Antimicrobial Antioxidant Daucane Sesquiterpenes from Ferula hermonis Boiss

Abstract

Seventeen daucane sesquiterpenoid esters, including a new one (4), were isolated from the root of Ferula hermonis Boiss. The structures of the isolated compounds were elucidated on the basis of spectroscopic evidence and correlated with known compounds. The relative stereochemistry of the new compound was determined using 2D NOESY and the most stable and the lowest energy conformation was determined using molecular modelling. The antimicrobial activity was evaluated by determination of MIC using the broth microdilution method against six bacterial strains and one fungal strain (Pseudomonas aeruginosa PAO1, Escherichia coli, Bacillus subtilis ATCC6633, Mycobacterium bovis BCG Pasteur, Mycobacterium tuberculosis H37Rv, Staphylococcus aureus ATCC6538 and Candida albicans SC5314). There was a significant indication that compounds 15, 16, 17 demonstrated potent activity against Gram +ve (S. aureus, B. subtilis), as well as Mycobacterium strains M. bovis BCG and M. tuberculosis H37Rv. None of the isolated compounds exhibited a significant antifungal activity. In the antioxidant study using the DPPH assay method, the highest radical scavenging activity was observed for compounds 15, 16, 17.

Simmondsia chinensis: A rich source of bioactive flavonoids and lignans

“…The experiment was carried out in triplicate, using BHT as a positive control. The percentage reduction of the DPPH, Q, referred to "inhibition or quenching" was calculated by the following formula (AbdelMageed et al, 2012;Ibraheim et al, 2012;Wagner et al, 2014):…”

Phytochemistry and Pharmacology of Ferula hermonis Boiss. – A Review

“…Ibraheim. et al [68] have recently evaluated the antimicrobial activity of seventeen daucane sesquiterpenes and determined their MICs using the broth micro dilution method against six bacterial strains and one fungal strain (Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis, Mycobacterium bovis, Mycobacterium tuberculosis, Staphylococcus aureus and Candida albicans). Teferidin (15), ferutinin (16) and teferin (17) showed potent activity against the Gram positive bacteria S. aureus and B. subtilis, as well as Mycobacterium strains, M. bovis and M. tuberculosis.…”

“…In 2005, Traboulsi et al [68] determined the insecticidal activities of essential oils from different parts of aromatic plants against larvae of the mosquito Culex pipiens molestus. The oils of F. hermonis were toxic on larvae with LC 50 value of 44.0 mg/l.…”

Antifungal Compounds from the Rhizome and Roots of Ferula hermonis

“…(in some papers referred as F. harmonis ), a perennial shrub that grows on the Hermon mountain, between Lebanon and Syria, commonly known as ‘Shirsh‐el‐Zallouh’ which means hairy root, is used in the Middle East to improve sexual behavior in the treatment of frigidity and impotence (Auzi et al ., ; El‐Taher et al ., ; Lev and Amar, ). Although some papers dealing on the sesquiterpene composition of different extracts (Al‐Sha'er et al ., ; Auzi et al ., ; Diab et al ., , ; Galal, ; Galal et al ., ; Ibraheim et al ., ; Lhuillier et al ., ) as well as on its antibacterial and insecticidal activities (Al‐Nahar et al ., ; Al‐Sha'er et al ., ; Galal et al ., ; Hilan et al ., ; Ibraheim et al ., ) have been previously published, little is known about its antifungal activity.…”