RESUMO
Anethum sowa L. has been used as a spice herb in the Asian and European culinary systems to add flavour and taste. The studied plant has diverse folkloric medicinal value. Present study was designed to isolate phytochemicals from the hexane, chloroform and ethyl acetate extracts of the roots by various chromatographic techniques. Based on spectral analysis (IR, LC-MS, NMR) the isolated compounds were identified as physcione (1), ß-sitosterol (2), stigmasterol (3), 2-oxo-3-propyl-2H-chromene-7-carboxylic acid (4), bergapten (5), 3-ethyl-7-hydroxy-2H-chromen-2-one (6) and graveolone (7). The mentioned compounds have been isolated for the first time from the roots part of the plant. Based on extensive literature review, physcione and bergapten were inferred to exhibit crucial bioactivities including inhibitory efficacy against various forms of cancer. Accordingly, in the present research approach molecular docking investigations of the isolated phytochemicals have been robustly executed with different oncogenes that have been reported to be actively involved in various forms of carcinoma. In silico investigations encompassing molecular docking analysis and drug-likeness profiling was executed to estimate the potential therapeutic tendencies of the phytochemicals targeted towards effective cancer therapy. Current investigation offers meaningful know-how pertaining to potential anticancer activities of the phytochemicals extracted from the roots of Anethum sowa L. and might open up new revenues towards effective drug development against cancer.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apiaceae/química , Simulação de Acoplamento Molecular , Extratos Vegetais/farmacologia , Raízes de Plantas/química , 5-Metoxipsoraleno/química , 5-Metoxipsoraleno/isolamento & purificação , 5-Metoxipsoraleno/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Benzopiranos/química , Benzopiranos/isolamento & purificação , Benzopiranos/farmacologia , Ácidos Carboxílicos/química , Ácidos Carboxílicos/isolamento & purificação , Ácidos Carboxílicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Metoxaleno/análogos & derivados , Metoxaleno/química , Metoxaleno/isolamento & purificação , Metoxaleno/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologiaRESUMO
BACKGROUND: Medicinal herbs are used for the treatment of different ailments since antiquity. Different parts of Anethum sowa L. is used in folk medicine as a carminative for the treatment of flatulence, colic and hiccups of infants and children, antioxidant, antimicrobial and antispasmodic agent. The aim of our present study is to evaluate the chemical composition of the essential oil, proximate and elemental composition, amino acid, fatty acid profile and thermal behaviour of its root part as well as different pharmacological activities like antioxidant, antimicrobial and cytotoxicity of the root essential oil. METHODS: The air-dried roots of Anethum sowa L. were subjected to hydro-distillation to yield the essential oil. The antioxidant activity of the essential oil was studied by DPPH radical scavenging activity. The antimicrobial activity was tested against four Gram-positive, six Gram-negative bacteria and four fungi species. The minimum inhibitory concentration (MIC) and Minimum bacterial concentration (MBC) for each examined microorganism were determined using the micro-dilution method. The LC50 value of the oil was also evaluated by brine shrimp lethality assay. The subsequent proximate analysis was also done by AOAC methods. The elemental analysis of the root powder was analysed by ICP-MS, AAS and FP system. The fatty acid was extracted by hot and cold extraction method and the analyses were carried out by GC. The amino acid profile was done by the amino acid analyzer. The DTA, DTG and TG of the root powder were taken by the thermogravimetric analyzer. RESULTS: A total of 24 constituents was identified and quantified in the essential oil and its water extract portion by GC and GC-MS. Apiol (81.99 and 74.779%) was found the highest phenylpropanoid constituent followed by m-diaminobenzene (10.446 and 8.778%) in the essential oil and aqueous extract portion. On the other hand, ß-butyrolactone (5.13%) and isobutyl acetone (3.73%) were found in the major constituents in the water extract part. The IC50 value of the essential oil was found to be 3.07 mg/mL by DPPH radical assay methods. The LC50 value of the brine shrimp cytotoxicity assay of the essential oil was observed at 0.81 µg/mL. The essential oil showed better activity on Gram-negative bacteria than Gram-positive bacteria and fungi. The proximate composition showed that root contained 5.29% ash, 2.01% protein, 54.09% crude fibre, 0.15% essential oil and 1.14% fatty oil for hot extract and 0.23% for cold extract on the dried basis. The palmitic (33.81 & 31.58%) and linoleic acid (30.03 & 23.79%) were the major saturated and unsaturated fatty acids in the cold and hot extracted root powder respectively. Ca (23,600 mg/kg), Mg (7620.33 mg/kg) and K (1286.15 mg/kg) were the most predominant elements followed by Ni (1187.30 mg/kg), Se (913.79 mg/kg), Li (317.84 mg/kg), Na (288.72 mg/kg) and Fe (206.88 mg/kg). The toxic elements were found to be within the permissible limit. Glutamic acid (19.37%), glycine (14.53%) and lysine (17.08%) were found as the major amino acids. The decomposition rates were obtained by TG, DTG and DTA curve of the powder sample at various temperature ranges. CONCLUSIONS: The results demonstrated that the root part of Anethum sowa L. is a rich source of mineral elements, essential amino acid and fatty acids. The essential oil is the highly potential as bioactive oil for pharmaceuticals and medical applications, possessing antioxidant, antimicrobial and cytotoxic activities. The thermal analysis suggested as a simple, effective and rapid method to characterize the Anethum sowa L. species as well as to assess for herbal formulation.
Assuntos
Apiaceae/química , Óleos Voláteis/química , Óleos de Plantas/química , Raízes de Plantas/química , Animais , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Artemia/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologiaRESUMO
BACKGROUND: Anethum sowa L. is widely used as an important spice and traditional medicinal plants to treat various ailments. On the basis of scientific ethnobotanical information, this study was undertaken to evaluate the antioxidant, antimicrobial and cytotoxic activity of the crude extracts of Anethum sowa L. roots as well as to identify the classes of phytochemicals by chemical tests. METHODS: The antioxidant potential of the extracts was ascertained with the stable organic free radical (2, 2-diphenyl-1-picryl-hydrazyl). The agar well diffusion method was used to determine the susceptibility of bacterial and fungal strains of the crude extracts. The minimum inhibitory concentration (MIC) and minimum bactericidal concentrations (MBC) were determined by the microdilution test. Cytotoxic activities were screened using brine shrimps (Artemia salina) lethality assay. Finally, phytochemicals were profiled using standard procedures. RESULTS: A preliminary phytochemical screening of the different crude extracts by methanol, ethyl acetate and chloroform showed the presence of secondary metabolites such as flavonoids, alkaloids, saponin, cardiac glycosides and tannins while cyanogenetic glycosides were not detected. The methanol, ethyl acetate and chloroform extracts displayed high antioxidant activity (IC50 = 13.08 ± 0.03, 33.48 ± 0.16 and 36.42 ± 0.41 µg/mL, respectively) in the DPPH assay comparable to that of the standard ascorbic acid and BHT (IC50 = 3.74 ± 0.05 and 11.84 ± 0.29 µg/mL). The cytotoxic activity of the crude ethyl acetate and chloroform extracts possessed excellent activity (LC50 = 5.03 ± 0.08, 5.23 ± 0.11 and 17.22 ± 0.14 µg/mL, respectively) against brine shrimp larvae after 24 h of treatment and compared with standard vincristine sulphate (LC50 = 0.46 ± 0.05 µg/mL). The extracts also showed good antimicrobial activity against both Gram-positive and Gram-negative bacteria when compared with two standard antibiotics ciprofloxacin and tetracycline. CONCLUSION: These results showed that the Anethum sowa root extracts are the important source of the antioxidant, antimicrobial and cytotoxic agent. So, further research is necessary to isolate and characterize of different phytoconstituents for pharmaceutical drug lead molecules and also to verify its traditional uses.
Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Apiaceae/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Animais , Anti-Infecciosos/química , Anti-Infecciosos/toxicidade , Antioxidantes/química , Antioxidantes/toxicidade , Artemia/efeitos dos fármacos , Bactérias/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos/química , Compostos Fitoquímicos/toxicidade , Extratos Vegetais/química , Extratos Vegetais/toxicidadeRESUMO
Usnea undulata Stirton (Usneaaceae) is a fruticose lichen used locally in ethnoveterinary medicine to treat mammary infections in cattle while human beings use it for the treatment of wounds in Eastern Cape, South Africa. Bioactivity-guided fractionation of its extracts led to the isolation and characterization of a new depsidone, 2'-O-methylhypostictic acid (8), together with seven known compounds, i.e. methyl ß-orsellinate, norstictic acid, menegazziaic acid, (+) usnic acid, hypoconstictic acid, salazinic acid, and galbinic acid. The structures of the compounds were elucidated on the basis of their spectral analysis including homo- and hetero-nuclear correlation NMR experiments (COSY, NOESY, HMQC, and HMBC) and mass spectra as well as by comparison with available data in the literature. The minimum inhibitory concentrations (MICs) values of the compounds against six bacteria were determined. Compound 8 showed inhibitory activity against Bacillus cereus, Bacillus subtilis, and Staphylococcus epidermidis with MICs of 31, 62.5, 62.5 µg/ml, respectively. (+) Usnic acid was most active against B. subtilis, B. cereus, Staphylococcus aureus, and Escherichia coli with MICs of 8, 8, 31, and 31 µg/ml, respectively, while other compounds exhibited moderate activity.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Depsídeos/isolamento & purificação , Depsídeos/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Usnea/química , Animais , Antibacterianos/química , Bacillus cereus/efeitos dos fármacos , Bacillus subtilis/efeitos dos fármacos , Benzofuranos/química , Benzofuranos/isolamento & purificação , Bovinos , Depsídeos/química , Escherichia coli/efeitos dos fármacos , Humanos , Lactonas/química , Testes de Sensibilidade Microbiana , Salicilatos/química , Salicilatos/isolamento & purificação , África do Sul , Staphylococcus aureus/efeitos dos fármacosRESUMO
Three novel flavonoid glycosides, 5,6-dimethyoxy-3',4''-dioxymethylene-7-O-(6''-beta-D-glucopyranosyl-beta-D-glucopyranosyl) flavanone (1), 5,4'-dihydroxy-3-O-alpha-L-rhamnopyranosyl-6-C-glucopyranosyl-7-O-(6''-para-coumaroyl-beta-D-glucopyranosyl) flavone (2) and 5,4'-dihydroxy-3-O-(2'''''-beta-glucopyranosyl-alpha-L-rhamnopyranosyl)-6-C-glucopyranosyl-7-O-(6''-para-coumaroyl-beta-D-glucopyranosyl) flavone (3) were isolated from the 1-butanol soluble fraction of the bulbs of the plant Urginea indica (Indian squill). The structures of the compounds were elucidated on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, NOESY, HSQC and HMBC) and mass spectra.
Assuntos
Drimia/química , Flavonoides/química , Glicosídeos/química , Raízes de Plantas/química , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
A new phenylpropanoid glycoside, alpha-L-rhamnopyranosyl-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 6)-1-O-caffeoyl-beta-D-glucopyranoside (1) along with two known phenylethanoid glycosides (2-3) has been isolated from the aerial parts of Leucas indica Linn. Their structures were deduced from the spectroscopic studies and compared with the literature values.
Assuntos
Glicosídeos/isolamento & purificação , Lamiaceae/química , Fenilpropionatos/isolamento & purificação , Bangladesh , Glicosídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenilpropionatos/química , EstereoisomerismoRESUMO
Arctotis arctotoides is a perennial herb used medicinally for the treatment of various ailments in the Eastern Cape, South Africa. Different extracts of the plant were investigated for their antimicrobial constituents. This led to the isolation and identification of a new daucosterol derivative 3-O-[beta-D-(6'-nonadeanoate)glucopyranosyl]-beta-sitosterol and seven known compounds namely: serratagenic acid, stigmasterol, daucosterol, zaluzanin D, dehydrocostuslactone, nepetin, and pedalitin. The structures of the compounds were elucidated on the basis of spectral analysis, including homo and hetero nuclear correlation NMR experiments (COSY, NOESY, HMQC, HMBC) and mass spectra as well as by comparison with available data in the literature. The compounds exhibited antibacterial activity except stigmasterol, daucosterol and dehydrocostuslactone. Nepetin was the most active against Bacillus subtilis and Staphylococcus aureus with the minimum inhibitory concentrations of 4 microg mL( - 1) and 31 microg mL( - 1), respectively, while others exhibited moderate activity.
Assuntos
Antibacterianos/farmacologia , Asteraceae , Bacillus subtilis/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/administração & dosagem , Antibacterianos/química , Antibacterianos/uso terapêutico , Humanos , Testes de Sensibilidade Microbiana , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Sitosteroides/administração & dosagem , Sitosteroides/química , Sitosteroides/farmacologia , Sitosteroides/uso terapêuticoRESUMO
A new triterpenoid 2alpha,3beta,21beta,23,28-penta hydroxyl 12-oleanene and two known compounds were isolated from the roots of Laportea crenulata Gaud. The structures of all compounds were elucidated on the basis of various spectroscopic data. The two known compounds beta-sitosterol and beta-sitosterol 3-beta-D-glucopyranoside are also the first report of isolation from this plant. The antifungal activity of new triterpenoid was studied against Aspergillus flavus, Aspergillus niger, Candida albicans, and Rhizopus aurizae, and compared with the activity of nystatin (30 microg disc(-1)). This compound has shown moderate activity against tested fungi.
Assuntos
Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Aspergillus/química , Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Urticaceae/química , Antifúngicos/química , Bangladesh , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Nistatina/farmacologia , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Raízes de Plantas/químicaRESUMO
A new complex iridoid, prismatomerin (1), has been isolated from the leaves of Prismatomeris tetrandra, together with the known glucoside gaertneroside (4). The structures of 1 and 4 were determined by spectroscopic analysis, notably 2D NMR techniques. The (1R,5S,8S,9S,10S)-(-) absolute configuration of prismatomerin (1) was determined by comparison of the vibrational circular dichroism (VCD) spectrum calculated using density functional theory and the experimental VCD spectrum of the O-acetyl derivative 3. Prismatomerin (1) showed remarkable antitumor activity and also interfered with mitotic spindle formation.
Assuntos
Antineoplásicos Fitogênicos , Iridoides , Rubiaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Bangladesh , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Iridoides/química , Iridoides/isolamento & purificação , Iridoides/farmacologia , Mitose/efeitos dos fármacos , Estrutura Molecular , Folhas de Planta/químicaRESUMO
Bioassay-guided investigation of the stems of Cornus kousa led to the isolation of 12 compounds such as four triterpenoids: betulinic acid (1), maslinic acid (2), arjunolic acid (3), 3-isoarjunolic acid (4), four flavanoids; catechin (5), epi-catechin (6), 2-hydroxynaringenin (7), 2-hydroxynaringenin-7-O-beta-D-glucopyranoside (8), two ellagic acid derivatives; 3,4,3'-tri-O-methylellagic acid (9), 3,4-di-O-methylellagic acid (10), a daucosterol (11) and a sucrose derivative; (3'-O-p-coumaroyl)-beta-D-fructofuranosy-(2?1)-(6-O-p-coumaroyl)-alpha-D-glucopyranoside (12). Their structures were elucidated on the basis of spectroscopic studies as well as by comparison with available data in the literature. The free radical scavenging activity and elastase inhibition activity were investigated for the development of antiaging ingredients as a raw material for use in cosmetics. Among these compounds, compounds 1, 2 and 8 showed significant elastase inhibition activity and IC(50) was 10.81 microg/mL, 21.21 microg/mL and 44.63 microg/mL, respectively, on porcine pancreatic elastase, whereas compounds 5, 6, 7 and 8 showed significant free radical scavenging activity and SC(50) was 8.37 microg/mL, 9.31 microg/mL, 9.23 microg/mL and 17.45 microg/mL, respectively.
Assuntos
Cornus/química , Sequestradores de Radicais Livres/análise , Monofenol Mono-Oxigenase/antagonistas & inibidores , Elastase Pancreática/antagonistas & inibidores , Caules de Planta/química , Compostos de Bifenilo , Picratos , Extratos Vegetais/químicaRESUMO
A series of cis-platinum ethynyl complexes with the general formula cis-[Pt(dppe)(C[triple bond]CR)2](dppe = 1,2-bis(diphenylphosphino)ethane; R = C6H4-p-NO2 1, C6H4-p-CH3 2, C6H4-p-C[triple bond]CH 3 and C6H4-p-C6H4-p-C[triple bond]CH 4) have been prepared by the coupling reaction of cis-[Pt(dppe)Cl2] with two equivalents of the appropriate alkyne. The new complexes have been fully characterized by spectroscopic techniques, and the cis square planar arrangement at the platinum centre has been confirmed by single-crystal X-ray diffraction studies of complexes 1, 2 and 4. The absorption spectra of the complexes 1-4 are dominated by a pi-->pi* band that contains some platinum (n + 1) p orbital character. The position of the band is dependent on the electron donating or withdrawing properties of the ethynyl substituents, R. Complex 1 displays a triplet emission in the green, at room temperature, while complexes 2-4, display singlet emissions in the blue. Again, the difference can be attributed to the nature of the R substituents.