Thuggacins, Macrolide Antibiotics Active againstMycobacterium tuberculosis: Isolation from Myxobacteria, Structure Elucidation, Conformation Analysis and Biosynthesis

Chemistry – A European Journal
2007.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Two novel antibiotics, thuggacin A (<jats:bold>1</jats:bold>) and B (<jats:bold>2</jats:bold>), were isolated from the myxobacterium<jats:italic>Sorangium cellulosum</jats:italic>.<jats:bold>1</jats:bold>and<jats:bold>2</jats:bold>are unique thiazole‐containing macrolides with side chains on both sides of the lactone group. Upon standing in solution, thuggacin A (<jats:bold>1</jats:bold>) rearranges by acyl migration of the lactone group to give a mixture with thuggacins B (<jats:bold>2</jats:bold>) and C (<jats:bold>3</jats:bold>). NOEs and vicinal coupling constants within the lactone ring provided distinct data for the generation of a structure model by PM3 calculations, which allowed an analysis of the conformation in solution and the relative configuration of six asymmetric centres. A minor sorangium metabolite was identified as 13‐methyl‐thuggacin A (<jats:bold>4</jats:bold>). Furthermore, two natural thuggacin variants,<jats:bold>5</jats:bold>and<jats:bold>6</jats:bold>, were found in another myxobacterium,<jats:italic>Chondromyces crocatus</jats:italic>. In these variants, one side chain is replaced by a methyl group and a hydroxy group is repositioned to give a primary alcohol at the former methyl site, in an α position with respect to the thiazole ring.<jats:bold>1</jats:bold>proved to be active against clinical isolates and reference strains of<jats:italic>Mycobacterium tuberculosis.</jats:italic>Preliminary studies on the mechanism of action indicate inhibition of the cellular electron‐transport chain.

Knowledge Graph

Similar Paper

Thuggacins, Macrolide Antibiotics Active against<i>Mycobacterium tuberculosis</i>: Isolation from Myxobacteria, Structure Elucidation, Conformation Analysis and Biosynthesis
Chemistry – A European Journal 2007.0
The Thuggacins, Novel Antibacterial Macrolides from Sorangium cellulosum Acting against Selected Gram-positive Bacteria
The Journal of Antibiotics 2007.0
Nannozinones and Sorazinones, Unprecedented Pyrazinones from Myxobacteria
Journal of Natural Products 2014.0
Nannozinones and Sorazinones, Unprecedented Pyrazinones from Myxobacteria
Journal of Natural Products 2014.0
Antibiotics from Gliding Bacteria, LXXX. Chivosazoles A–F: Novel Antifungal and Cytotoxic Macrolides from <i>Sorangium cellulosum</i> (myxobacteria)
Liebigs Annalen 1997.0
Antibiotics from gilding bacteria. No.67. Sorangiolid A, a New Antibiotic Isolated from the Myxobacterium Sorangium cellulosumSo ce 12.
The Journal of Antibiotics 1995.0
Antibiotics from gliding bacteria. No.60. The Tartrolons, New Boron-containing Antibiotics from a Myxobacterium, Sorangium cellulosum.
The Journal of Antibiotics 1995.0
Thiomycalolides:  New Cytotoxic Trisoxazole-Containing Macrolides Isolated from a Marine Sponge Mycale sp.
Journal of Natural Products 1998.0
Antibiotics from Gliding Bacteria, LIX. Disorazoles, Highly Cytotoxic Metabolites from the Sorangicin‐Producing Bacterium <i>Sorangium Cellulosum</i>, Strain So ce12
Liebigs Annalen der Chemie 1994.0
Etnangien, a Macrolide-Polyene Antibiotic from <i>Sorangium cellulosum</i> That Inhibits Nucleic Acid Polymerases
Journal of Natural Products 2007.0