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Stoffwechselprodukte von Mikroorganismen

149. Mitteilung. Lysolipin I, ein neues Antibioticum aus Streptomyces violaceoniger

Metabolic products of microorganisms

149. Lysolipin I, a new antibiotic from Streptomyces violaceoniger

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Abstract

From the cultures of Streptomyces violaceoniger, strain Tü 96, two new lipophilic antibioties, Lysolipin I and Lysolipin X were isolated. The latter one is chemically unstable and is easily transformed to Lysolipin I.

The deeply yellow Lysolipin I has a molecular formula C29H24CINO11. It was characterized by the ir, uv, H-nmr and 13C-nmr spectra, which make a quinone structure very probable.

Lysolipin I is active against Gram-positive and Gram-negative bacteria. However, enterobacteriae are only inhibited in high dilution, when the membrane permeation is damaged.

Lysolipin I acts lytically against bacterial cells. Its activity is decreased by several lipids. The site of action is the biosynthesis of bacterial cell walls, an interaction with the carrier lipid for mureine intermediates being probable.

Zusammenfassung

Aus den Kulturen von Streptomyces violaceoniger, Stamm Tü 96, wurden zwei neue lipophile Antibiotica, Lysolipin I und Lysolipin X, isoliert. Das letztere ist sehr unstabil und geht leicht in Lysolipin I über. Das tief gelb gefärbte, optisch aktive Lysolipin I besitzt die Bruttoformel C29H24CINO11 und wurde durch das IR-, UV-, das H-NMR-und das 13C-NMR-Spektrum charakterisiert. Es liegt ein neuartiges Chinon-Antibioticum vor.

Lysolipin I ist hoch wirksam gegen Gram-positive und Gram-negative Bakterien, gegen Enterobakterien allerdings nur bei permeationsgeschädigten Stämmen. Lysolipin I übt auf Bakterienzellen eine lytische Wirkung aus. Sie wird durch verschiedene Lipide antagonisiert. Angriffsort des Antibioticums ist die Biosynthese der Bakterienzellwand. Eine Wechselwirkung mit dem Carrier-Lipid von Murein-Zwischenstufen wurde wahrscheinlich gemacht.

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Authors and Affiliations

  1. Lehrbereich Mikrobiologie, Institut für Biologie II der Universität, Tübingen

    H. Drautz, W. Keller-Schierlein & H. Zähner

  2. Laboratorium für organische Chemie der Eidgenössischen Technischen Hochschule, Zürich

    H. Drautz, W. Keller-Schierlein & H. Zähner

Authors
  1. H. Drautz
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  2. W. Keller-Schierlein
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  3. H. Zähner
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Additional information

148. Mitteilung: W. Keller-Schierlein, A. Klaus, H. U. Naegeli, G. Wolf, H. Zähner: (S)-3-p-Methoxylphenyl-3-acetylaminopropan-1-ol, a new metabolite of an actinomycete. Experientia (Basel) 31, 1001 (1975).

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Drautz, H., Keller-Schierlein, W. & Zähner, H. Stoffwechselprodukte von Mikroorganismen. Arch. Microbiol. 106, 175–190 (1975). https://doi.org/10.1007/BF00446521

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