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Six Heterocyclic Metabolites from the Myxobacterium Labilithrix Luteola

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2018 Mar 3
PMID 29495640
Citations 14
Authors
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Abstract

Two new secondary metabolites, labindole A [2-methyl-3-(2-nitroethyl)-3H-indole] () and labindole B [2-methyl-3-(2-nitrovinyl)-3H-indole] (), were isolated from the myxobacterium (DSM 27648). Additionally, four metabolites , , and 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 () and B () exhibited significant activity against Hepatitis C Virus, 9-carbazole (), 3-chloro-9-carbazole () and 4-hydroxymethyl-quinoline () showed antifungal activities. Moreover, compound had weak to moderate antibacterial activities, while labindoles A () and B () were devoid of significant antifungal and antibacterial effects.

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References
1.
Plaza A, Garcia R, Bifulco G, Martinez J, Huttel S, Sasse F . Aetheramides A and B, potent HIV-inhibitory depsipeptides from a myxobacterium of the new genus "Aetherobacter". Org Lett. 2012; 14(11):2854-7. DOI: 10.1021/ol3011002. View

2.
Sasse F, Steinmetz H, Schupp T, Petersen F, Memmert K, Hofmann H . Argyrins, immunosuppressive cyclic peptides from myxobacteria. I. Production, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 2002; 55(6):543-51. DOI: 10.7164/antibiotics.55.543. View

3.
Elander R, Mabe J, Hamill R, Gorman M . Metabolism of tryptophans by Pseudomonas aureofaciens. VI. Production of pyrrolnitrin by selected Pseudomonas species. Appl Microbiol. 1968; 16(5):753-8. PMC: 547512. DOI: 10.1128/am.16.5.753-758.1968. View

4.
Garozzo A, Pinizzotto M, Guerrera F, Tempera G, Castro A, Geremia E . Antipoliovirus activity of isothiazole derivatives: mode of action of 5,5'-diphenyl-3,3'-diisothiazole disulfide (DID). Arch Virol. 1994; 135(1-2):1-11. DOI: 10.1007/BF01309761. View

5.
Luk K, Stern L, Weigele M, OBrien R, Spirt N . Isolation and identification of "diazepam-like" compounds from bovine urine. J Nat Prod. 1983; 46(6):852-61. DOI: 10.1021/np50030a005. View