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Publikation

Reisberg, M., Arnold, N., Porzel, A., Neubert Reinhard, H. H. & Dräger, B. Malusides, novel glucosylceramides isolated from apple pomace (Malus domestica). Z NATURFORSCH C 73, 33-39, (2018) DOI: org.10.1515/znc-2017-0059

Three new glucosylceramides (GluCers) named malusides I–III (1–3) were isolated from apple (cultivars of Malus domestica) pomace (fruit material remaining after juice extraction). An unusual oxo/hydroxy group pattern within the sphingadienine (d18:2) type sphingoid base was observed. All compounds contained the same α-hydroxylated fatty acid (h16:0) and a β-D-glucose moiety. Their structures were assigned on the basis of one- and two-dimensional (1D and 2D) nuclear magnetic resonance (NMR) spectroscopic analyses and mass spectrometry (MS) measurements.
Publikation

Schober, D., Jacob, D., Wilson, M., Cruz, J. A., Marcu, A., Grant, J. R., Moing, A., Deborde, C., de Figueiredo, L. F., Haug, K., Rocca-Serra, P., Easton, J., Ebbels, T. M. D., Hao, J., Ludwig, C., Günther, U. L., Rosato, A., Klein, M. S., Lewis, I. A., Luchinat, C., Jones, A. R., Grauslys, A., Larralde, M., Yokochi, M., Kobayashi, N., Porzel, A., Griffin, J. L., Viant, M. R., Wishart, D. S., Steinbeck, C., Salek, R. M. & Neumann, S. nmrML: A community supported open data standard for the description, storage, and exchange of NMR data. Anal Chem. 90 , 649–656, (2018) DOI: 10.1021/acs.analchem.7b02795

NMR is a widely used analytical technique with a growing number of repositories available. As a result, demands for a vendor-agnostic, open data format for long-term archiving of NMR data have emerged with the aim to ease and encourage sharing, comparison, and reuse of NMR data. Here we present nmrML, an open XML-based exchange and storage format for NMR spectral data. The nmrML format is intended to be fully compatible with existing NMR data for chemical, biochemical, and metabolomics experiments. nmrML can capture raw NMR data, spectral data acquisition parameters, and where available spectral metadata, such as chemical structures associated with spectral assignments. The nmrML format is compatible with pure-compound NMR data for reference spectral libraries as well as NMR data from complex biomixtures, i.e., metabolomics experiments. To facilitate format conversions, we provide nmrML converters for Bruker, JEOL and Agilent/Varian vendor formats. In addition, easy-to-use Web-based spectral viewing, processing, and spectral assignment tools that read and write nmrML have been developed. Software libraries and Web services for data validation are available for tool developers and end-users. The nmrML format has already been adopted for capturing and disseminating NMR data for small molecules by several open source data processing tools and metabolomics reference spectral libraries, e.g., serving as storage format for the MetaboLights data repository. The nmrML open access data standard has been endorsed by the Metabolomics Standards Initiative (MSI), and we here encourage user participation and feedback to increase usability and make it a successful standard.
Bücher und Buchkapitel

Chini, A., Monte, I., Zamarreño, A. M., Hamberg, M., Lassueur, S., Reymond, P., Weiss, S., Stintzi, A., Schaller, A., Porzel, A., García-Mina, J. M. & Solano, R. An OPR3-independent pathway uses 4,5-didehydrojasmonate for jasmonate synthesis. Nat Chem Biol 14, 171-178, (2018) DOI: 10.1038/nchembio.2540

Biosynthesis of the phytohormone jasmonoyl-isoleucine (JA-Ile) requires reduction of the JA precursor 12-oxo-phytodienoic acid (OPDA) by OPDA reductase 3 (OPR3). Previous analyses of the opr3-1 Arabidopsis mutant suggested an OPDA signaling role independent of JA-Ile and its receptor COI1; however, this hypothesis has been challenged because opr3-1 is a conditional allele not completely impaired in JA-Ile biosynthesis. To clarify the role of OPR3 and OPDA in JA-independent defenses, we isolated and characterized a loss-of-function opr3-3 allele. Strikingly, opr3-3 plants remained resistant to necrotrophic pathogens and insect feeding, and activated COI1-dependent JA-mediated gene expression. Analysis of OPDA derivatives identified 4,5-didehydro-JA in wounded wild-type and opr3-3 plants. OPR2 was found to reduce 4,5-didehydro-JA to JA, explaining the accumulation of JA-Ile and activation of JA-Ile-responses in opr3-3 mutants. Our results demonstrate that in the absence of OPR3, OPDA enters the β-oxidation pathway to produce 4,5-ddh-JA as a direct precursor of JA and JA-Ile, thus identifying an OPR3-independent pathway for JA biosynthesis.

Publikation

Morejon, M. C., Laub, A., Kaluderovic, G. N., Puentes, A. R., Hmedat, A. N., Otero-Gonzalez, A. J., Rivera, D. G. & Wessjohann, L. A. A multicomponent macrocyclization strategy to natural product-like cyclic lipopeptides: synthesis and anticancer evaluation of surfactin and mycosubtilin analogues.  Org Biomol Chem 15, 3628-3637, (2017) DOI: 10.1039/C7OB00459A

A multicomponent macrocyclization strategy towards cyclic lipopeptides is described. The approach relies on the utilization of the Ugi and Passerini multicomponent reactions for the cyclization of peptides and oxo-peptides, and here it is employed for the construction of a small library of analogues of the natural products mycosubtilin and surfactin A. A key feature of this method is the simultaneous incorporation of either one or two exocyclic lipid tails along with the macrocyclic ring closure, which is only possible due to the multicomponent nature of the macrocyclization step. The evaluation of the anticancer activity of the lipopeptide library showed that the installation of a second lipid moiety in the surfactin scaffold leads to a more potent cytotoxicity in cancer cells. This is a new example of the multicomponent reaction potential in rapidly producing natural product analogues for biological screening.
Publikation

El-Sayed, M. T., Wessjohann, L., Porzel, A. & Hilgeroth, A. Diazatruxenes from the condensation reaction of indoles with ninhydrin.  J Heterocycl Chem. 54, 1077-1083, (2017) DOI: 10.1002/jhet.2677

The reaction of indoles with ninhydrin has been reported to provide only 1:1 condensation products (cf. A or 8) that show good antioxidant and anti-inflammatory activity. In the present work, our synthetic challenge for the synthesis of innovative, highly substituted tetra-indole indanes of type 1 via a 4:1 condensation reaction in acetic acid gave two unexpected new products, the diazatruxene derivatives 3 and 4. The novel structures have been characterized by their analytical and spectral data including 1D- and 2D-NMR. With 5-chloroindole, only the known 1:1 reaction.
Publikation

Farag, M. A. Ali., S. E., Hodaya, R. H., El-Seedi, H. R., Sultani, H. N., Laub, A., Eissa, T. F., Abou-Zaid, F. O. F. & Wessjohann, L. A. Molecules 22, 761, (2017) DOI: 10.3390/molecules22050761

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Publikation

Reisberg, M., Arnold, N., Porzel, A., Neubert, R. H. H. & Dräger, B. Production of rare phyto-ceramides from abundant food plant residues. J Agr Food Chem. 65, 1507-1517, (2017) DOI: 10.1021/acs.jafc.6b04275

Ceramides (Cers) are major components of the outermost layer of the skin, the stratum corneum, and play a crucial role in permeability barrier functions. Alterations in Cer composition causing skin diseases are compensated with semisynthetic skin-identical Cers. Plants constitute new resources for Cer production as they contain glucosylceramides (GluCers) as major components. GluCers were purified from industrial waste plant materials, apple pomace (Malus domestica), wheat germs (Triticum sp.), and coffee grounds (Coffea sp.), with GluCer contents of 28.9 mg, 33.7 mg, and 4.4 mg per 100 g of plant material. Forty-five species of GluCers (1–45) were identified with different sphingoid bases, saturated or monounsaturated α-hydroxy fatty acids (C15–28), and β-glucose as polar headgroup. Three main GluCers were hydrolyzed by a recombinant human glucocerebrosidase to produce phyto-Cers (46–48). These studies showed that rare and expensive phyto-Cers can be obtained from industrial food plant residues.
Publikation

Frolov, A., Bilova, T., Paudel, G., Greifenhagen, U., Lukasheva, E., Schilyaev, N., Brauch, D., Soboleva, A., Didio, A., Chantseva, V., Mavropolo-Stolyarenko, G., Grishina, T., Smolikova, G., Osmolovskaya, N., Balcke, G. U., Milkowski, C., Stefanov, V., Medvedev, S., Birkemeyer, C. & Wessjohann, L. A. Impact of plant proteine glycation in ageing and stress response: potential mechanisms, biochemistry and biological role. ActaNaturae 8, 225, (2016)

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Publikation

Treutler, H., Tsugawa, H., Porzel, A., Gorzolka, K., Tissier, A., Neumann, S. & Balcke, G. U. Discovering regulated metabolite families in untargeted metabolomics studies. Anal Chem 88, 8082-8090, (2016) DOI: 10.1021/acs.analchem.6b01569

The identification of metabolites by mass spectrometry constitutes a major bottleneck which considerably limits the throughput of metabolomics studies in biomedical or plant research. Here, we present a novel approach to analyze metabolomics data from untargeted, data-independent LC-MS/MS measurements. By integrated analysis of MS1 abundances and MS/MS spectra, the identification of regulated metabolite families is achieved. This approach offers a global view on metabolic regulation in comparative metabolomics. We implemented our approach in the web application “MetFamily”, which is freely available at http://msbi.ipb-halle.de/MetFamily/. MetFamily provides a dynamic link between the patterns based on MS1-signal intensity and the corresponding structural similarity at the MS/MS level. Structurally related metabolites are annotated as metabolite families based on a hierarchical cluster analysis of measured MS/MS spectra. Joint examination with principal component analysis of MS1 patterns, where this annotation 

Publikation

Alresly, Z., Lindequist, U., Lalk, M., Porzel, A., Arnold, N. & Wessjohann, L. A. Bioactive triterpenes from the fungus Piptoporus betulinus  Piptoporus betulinus. Rec Nat Prod 10, 103-108, (2016)

Phytochemical investigation of the ethyl acetate extract of the fruiting bodies from the basidiomycete  Piptoporus  betulinus led  to  the  isolation  of  a  new  bioactive  lanostane  triterpene  identified  as 3ß-acetoxy-16-hydroxy-24-oxo-5α-lanosta-8-ene-21-oic acid (1). In addition, ten know n triterpenes, polyporenic acid A (5), polyporenic  acid  C (4),  three  derivatives  of  polyporenic  acid  A (8,  10,  11),  betulinic  acid (3), betulin  (2), ergosterol peroxide (6), 9,11-dehydroergosterol peroxide (7), and fomefficinic acid (9), were also isolated from the fungus. All isolated compounds were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria as well as against a fungal strain. The new triterpene and some of the other compounds showed antimicrobial activity against Gram-positive bacteria.

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