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Noleto‐Dias, C.; Farag, M. A.; Porzel, A.; Tavares, J. F.; Wessjohann, L. A.; A multiplex approach of MS, 1D‐, and 2D‐NMR metabolomics in plant ontogeny: A case study on Clusia minor L. organs (leaf, flower, fruit, and seed) Phytochem. Anal. 1-24, (2023) DOI: 10.1002/pca.3300

Introduction: The genus Clusia L. is mostly recognised for the production of prenylated benzophenones and tocotrienol derivatives.Objectives: The objective of this study was to map metabolome variation within Clusia minor organs at different developmental stages.Material and Methods: In total 15 organs/stages (leaf, flower, fruit, and seed) were analysed by UPLC‐MS and 1H‐ and heteronuclear multiple‐bond correlation (HMBC)‐NMR‐based metabolomics.Results: This work led to the assignment of 46 metabolites, belonging to organic acids(1), sugars(2) phenolic acids(1), flavonoids(3) prenylated xanthones(1) benzophenones(4) and tocotrienols(2). Multivariate data analyses explained the variability and classification of samples, highlighting chemical markers that discriminate each organ/stage. Leaves were found to be rich in 5‐hydroxy‐8‐methyltocotrienol (8.5 μg/mg f.w.), while flowers were abundant in the polyprenylated benzophenone nemorosone with maximum level detected in the fully mature flower bud (43 μg/mg f.w.). Nemorosone and 5‐hydroxy tocotrienoloic acid were isolated from FL6 for full structural characterisation. This is the first report of the NMR assignments of 5‐hydroxy tocotrienoloic acid, and its maximum level was detected in the mature fruit at 50 μg/mg f.w. Seeds as typical storage organ were rich in sugars and omega‐6 fatty acids.Conclusion: To the best of our knowledge, this is the first report on a comparative 1D‐/2D‐NMR approach to assess compositional differences in ontogeny studies compared with LC‐MS exemplified by Clusia organs. Results derived from this study provide better understanding of the stages at which maximal production of natural compounds occur and elucidate in which developmental stages the enzymes responsible for the production of such metabolites are preferentially expressed.
Publikation

Noleto-Dias, C.; Picoli, E. A. T.; Porzel, A.; Wessjohann, L. A.; Tavares, J. F.; Farag, M. A.; Metabolomics characterizes early metabolic changes and markers of tolerant Eucalyptus ssp. clones against drought stress Phytochemistry 212, 113715, (2023) DOI: 10.1016/j.phytochem.2023.113715

L’Hér. (Myrtaceae) is one of the economically most important and widely cultivated trees for wood crop purposes worldwide. Climatic changes together with the constant need to expand plantations to areas that do not always provide optimal conditions for plant growth highlight the need to assess the impact of abiotic stresses on eucalypt trees. We aimed to unveil the drought effect on the leaf metabolome of commercial clones with differential phenotypic response to this stress. For this, seedlings of 13 clones were grown at well-watered (WW) and water-deficit (WD) conditions and their leaf extracts were subjected to comparative analysis using ultra-high performance liquid chromatography coupled to mass spectrometry (UPLC-MS) and nuclear magnetic resonance spectroscopy (NMR). UPLC-MS and NMR analyses led to the annotation of over 100 molecular features of classes such as cyclitols, phenolics, flavonoids, formylated phloroglucinol compounds (FPCs) and fatty acids. Multivariate data analysis was employed for specimens\' classifications and markers identification from both platforms. The results obtained in this work allowed us to classify clones differing in drought tolerance. Classification models were validated using an extra subset of samples. Tolerant plants exposed to water deficit accumulated arginine, gallic acid derivatives, caffeic acid and tannins at higher levels. In contrast, stressed drought-sensitive clones were characterised by a significant reduction in glucose, inositol and shikimic acid levels. These changes in contrasting drought response eucalypt pave ways for differential outcomes of tolerant and susceptible phenotypes. Under optimal growth conditions, all clones were rich in FPCs. These results can be used for early screening of tolerant clones and to improve our understanding of the role of these biomarkers in Eucalyptus tolerance to drought stress.
Publikation

Lam, Y. T. H.; Hoppe, J.; Dang, Q. N.; Porzel, A.; Soboleva, A.; Brandt, W.; Rennert, R.; Hussain, H.; Davari, M. D.; Wessjohann, L.; Arnold, N.; Purpurascenines A–C, azepino-indole alkaloids from Cortinarius purpurascens: Isolation, biosynthesis, and activity studies on the 5-HT2A receptor J. Nat. Prod. 86, 1373-1384, (2023) DOI: 10.1021/acs.jnatprod.2c00716

Three previously undescribed azepino-indole alkaloids, named purpurascenines A−C (1−3), together with the new-to-nature 7-hydroxytryptophan (4) as well as two known compounds, adenosine (5) and riboflavin (6), were isolated from fruiting bodies of Cortinarius purpurascens Fr. (Cortinariaceae). The structures of 1−3 were elucidated based on spectroscopic analyses and ECD calculations. Furthermore, the biosynthesis of purpurascenine A (1) was investigated by in vivo experiments using 13C-labeled sodium pyruvate, alanine, and sodium acetate incubated with fruiting bodies of C. purpurascens. The incorporation of 13C into 1 was analyzed using 1D NMR and HRESIMS methods. With [3-13C]-pyruvate, a dramatic enrichment of 13C was observed, and hence a biosynthetic route via a direct Pictet−Spengler reaction between α-keto acids and 7-hydroxytryptophan (4) is suggested for the biosynthesis of purpurascenines A−C (1−3). Compound 1 exhibits no antiproliferative or cytotoxic effects against human prostate (PC-3), colorectal (HCT-116), and breast (MCF-7) cancer cells. An in silico docking study confirmed the hypothesis that purpurascenine A (1) could bind to the 5-HT2A serotonin receptor’s active site. A new functional 5-HT2A receptor activation assay showed no functional agonistic but some antagonistic effects of 1 against the 5-HT-dependent 5-HT2A activation and likely antagonistic effects on putative constitutive activity of the 5-HT2A receptor.
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

Agzamova, M. A.; Mamadalieva, N. Z.; Porzel, A.; Hussain, H.; Dube, M.; Franke, K.; Janibekov, A.; Wessjohann, L. A.; Lehmanniaside, a new cycloartane triterpene glycoside from Astragalus lehmannianus Nat. Prod. Res. 37, 354-359, (2023) DOI: 10.1080/14786419.2021.1969563

Chemical investigation of the aerial parts of Astragalus lehmannianus Bunge (Leguminosae) led to the isolation and identification of a new cycloartane triterpene glycoside – lehmanniaside (2\'-O-acetyl-3-β-O-D-xylopyranosyl-3β,6α,16β,24α-tetrahydroxy-20,25-epoxycycloartane). Its structure was elucidated by means of spectroscopic analysis (HR-MS, 1D and 2D NMR). Bioassays showed that lehmanniaside exhibits weak anthelmintic, antifungal, and cytotoxic activities.
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

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

Otify, A. M.; Serag, A.; Porzel, A.; Wessjohann, L. A.; Farag, M. A.; NMR metabolome-based classification of Cymbopogon Species: a prospect for phyto-equivalency of its different accessions using chemometric tools Food Analytical Methods 15, 2095-2106, (2022) DOI: 10.1007/s12161-022-02257-8

Cymbopogon species are widely distributed worldwide and known for their high essential oil content with potential commercial and medicinal benefits justifying for their inclusion in food and cosmetics. Most species received scant characterization regarding their full complement of bioactive constituents necessary to explain their medicinal activities. In this study, the metabolite profiles of 5 Cymbopogon species, C. citratus, C. flexuosus, C. procerus, C. martini, and C. nardus, were characterized via NMR-based metabolomics. The results of 13 shoot accessions revealed the identification and quantification of 23 primary and secondary metabolites belonging to various compound classes. Multivariate analyses were used for species classification, though found not successful in discrimination based on geographical origin. Nevertheless, C. citratus was found particularly enriched in neral, geranial, (E)-aconitic acid, isoorientin, and caffeic acid as the major characterizing metabolites compared to other species, while an unknown apigenin derivative appeared to discriminate C. martini. The high essential oil and phenolic content in C. citratus emphasizes its strong antioxidant activity, whereas (E)-aconitic acid accounts for its traditional use as insecticide. This study affords the first insight into metabolite compositional differences among Cymbopogon species. Moreover, antimicrobial, insecticidal, antidiabetic, and antioxidant compounds were identified that can be utilized as biomarkers for species authentication.
Publikation

Moura, P. H. B.; Brandt, W.; Porzel, A.; Martins, R. C. C.; Leal, I. C. R.; Wessjohann, L. A.; Structural elucidation of an atropisomeric entcassiflavan-(4β→8)-epicatechin isolated from Dalbergia monetaria L.f. based on NMR and ECD calculations in comparison to experimental data Molecules 27, 2512, (2022) DOI: 10.3390/molecules27082512

A rare dihydoxyflavan-epicatechin proanthocyanidin, entcassiflavan-(4β→8)-epicatechin, was isolated from Dalbergia monetaria, a plant widely used by traditional people from the Amazon to treat urinary tract infections. The constitution and relative configuration of the compound were elucidated by HR-MS and detailed 1D- and 2D-NMR measurements. By comparing the experimental electronic circular dichroism (ECD) spectrum with the calculated ECD spectra of all 16 possible isomers, the absolute configuration, the interflavan linkage, and the atropisomers could be determined.
Publikation

Zabel, S.; Brandt, W.; Porzel, A.; Athmer, B.; Bennewitz, S.; Schäfer, P.; Kortbeek, R. W. J.; Bleeker, P. M.; Tissier, A.; A single cytochrome P450 oxidase from Solanum habrochaites sequentially oxidizes 7-epi-zingiberene to derivatives toxic to whiteflies and various microorganisms Plant J. 105, 1309-1325, (2021) DOI: 10.1111/tpj.15113

Secretions from glandular trichomes potentially protect plants against a variety of aggressors. In the tomato clade of the Solanum genus, glandular trichomes of wild species produce a rich source of chemical diversity at the leaf surface. Previously, 7-epi-zingiberene produced in several accessions of Solanum habrochaites was found to confer resistance to whiteflies (Bemisia tabaci) and other insect pests. Here, we report the identification and characterisation of 9-hydroxy-zingiberene (9HZ) and 9-hydroxy-10,11-epoxyzingiberene (9H10epoZ), two derivatives of 7-epi-zingiberene produced in glandular trichomes of S. habrochaites LA2167. Using a combination of transcriptomics and genetics, we identified a gene coding for a cytochrome P450 oxygenase, ShCYP71D184, that is highly expressed in trichomes and co-segregates with the presence of the zingiberene derivatives. Transient expression assays in Nicotiana benthamiana showed that ShCYP71D184 carries out two successive oxidations to generate 9HZ and 9H10epoZ. Bioactivity assays showed that 9-hydroxy-10,11-epoxyzingiberene in particular exhibits substantial toxicity against B. tabaci and various microorganisms including Phytophthora infestans and Botrytis cinerea. Our work shows that trichome secretions from wild tomato species can provide protection against a wide variety of organisms. In addition, the availability of the genes encoding the enzymes for the pathway of 7-epi-zingiberene derivatives makes it possible to introduce this trait in cultivated tomato by precision breeding.
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