TY - JOUR A1 - Vijayakrishnan, Balakumar A1 - Issaree, Arisara A1 - Corilo, Yuri E. A1 - Ferreira, Christina Ramires A1 - Eberlin, Marcos N. A1 - Peter, Martin G. T1 - MSn of the six isomers of (GlcN)(2)(GlcNAc)(2) aminoglucan tetrasaccharides (diacetylchitotetraoses) rules of fragmentation for the sodiated molecules and application to sequence analysis of hetero-chitooligosaccharides JF - Carbohydrate polymers : an international journal devoted to scientific and technological aspects of industrially important polysaccharides N2 - The six possible isomers of di-N-acetylchitotetraoses [AADD, ADDA, ADAD, DADA, DAAD, and DDAA, where D stands for 2-amino-2-deoxy-3-D-glucose (GlcN) and A for 2-acetamido-2-deoxy-beta-D-glucose (GlcNAc)] were analyzed by ESI(+)-MSn. Collision induced dissociation via MSn experiments were performed for the sodiated molecules of m/z 769 [M+Na](+) for each isomer, and fragments were generated mainly by glycosidic bond and cross-ring cleavages. Rules of fragmentation were then established. A reducing end D residue yields the (O.2)A(4) cross-ring [M-59+Na](+) fragment of m/z 710 as the most abundant, whereas isomers containing a reducing end A prefer to lose water to form the [M-18+Na](+) ion of m/z 751, as well as abundant (O.2)A(4) cross-ring [M-101+Na](+) fragments of m/z 668 and B-3 [M-221+Na](+) ions of m/z 548. MS3 of C- and Y-type ions shows analogous fragmentation behaviour that allows identification of the reducing end next-neighbour residue. Due to gas-phase anchimeric assistance, B-type cleavage between the glycosidic oxygen and the anomeric carbon atom is favoured when the glycon is an A residue. Relative ion abundances are generally in the order B >> C > Y, but may vary depending on the next neighbour towards the non-reducing end. These fragmentation rules were used for partial sequence analysis of hetero-chitooligosaccharides of the composition D(2)A(3), D(3)A(3), D(2)A(4), D(4)A(3), and D(3)A(4). KW - Chitosan KW - Fragmentation KW - Oligosaccharides KW - Sequence analysis KW - Tandem mass spectrometry Y1 - 2011 U6 - https://doi.org/10.1016/j.carbpol.2010.04.041 SN - 0144-8617 VL - 84 IS - 2 SP - 713 EP - 726 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Mengibar, M. A1 - Ganan, M. A1 - Miralles, B. A1 - Carrascosa, A. V. A1 - Martinez-Rodriguez, Adolfo J. A1 - Peter, Martin G. A1 - Heras, A. T1 - Antibacterial activity of products of depolymerization of chitosans with lysozyme and chitosanase against Campylobacter jejuni JF - Carbohydrate polymers : an international journal devoted to scientific and technological aspects of industrially important polysaccharides N2 - Chitosan has several biological properties useful for the food industry, but the most attractive is its potential use as a food preservative of natural origin due to its antimicrobial activity against a wide range of food-borne microorganisms. Among food-borne pathogens, Campylobacter jejuni and related species are recognised as the most common causes of bacterial food-borne diarrhoeal disease throughout the world. Recently, it has been demonstrated that campylobacters are highly sensitive to chitosan. Even though chitosan is known to have important functional activities, poor solubility makes them difficult to use in food and biomedical applications. Unlike chitosan, the low viscosity and good solubility of chitosan oligosaccharides (COS) make them especially attractive in an important number of useful applications. In the present work, the effect of different COS on C. jejuni was investigated. Variables such as the physicochemical characteristics of chitosan and the enzyme used in COS preparation were studied. The COS had been fractioned using ultrafiltration membranes and each fraction was characterized regarding its FA and molecular weight distribution. It has been demonstrated that the biological properties of COS on Campylobacter depend on the composition of the fraction analysed. COS prepared by enzymatic hydrolysis with chitosanase were more active against Campylobacter that lysozyme-derived COS, and this behaviour seems to be related with the acetylation of the chains. On the other hand. the 10-30 kDa fraction was the most active COS fraction, independently of the enzyme used for the hydrolysis. These results have shown that COS could be useful as antimicrobial in the control of C. jejuni. KW - Campylobacter jejuni KW - Chitooligosaccharides KW - Chitosanase KW - Lysozyme KW - Depolymerization Y1 - 2011 U6 - https://doi.org/10.1016/j.carbpol.2010.04.042 SN - 0144-8617 VL - 84 IS - 2 SP - 844 EP - 848 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Juma, Wanyama P. A1 - Akala, Hoseah M. A1 - Eyase, Fredrick L. A1 - Muiva, Lois M. A1 - Heydenreich, Matthias A1 - Okalebo, Faith A. A1 - Gitu, Peter M. A1 - Peter, Martin G. A1 - Walsh, Douglas S. A1 - Imbuga, Mabel A1 - Yenesew, Abiy T1 - Terpurinflavone an antiplasmodial flavone from the stem of Tephrosia Purpurea JF - Phytochemistry letters N2 - The stem extract of Tephrosia purpurea showed antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) strains of Plasmodium falciparum with IC(50) values of 10.47 +/- 2.22 mu g/ml and 12.06 +/- 2.54 mu g/ml, respectively. A new prenylated flavone, named terpurinflavone, along with the known compounds lanceolatin A, (-)-semiglabrin and lanceolatin B have been isolated from this extract. The new compound, terpurinflavone, showed the highest antiplasmodial activity with IC(50) values of 3.12 +/- 0.28 mu M (D6) and 6.26 +/- 2.66 mu M (W2). The structures were determined on the basis of spectroscopic evidence. KW - Tephrosia purpurea KW - Leguminosae KW - Stem KW - Flavone KW - Terpurinflavone KW - Antiplasmodial Y1 - 2011 U6 - https://doi.org/10.1016/j.phytol.2011.02.010 SN - 1874-3900 VL - 4 IS - 2 SP - 176 EP - 178 PB - Elsevier CY - Amsterdam ER - TY - JOUR A1 - Yenesew, Abiy A1 - Twinomuhwezi, Hannington A1 - Kiremire, Bernard T. A1 - Mbugua, Martin N. A1 - Gitu, Peter M. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - 8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica N2 - A new pterocarpan (named 8-methoxyneorautenol) was isolated from the acetone ext. of the root bark of Erythrina abyssinica. In addn., the known isoflavonoid derivs. eryvarin L, erycristagallin and shinpterocarpin were identified for the first time from the roots of this plant. The structures were detd. on the basis of spectroscopic evidence. The new compd. showed selective antimicrobial activity against Trichophyton mentagrophytes. The acetone ext. of the root bark of E. abyssinica showed radical scavenging activity towards 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The pterocarpenes, 3-hydroxy-9-methoxy-10-(3,3-dimethylallyl)pterocarpene and erycristagallin, were the most active constituents of the roots of this plant and showing dose-dependent activities similar to that of the std. quercetin. [on SciFinder (R)] Y1 - 2009 UR - http://www.ajol.info/journal_index.php?jid=120&ab=bcse SN - 1011-3924 ER - TY - JOUR A1 - Menezes, Bruno M. A1 - Grigolon, Lisanne A1 - Todorovic, Zoran A1 - Peter, Martin G. A1 - Franco, Telma T. T1 - On the depolymerization of chitosan by papain : a re-assessment Y1 - 2009 ER - TY - JOUR A1 - Issaree, Arisara A1 - Vijayakrishnan, Balakumar A1 - Abdelnur, Patricia V. A1 - Corilo, Yuri E. A1 - Riccio, Maria F. A1 - Sanvido, Gustavo B. A1 - Eberlin, Marcos N. A1 - Peter, Martin G. T1 - Mass spectrometry of aminoglucan oligosaccharides using electrospray ionization MS/MS and MS/MS/MS Y1 - 2009 ER - TY - GEN A1 - Peter, Martin G. A1 - Yenesew, Abiy A1 - Twinomuhwezi, Hannington A1 - Kabaru, Jacques M. A1 - Akala, Hoseah M. A1 - Kiremire, Bernard T. A1 - Heydenreich, Matthias A1 - Eyase, Fredrick A1 - Waters, Norman C. A1 - Walsh, Douglas S. T1 - Antiplasmodial and larvicidal flavonoids from Derris trifoliata N2 - From the dichloromethane-methanol (1:1) extract of the seed pods of Derris trifoliata, a new flavanone derivative (S)-lupinifolin 4´-methyl ether was isolated. In addition, the known flavonoids lupinifolin and rotenone were identified. The structures were determined on the basis of spectroscopic evidence. Lupinfolin showed moderate in vitro antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquineresistant) strains of Plasmodium falciparum. The different parts of this plant showed larvicidal activities against Aedes aegypti and rotenoids were identified as the active principles. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - paper 121 KW - Derris trifoliata KW - Leguminosae KW - Flavanone KW - (S)-Lupinifolin 4´-methyl ether KW - Lupinifolin Y1 - 2009 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus-44614 ER - TY - GEN A1 - Peter, Martin G. A1 - Muiva, Lois M. A1 - Yenesew, Abiy A1 - Derese, Solomon A1 - Heydenreich, Matthias A1 - Akala, Hoseah M. A1 - Eyase, Fredrick A1 - Waters, Norman C. A1 - Mutai, Charles A1 - Keriko, Joseph M. A1 - Walsh, Douglas S. T1 - Antiplasmodial β-hydroxydihydrochalcone from seedpods of Tephrosia elata N2 - From the seedpods of Tephrosia elata, a new β-hydroxydihydrochalcone named (S)-elatadihydrochalcone was isolated. In addition, the known flavonoids obovatachalcone, obovatin, obovatin methyl ether and deguelin were identified. The structures were determined on the basis of spectroscopic evidence. The crude extract and the flavonoids obtained from the seedpods of this plant showed antiplasmodial activities. The literature NMR data on β-hydroxydihydrochalcones is reviewed and the identity of some of the compounds assigned β-hydroxydihydrochalcone skeleton is questioned. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - paper 118 KW - Tephrosia elata KW - Leguminosae KW - Seedpods KW - (S)-Elatadihydrochalcone KW - β-Hydroxydihydrochalcone Y1 - 2009 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus-44437 ER - TY - JOUR A1 - Fettke, Anja A1 - Peikow, Dirk A1 - Peter, Martin G. A1 - Kleinpeter, Erich T1 - Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose N2 - The synthesis of six analogs of N,N;-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, ;; and ;; and of the S-arylglycoside bonds, ; and ;, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies. Y1 - 2009 UR - http://www.sciencedirect.com/science/journal/00404020 U6 - https://doi.org/10.1016/j.tet.2009.03.067 SN - 0040-4020 ER - TY - GEN A1 - Bringmann, Gerhard A1 - Mutanyatta-Comar, Joan A1 - Maksimenka, Katja A1 - Wanjohi, John M. A1 - Heydenreich, Matthias A1 - Brun, Reto A1 - Müller, Werner E. G. A1 - Peter, Martin A1 - Midiwo, Jacob O. A1 - Yenesew, Abiy T1 - Joziknipholones A and B : the First Dimeric Phenylanthraquinones, from the Roots of Bulbine frutescens N2 - From the roots of the African plant Bulbine frutescens (Asphodelaceae), two unprecedented novel dimeric phenylanthraquinones, named joziknipholones A and B, possessing axial and centrochirality, were isolated, together with six known compounds. Structural elucidation of the new metabolites was achieved by spectroscopic and chiroptical methods, by reductive cleavage of the central bond between the monomeric phenylanthraquinone and -anthrone portions with sodium dithionite, and by quantum chemical CD calculations. Based on the recently revised absolute axial configuration of the parent phenylanthraquinones, knipholone and knipholone anthrone, the new dimers were attributed to possess the P-configuration (i.e., with the acetyl portions below the anthraquinone plane) at both axes in the case of joziknipholone A, whereas in joziknipholone B, the knipholone part was found to be M-configured. Joziknipholones A and B are active against the chloroquine resistant strain K1 of the malaria pathogen, Plasmodium falciparum, and show moderate activity against murine leukemic lymphoma L5178y cells. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - paper 104 KW - antimalarial activity KW - chirality KW - joziknipholones KW - natural products KW - structure elucidation Y1 - 2008 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus-42638 ER -