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Laub, A.; Sendatzki, A.-K.; Palfner, G.; Wessjohann, L. A.; Schmidt, J.; Arnold, N. HPTLC-DESI-HRMS-Based Profiling of Anthraquinones in Complex Mixtures—A Proof-of-Concept Study Using Crude Extracts of Chilean Mushrooms Foods 9, 156, (2020) DOI: 10.3390/foods9020156

High-performance thin-layer chromatography (HPTLC) coupled with negative ion desorption electrospray ionization high-resolution mass spectrometry (DESI-HRMS) was used for the analysis of anthraquinones in complex crude extracts of Chilean dermocyboid Cortinarii. For this proof-of-concept study, the known anthraquinones emodin, physcion, endocrocin, dermolutein, hypericin, and skyrin were identified by their elemental composition. HRMS also allowed the differentiation of the investigated anthraquinones from accompanying compounds with the same nominal mass in the crude extracts. An investigation of the characteristic fragmentation pattern of skyrin in comparison with a reference compound showed, exemplarily, the feasibility of the method for the determination of these coloring, bioactive and chemotaxonomically important marker compounds. Accordingly, we demonstrate that the coupling of HPTLC with DESI-HRMS represents an advanced and efficient technique for the detection of anthraquinones in complex matrices. This analytical approach may be applied in the field of anthraquinone-containing food and plants such as Rheum spp. (rhubarb), Aloe spp., Morinda spp., Cassia spp. and others. Furthermore, the described method can be suitable for the analysis of anthraquinone-based colorants and dyes, which are used in the food, cosmetic, and pharmaceutical industry.

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.

Noviana, Z.; Vieira, S.; Pascual, J.; Fobofou, S. A. T.; Rohde, M.; Spröer, C.; Bunk, B.; Overmann, J. Hypericibacter terrae gen. nov., sp. nov. and Hypericibacter adhaerens sp. nov., two new members of the family Rhodospirillaceae isolated from the rhizosphere of Hypericum perforatum Int J Syst Evol Microbiol 70, 1850-1860, (2020) DOI: 10.1099/ijsem.0.003983

Two strains of the family Rhodospirillaceae were isolated from the rhizosphere of the medicinal plant Hypericum perforatum. Cells of both strains were Gram-stain-negative, motile by means of a single polar flagellum, non-spore-forming, non-capsulated, short rods that divided by binary fission. Colonies were small and white. Strains R5913T and R5959T were oxidase-positive, mesophilic, neutrophilic and grew optimally without NaCl. Both grew under aerobic and microaerophilic conditions and on a limited range of substrates with best results on yeast extract. Major fatty acids were C19 : 0 cyclo ω8c and C16 : 0; in addition, C18 : 1ω7c was also found as a predominant fatty acid in strain R5913T. The major respiratory quinone was ubiquinone 10 (Q-10). The DNA G+C contents of strains R5913T and R5959T were 66.0 and 67.4 mol%, respectively. 16S rRNA gene sequence comparison revealed that the closest relatives (<92 % similarity) of the strains are Oceanibaculum pacificum MCCC 1A02656T, Dongia mobilis CGMCC 1.7660T, Dongia soli D78T and Dongia rigui 04SU4-PT. The two novel strains shared 98.6 % sequence similarity and represent different species on the basis of low average nucleotide identity of their genomes (83.8 %). Based on the combined phenotypic, genomic and phylogenetic investigations, the two strains represent two novel species of a new genus in the family Rhodospirillaceae , for which the name Hypericibacter gen. nov. is proposed, comprising the type species Hypericibacter terrae sp. nov. (type strain R5913T=DSM 109816T=CECT 9472T) and Hypericibacter adhaerens sp. nov. (type strain R5959T=DSM 109817T=CECT 9620T).

Tchatchouang Noulala, C. G.; Fotso, G. W.; Rennert, R.; Lenta, B. N.; Sewald, N.; Arnold, N.; Happi, E. N.; Ngadjui, B. T. Mesomeric form of quaternary indoloquinazoline alkaloid and other constituents from the Cameroonian Rutaceae Araliopsis soyauxii Engl. Biochem Syst Ecol 91, 104050, (2020) DOI: 10.1016/j.bse.2020.104050

A mesomeric form of quaternary indoloquinazoline alkaloid, soyauxinium chloride (1) was obtained through the chemical investigation of stem bark and roots of Araliopsis soyauxii Engl. [syn. Vepris soyauxii (Engl.) Mziray] (Rutaceae) together with fifteen known compounds, including three furoquinoline alkaloids, three 2-quinolones, two limonoids, two triterpenes, two steroids, a coumarin, an acridone alkaloid, and a flavonoid glycoside. Their structures were established by comprehensive spectroscopic and spectrometric analyses (1D and 2D NMR, ESI-HR-MS) and by comparison with previously reported data. 13C NMR data of araliopsinine are also reported here for the first time. The isolated compounds were screened in vitro for their effects on the viability of two different human cancer cell lines, namely prostate PC-3 adenocarcinoma cells and colorectal HT-29 adenocarcinoma cells. However, none of the tested compounds exhibited strong anti-proliferative or cytotoxic activities, to either prostate PC-3 cells or colon HT-29 cells. At 100 μM, the furoquinoline maculine showed a slightly increased anti-proliferative effect, however, exclusively on HT-29 cells. The chemotaxonomic significance of the isolated compounds has also been discussed.
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Nugraha, A. S.; Untari, L. F.; Laub, A.; Porzel, A.; Franke, K.; Wessjohann, L. A. Anthelmintic and antimicrobial activities of three new depsides and ten known depsides and phenols from Indonesian lichen: Parmelia cetrata Ach. Nat Prod Res (2020) DOI: 10.1080/14786419.2020.1761361

An extensive phytochemical study of a foliose lichen from Indonesia, Parmelia cetrata, resulted in the successful isolation of 13 phenol and depside derivatives (1–13) including the previously unreported depsides 3′-hydroxyl-5′-pentylphenyl 2,4-dihydroxyl-6-methylbenzoate (7), 3′-hydroxyl-5′-propylphenyl 2,4-dihydroxyl-6-methylbenzoate (8) and 3′-hydroxyl-5′-methylphenyl 2-hydroxyl-4-methoxyl-6-propylbenzoate (9). The anti-infective activity of isolated compounds was evaluated against the gram-negative bacterium Aliivibrio fischeri and the nematode Caenorhabditis elegans. 2,4-Dihydroxyl-6-pentylbenzoate (5) and lecanoric acid (6) induced growth inhibition of A. fischeri with inhibition values of 49% and 100% at a concentration of 100 µM, respectively. The antibacterial activity might be due to their free carboxyl group. A phenolic group at C4 also contributed to the antimicrobial activity of the depsides as shown for compounds 7 and 8, which caused 89% and 96% growth inhibition at 100 µM, respectively. Lecanoric acid (6) in addition possesses significant anthelmintic effects causing 80% mortality of C. elegans at 100 µg/mL.

Holzmeyer, L.; Hartig, A.-K.; Franke, K.; Brandt, W.; Muellner-Riehl, A. N.; Wessjohann, L. A.; Schnitzler, J. Evaluation of plant sources for antiinfective lead compound discovery by correlating phylogenetic, spatial, and bioactivity data Proc Natl Acad Sci USA 117, 12444-12451, (2020) DOI: 10.1073/pnas.1915277117

The continued high rates of using antibiotics in healthcare and livestock, without sufficient new compounds reaching the market, has led to a dramatic increase in antimicrobial resistance, with multidrug-resistant bacteria emerging as a major public health threat worldwide. Because the vast majority of antiinfectives are natural products or have originated from them, we assessed the predictive power of plant molecular phylogenies and species distribution modeling in the search for clades and areas which promise to provide a higher probability of delivering new antiinfective compound leads. Our approach enables taxonomically and spatially targeted bioprospecting and supports the battle against the global antimicrobial crisis.

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.

Deising, H. B.; Amorim, R.; De Oliveira Silva, A.; Raschke, A.; Eisermann, I.; Wirsel, S. G. R.; Csuk, R.; Schmitz, L. M.; Arnold, N. Antagonistic Microorganisms in Plant Protection: Consumers’ Friends or Foes? (Deising, H. B. et al., eds.). Modern Fungicides and Antifungal Compounds IX, 217-228, (2020) ISBN: 978-3-941261-16-7


Farag, M. A.; El Senousy, A. S.; El-Ahmady, S. H.; Porzel, A.; Wessjohann, L. A. Comparative metabolome-based classification of Senna drugs: a prospect for phyto-equivalency of its different commercial products Metabolomics 15, 80, (2019) DOI: 10.1007/s11306-019-1538-x

IntroductionThe demand to develop efficient and reliable analytical methods for the quality control of nutraceuticals is on the rise, together with an increase in the legal requirements for safe and consistent levels of its active principles.ObjectiveTo establish a reliable model for the quality control of widely used Senna preparations used as laxatives and assess its phyto-equivalency.MethodsA comparative metabolomics approach via NMR and MS analyses was employed for the comprehensive measurement of metabolites and analyzed using chemometrics.ResultsUnder optimized conditions, 30 metabolites were simultaneously identified and quantified including anthraquinones, bianthrones, acetophenones, flavonoid conjugates, naphthalenes, phenolics, and fatty acids. Principal component analysis (PCA) was used to define relative metabolite differences among Senna preparations. Furthermore, quantitative 1H NMR (qHNMR) was employed to assess absolute metabolites levels in preparations. Results revealed that 6-hydroxy musizin or tinnevellin were correlated with active metabolites levels, suggesting the use of either of these naphthalene glycosides as markers for official Senna drugs authentication.ConclusionThis study provides the first comparative metabolomics approach utilizing NMR and UPLC–MS to reveal for secondary metabolite compositional differences in Senna preparations that could readily be applied as a reliable quality control model for its analysis.

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.
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