Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran

Abstract

Phytochemical analysis of the Ferulago trifida Boiss. from Apiaceae family led to the isolation and identification of suberosin (1), isoimperatorin (2), prantschimgin (3), oxypeucedanin (4), oxypeucedanin methanolate (5), suberenol (6), 6-hydroxymethylherniarin (7), oxypeucedanin hydrate (8), ulopterol (9), bergapten (10), xanthotoxin (11), imperatorin (12) and grandivittin (13) from chloroform extracts of the roots (1-9) and fruits (1, 2, 8, 10-13) of this species. Oxypeucedanin methanolate and suberenol demonstrated a potent antioxidant power with 268.2 ± 5.4 and 251.2 ± 6.2 mmol FSE/100 g, respectively, compared by BHT (267.2 ± 4.2 mmol FSE/100 g) in FRAP method. The potent antibacterial effects were found for oxypeucedanin methanolate on S. epidermidis (IZ; 26 mm, MIC; 250 μg mL) an oxypeucedanin hydrate on K. pneumoniae (IZ: 21 mm, MIC: 250 μg mL). Moreover, suberosin showed higher preferential toxicity against MDA-MB-23 cells (IC: 0.21 mM, SI: 5.0), in comparison with tamoxifen (IC: 0.012 mM, SI: 2.45) in MTT assay.

Variation of Chemical Constituents and Antiradical Capacity of Nine Ferulago angulata Populations from Iran

“…The bioactivities of the extract of aerial parts and of the EO have been previously studied. For instance, different extracts and coumarins of the plant exerted moderate antiradical scavenging, antibacterial, and antioxidant activities . Moreover, in the literature antioxidant activity, in vivo anxiolytic and antidepressant for the EO, along with cytotoxicity, apoptosis‐inducing, and in vitro anticancer effects of the extracts were reported.…”

“…For instance, different extracts and coumarins of the plant exerted moderate antiradical scavenging, [15][16][17][18] antibacterial, [19] and antioxidant activities. [20] Moreover, in the literature antioxidant activity, [4,7,10,21 -25] in vivo anxiolytic and antidepressant for the EO, [4] along with cytotoxicity, apoptosis-inducing, [16] and in vitro anticancer effects [26] of the extracts were reported. Furthermore, the AcOEt and methanolic extract of F. angulata previously revealed the highest levels of phenolic compounds among its various extracts.…”

Essential Oil Analysis and Isolation of Coumarins and Flavonol Glycosides of Ferulago angulata (Schltdl.) Boiss. Fruits

“…In 2018, Tavakoli et al reported the isolation of thirteen coumarin derivatives from the roots and fruits of Ferulago trifida, among them suberosin showed higher preferential toxicity against MDA-MB-23 cells (IC 50 : 0.21 mM, Selectivity index: 5.0), in comparison with tamoxifen (IC 50 : Pharmaceutical Sciences, 2021, 27(1), 139-146 | 143 0.012 mM, Selectivity index: 2.45) and strong antibacterial activity against S. epidermidis (Inhibition zone; 19 mm, MIC; 250 μg/ml). 25 In the mentioned study, suberenol was also found as a potent antioxidant in ferric reducing antioxidant power (FRAP) test (251.2 ± 6.2 mmol FSE/100 g). 25 In another study, phytochemical analysis of Ferulago bracteata roots using a bioassay guided approach resulted in the isolation of suberosin, bergapten, imperatorin, and other nine compounds, of which suberosin showed the potent α-glucosidase inhibitory activity (IC 50 : 0.89 mg/ ml) in comparison with reference standard acarbose (IC 50 4.95 mg/ml).…”

“…25 In the mentioned study, suberenol was also found as a potent antioxidant in ferric reducing antioxidant power (FRAP) test (251.2 ± 6.2 mmol FSE/100 g). 25 In another study, phytochemical analysis of Ferulago bracteata roots using a bioassay guided approach resulted in the isolation of suberosin, bergapten, imperatorin, and other nine compounds, of which suberosin showed the potent α-glucosidase inhibitory activity (IC 50 : 0.89 mg/ ml) in comparison with reference standard acarbose (IC 50 4.95 mg/ml). 31 Anti-inflammatory potential of suberosin, a major prenylated coumarin isolated from F. angulata fruits, has been demonstrated by its inhibitory effects of proliferation of human peripheral blood mononuclear cells (HPBC) proliferation through reduction of intracellular Ca 2+ concentration and inhibition of ERK, NF-AT, and NF-κB activation.…”

Deverra tortuosa (Desf.) DC from Saudi Arabia as a new source of marmin and furanocoumarins derivatives with α-glucosidase, antibacterial and cytotoxic activities

“…However, these compounds did not seem to be active against 4 bacterial strains (S. typhimurium, K. pneumonia, E. faecalis and P. mirabilis). The antimicrobial properties of several furanocoumarins have been reported previously, for Bergapten isolated from Treculia obovoidea (Kuete et al, 2007) and for Isoimperatorin isolated from the roots and fruits of Ferulago trifida Boiss (Tavakoli et al, 2018). and isopimpinellin isolated from Prangos uloptera roots (Razavi et al, 2009) and from Peucedanum zenkeri seeds (Ngwendson et al, 2003).…”