3-29 µM [127]. Morphological assessment of these oxylipins' effect on SKMEL-28 melanoma cells using video-enhanced phase-contrast microscopy suggested a similar mechanism of apoptosis induction to that observed upon falcarindiol (33) treatment of colon cancer [127].…”

Polyacetylene Isomers Isolated from Bidens pilosa L. Suppress the Metastasis of Gastric Cancer Cells by Inhibiting Wnt/β-Catenin and Hippo/YAP Signaling Pathways

“…For example, phenyl-1,3,5-heptatriyne showed significant cytotoxicity against human hepatoma HepG2 cells and human colon cancer CaCO-2 cells with IC 50 values of 0.49 and 0.7 µg/mL, respectively [ 16 ]. In addition, four falcarindiol-type polyacetylenes isolated from E. tricuspidatum exhibited significant inhibition of cell proliferation on human malignant melanoma SK-MEL-28 cells, human pulmonary carcinoma A549 cells, and human breast cancer MCF-7 cells with IC 50 values ranging from 0.3 to 29 μM [ 17 ]. It is worth mentioning that these polyacetylenes with anti-tumor activity in vitro shared a conjugated system of two carbon–carbon triple bonds and a double bond.…”

PHYTOCHEMICAL ANALYSIS AND ANTIBACTERIAL ACTIVITY OF ERYNGIUM PYRAMIDALE BOISS. & HAUSSKN

“…Various species of the genus Eryngium like other Apiaceae family members have been reported to possess ornamental, culinary, agricultural, and medicinal applications. Moreover, many Eryngium species have been widely employed in folk medicine as hypoglycemic, antitussive, poison antidote, kidney stone inhibitor, stimulant, diuretic, aphrodisiac, and anti-inflammatory agents [7][8][9]. On the other hand, Eryngium species demonstrate a wide variety of biological and pharmacological activities such as antibacterial, antitumor, antifungal, antiinflammatory, anti-snake and scorpion venoms, antimalarial, antioxidant, and antihyperglycemic activities [9,10] due to having a considerable amount of secondary metabolites and biologically active chemical compounds such as polyacetylenes [11,12], coumarins [13,14], flavonoids [14], phenolics [15,16], terpenoids [17,18], triterpenoid saponins [19], and steroids [20,21].…”