zur Suche springenzur Navigation springenzum Inhalt springen

Publikationen - Natur- und Wirkstoffchemie

Sortieren nach: Erscheinungsjahr Typ der Publikation

Zeige Ergebnisse 1 bis 9 von 9.

Publikation

Ramadan, N. S.; Wessjohann, L. A.; Mocan, A.; Vodnar, D. C.; El-Sayed, N. H.; El-Toumy, S. A.; Mohamed, D. A.; Aziz, Z. A.; Ehrlich, A.; Farag, M. A.; Nutrient and Sensory Metabolites Profiling of Averrhoa Carambola L. (Starfruit) in the Context of Its Origin and Ripening Stage by GC/MS and Chemometric Analysis Molecules 25, 2423, (2020) DOI: 10.3390/molecules25102423

Averrhoa carambola L. is a tropical tree with edible fruit that grows at different climatic conditions. Despite its nutritive value and reported health benefits, it is a controversial fruit owing to its rich oxalate content. The present study aimed at investigating aroma and nutrient primary metabolites distribution in A. carambola fruits grown in Indonesia, Malaysia (its endemic origin) versus Egypt, and at different ripening stages. Two techniques were employed to assess volatile and non-volatile metabolites including headspace solid-phase micro-extraction (HS-SPME) joined with gas chromatography coupled with mass-spectrometry (GC-MS) and GC-MS post silylation, respectively. Twenty-four volatiles were detected, with esters amounting for the major class of volatiles in Egyptian fruit at ca. 66%, with methyl caproate as the major component, distinguishing it from other origins. In contrast, aldehydes predominated tropically grown fruits with the ether myristicin found exclusively in these. Primary metabolites profiling led to the identification of 117 metabolites viz. sugars, polyols and organic acids. Fructose (38–48%) and glucose (21–25%) predominated sugar compositions in ripe fruits, whereas sorbitol was the major sugar alcohol (2.4–10.5%) in ripe fruits as well. Oxalic acid, an anti-nutrient with potential health risks, was the major organic acid detected in all the studied fruits (1.7–2.7%), except the Malaysian one (0.07%). It increases upon fruit ripening, including considerable amounts of volatile oxalate esters detected via SPME, and which must not be omitted in total oxalate determinations for safety assessments.
Publikation

Farag, M. A.; Abdelwareth, A.; Sallam, I. E.; el Shorbagi, M.; Jehmlich, N.; Fritz-Wallace, K.; Serena Schäpe, S.; Rolle-Kampczyk, U.; Ehrlich, A.; Wessjohann, L. A.; von Bergen, M.; Metabolomics reveals impact of seven functional foods on metabolic pathways in a gut microbiota model J. Adv. Res. 23, 47-59, (2020) DOI: 10.1016/j.jare.2020.01.001

Functional food defined as dietary supplements that in addition to their nutritional values, can beneficially modulate body functions becomes more and more popular but the reaction of the intestinal microbiota to it is largely unknown. In order to analyse the impact of functional food on the microbiota itself it is necessary to focus on the physiology of the microbiota, which can be assessed in a whole by untargeted metabolomics. Obtaining a detailed description of the gut microbiota reaction to food ingredients can be a key to understand how these organisms regulate and bioprocess many of these food components. Extracts prepared from seven chief functional foods, namely green tea, black tea, Opuntia ficus-indica (prickly pear, cactus pear), black coffee, green coffee, pomegranate, and sumac were administered to a gut consortium culture encompassing 8 microbes which are resembling, to a large extent, the metabolic activities found in the human gut. Samples were harvested at 0.5 and 24 h post addition of functional food extract and from blank culture in parallel and analysed for its metabolites composition using gas chromatography coupled to mass spectrometry detection (GC-MS). A total of 131 metabolites were identified belonging to organic acids, alcohols, amino acids, fatty acids, inorganic compounds, nitrogenous compounds, nucleic acids, phenolics, steroids and sugars, with amino acids as the most abundant class in cultures. Considering the complexity of such datasets, multivariate data analyses were employed to classify samples and investigate how functional foods influence gut microbiota metabolisms. Results from this study provided a first insights regarding how functional foods alter gut metabolism through either induction or inhibition of certain metabolic pathways, i.e. GABA production in the presence of higher acidity induced by functional food metabolites such as polyphenols. Likewise, functional food metabolites i.e., purine alkaloids acted themselves as direct substrate in microbiota metabolism.
Publikation

Farag, M. A.; El-Kersh, D. M.; Ehrlich, A.; Choucry, M. A.; El-Seedi, H.; Frolov, A.; Wessjohann, L. A.; Variation in Ceratonia siliqua pod metabolome in context of its different geographical origin, ripening stage and roasting process Food Chem. 283, 675-687, (2019) DOI: 10.1016/j.foodchem.2018.12.118

Carob is a legume tree of a considerable commercial importance for the flavor and sweet industry. In this context, it is cultivated mostly for its pods, which are known for their nutritive value and multiple health benefits. However, metabolite patterns, underlying these properties are still mostly uncharacterized. In this study, the role of geographical origin, ontogenetic changes and thermal processing on the Ceratonia siliqua pod metabolome was assessed by mass spectrometry (MS)-based metabolomics. Thereby, a total of 70 fruits primary metabolites, represented mainly by carbohydrates, organic and amino acids were detected. Analysis of secondary bioactive metabolites assessed by ultra-high-performance liquid chromatography-electrospray ionization high resolution mass spectrometry (UHPLC-ESI-HR-MS) revealed in total 83 signals. The major signals, most significantly contributing in discrimination of C. siliqua specimens were assigned to tannins and flavonoids. PCA models derived from either UHPLC-MS or GC-MS proved to be powerful tools for discrimination of C. siliqua specimens.
Publikation

Farag, M. A.; Otify, A. M.; El-Sayed, A. M.; Michel, C. G.; ElShebiney, S. A.; Ehrlich, A.; Wessjohann, L. A.; Sensory Metabolite Profiling in a Date Pit Based Coffee Substitute and in Response to Roasting as Analyzed via Mass Spectrometry Based Metabolomics Molecules 24, 3377, (2019) DOI: 10.3390/molecules24183377

Interest in developing coffee substitutes is on the rise, to minimizing its health side effects. In the Middle East, date palm (Phoenix dactylifera L.) pits are often used as a coffee substitute post roasting. In this study, commercially-roasted date pit products, along with unroasted and home-prepared roasted date pits, were subjected to analyses for their metabolite composition, and neuropharmacological evaluation in mice. Headspace SPME-GCMS and GCMS post silylation were employed for characterizing its volatile and non-volatile metabolite profile. For comparison to roasted coffee, coffee product was also included. There is evidence that some commercial date pit products appear to contain undeclared additives. SPME headspace analysis revealed the abundance of furans, pyrans, terpenoids and sulfur compounds in roasted date pits, whereas pyrroles and caffeine were absent. GCMS-post silylation employed for primary metabolite profiling revealed fatty acids’ enrichment in roasted pits versus sugars’ abundance in coffee. Biological investigations affirmed that date pit showed safer margin than coffee from its LD50, albeit it exhibits no CNS stimulant properties. This study provides the first insight into the roasting impact on the date pit through its metabolome and its neuropharmacological aspects to rationalize its use as a coffee substitute.
Publikation

Farag, M. A.; Tawfike, A. F.; Donia, M. S.; Ehrlich, A.; Wessjohann, L. A.; Influence of Pickling Process on Allium cepa and Citrus limon Metabolome as Determined via Mass Spectrometry-Based Metabolomics Molecules 24, 928, (2019) DOI: 10.3390/molecules24050928

Brine, the historically known food additive salt solution, has been widely used as a pickling media to preserve flavor or enhance food aroma, appearance, or other qualities. The influence of pickling, using brine, on the aroma compounds and the primary and secondary metabolite profile in onion bulb Allium cepa red cv. and lemon fruit Citrus limon was evaluated using multiplex metabolomics technologies. In lemon, pickling negatively affected its key odor compound “citral”, whereas monoterpene hydrocarbons limonene and γ-terpinene increased in the pickled product. Meanwhile, in onion sulphur rearrangement products appeared upon storage, i.e., 3,5-diethyl-1,2,4-trithiolane. Profiling of the polar secondary metabolites in lemon fruit via ultra-performance liquid chromatography coupled to MS annotated 37 metabolites including 18 flavonoids, nine coumarins, five limonoids, and two organic acids. With regard to pickling impact, notable and clear separation among specimens was observed with an orthogonal projections to least squares-discriminant analysis (OPLS-DA) score plot for the lemon fruit model showing an enrichment of limonoids and organic acids and that for fresh onion bulb showing an abundance of flavonols and saponins. In general, the pickling process appeared to negatively impact the abundance of secondary metabolites in both onion and lemon, suggesting a decrease in their food health benefits.
Publikation

D’Eustacchio, D.; Centorame, M.; Fanfani, A.; Senczuk, G.; Jiménez-Alemán, G. H.; Vasco-Vidal, A.; Méndez, Y.; Ehrlich, A.; Wessjohann, L.; Francioso, A.; Iridoids and volatile pheromones of Tapinoma darioi ants: chemical differences to the closely related species Tapinoma magnum Chemoecology 29, 51-60, (2019) DOI: 10.1007/s00049-018-00275-9

Tapinoma species, and more general dolichoderine ants, are able to produce a variety of volatile compounds they use as chemical defense, alarm, and communication pheromones. Among these, iridoids and volatile ketones are the predominant molecule classes produced by the anal glands of these ants. A recent taxonomic revision of the genus Tapinoma in Europe revealed that the supercolonial species Tapinoma nigerrimum consists of a complex of four cryptic species. Two of them, Tapinoma magnum and the newly described Tapinoma darioi, are closely related species that evolutionary diverged recently. In this work, we determine and characterize the chemical profile of pheromones and volatile compounds of two Tapinoma species. From a chemical point of view, T. darioi and T. magnum show both qualitative and quantitative differences in the pheromones produced, supporting the taxonomic revision of the T. nigerrimum complex. Our data confirm T. darioi and T. magnum as separate species also from a biochemical point of view demonstrating the value of chemotaxonomy as a suitable tool for integrative studies of species differentiation even for closely related taxa.
Publikation

Farag, M. A.; Khattab, A. R.; Ehrlich, A.; Kropf, M.; Heiss, A. G.; Wessjohann, L. A.; Gas Chromatography/Mass Spectrometry-Based Metabolite Profiling of Nutrients and Antinutrients in Eight Lens and Lupinus Seeds (Fabaceae) J. Agr. Food Chem. 66, 4267-4280, (2018) DOI: 10.1021/acs.jafc.8b00369

Lens culinaris and several Lupinus species are two legumes regarded as potential protein resources aside from their richness in phytochemicals. Consequently, characterization of their metabolite composition seems warranted to be considered as a sustainable commercial functional food. This study presents a discriminatory holistic approach for metabolite profiling in accessions of four lentil cultivars and four Lupinus species via gas chromatography/mass spectrometry. A total of 107 metabolites were identified, encompassing organic and amino acids, sugars, and sterols, along with antinutrients, viz., alkaloids and sugar phosphates. Among the examined specimens, four nutritionally valuable accessions ought to be prioritized for future breeding to include Lupinus hispanicus, enriched in organic (ca. 11.7%) and amino acids (ca. 5%), and Lupinus angustifolius, rich in sucrose (ca. 40%), along with two dark-colored lentil cultivars ‘verte du Puy’ and ‘Black Beluga’ enriched in peptides. Antinutrient chemicals were observed in Lupinus polyphyllus, owing to its high alkaloid content. Several species-specific markers were also revealed using multivariate data analyses.
Publikation

Farag, M. A.; Maamoun, A. A.; Ehrlich, A.; Fahmy, S.; Wessjohann, L. A.; Assessment of sensory metabolites distribution in 3 cactus Opuntia ficus-indica fruit cultivars using UV fingerprinting and GC/MS profiling techniques LWT 80, 145-154, (2017) DOI: 10.1016/j.lwt.2017.02.014

Among most propagated and worldwide cacti used for commercial (food) production is Opuntia ficus-indica. The present study aimed at investigating aroma compound and metabolites distribution in cactus fruits from 3 cultivars (cvs): red ‘Rose’, yellow-orange ‘Gialla’ and greenish-white ‘Bianca’ represented by both its pulp and skin samples. Two methods were applied including UV-vis fingerprinting versus gas chromatography coupled to mass spectrometry (GC-MS). Betalains predominated in red fruits, whereas carotenoids and chlorophyll were more abundant in orange and green fruits, respectively, as revealed from their crude extracts UV absorption spectra. Volatiles were profiled using headspace solid-phase micro-extraction (SPME) coupled to GC-MS. 40 Volatiles were identified with short chain aldehydes (25–32%) and acids (25–29%) as the major volatile classes. Cultivars exhibited comparable aroma profiles suggesting that volatiles cannot serve as a chemical fingerprint to distinguish between cvs. Primary metabolites mediating for fruit taste and nutritional value viz. sugars and amino acid were profiled using GC-MS post silylation with 82 identified metabolites. Glucose (62%) and fructose (16%) were found to predominate sugar composition, whereas proline was the major amino acid (3–8%). Multivariate data analyses revealed for betalain and disaccharides enrichment i.e., turanose and sucrose in fruit skin versus proline, talopyranose and lyxopyranose abundance in pulp tissue.
Publikation

Welsch, S. J.; Umkehrer, M.; Kalinski, C.; Ross, G.; Burdack, C.; Kolb, J.; Wild, M.; Ehrlich, A.; Wessjohann, L. A.; Synthesis of substituted imidazolines by an Ugi/Staudinger/aza-Wittig sequence Tetrahedron Lett. 56, 1025-1029, (2015) DOI: 10.1016/j.tetlet.2015.01.043

A series of 2-(acetamide-2-yl)-imidazolines (II) with 5 points of diversity were prepared by an Ugi-4CR–Staudinger–aza-Wittig-sequence starting from simple azidoalkylamines. The intramolecular aza-Wittig cyclization between the iminophosphane and the tertiary amide of the Ugi product (I) was effected by short microwave irradiation. Competitive cyclization to the secondary amide was not relevant, however, in some cases subsequent formation of the bicyclic ortho-amidines (III) was observed.
IPB Mainnav Search