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New Peptaibols from Mycogone cervina

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    New Peptaibols from Mycogone cervina†
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    Institute for Biotechnology and Drug Research, Erwin-Schroedinger-Strasse 56, D-67663 Kaiserslautern, Germany, and Department of Organic and Bioorganic Chemistry, Lund University, P.O. Box 124, S-221 00 Lund, Sweden
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2004, 67, 3, 466–468
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    https://doi.org/10.1021/np0302899
    Published January 14, 2004
    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    From cultures of Mycogone cervina, a mycophilic fungus growing on the fruit bodies of ascomycete Paxina acetabulum, two new peptaibols (cervinin, N-Ac-Leu−Aib−Pro−Aib−Leu−Aib−Pro−Ala−Aib−Pro−Val−red-Leu (1) and the red-Leu O-acetylated derivative 2) were isolated. The structures of 1 and 2 were elucidated by spectroscopic techniques. They exhibited weak antibacterial as well as cytotoxic activities. They are the first secondary metabolites described from M. cervina.

    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy

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    †

     Dedicated to the memory of the late Dr. U. Gräfe.

    ‡

     Institute for Biotechnology and Drug Research, Kaiserslautern.

    §

     Lund University.

    *

     To whom correspondence should be addressed. Tel:  +46-462228213. Fax:  +46-462228209. E-mail:  [email protected].

    Cited By

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    This article is cited by 16 publications.

    1. Dong Liu, Hong Lin, Peter Proksch, Xixiang Tang, Zhongze Shao, and Wenhan Lin . Microbacterins A and B, New Peptaibols from the Deep Sea Actinomycete Microbacterium sediminis sp. nov. YLB-01(T). Organic Letters 2015, 17 (5) , 1220-1223. https://doi.org/10.1021/acs.orglett.5b00172
    2. Hilaire V. Kemami Wangun, Hans-Martin Dahse and Christian Hertweck. Epicoccamides B–D, Glycosylated Tetramic Acid Derivatives from an Epicoccum sp. Associated with the Tree Fungus Pholiota squarrosa. Journal of Natural Products 2007, 70 (11) , 1800-1803. https://doi.org/10.1021/np070245q
    3. Thomas Degenkolb,, Tom Gräfenhan,, Helgard I. Nirenberg,, Walter Gams, and, Hans Brückner. Trichoderma brevicompactum Complex: Rich Source of Novel and Recurrent Plant-Protective Polypeptide Antibiotics (Peptaibiotics). Journal of Agricultural and Food Chemistry 2006, 54 (19) , 7047-7061. https://doi.org/10.1021/jf060788q
    4. Varun Pratap Singh, Anup Singh Pathania, Manoj Kushwaha, Samsher Singh, Vandana Sharma, Fayaz A. Malik, Inshad A. Khan, Anil Kumar, Deepika Singh, Ram A. Vishwakarma. 14-Residue peptaibol velutibol A from Trichoderma velutinum : its structural and cytotoxic evaluation. RSC Advances 2020, 10 (52) , 31233-31242. https://doi.org/10.1039/D0RA05780K
    5. Lin Du, April L. Risinger, Carter A. Mitchell, Jianlan You, Blake W. Stamps, Ning Pan, Jarrod B. King, Jean C. Bopassa, Susan I. V. Judge, Zhibo Yang, Bradley S. Stevenson, Robert H. Cichewicz. Unique amalgamation of primary and secondary structural elements transform peptaibols into potent bioactive cell-penetrating peptides. Proceedings of the National Academy of Sciences 2017, 114 (43) https://doi.org/10.1073/pnas.1707565114
    6. César de la Fuente-Núñez, L. Whitmore, B.A. Wallace. Peptaibols. 2013, 150-156. https://doi.org/10.1016/B978-0-12-385095-9.00022-1
    7. Wei Zhang, Xiangpeng Li, Ning Ding, Yingxia Li. Stereoselective synthesis of fully protected (2 S ,4 S ,6 S )‐2‐amino‐6‐hydroxy‐4‐methyl‐8‐oxodecanoic acid (AHMOD). Journal of Peptide Science 2012, 18 (3) , 163-169. https://doi.org/10.1002/psc.1433
    8. Thomas Degenkolb, Hans Brückner. Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing C α ‐Dialkylamino Acids?. Chemistry & Biodiversity 2008, 5 (9) , 1817-1843. https://doi.org/10.1002/cbdv.200890171
    9. Hilaire V. Kemami Wangun, Keishi Ishida, Christian Hertweck. Epicoccalone, a Coumarin‐Type Chymotrypsin Inhibitor, and Isobenzofuran Congeners from an Epicoccum sp. Associated with a Tree Fungus. European Journal of Organic Chemistry 2008, 2008 (22) , 3781-3784. https://doi.org/10.1002/ejoc.200800447
    10. Norbert Stoppacher, Susanne Zeilinger, Markus Omann, Paul‐Gerhard Lassahn, Andreas Roitinger, Rudolf Krska, Rainer Schuhmacher. Characterisation of the peptaibiome of the biocontrol fungus Trichoderma atroviride by liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2008, 22 (12) , 1889-1898. https://doi.org/10.1002/rcm.3568
    11. Nicolas Ruiz, Gaëtane Wielgosz-Collin, Laurence Poirier, Olivier Grovel, Karina Ethel Petit, Mustapha Mohamed-Benkada, Thibaut Robiou du Pont, John Bissett, Philippe Vérité, Gilles Barnathan, Yves François Pouchus. New Trichobrachins, 11-residue peptaibols from a marine strain of Trichoderma longibrachiatum. Peptides 2007, 28 (7) , 1351-1358. https://doi.org/10.1016/j.peptides.2007.05.012
    12. Thomas Degenkolb, Jochen Kirschbaum, Hans Brückner. New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review. Chemistry & Biodiversity 2007, 4 (6) , 1052-1067. https://doi.org/10.1002/cbdv.200790096
    13. Chiara Baldini, Massimo Bellanda, Cristina Peggion, Albert Legrand Djontu, Come Atagua, Stefano Mammi, Claudio Toniolo. Total Synthesis in Solution and Conformational Analysis of the Peptaibol Cervinin and Selected Analogues. Chemistry & Biodiversity 2007, 4 (6) , 1129-1143. https://doi.org/10.1002/cbdv.200790101
    14. L. WHITMORE, B.A. WALLACE. Peptaibols. 2006, 83-88. https://doi.org/10.1016/B978-012369442-3/50017-9
    15. Nina-A. Lehr, Anja Meffert, Luis Antelo, Olov Sterner, Heidrun Anke, Roland W. S. Weber. Antiamoebins, myrocin B and the basis of antifungal antibiosis in the coprophilous fungus Stilbella erythrocephala (syn. S. fimetaria). FEMS Microbiology Ecology 2006, 55 (1) , 105-112. https://doi.org/10.1111/j.1574-6941.2005.00007.x
    16. Nicolas Pradeille, Oliver Zerbe, Kerstin Möhle, Anthony Linden, Heinz Heimgartner. The First Total Synthesis of the PeptaibolHypomurocin A1 and Its Conformation Analysis: an Application of the ‘Azirine/Oxazolone Method’. Chemistry & Biodiversity 2005, 2 (9) , 1127-1152. https://doi.org/10.1002/cbdv.200590084
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2004, 67, 3, 466–468
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np0302899
    Published January 14, 2004
    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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