Z. Naturforsch. 2012,
67b, 417 – 420
doi:10.5560/ZNB.2011-0277
Barakacin: A Thiazolyl-indole Alkaloid Isolated from a Ruminal Pseudomonas sp.
Imene
Zendah1,
Khaled A.
Shaaban1,
Elisabeth
Helmke2,
Armin
Maier3,
Heinz H.
Fiebig3, and
Hartmut
Laatsch1
1 Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
2 Alfred-Wegener-Institute for Polar and Marine Research, Am Handelshafen 12, 27570 Bremerhaven, Germany
3 Oncotest GmbH, Am Flughafen 12–14, 79108 Freiburg, Germany
Reprint requests to Prof. Dr. H. Laatsch. Fax: +49(0)551-399660. E-mail:
hlaatsc@gwdg.de
Received December 9, 2011 / published online May 31, 2012
A new thiazolyl-indole alkaloid, barakacin (1), has been isolated from the ruminal bacterium Pseudomonas aeruginosa strain ZIO. On the basis of detailed spectroscopic analyses and comparison with the data of related compounds, its structure has been determined as 2-{4-[bis-(1H-indol-3-yl)-methyl]-thiazol-2-yl}-phenol. In addition, the known compounds phenazine-1-carboxylic acid, 3-(hydroxyacetyl)-indole, indole-3-carbaldehyde, and glycolipid A were isolated. The discovery of compounds with a new skeleton emphasizes the importance for exploring new ecological niches like the rumen of bovines for the detection of new natural products. This paper describes the fermentation, isolation, structure elucidation and biological activities of compound 1.
Key words: Barakacin, Indole Derivatives, Thiazolyl Antibiotics, Ruminal Bacterium