ABSTRACT
Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2), anthemin C (3), tatridin A (4), 1-epi-tatridin B (5), anthemin B (6), 6-deacetyl-beta-cyclopyrethrosin (7), elegalactone A (8), and 1beta,4alpha,6alpha-trihydroxyeudesm-11-en-8alpha-12-olide (9), were isolated from the aerial parts of A. melanolepis in addition to eight known flavonoids and three phenolic acids. Compounds 1, 3, and 6 are new natural products. The structures of the compounds were deduced by spectroscopic methods. The in vitro antimicrobial potential of the isolated sesquiterpene lactones against four Gram-positive and five Gram-negative bacteria and one fungus was evaluated using the microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines. Furthermore, the pharmacokinetic profile of the sesquiterpene lactones was investigated using computational methods.
Subject(s)
Anthemis/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Lactones/isolation & purification , Lactones/pharmacology , Plants, Medicinal/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Anti-Bacterial Agents/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Drug Screening Assays, Antitumor , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Greece , Humans , Lactones/chemistry , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistryABSTRACT
The volatile composition of eight Anthemis species has been studied. The essential oils were obtained by hydrodistillation in a modified Clevenger-type apparatus, and their analyses were performed by GC and GC-MS. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. A total of 284 different compounds were identified and significant qualitative and quantitative differences and similarities were observed among the samples. The main constituents of the investigated populations of each taxon have been revealed as follows: A. altissima: (-)-linalool, trans-caryophyllene, cis-chrysanthenyl acetate; A. auriculata: spathulenol, trans-caryophyllene, beta-eudesmol; A. chia: cis-chrysanthenyl acetate, trans-caryophyllene, germacrene-d; A. cotula: germacrene-d, spathulenol A. tinctoria: spathulenol, (-)-caryophyllene oxide, T-cadinol; A. melanolepis: p-cymene, chrysanthenone, trans-verbenol, (-)-caryophyllene oxide; A. tomentosa: (-)-linalool, 1,8-cineole; A. werneri subsp. werneri: nopol, terpineol-4, trans-caryophyllene. Sesquiterpene hydrocarbons were shown to be the main group of constituents of all taxa.
Subject(s)
Anthemis/chemistry , Oils, Volatile/chemistry , Chromatography, Gas , Gas Chromatography-Mass Spectrometry , Greece , Species SpecificityABSTRACT
Ten sesquiterpene lactones, 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)sonchucarpolide (4-epi-malacitanolide) (1), 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)-4-epi-sonchucarpolide (2), malacitanolide (3), its 4'-acetyl derivative (4), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensine (5), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7alphaH,6betaH-eleman-1,3,11(13)-trien-6,12-olide (6), the germacranolides 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)salonitenolide (7), cnicin (8), and 4'-acetylcnicin (9), and the sesquiterpene methyl 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-6alpha,15-dihydroxyelema-1,3,11(13)-trien-12-oate (10), were isolated from the aerial parts of Centaurea spinosa. Nine known flavonoids were also isolated. The structures and the stereochemistry of the new compounds 1 and 2 were deduced by spectroscopic methods. The in vitro activity of 1-10 against three Gram-positive and three Gram-negative bacteria was evaluated using a microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines.