RESUMO
The structures and anticancer effects of two sesquiterpene lactones, 1 R,10S,3S,4R-diepoxyguai-5S,6S,7S-11(13)-en-6,12-olide (1) and hanphyllin (2) isolated from the aerial part of Tanacetopsis karataviensis (Kovalevsk.) Kovalevsk were investigated. The compound 1 was isolated for the first time as a natural compound and its structure was investigated by HR-ESI-MS, IR and NMR techniques. The X-ray diffraction analysis was performed to accurately determine the spatial structures of 1 and 2. Furthermore, we evaluated the cytotoxic activity of 1 and 2, and the chloroform fraction which contains both of them. Cytotoxic activity revealed that the effect of the chloroform fraction is stronger in growth inhibition of HeLa (89.7%) and HEp-2 (63.0%) cancer cells than the effect of individual compounds 1 (55.9 and 36.3%), 2 (78.6 and 50.3%) and the reference cisplatin (58.0 and 46.8%) respectively. Moreover, the chloroform fraction is less toxic to the hepatocytes.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Lactonas/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Lagochilus species are mainly distributed in Central Asia and widely used in folk medicine as a sedative and haemostatic. The present investigation reports on the extraction by hydrodistillation and the chemical composition of three Lagochilus species (L. gypsaceus, L. inebrians and L. setulosus) essential oils from Uzbekistan. The chemical composition of these essential oils was determined by GC-MS. The results showed that the studied essential oils are made up mainly of linalool (11.97%), ß-ionone (11.75%), trans-chrysanthenyl acetate (7.15%), α-terpineol (7.40%) for L. gypsaceus; trans-chrysanthenyl acetate (9.40%), eugenol (7.01%), trans-verbenol (3.85%), bicyclo[3.1.1]hept-3-en-2-one (3.76%), pinocarvone (3.43%) for L. inebrians; and finally 2,4-bis(1,1-dimethylethyl)phenol (19.78%), bicyclo[3.1.1]hept-2-en-4-ol (5.43%), hexadecanoic acid (5.39%), limonene (5.19%), 2-hexenal (5.03%) for L. setulosus. The best antioxidant and tyrosinase inhibitory activity was observed for the essential oil of L. inebrians. However, L. setulosus essential oil exhibited the strongest inhibitory effect against amylase.
Assuntos
Lamiaceae/química , Óleos Voláteis , Amilases/antagonistas & inibidores , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Limoneno , Monofenol Mono-Oxigenase/antagonistas & inibidores , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , UzbequistãoRESUMO
Plants of the Lamiaceae family are important ornamental, medicinal, and aromatic plants, many of which produce essential oils that are used in traditional and modern medicine, and in the food, cosmetics, and pharmaceutical industry. Various species of the genera Hyssopus, Leonurus, Mentha, Nepeta, Origanum, Perovskia, Phlomis, Salvia, Scutellaria, and Ziziphora are widespread throughout the world, are the most popular plants in Uzbek traditional remedies, and are often used for the treatment of wounds, gastritis, infections, dermatitis, bronchitis, and inflammation. Extensive studies of the chemical components of these plants have led to the identification of many compounds, as well as essentials oils, with medicinal and other commercial values. The purpose of this review is to provide a critical overview of the literature surrounding the traditional uses, ethnopharmacology, biological activities, and essential oils composition of aromatic plants of the family Lamiaceae, from the Uzbek flora.
RESUMO
The chemical composition of the essential oils obtained from aerial parts of Nepeta alatavica Lipsky, N. nuda L, and N. olgae Regel (Lamiaceae), growing wild in Central Asia (Tajikistan and Uzbekistan), were analyzed by GLC and GLC-MS. The main constituents of the essential oil from N. nuda were 1,8-cineole (24.6%), 4a-α,7-ß,7a-α-nepetalactone (21.0%), germacrene D (13.5%), and ß-caryophyllene (12.7%), whereas those of N. alatavica were thymol (48.5%) verbenone (7.7%), and carvacrol (7.5%). In the essential oil of N. olgae the most abundant compounds were acetylcyclohexene (31.5%), 4-tridecyne (13.2%), 2-methyl cyclopentanone (6.8%) and 1,8-cineole (6.0%). The potential antioxidant activity of these essential oils was studied by using DPPH, ABTS and FRAP assays. The essential oil of N. alatavica showed the highest in vitro free radical scavenging activity, probably due to its high thymol and carvacrol content.
Assuntos
Antioxidantes/química , Nepeta/química , Óleos Voláteis/química , Benzotiazóis/química , Compostos de Bifenilo/química , Cromatografia Líquida , Cromatografia Gasosa-Espectrometria de Massas , Oxirredução , Picratos/química , Componentes Aéreos da Planta/química , Ácidos Sulfônicos/químicaRESUMO
OBJECTIVES: The aim of this study was to investigate the flavonoid composition of Scutellaria immaculata and S. ramosissima (Lamiaceae) and the in-vitro biological activity of their extracts and flavonoids. METHODS: The flavonoid composition of S. immaculata (Si) and S. ramosissima (Sr) were analysed using LC-MS. Antimicrobial activity was studied in vitro against a range of bacteria and fungi using diffusion and microdilution methods. Anti-trypanosomal and cell proliferation inhibitory activity of the extracts and flavonoids was assessed using MTT. The antioxidant activity of the flavonoids and extracts were evaluated using DPPH* test. KEY FINDINGS: LC-MS investigation of Si and Sr plants allowed the identification, for the first time, of an additional 9 and 16 flavonoids, respectively. The methanol, chloroform and water extracts from these plants and six flavonoids (scutellarin, chrysin, apigenin, apigenin-7-O-glucoside, cynaroside and pinocembrine) exhibited significant inhibition of cell growth against HeLa, HepG-2 and MCF-7 cells. The chloroform extract of Sr showed potent cytotoxic effects with IC50 (drug concentration which resulted in a 50% reduction in cell viability) values of 9.25 ± 1.07 µg/ml, 12.83 ± 1.49 µg/ml and 17.29 ± 1.27 µg/ml, respectively. The highest anti-trypanosomal effect against T. b. brucei was shown by the chloroform extract of Sr with an IC50 (drug concentration which resulted in a 50% inhibition of the biological activity) of 61 µg/ml. The pure flavonoids showed an IC50 range between 3 and 29 µm, with cynaroside as the most active compound with an IC50 value of 3.961 ± 0.133 µm. The chloroform extract of Sr has potent antimicrobial activity against Streptococcus pyogenes (minimum inhibitory concentration, MIC = 0.03 mg/ml). Pinocembrine exhibited a strong activity against the all bacteria except Escherichia coli and yeasts. Water extracts of Sr and Si exhibited potent antioxidant activity with IC50 values of 5.62 ± 0.51 µg/ml and 3.48 ± 0.02 µg/ml, respectively. Scutellarin exerted stronger antioxidant activity than other flavonoids. CONCLUSIONS: This is the first study reporting an in-vitro biological investigation for Si and Sr. Especially the chloroform extract of Sr showed potent anticancer and antimicrobial activity. Cynaroside had a highly selective and strong cytotoxicity against T. b. brucei while showing only mild effects against cancer cells.