Characterization Of Coumarin Research Articles

Metabolic profiling of coumarins by the combination of UPLC-MS-based metabolomics and multiple mass defect filter

Coumarins have aroused high interests due to their diverse bioactivities. Understanding of its metabolism contributes to determine the druggability of coumarin in vivo.A sensitive and efficient strategy based on ultra-performance liquid chromatography-mass spectrometer (UPLC-MS) analysis combined with various data-processing techniques including metabolomics and multiple mass defect filter (MMDF) was established for the comprehensive screening and elucidation of potential coumarin metabolites.Total 20 metabolites of scoparone were identified in this study, including 14 undescribed metabolites. The metabolism of two other similar coumarins scopoletin and esculetin also could be determined using this strategy.By the established strategy, this study gives the insights about the major metabolic pathways of scoparone in vivo and in vitro metabolism, including demethylation, hydroxylation, hydration, cysteine conjugation, glucuronide conjugation and sulfate conjugation. Additionally, the metabolic pathways of scopoletin and esculetin were determined as hydroxylation, glucuronidation and sulfation. These results contribute to the understanding of metabolic characterization of coumarins, and demonstrate that the combination of UPLC-MS-based metabolomics and MMDF is a powerful approach to determine the metabolic pathways of coumarin compounds.

Microwave Assisted Rapid Extraction and Characterization of Coumarin from Fig Plant (Ficus carica)

Coumarins are fragrant natural bioactive organic compound find application as aroma, flavor and wide medicinal use. Fig plant (Ficus Carica) is a very good source of Coumarins. Coumarins are a member of the benzopyrone family and it has a benzene ring joined to a pyrone ring. There is a need for effective extraction and purification of Coumarins from plant materials. Different methods of extraction of Courmarin from Ficus Carica has been studied in this paper, among them, microwave extraction (180 W power) provided rapid extraction with 10 minutes time with extract yield of 0.67 g as compared to that of 1 hour of water bath extraction at 60C. Coumarin was isolated from the crude extract using NaOH and petroleum ether and their presence was characterized confirmed using UV spectroscopy, IR spectroscopy, TLC and fluorescence test. The antibacterial activity of coumarin was also evaluated using disc diffusion method and Minimum Inhibition Count (MIC). The present study analyzes and provides method of microwave assisted rapid extraction of Coumarin from Fig plant (Ficus Carica) and its characterization, which could be widely used as generic method from natural materials for different applications.

Comprehensive profiling and characterization of coumarins from roots, stems, leaves, branches, and seeds of Chimonanthus nitensOliv. using ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry combined with modified mass defect filter

Chimonanthus nitensOliv. (CNO), having been studied and developed as the tea beverages, tea raw materials and preparations, an unique species in China, have been extensively used for treating colds and influenza for centuries. In the present study, a method based on the modified mass defect filter (MDF) was firstly developed and validated for comprehensive profiling of coumarins in the different parts of CNO via ultra-performance liquid chromatography tandem quadrupole time-of-flight mass spectrometry (UPLC-QTOF/MS). The five-point screening approach based on MDF and the visual isotopic ion technique could rapidly screen the interested precursor ions. The fragmentation behavior of coumarins was systematically investigated and a total of 42 coumarins including 27 potential new ones were unambiguously or tentatively identified in the CNO. Collectively, the results obtained in the present work may provide useful information for future utilization of CNO.

Phytochemical Investigation, Isolation and Characterization of Coumarins from Aerial Parts and Roots of Tunisian Pituranthos chloranthus (Apiaceae)

Pituranthos chloranthus, commonly known in Arabic as ‘Aljen,’ is a small aromatic plant which grows spontaneously in North Africa and it is widespread in central and southern Tunisia. This paper is the first report of its kind on the isolation and characterization of certain coumarin derivatives from the extract of the roots and aerial parts of this plant. Background: Pituranthos chloranthus (Apiaceae) commonly known as ‘Aljen’ is an endemic Tunisian aromatic plant, largely used in folk medicine. This plant contains bioactive compounds, particularly coumarin derivatives. The objective of the present study was to isolate and characterize some bioactive phytochemical constituents from the extract of the aerial parts and roots of Pituranthos chloranthus. Methods: Different extracts were subjected to column chromatography and eluted with solvent mixtures of increasing polarity (petroleum ether, ethyl acetate and methanol) to isolate five pure Products. The structure of the isolated compound was established using spectroscopic methods (UV, 1 H-NMR, 13 C-NMR, DEPT, HMBC, HSQC, COSY), and HRMS. Results: Isoimperatorin, osthol and oxypeucedanin were isolated from the n-hexane and ethyl acetate extract of the aerial part of the plant. Bergapten and nodakenetin were isolated from the methanolic extract of the roots. Conclusion: Pituranthos chloranthus contains bergapten, isoimperatorin, nodakenetin, osthol and oxypeucedanin which may be responsible for various pharmacological activities of the plant.

Synthesis and Characterisation of Coumarins from H-Cardanol

A facile conversion of H-cardanol (side-chain hydrogenated cardanol, 3-pentadecylphenol; renewable fine chemical from the cashew industry) into value added 3-acylcoumarins, including those incorporating (+) menthol or cholesterol, has been achieved. The H-cardanol coumarin hybrid compounds were low melting, lipophilic and soluble in hydrocarbon solvents. They exhibit UV characteristics typical of 7-alkyl-3-acylcoumarins.

Isolation and Characterization of Coumarin Isolated from Endophyte, Alternaria Species -1 of Crotalaria pallida and Its Apoptotic Action on HeLa Cancer Cell Line

Endophyte, Alternaria species-1 isolated from leaf part of Crotalaria pallida was selected in isolation, identification and purification of coumarin. HPLC, UV-spectrophotometry, FTIR, NMR and XRD studies were carried out on characterization of endophytic fungal coumarin. In vitro apoptotic activity was carried out against HeLa cervical cancer cell lines. The results of MTT studies, acridine staining activity revealed the coumarin as an effective in inducing apoptotic activity in HeLa cells. The coumarin significantly inhibited the proliferation of HeLa cells and it’s a concentration and time dependent manner. Significant elevation of caspase 3 and 9 and activity was observed in coumarin treated HeLa cells but no elevation or activity of caspase 7, 8, 10 was not observed. Coumarin has shown 0.156 μg/ml of significant IC50 value against viable of HeLa cell lines. Thus, coumarin exerts apoptotic activity by caspase dependent apoptosis by enhancing the caspase 3 and 9 and it degraded the DNA (avoided the further replication). This is the first report in internationally that coumarin isolated from endophyte, Alternaria species-1, purified and characterized and its role was identified in apoptotic activity.

Photophysical Properties of Coumarin Compounds in Neat and Binary Solvent Mixtures: Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters

This work studied the fluorescent and solvatochromic properties of coumarin and its derivatives aiming to contribute in the elucidation of the excited state behavior of the molecule in solvent mixtures. This approach has been developed through a set of measurements involving different solvent ratios, which present distinct dielectric constants. The excitation and fluorescence maxima were largely blue-shifted with increasing participation of the organic solvent and the Stokes shifts were unusually low in mixtures with lower solvent polarity parameter, Δf. The emission intensity of coumarin was extremely sensitive to the polarity and the different structural conformations of solvents. These results influenced the spectroscopic behavior and explain the deviation from the linearity of the Lippert-Mataga relationship. The use of fluorescence spectroscopy makes the understanding of the behavior of the systems studied when in the presence of different environments being extremely important for the identification and characterization of coumarin in different pharmaceutical formulations.

Identification and characterisation of coumarins from the roots of Angelica dahurica and their inhibitory effects against cholinesterase

The current research was the first to investigate coumarins and their cholinesterase inhibitory activities from Angelica dahurica roots. The ethanol extract of this species (100μg/ml) possessed inhibitory effects against human acetylcholinesterase (hAChE) and butylcholinesterase (BChE) with IC50 values of 26.40 and 14.71μg/ml, respectively. To evaluate the compounds responsible for these activities, the ethanol extract was chromatographed, which yielded ten coumarins, including isoimperatorin (1), imperatorin (2), senbyakangelicol (3), oxypeucedanin (4), byakangelicol (5), t-OMe-oxypeucedanin hydrate (6), t-OMe-byakangelicin (7), angelol H (8), byakangelicin (9), and oxypeucedanin hydrate (10). Among them, coumarin 5, 7, and 9 showed potent inhibition with IC50s of 46.3, 39.0, and 55.4μM (hAChE) as well as 45.2, 25.6, and 42.4μM (BChE), respectively. Moreover, their inhibition modes against two cholinesterases exhibited noncompetitive. The individual coumarin contents were remarkable differences, especially, oxypeucedanin (4) was the most predominant compound (8710.9μg/g), representing approximately 55.0% of the total content.

The characterisation of coumarins from selected structural classes by electrospray ionisation quadrupole time‐of‐flight tandem mass spectrometry

Electrospray ionisation quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS) has been used for characterisation of a selection of naturally occurring and synthetic coumarins from different structural classes. The product ions, suggested in earlier studies by electrospray ionisation ion trap mass spectrometry (ESI-MS(n)), are unequivocally established for the representative coumarins by virtue of accurate mass measurement. Synthetic coumarins that are unsubstituted in the heterocyclic ring give rise to a major product ion by loss of CO(2), whereas those substituted in the heterocyclic ring generally undergo alternative fragmentation releasing neutral species such as ketene or methyl ketene. Naturally occurring coumarins, unsubstituted in the heterocyclic ring and substituted in the benzene ring with chains or rings of hydrocarbons and oxygen, principally fragment at the side chain releasing unsaturated hydrocarbons. The ESI-QTOF-MS/MS behaviour of some naturally occurring and synthetic quinolines which are structurally similar or fragment similarly are included where appropriate.

Synthesis and characterization of coumarin and dimedone-derived diazabicycles

A series of diazabicyclic derivatives were prepared in three to four steps from p-anisidine and p-nitrobenzaldehyde. The key step of the synthesis involved the acid-catalyzed coupling of 4-aminocoumarin or dimedone derivatives with amino alcohols 3 or 7 to give the ring-opened forms 4, 10, 12 and the ring-closed diazabicycles 5, 6, 9, 11. When 4-alkylaminocoumarins were used as the coupling reagents, the major cyclized product was N-dealkylated diazabicycle 5, rather than the corresponding N-alkylated products. Alternatively, compound 4 was cyclized by DDQ oxidation to produce quinone imine 13. The molecular structures of the synthesized compounds were characterized by X-ray crystallography.

Characterization of Coumarins in Chamomile Preparations Sold in Italy

AbstractThe umbelliferone/herniarin ratio in herbal preparations of chamomile was determined by high-performance thin-layer chromatographic analysis (HPTLC). Plant material was extracted in 150 ml of warm H2O for 10 min, then the residual plant material was extracted with 150 ml of MeOH for 1 h. The herbal preparations containing ligulate florets showed higher content of coumarin if compared to other parts of the flower-heads. The ratio umbelliferonel hemiarin was lower than 1:5 in technological preparations.