Institut für Chemie

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Browsing Institut für Chemie by Classification "660"

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    Structure elucidation and characterization of novel glycolipid biosurfactant produced by Rouxiella badensis DSM 100043T
    (2025) Harahap, Andre Fahriz Perdana; Conrad, Jürgen; Wolf, Mario; Pfannstiel, Jens; Klaiber, Iris; Grether, Jakob; Hiller, Eric; Vahidinasab, Maliheh; Salminen, Hanna; Treinen, Chantal; Perino, Elvio Henrique Benatto; Hausmann, Rudolf; Harahap, Andre Fahriz Perdana; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Conrad, Jürgen; Department of Organic Chemistry (130b), Institute of Chemistry, University of Hohenheim, Garbenstr. 30, 70599 Stuttgart, Germany; (J.C.); (M.W.); Wolf, Mario; Department of Organic Chemistry (130b), Institute of Chemistry, University of Hohenheim, Garbenstr. 30, 70599 Stuttgart, Germany; (J.C.); (M.W.); Pfannstiel, Jens; Mass Spectrometry Unit, Core Facility Hohenheim, University of Hohenheim, Ottilie-Zeller-Weg 2, 70599 Stuttgart, Germany; (J.P.); (I.K.); Klaiber, Iris; Mass Spectrometry Unit, Core Facility Hohenheim, University of Hohenheim, Ottilie-Zeller-Weg 2, 70599 Stuttgart, Germany; (J.P.); (I.K.); Grether, Jakob; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Hiller, Eric; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Vahidinasab, Maliheh; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Salminen, Hanna; Department of Food Material Science (150g), Institute of Food Science and Biotechnology, University of Hohenheim, Garbenstr. 21/25, 70599 Stuttgart, Germany;; Treinen, Chantal; Cellular Agriculture, TUM School of Life Sciences, Technical University of Munich, 85354 Freising, Germany;; Perino, Elvio Henrique Benatto; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Hausmann, Rudolf; Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany; (A.F.P.H.); (J.G.); (E.H.); (M.V.); (E.H.B.P.); Serianni, Anthony S.
    Microbial biosurfactants have become increasingly attractive as promising ingredients for environmentally friendly products. The reasons for this are their generally good performance and biodegradability, low toxicity, production from renewable raw materials, and benefits for the environment perceived by consumers. In this study, we investigated the chemical structure and properties of a novel glycolipid from a new biosurfactant-producing strain, Rouxiella badensis DSM 100043 T . Bioreactor cultivation was performed at 30 °C and pH 7.0 for 28 h using 15 g/L glycerol as a carbon source. The glycolipid was successfully purified from the ethyl acetate extract of the supernatant using medium pressure liquid chromatography (MPLC). The structure of the glycolipid was determined by one- and two-dimensional ( 1 H and 13 C) nuclear magnetic resonance (NMR) and confirmed by liquid chromatography electrospray ionization mass spectrometry (LC-ESI/MS). NMR analysis revealed the hydrophilic moiety as a glucose molecule and the hydrophobic moieties as 3-hydroxy-5-dodecenoic acid and 3-hydroxydecanoic acid, which are linked with the glucose by ester bonds at the C2 and C3 positions. Surface tension measurement with tensiometry indicated that the glucose–lipid could reduce the surface tension of water from 72.05 mN/m to 24.59 mN/m at 25 °C with a very low critical micelle concentration (CMC) of 5.69 mg/L. Moreover, the glucose–lipid demonstrated very good stability in maintaining emulsification activity at pH 2–8, a temperature of up to 100 °C, and a NaCl concentration of up to 15%. These results show that R. badensis DSM 100043 T produced a novel glycolipid biosurfactant with excellent surface-active properties, making it promising for further research or industrial applications.
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    Publication
    Synthesis, characterization, theoretical and experimental anticancer evaluation of novel cocrystals of 5-fluorouracil and Schiff bases against SW480 colorectal carcinoma
    (2023) Jubeen, Farhat; Jabeen, Ishrat; Aftab, Usman; Noor, Sadia; e Hareem, Mah ; Sultan, Misbah; Kazi, Mohsin
    The chemotherapeutic agent known as 5-fluorouracil (5-FU) is an artificial fluoropyrimidine antimetabolite that has been widely used for its antineoplastic properties. Cocrystals of 5-fluorouracil (5-FU) with five different Schiff bases (benzylidene-urea (BU), benzylidene-aniline (BA), salicylidene-aniline (SA), salicylidene-phenylhydrazine (SPH), and para-hydroxy benzylideneaniline (HBA)) are reported in this study. The newly synthesized cocrystals were analyzed by FTIR and PXRD. In this study, we investigated the antitumor efficacy of 5-FU derivatives in SW480 colon cancer cells via MTT assay at varying dose concentrations. Molecular docking was performed to predict the binding mechanism of TS with various 5-FU complexes. FTIR revealed the presence of respective functional groups in the prepared cocrystals. The frequencies (v) of N-H (3220.24 cm−1) and carbonyl groups (1662.38 cm−1) in the spectrum of 5-FU shifted considerably in all derivative cocrystal new interactions. There was a noticeable transformation in the PXRD peak of 5-FU at 2θ = 28.37° in all derivatives. The novelty of the present study lies in the fact that 5-FU-BA showed an anticancer potential IC50 (6.4731) far higher than that of 5-FU (12.116), almost comparable to that of the reference drug doxorubicin (3.3159), against SW480 cancel cell lines, followed by 5-Fu-HBA (10.2174). The inhibition rates of 5-FU-BA and 5-FU-HBA were highest among the derivatives (99.85% and 99.37%, respectively) in comparison with doxorubicin (97.103%). The results revealed that the synthesized 5-FU cocrystals have promising antitumor efficacy compared with previously reported 5-FU and 5-FU. The activities of the cocrystals were rationalized by a molecular modeling approach to envisage binding modes with the target cancer protein.