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Viennamycins: Lipopeptides Produced by a Streptomyces sp.

Authors
  • Bekiesch, Paulina1
  • Zehl, Martin1
  • Domingo-Contreras, Elizabeth2
  • Martín, Jesús2
  • Pérez-Victoria, Ignacio2
  • Reyes, Fernando2
  • Kaplan, Arthur1
  • Rückert, Christian3
  • Busche, Tobias3
  • Kalinowski, Jörn3
  • Zotchev, Sergey B.1
  • 1 University of Vienna, Austria , (Austria)
  • 2 Fundación Medina, Spain , (Spain)
  • 3 Bielefeld University, Germany , (Germany)
Type
Published Article
Journal
Journal of Natural Products
Publisher
American Chemical Society
Publication Date
Jul 31, 2020
Volume
83
Issue
8
Pages
2381–2389
Identifiers
DOI: 10.1021/acs.jnatprod.0c00152
PMID: 32786880
PMCID: PMC7460545
Source
PubMed Central
License
Unknown

Abstract

Extracts from Streptomyces sp. S4.7 isolated from the rhizosphere of edelweiss, an alpine medicinal plant, exhibited activity against Gram-positive bacteria. LC-HRMS analyses of the extracts resulted in the detection of two unknown, structurally related lipopeptides that were assumed to be responsible for the antibiotic activity. LC-MS guided isolation and structure elucidation of viennamycins A and B ( 1 and 2 ) by HR-MS/MS, 1D and 2D NMR, and Marfey’s analyses revealed them to be novel compounds, with viennamycin A containing cysteic acid, a unique feature for lipopeptides. Tests for antibacterial, antifungal, and cytotoxic activities of purified viennamycins, both with and without divalent cations, did not reveal any bioactivity, suggesting that their biological function, which could not be determined in the tests used, is atypical for lipopeptides. The genome of Streptomyces sp. S4.7 was sequenced and analyzed, revealing the viennamycin biosynthetic gene cluster. Detailed bioinformatics-based analysis of the viennamycin gene cluster allowed elucidation of the biosynthetic pathway for these lipopeptides.

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