Omanische Heilpflanze im Fokus der Phytochemie IPB-Wissenschaftler und Partner aus Dhofar haben jüngst die omanische Heilpflanze Terminalia dhofarica unter die phytochemische Lupe genommen. Die Pflanze ist reich an…
Geschmack ist vorhersagbar: Mit FlavorMiner. FlavorMiner heißt das Tool, das IPB-Chemiker und Partner aus Kolumbien jüngst entwickelt haben. Das Programm kann, basierend auf maschinellem Lernen (KI), anhand der…
Farag, M. A.; Porzel, A.; Schmidt, J.; Wessjohann, L. A.;Metabolite profiling and fingerprinting of commercial cultivars of Humulus lupulus L. (hop): a comparison of MS and NMR methods in metabolomicsMetabolomics8492-507(2012)DOI: 10.1007/s11306-011-0335-y
Hop (Humulus lupulus L. Cannabaceae) is an economically important crop. In addition to its role in beer brewing, its pharmaceutical applications have been of increasing importance in recent years. Bitter acids (prenylated polyketides), prenylflavonoids and essential oils, are the primary phytochemical components that account for hop medicinal value. An integrated approach utilizing nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques was used for the first large-scale metabolite profiling in Humulus lupulus. Resins and extracts prepared from 13 hop cultivars were analysed using NMR, liquid chromatography (LC)-MS and fourier transform ion cyclotron resonance (FTICR)-MS in parallel and subjected to principal component analysis (PCA). A one pot extraction method, compatible with both MS and NMR measurement was developed to help rule out effects due to differences in extraction protocols. Under optimised conditions, we were able to simultaneously quantify and identify 46 metabolites including 18 bitter acids, 12 flavonoids, 3 terpenes, 3 fatty acids and 2 sugars. Cultivars segregation in PCA plots generated from both LC-MS and NMR data were found comparable and mostly influenced by differences in bitter acids composition among cultivars. FTICR-MS showed inconsistent PCA loading plot results which are likely due to preferential ionisation and also point to the presence of novel isoprenylated metabolites in hop. This comparative metabolomic approach provided new insights for the complementariness and coincidence for these different technology platform applications in hop and similar plant metabolomics projects.
Publikation
Farag, M. A.; Porzel, A.; Wessjohann, L. A.;Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC–MS, LC–MS and 1D NMR techniquesPhytochemistry7660-72(2012)DOI: 10.1016/j.phytochem.2011.12.010
Glycyrrhiza glabra, commonly known as licorice, is a popular herbal supplement used for the treatment of chronic inflammatory conditions and possesses anticancer and antiviral activities. This species contains a plethora of phytochemicals including terpenoids, saponins, flavonoids, polyamines and polysaccharides. The full complement of bioactive compounds has yet to be elucidated, a step necessary in order to explain its medicinal use. There are over 30 species in the Glycyrrhiza genus world-wide, most of which have been little characterized in terms of phytochemical or pharmacological properties. Here, large scale multi-targeted metabolic profiling and fingerprinting techniques were utilized to help gain a broader insight into Glycyrrhiza species chemical composition. UV, MS and NMR spectra of extracted components were connected with NMR, MS, and multivariate analyses data from Glycyrrhiza glabra, Glycyrrhiza uralensis, Glycyrrhiza inflata and Glycyrrhiza echinata. Major peaks in 1H NMR and MS spectra contributing to the discrimination among species were assigned as those of glycyrrhizin, 4-hydroxyphenyl acetic acid, and glycosidic conjugates of liquiritigenin/isoliquiritigenin. Primary metabolites profiling using GC–MS revealed the presence of cadaverine, an amino acid, exclusively found in G. inflata roots. Both LC–MS and NMR were found effective techniques in sample classification based on genetic and or geographical origin as revealed from derived PCA analysis.
Publikation
Pereira, C.; Barreto Júnior, C. B.; Kuster, R. M.; Simas, N. K.; Sakuragui, C. M.; Porzel, A.; Wessjohann, L.;Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)Quím. Nova351123-1126(2012)DOI: 10.1590/S0100-40422012000600010
This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-β-D-glucopyranoside) and a neolignan glucoside, dehydrodiconiferyl alcohol-4-β-D-glucoside. All compounds were identified by a combination of spectroscopic methods (1H, 1D, 2D NMR, 13C and UV), ESI-MS and comparison with the literature data. This is the first report of flavonoids in the genus Guarea and of a neolignan glucoside in the Meliaceae family.
Publikation
Ali, N. A. A.; Sharopov, F. S.; Alhaj, M.; Hill, G. M.; Porzel, A.; Arnold, N.; Setzer, W. N.; Schmidt, J.; Wessjohann, L.;Chemical Composition and Biological Activity of Essential Oil from Pulicaria undulata from YemenNat. Prod. Commun.7257-260(2012)DOI: 10.1177/1934578X1200700238
The chemical composition of the essential oil obtained from the leaves of Pulicaria undulata Gamal Ed Din (syn P. oriental sensu Schwartz and P. jaubertii Gamal Ed Din) was analyzed by GC-MS. Major compounds of P. undulata oil were the oxygenated monoterpenenes, carvotanacetone (91.4%) and 2,5-dimethoxy-p-cymene (2.6.%). The antimicrobial activity of the essential oil was evaluated against six microorganisms, Escherichia coli Pseudomonas aeruginosa, Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, and Candida albicans, using disc diffusion and broth microdilution methods. The oil showed the strongest bactericidal activity against Staphylococcus aureus and methicillin-resistant S. aureus, as well as Candida albicans. The essential oil showed moderate cytotoxic activity against MCF-7 breast tumor cells, with an IC50 of 64.6 ±13.7 μg/mL. Bioautographic assays were used to evaluate the acetylcholinesterase inhibitory effect as well as antifungal activity of the oil against Cladosporium cucumerinum.