A new Tetrahydrofuran sesquiterpene skeleton from Artemisia sieberi

Abstract

A new Tetrahydrofuran sesquiterpene 7,10‐Epoxy‐10‐methy‐dodeca‐1,6(14)‐diene‐3,4‐diol (1) along with three known Tetrahydrofuran sesquiterpene compounds 2,6,10‐trimethyl‐2,5:7,10‐dioxido‐dodeca‐3,11‐dien‐5‐ol (2), cis‐hydroxydavanone (3), and davana acid (4). All isolated metabolites were tested against MCF‐7, HCT‐116, and HepG‐2 cancer cell lines. Compound 2 showed potent activity against MCF‐7 (IC50 = 26 ± 0.4 μg/ml), HCT‐116 (IC50 = 30.4 ± 0.9 μg/ml), and HepG‐2 (IC50 = 20.5 ± 0.3 μg/ml) cancer cells.

Isochlorogenic Acid Glucosides from the Arabian Medicinal Plant Artemisia sieberi and Their Antimicrobial Activities

“…The non-water soluble parts were chromatographed by using silica gel and then further divided by repeated column and LC fractionations to acquired sixteen compounds (1-16, Figure 1). These comprised the new compounds isochlorogenic acid A-3 -O-β-glucopyranoside (1), isochlorogenic acid A-3 -O-β-glucopyranoside methyl ester (2), and isochlorogenic acid C-3 -O-β-glucopyranoside (3), and thirteen known secondary metabolites: dehydrodiconiferyl alcohol 9 -β-D-glucopyranoside (4) [8], dehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (5) [9], 3α,4α-10β-trihydroxy-8α-acetyloxyguaian-12,6α-olide (6), 3α,4α-10β-trihydroxy-guaian-12,6α-olide (7), epi-vulgarin (8) [10], angelicoidenol 2-O-β-D-glucopyranoside (9) [11], betulabuside A (10) [12], skimmin (11), yangambin (12) [13], isoquercetin (13), p-arbutin (14), chlorogenic acid (15) and its methyl ester (16). All the previously known compounds were recognised via correlation of their spectroscopic details with those described in the literature or with those of standards available in our laboratories.…”

“…Belonging to the Asteraceae family, it is not surprising that sesquiterpene lactones and flavonoids have been reported as the dominating class of secondary metabolites purified from the medium polarity fractions of the plant extracts. Only a specific and mild antioxidant and antitumor activities have been associated with these compounds [7].…”

Chemical Constituents of the Artemisia ciniformis Aerial Parts Grown in the Northeast of Iran and Their Chemotaxonomic Significance

“…There are several reports of the anti-cancer activity of davanone derivatives from different Artemisia species against cancerous cell lines (18,(38)(39)(40)(41)(42)(43). The mechanism of action of davanone derivatives against cancer cells involves apoptosis induction through a caspasedependent process, loss of mitochondrial membrane potential (MMP), inhibition of cell migration and invasion, and targeting of the PI3K/AKT/MAPK signaling pathway (18,(38)(39)(40)(41). Additionally, other biological activities such as antifungal and antiosteoclastogenic activities have been reported for davanone derivatives (44,45).…”

Chemical Profiles, Anticancer, and Anti-Aging Activities of Essential Oils of Pluchea dioscoridis (L.) DC. and Erigeron bonariensis L.

“…The sesquiterpenes in both forms, oxygenated and hydrocarbons, represented very effective The significant activities of the two EOs might be attributed to the chemical composition in which the synergetic effect of the compounds contributes to this activity [48]. The sesquiterpenes in both forms, oxygenated and hydrocarbons, represented very effective compounds as anticancer leaders [49,50]. Several reports deduced that the increasing of sesquiterpene contents in EOs caused increasing in anticancer activity [51,52].…”