Journal article
Cicadapeptins I and II: New aib-containing peptides from the entomopathogenic fungus Cordyceps heteropoda
Journal of natural products (Washington, D.C.), Vol.68(1), pp.50-55
2005
DOI: 10.1021/np0497189
PMID: 15679316
Abstract
Fermentation extracts of Cordyceps heteropoda (ARSEF #1880), an entomopathogenic fungus isolated from an Australian cicada, yielded a known antifungal compound, myriocin, and a complex microheterogeneous family of novel nonribosomal peptides, each containing two residues of α-aminoisobutyric acid (Aib). Structure elucidation of two major components of the peptide mixture, cicadapeptins I and II (1 and 2), was accomplished by amino acid analysis and various MS, 1-D NMR, and 2-D NMR experiments. Both compounds are acylated at the N-terminus by n-decanoic acid and amidated at the C-terminus by 1,2-diamino-4-methylpentane. The amino acid sequence of cicadapeptin I is N-terminus-Hyp-Hyp-Val-Aib-Gln-Aib-Leu-C-terminus. Ile substitutes for Leu in cicadapeptin II. To our knowledge, this is the first report from fungi of consecutive Hyp or Pro residues in a nonribosomal linear peptide. ROESY data indicated that the cicadapeptins adopt a helical conformation. Cicadapeptins I and II displayed antibacterial activity and limited antifungal activity.
Details
- Title: Subtitle
- Cicadapeptins I and II: New aib-containing peptides from the entomopathogenic fungus Cordyceps heteropoda
- Creators
- Stuart B Krasnoff - Department of Plant Pathology, Cornell University, Ithaca, New York 14853, United StatesRicardo F Reategui - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesMelissa M Wagenaar - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesJames B Gloer - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesDonna M Gibson - USDA-ARS-Plant Protection Research Unit, Ithaca, New York 14853, United States
- Resource Type
- Journal article
- Publication Details
- Journal of natural products (Washington, D.C.), Vol.68(1), pp.50-55
- Publisher
- American Society of Pharmacognosy
- DOI
- 10.1021/np0497189
- PMID
- 15679316
- ISSN
- 0163-3864
- eISSN
- 1520-6025
- Language
- English
- Date published
- 2005
- Academic Unit
- Chemistry
- Record Identifier
- 9984216699502771
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