Abstract
Two new secondary metabolites, labindole A [2-methyl-3-(2-nitroethyl)-3H-indole] (1) and labindole B [2-methyl-3-(2-nitrovinyl)-3H-indole] (2), were isolated from the myxobacterium Labilithrixluteola (DSM 27648T). Additionally, four metabolites 3, 4, 5 and 6 already known from other sources were obtained. Their structures were elucidated from high resolution electrospray ionisation mass spectrometry (HRESIMS) and 1D and 2D nuclear magnetic resonance (NMR) spectroscopy data and their relative configuration was assigned based on nuclear Overhauser effect (NOE) and vicinal ¹H-NMR coupling data. The compounds where tested for biological activities; labindoles A (1) and B (2) exhibited significant activity against Hepatitis C Virus, 9H-carbazole (3), 3-chloro-9H-carbazole (4) and 4-hydroxymethyl-quinoline (5) showed antifungal activities. Moreover, compound 3 had weak to moderate antibacterial activities, while labindoles A (1) and B (2) were devoid of significant antifungal and antibacterial effects.
References
Apr 1, 1990·Archives of Biochemistry and Biophysics·T FrenzelH G Floss
May 22, 1986·Journal of Immunological Methods·F Denizot, R Lang
Nov 1, 1983·Journal of Natural Products·K C LukN Spirt
Aug 1, 1982·The Journal of Antibiotics·K GerthH Reichenbach
Jan 1, 1994·Archives of Virology·A GarozzoE Geremia
Dec 1, 2000·The Journal of Antibiotics·F SasseH Reichenbach
Oct 11, 2002·The Journal of Antibiotics·Larissa VollbrechtPeter von Matt
Jan 1, 1993·Biotechnology Advances·H Reichenbach, G Höfle
Jul 17, 2008·Journal of Enzyme Inhibition and Medicinal Chemistry·Vijayakumar N Sonar, Peter A Crooks
Aug 13, 2011·Hepatology : Official Journal of the American Association for the Study of Liver Diseases·Sandra CiesekEike Steinmann
May 24, 2012·Organic Letters·Alberto PlazaRolf Müller
Jan 8, 2014·Organic & Biomolecular Chemistry·Rahul Kisan KawadeRai-Shung Liu
Jan 28, 2014·Journal of Natural Products·Rolf JansenRolf Müller
Jul 23, 2014·International Journal of Systematic and Evolutionary Microbiology·Eisaku YamamotoKoji Nagai
Oct 9, 2014·Angewandte Chemie·Frank SurupRolf Müller
Dec 17, 2015·MicrobiologyOpen·Kathrin I MohrMarc Stadler
Feb 13, 2016·Journal of Natural Products·Sabrina KarwehlMarc Stadler
Dec 3, 2016·Natural Product Reports·J HerrmannR Müller
Jan 24, 2017·Cell·Chun-Jun GuoMichael A Fischbach
Citations
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Lucky S MulwaMarc Stadler
Dec 12, 2019·Frontiers in Microbiology·Weiming HuKathryn E Bushley
Jun 20, 2020·Archiv der Pharmazie·Yang LiuGuishun Piao
Oct 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Birthe SandargoFrank Surup
Nov 30, 2018·Frontiers in Microbiology·Zina NasfiRafik Bachoual
Jul 22, 2018·Microorganisms·Lucky S Mulwa, Marc Stadler
Dec 2, 2020·Microorganisms·Omar MessaoudiMourad Bendahou
Nov 26, 2020·The Science of the Total Environment·R Sagaya JansiAmal Al-Tamimi
Apr 4, 2021·Antibiotics·Yumei YanMinhui Li
Jun 2, 2021·Folia Microbiologica·Akansha Shrivastava, Rakesh Kumar Sharma
Apr 24, 2019·Journal of Natural Products·Jiao LiMaoluo Gan
Apr 26, 2019·Journal of Natural Products·Omar MessaoudiJoachim Wink
Aug 29, 2021·Pharmaceutics·Mudasir Ahmad BhatArif Tasleem Jan
Oct 2, 2021·Organic & Biomolecular Chemistry·Hugues FouotsaMehdi A Beniddir