Identification and Characterization of a Library of Microheterogeneous Cyclohexadepsipeptides from the Fungus Isaria
| Autor: | R. S. Ranganayaki, Hemalatha Balaram, Monnanda P. Bopanna, S. Raghothama, Padmanabhan Balaram, M. C. Srinivasan, Varatharajan Sabareesh |
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| Rok vydání: | 2007 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Stereochemistry Electrospray ionization Plasmodium falciparum Pharmaceutical Science Mass spectrometry Analytical Chemistry Antimalarials Residue (chemistry) Depsipeptides Drug Discovery Animals Molecule Amino Acid Sequence Peptide sequence Pharmacology chemistry.chemical_classification Molecular Structure biology Organic Chemistry Nuclear magnetic resonance spectroscopy biology.organism_classification Cyclic peptide Complementary and alternative medicine chemistry Isaria sinclairii Molecular Medicine Mitosporic Fungi |
| Zdroj: | Journal of Natural Products. 70:715-729 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np060532e |
| Popis: | Ten new cyclic hexadepsipeptides, six isariins and four isaridins, from the fungus Isaria have been identified and characterized by high-performance liquid chromatography, coupled to tandem electrospray ionization mass spectrometry (LC-ESIMS/MS). The isariins possess a beta-hydroxy acid residue and five alpha-amino acids, while isaridins contain a beta-amino acid, an alpha-hydroxy acid, and four alpha-amino acids. One- and two-dimensional NMR spectroscopy confirmed the chemical identity of some of the isariin fractions. Mass spectral fragmentation patterns of [M + H]+ ions reveal clear diagnostic fragment ions for the isariins and isaridins. Previously described cyclic depsipeptides, isarfelins from Isaria felina (Guo, Y. X.; Liu, Q. H.; Ng, T. B.; Wang H. X. Peptides 2005, 26, 2384), are now reassigned as members of the isaridin family. Examination of isaridin sequences revealed significant similarities with cyclic hexadepsipeptides such as destruxins and roseotoxins. The structure of an isariin (isariin A) investigated by NMR spectroscopy indicated the presence of a hybrid alphabeta C11 turn, formed by the beta-hydroxy acid and glycine residues and a D Leu-L Ala type II' beta-turn. Additionally, the inhibitory effect of isariins and an isaridin on the intra-erythrocytic growth of Plasmodium falciparum is presented. |
| Databáze: | OpenAIRE |
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