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Nagia, M.; Morgan, I.; Gamel, M. A.; Farag, M. A.; Maximizing the value of indole-3-carbinol, from its distribution in dietary sources, health effects, metabolism, extraction, and analysis in food and biofluids Crit. Rev. Food Sci. Nutr. 1-22, (2023) DOI: 10.1080/10408398.2023.2197065

Indole-3-carbinol (I3C) is a major dietary component produced in Brassica vegetables from glucosinolates (GLS) upon herbivores’ attack. The compound is gaining increasing interest due to its anticancer activity. However, reports about improving its level in plants or other sources are still rare. Unfortunately, I3C is unstable in acidic media and tends to polymerize rendering its extraction and detection challenging. This review presents a multifaceted overview of I3C regarding its natural occurrence, biosynthesis, isolation, and extraction procedure from dietary sources, and optimization for the best recovery yield. Further, an overview is presented on its metabolism and biotransformation inside the body to account for its health benefits and factors to ensure the best metabolic yield. Compile of the different analytical approaches for I3C analysis in dietary sources is presented for the first time, together with approaches for its detection and its metabolism in body fluids for proof of efficacy. Lastly, the chemopreventive effects of I3C and the underlying action mechanisms are summarized. Optimizing the yield and methods for the detection of I3C will assist for its incorporation as a nutraceutical or adjuvant in cancer treatment programs. Highlighting the complete biosynthetic pathway and factors involved in I3C production will aid for its future biotechnological production.
Publikation

S. Ramadan, N.; Fayek, N. M.; M. El-Sayed, M.; S. Mohamed, R.; Wessjohann, L. A.; Farag, M. A.; Averrhoa carambola L. fruit and stem metabolites profiling and immunostimulatory action mechanisms against cyclosporine induced toxic effects in rat model as analyzed using UHPLC/MS-MS-based chemometrics and bioassays Food Chem. Toxicol. 179, 114001, (2023) DOI: 10.1016/j.fct.2023.114001

The Averrhoa carambola L. tree encompasses a myriad of phytochemicals contributing to its nutritional and health benefits. The current study aims at investigating the A. carambola L. the metabolite profile grown in tropical and temperate regions represented by fruit and stem, for the first time using UPLC/MS-based molecular networking and chemometrics. Asides, assessment of the immunostimulatory effect of ripe fruit and stem, was compared in relation to metabolite fingerprints. Eighty metabolites were identified, 8 of which are first-time to be reported including 3 dihydrochalcone-C-glycosides, 4 flavonoids, and one phenolic. Multivariate data analysis revealed dihydrochalcones as origin-discriminating metabolites between temperate and tropical grown fruits. Further, an in vivo immunomodulatory assay in a cyclosporine A-induced rat model revealed a potential immune-enhancing effect as manifested by down-regulation of inflammatory markers (IL-6, INF-γ, IL-1, TLR4, and ESR) concurrent with the up-regulation of CD4 level and the CD4/CD8 ratio. Moreover, both extracts suppressed elevation of liver and kidney functions in serum as well as reduction in oxidative stress with concurrent increased levels of T-protein, albumin, globulin, and A/G ratio. This study pinpoints differences in secondary metabolite profiles amongst A. carambola L. accessions from different origins and organ type and its immunomodulatory action mechanisms.
Publikation

Abdel Shakour, Z. T.; El-Akad, R. H.; Elshamy, A. I.; El Gendy, A. E.-N. G.; Wessjohann, L. A.; Farag, M. A.; Dissection of Moringa oleifera leaf metabolome in context of its different extracts, origin and in relationship to its biological effects as analysed using molecular networking and chemometrics Food Chem. 399, 133948, (2023) DOI: 10.1016/j.foodchem.2022.133948

M. oleifera known as “miracle tree” is increasingly used in nutraceuticals for the reported health effects and nutritional value of its leaves. This study presents the first metabolome profiling of M. oleifera leaves of African origin using different solvent polarities via HR-UPLC/MS based molecular networking followed by multivariate data analyses for samples classification. 119 Chemicals were characterized in both positive and negative modes belonging to 8 classes viz. phenolic acids, flavonoids, peptides, fatty acids/amides, sulfolipids, glucosinolates and carotenoids. New metabolites i.e., polyphenolics, fatty acids, in addition to a new class of sulfolipids were annotated for the first time in Moringa leaves. In vitro anti-inflammatory and anti-aging bioassays of the leaf extracts were assessed and in correlation to their metabolite profile via multivariate data analyses. Kaempferol, quercetin and apigenin-O/C-glycosides, fatty acyl amides and carotenoids appeared crucial for biological activities and leaves origin discrimination.
Publikation

Farag, M. A.; Baky, M. H.; Morgan, I.; Khalifa, M. R.; Rennert, R.; Mohamed, O. G.; El-Sayed, M. M.; Porzel, A.; Wessjohann, L. A.; Ramadan, N. S.; Comparison of Balanites aegyptiaca parts: metabolome providing insights into plant health benefits and valorization purposes as analyzed using multiplex GC-MS, LC-MS, NMR-based metabolomics, and molecular networking RSC Adv. 13, 21471-21493, (2023) DOI: 10.1039/d3ra03141a

Balanites aegyptiaca (L.) Delile (Zygophyllaceae), also known as the desert date, is an edible fruit-producing tree popular for its nutritional and several health benefits. In this study, multi-targeted comparative metabolic profiling and fingerprinting approaches were conducted for the assessment of the nutrient primary and secondary metabolite heterogeneity in different parts, such as leaves, stems, seeds, unripe, and ripe fruits of B. aegyptiaca using nuclear magnetic resonance (NMR), ultra-performance liquid chromatography (UPLC-MS), and gas chromatography mass-spectrometry (GC-MS) based metabolomics coupled to multivariate analyses and in relation to its cytotoxic activities. NMR-based metabolomic study identified and quantified 15 major primary and secondary metabolites belonging to alkaloids, saponins, flavonoids, sugars, and amino and fatty acids. Principal component analysis (PCA) of the NMR dataset revealed α-glucose, sucrose, and isorhamnetin as markers for fruit and stem and unsaturated fatty acids for predominated seeds. Orthogonal projections to latent structure discriminant analysis (OPLS-DA) revealed trigonelline as a major distinctive metabolite in the immature fruit and isorhamnetin as a major distinct marker in the mature fruit. UPLC-MS/MS analysis using feature-based molecular networks revealed diverse chemical classes viz. steroidal saponins, N-containing metabolites, phenolics, fatty acids, and lipids as the constitutive metabolome in Balanites. Gas chromatography-mass spectroscopy (GC-MS) profiling of primary metabolites led to the detection of 135 peaks belonging to sugars, fatty acids/esters, amino acids, nitrogenous, and organic acids. Monosaccharides were detected at much higher levels in ripe fruit and disaccharides in predominate unripe fruits, whereas B. aegyptiaca vegetative parts (leaves and stem) were rich in amino acids and fatty acids. The antidiabetic compounds, viz, nicotinic acid, and trigonelline, were detected in all parts especially unripe fruit in addition to the sugar alcohol D-pinitol for the first time providing novel evidence for B. aegyptiaca use in diabetes. In vitro cytotoxic activity revealed the potential efficacy of immature fruit and seeds as cytotoxic agents against human prostate cancer (PC3) and human colorectal cancer (HCT-116) cell lines. Collectively, such detailed profiling of parts provides novel evidence for B. aegyptiaca medicinal uses.
Publikation

Zayed, A.; Abdelwareth, A.; Mohamed, T. A.; Fahmy, H. A.; Porzel, A.; Wessjohann, L. A.; Farag, M. A.; Dissecting coffee seeds metabolome in context of genotype, roasting degree, and blending in the Middle East using NMR and GC/MS techniques Food Chem. 373, 131452, (2022) DOI: 10.1016/j.foodchem.2021.131452

With a favored taste and various bioactivities, coffee has been consumed as a daily beverage worldwide. The current study presented a multi-faceted comparative metabolomics approach dissecting commercially available coffee products in the Middle East region for quality assessment and functional food purposes using NMR and GC/MS platforms. NMR metabolites fingerprinting led to identification of 18 metabolites and quantification (qNMR) of six prominent markers for standardization purposes. An increase of β-ethanolamine (MEA) reported for the first time, 5-(hydroxymethyl) furfural (5-HMF), concurrent with a reduction in chlorogenic acid, kahweol, and sucrose levels post roasting as revealed using multivariate data analyses (MVA). The diterpenes kahweol and cafestol were identified in green and roasted Coffea arabica, while 16-O-methyl cafestol in roasted C. robusta. Moreover, GC/MS identified a total of 143 metabolites belonging to 15 different chemical classes, with fructose found enriched in green C. robusta versus fatty acids abundance, i.e., palmitic and stearic acids in C. arabica confirming NMR results. These potential results aided to identify novel quality control attributes, i.e., ethanolamine, for coffee in the Middle East region and have yet to be confirmed in other coffee specimens.
Publikation

Hegazi, N. M.; Khattab, A. R.; Frolov, A.; Wessjohann, L. A.; Farag, M. A.; Authentication of saffron spice accessions from its common substitutes via a multiplex approach of UV/VIS fingerprints and UPLC/MS using molecular networking and chemometrics Food Chem. 367, 130739, (2022) DOI: 10.1016/j.foodchem.2021.130739

Saffron is a spice revered for its unique flavor and health attributes often subjected to fraudulence. In this study, molecular networking as a visualization tool for UPLC/MS dataset of saffron and its common substitutes i.e. safflower and calendula (n = 21) was employed for determining genuineness of saffron and detecting its common substitutes i.e. safflower and calendula. Saffron was abundant in flavonol-O-glycosides and crocetin esters versus richness of flavanones/chalcones glycosides in safflower and cinnamates/terpenes in calendula. OPLS-DA identified differences in UPLC/MS profiles of different saffron accessions where oxo-hydroxy-undecenoic acid-O-hexoside was posed as saffron authentication marker and aided in discrimination between Spanish saffron of high quality from its inferior grade i.e. Iranian saffron along with crocetin di-O-gentiobiosyl ester and kaempferol-O-sophoroside. Kaempferol-O-neohesperidoside and N,N,N,-p-coumaroyl spermidine were characteristic safflower metabolites, whereas, calendulaglycoside C and di-O-caffeoyl quinic acid were unique to calendula. UV/VIS fingerprint spectral regions of picrocrocin (230–260 nm) and crocin derivatives (400–470 nm) were posed as being discriminatory of saffron authenticity and suggestive it can replace UPLC/MS in saffrom quality determination.
Publikation

Farag, M. A.; Zayed, A.; Sallam, I. E.; Abdelwareth, A.; Wessjohann, L. A.; Metabolomics-based approach for coffee beverage improvement in the context of processing, brewing methods, and quality attributes Foods 11, 864, (2022) DOI: 10.3390/foods11060864

Coffee is a worldwide beverage of increasing consumption, owing to its unique flavor and several health benefits. Metabolites of coffee are numerous and could be classified on various bases, of which some are endogenous to coffee seeds, i.e., alkaloids, diterpenes, sugars, and amino acids, while others are generated during coffee processing, for example during roasting and brewing, such as furans, pyrazines, and melanoidins. As a beverage, it provides various distinct flavors, i.e., sourness, bitterness, and an astringent taste attributed to the presence of carboxylic acids, alkaloids, and chlorogenic acids. To resolve such a complex chemical makeup and to relate chemical composition to coffee effects, large-scale metabolomics technologies are being increasingly reported in the literature for proof of coffee quality and efficacy. This review summarizes the applications of various mass spectrometry (MS)- and nuclear magnetic resonance (NMR)-based metabolomics technologies in determining the impact of coffee breeding, origin, roasting, and brewing on coffee chemical composition, and considers this in relation to quality control (QC) determination, for example, by classifying defected and non-defected seeds or detecting the adulteration of raw materials. Resolving the coffee metabolome can aid future attempts to yield coffee seeds of desirable traits and best flavor types.
Publikation

Khattab, A. R.; Rasheed, D. M.; El-Haddad, A. E.; Porzel, A.; Wessjohann, L. A.; Farag, M. A.; Assessing phytoequivalency of four Zingiberaceae spices (galangals, turmeric and ginger) using a biochemometric approach: A case study Industrial Crops and Products 188, 115722, (2022) DOI: 10.1016/j.indcrop.2022.115722

The Zingiberaceae family (the ginger family) encompasses featured candidates used extensively in perfume, dyes, medicine as well as food industries. This study provides NMR metabolite fingerprinting, quantification and biological evaluation of four major plants viz. lesser and greater galangal, curcuma and ginger. 1H NMR derived metabolite profiles of the four spices were modeled via orthogonal partial least squares discriminate analysis (OPLS-DA). The cytotoxic activity of the four plants against colon and prostate cancer cell lines and in-vitro cyclooxygenase-1 inhibition activity were also evaluated. A correlation between the plants’ bioactivities and their 1H NMR metabolite profiles was established using OPLS and revealed putative metabolites responsible for these bioactivities. The most active cytotoxic plant was greater galangal due to its enrichment in galangal acetate. In contrast, lesser galangal exhibited the strongest anti-inflammatory action being enriched in 5-hydroxy-7-(4ꞌ-hydroxy-3 ꞌ-methoxyphenyl)-1-phenyl-3-heptanone and kaempferide. This study provides insight on the potential medicinal merit of genus Alpinia comparable to the more explored drugs turmeric and ginger within the Zingiberaceae family.
Publikation

Fayek, N. M.; Mekky, R. H.; Dias, C. N.; Kropf, M.; Heiss, A. G.; Wessjohann, L. A.; Farag, M. A.; UPLC-MS Metabolome-Based Seed Classification of 16 Vicia Species: A Prospect for Phyto-Equivalency and Chemotaxonomy of Different Accessions J. Agr. Food Chem. 69, 5252-5266, (2021) DOI: 10.1021/acs.jafc.0c06054

Seeds of domesticated Vicia (vetch) species (family Fabaceae-Faboideae) are produced and consumed worldwide for their nutritional value. Seed accessions belonging to 16 different species of Vicia—both domesticated and wild taxa—were subjected to a chemotaxonomic study using ultraperformance liquid chromatography–mass spectrometry (UPLC-MS) analyzed by chemometrics. A total of 89 metabolites were observed in the examined Vicia accessions. Seventy-eight out of the 89 detected metabolites were annotated. Metabolites quantified belonged to several classes, viz., flavonoids, procyanidins, prodelphinidins, anthocyanins, stilbenes, dihydrochalcones, phenolic acids, coumarins, alkaloids, jasmonates, fatty acids, terpenoids, and cyanogenics, with flavonoids and fatty acids amounting to the major classes. Flavonoids, fatty acids, and anthocyanins showed up as potential chemotaxonomic markers in Vicia species discrimination. Fatty acids were more enriched in Vicia faba specimens, while the abundance of flavonoids was the highest in Vicia parviflora. Anthocyanins allowed for discrimination between Vicia hirsuta and Vicia sepium. To the best of our knowledge, this is the first report on employing UPLC-MS metabolomics to discern the diversity of metabolites at the intrageneric level among Vicia species.
Publikation

Farag, M. A.; Shakour, Z. T.; Lübken, T.; Frolov, A.; Wessjohann, L. A.; Mahrous, E.; Unraveling the metabolome composition and its implication for Salvadora persica L. use as dental brush via a multiplex approach of NMR and LC–MS metabolomics J. Pharm. Biomed. Anal. 193, 113727, (2021) DOI: 10.1016/j.jpba.2020.113727

Salvadora persica L. (toothbrush tree, Miswak) is well recognized in most Middle Eastern and African countries for its potential role in dental care, albeit the underlying mechanism for its effectiveness is still not fully understood. A comparative MS and NMR metabolomics approach was employed to investigate the major primary and secondary metabolites composition of S. persica in context of its organ type viz., root or stem to rationalize for its use as a tooth brush. NMR metabolomics revealed its enrichment in nitrogenous compounds including proline-betaines i.e., 4-hydroxy-stachydrine and stachydrine reported for the first time in S. persica. LC/MS metabolomics identified flavonoids (8), benzylurea derivatives (5), butanediamides (3), phenolic acids (8) and 5 sulfur compounds, with 21 constituents reported for the first time in S. persica. Principal component analysis (PCA) and hierarchical cluster analysis (HCA) of either NMR or LC/MS dataset clearly separated stem from root specimens based on nitrogenous compounds abundance in roots and is justifying for its preference as toothbrush versus stems. The presence of betaines at high levels in S. persica (9−12 μg/mg dry weight) offers novel insights into its functioning as an osmoprotectant that maintains the hydration of oral mucosa. Additionally, the previously described anti-inflammatory activity of stachydrine along with the antimicrobial effects of sulfonated flavonoids, benzylisothiocynate and ellagic acid derivatives are likely contributors to S. persica oral hygiene health benefits. Among root samples, variation in sugars and organic acids levels were the main discriminatory criterion. This study provides the first standardization of S. persica extract using qNMR for further inclusion in nutraceuticals.

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