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Petrosifungins A and B, Novel Cyclodepsipeptides from a Sponge-Derived Strain of Penicillium brevicompactum

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    Petrosifungins A and B, Novel Cyclodepsipeptides from a Sponge-Derived Strain of Penicillium brevicompactum§
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    Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, and Alfred-Wegener-Institut für Polar- und Meeresforschung, Am Handelshafen 12, D-27570 Bremerhaven, Germany
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2004, 67, 3, 311–315
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    https://doi.org/10.1021/np034015x
    Published January 8, 2004
    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    A strain of Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis was investigated for its secondary metabolites. Using fast centrifugal partitioning chromatography (FCPC) two previously unknown cyclodepsipeptides, petrosifungins A (1) and B (2), were isolated, both containing two neighboring units of the nonproteinogenic amino acid l-pipecolinic acid. The absolute configurations of all amino acids were established to be l using GITC derivatization and Marfey's method. Furthermore, the known metabolite brevianamide A (3) was isolated. The likewise known compounds mycophenolic acid (4) and asperphenamate (5) were identified from their spectroscopic properties directly in the extract using HPLC-UV, -MS, and -NMR coupling.

    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy

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    §

     Part 6 in the series Novel Marine Natural Products. For part 5, see ref 5.

    *

     To whom correspondence should be addressed. Tel:  +49-931-888-5323. Fax:  +49-931-888-4755. E-mail:  [email protected].

    †

     Universität Würzburg.

    ‡

     Alfred-Wegener-Institut.

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    Cite this: J. Nat. Prod. 2004, 67, 3, 311–315
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np034015x
    Published January 8, 2004
    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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