Περίληψη:
In the framework of phytochemical studies on Greek endemic Inula species, Inula candida subsp. candida and Inula candida subsp. decalvans have been analyzed. The aerial parts were extracted with increasing polarity solvents and sixteen secondary metabolites from I. candida subsp. candida and eight from I. candida subsp. decalvans were isolated. From I. candida subsp. decalvans a sesquiterpene lactone (3aS,8aR)-6-methyl-3-methylidene-7-(3-oxobutyl)-3a,4,5,8a-tetrahydro-2H-cyclohepta[b]furan-2,8(3H)dione (1), was determined as a new natural product, additionally to five known triterpenes: β-amyrin (2), dammaradienol (3), dammaradienyl acetate (4), epifriedelanol (5), stigmasterol (6) and two known lactones: inusoniolide (7) and tomentosine (8). The chemical investigation of I. candida subsp. candida resulted in the isolation of ten known triterpenes: β-amyrin (2), stigmasterol (6), β-sitosterol (9), α-amyrone (10), α-amyrin (11), friedelin (12), lupenone (13), 3β-acetoxy-24-hydroxydammara-20,25-diene (14), 3β-acetoxy-25-hydroxydammara-20,23-diene (15), 3β-acetoxy-24-oxo-dammara-20,25-diene (16), as well as five lactones: inusoniolide (7), 4-O-dihydroinusoniolide (17), 9β-(3-hydroxyisovaleryloxy) parthenolide (18), 9β-hydroxyparthenolide (19), 9β-(3-hydroxy-2-methylbutyryloxy) parthenolide (20), together with the phenolic aldehyde: vanillin (21). The crude extracts and the isolated compounds were also evaluated for their antimicrobial activity against a panel of selected human pathogenic bacteria and fungi showing that the new lactone (1) and 9β-hydroxyparthenolide (19) showed the strongest activity against the tested bacteria (MIC 3•10 −2 –5•10 −1 μg/ml), while (1) and tomentosin (8) appeared as the most active against the assayed fungi (MIC 2,5•10 −2 –12•10 −2 μg/ml). The antiproliferative effect for the new lactone was also evaluated in vitro against the human non-small-cell bronchopulmonary carcinoma cell line NSCLC-N6 and the epidermoid lung cancer cell line A549. © 2019
Συγγραφείς:
Michalakea, E.
Graikou, K.
Aligiannis, N.
Panoutsopoulos, G.
Kalpoutzakis, E.
Roussakis, C.
Chinou, I.
Λέξεις-κλειδιά:
3beta acetoxy 24 hydroxydammara 20,25 diene; 3beta acetoxy 24 oxo dammara 20,25 diene; 3beta acetoxy 25 hydroxydammara 20,23 diene; 4 o dihydroinusoniolide; 5 fluocitocine; 6 methyl 3 methylidene 7 (3 oxobutyl) 3a,4,5,8a tetrahydro 2h cyclohepta[b]furan 2,8(3h) dione; 9beta (3 hydroxy 2 methylbutyryloxy)parthenolide; 9beta (3 hydroxyisovaleryloxy)parthenolide; 9beta hydroxyparthenolide; alpha amyrone; amoxicillin; amphotericin B; antibiotic agent; antifungal agent; beta amyrin; clavulanic acid; cytotoxic agent; dammaradienol; dammaradienyl acetate; drug metabolite; epifriedelanol; inusoniolide; netilmicin; plant extract; sesquiterpene lactone derivative; sitosterol; stigmasterol; tomentosine; unclassified drug; unindexed drug; vinorelbine tartrate, antibacterial activity; antifungal activity; antiproliferative activity; Article; biological activity; Candida albicans; Candida glabrata; Candida tropicalis; carbon nuclear magnetic resonance; controlled study; drug binding site; drug cytotoxicity; drug identification; drug isolation; drug purification; drug screening; drug selectivity; drug structure; endemic species; Enterobacter cloacae; Escherichia coli; heteronuclear multiple quantum coherence; human; human cell; IC50; Inula; Inula candida; Inula decalvans; lung carcinoma cell line; minimum inhibitory concentration; nonhuman; priority journal; proton nuclear magnetic resonance; Pseudomonas aeruginosa; Staphylococcus aureus; Staphylococcus epidermidis; thin layer chromatography
