AI Article Synopsis
- Fungal species in the genus studied produce a variety of secondary metabolites, including two new peptaibols, ampullosporin F and ampullosporin G, alongside five known compounds.
- The structures of ampullosporin F and G were determined using advanced analytical techniques, revealing differences in amino acid sequences that affect their biological activities.
- Both new compounds showed promising antifungal properties and significant anticancer effects in human prostate and colorectal cancer cell lines, with a molecular docking study conducted to explore their structure-activity relationships.
Article Abstract
Fungal species of genus are rich sources of diverse secondary metabolites (e.g., alkaloids, peptaibols), which exhibit variable biological activities. Herein, two new peptaibols, named ampullosporin F () and ampullosporin G (), together with five known compounds, ampullosporin A (), peptaibolin (), chrysosporide (), c(Trp-Ser) () and c(Trp-Ala) (), have been isolated from the culture of Damon strain KSH534. The structures of and were elucidated based on ESI-HRMS experiments and intense 1D and 2D NMR analyses. The sequence of ampullosporin F () was determined to be Ac-Trp-Ala-Aib-Aib-Leu-Aib-Gln-Aib-Aib-Aib-GluOMe-Leu-Aib-Gln-Leuol, while ampullosporin G () differs from by exchanging the position of Gln with GluOMe. Furthermore, the total synthesis of and was carried out on solid-phase to confirm the absolute configuration of all chiral amino acids as L. In addition, ampullosporin F () and G () showed significant antifungal activity against and , but were inactive against . Cell viability assays using human prostate (PC-3) and colorectal (HT-29) cancer cells confirmed potent anticancer activities of and . Furthermore, a molecular docking study was performed in silico as an attempt to explain the structure-activity correlation of the characteristic ampullosporins (-).
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8657771 | PMC |
| http://dx.doi.org/10.3390/ijms222312718 | DOI Listing |
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Article Synopsis
- Fungal species in the genus studied produce a variety of secondary metabolites, including two new peptaibols, ampullosporin F and ampullosporin G, alongside five known compounds.
- The structures of ampullosporin F and G were determined using advanced analytical techniques, revealing differences in amino acid sequences that affect their biological activities.
- Both new compounds showed promising antifungal properties and significant anticancer effects in human prostate and colorectal cancer cell lines, with a molecular docking study conducted to explore their structure-activity relationships.
Correction: An EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles.
Phys Chem Chem Phys
October 2019
Dipartimento di Scienze Chimiche, Università degli Studi di Padova, 35131 Padova, Italy.
Correction for 'An EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles' by Marco Bortolus et al., Phys. Chem.
View Article and Find Full Text PDFThe solid-state NMR measurements play an indispensable role in studies of interactions between biological membranes and peptaibols, which are amphipathic oligopeptides with a high abundance of alpha-aminobutyric acid (Aib). The solid-state NMR investigations are important in establishing the molecular models of the pore forming and antimicrobial properties of peptaibols, but rely on certain simplifications. Some of the underlying assumptions concern the parameters describing the 15N NMR chemical shielding tensor (CST) of the amide nitrogens in Aib and in conventional amino acids.
View Article and Find Full Text PDFAn EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles.
Phys Chem Chem Phys
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Ampullosporin A is a medium-length (14-amino acid long) hydrophobic peptide of the peptaibol family. In this work, electron paramagnetic resonance and circular dichroism spectroscopies were applied to study the interaction of synthetic ampullosporin A and three spin-labeled analogs with small unilamellar vesicles and bicelles. Zwitterionic vesicles were used to investigate the conformation and the penetration depth of the peptide at room temperature.
View Article and Find Full Text PDFSynthesis and conformational properties of a TOAC doubly spin-labeled analog of the medium-length, membrane active peptaibiotic ampullosporin A as revealed by CD, fluorescence, and EPR spectroscopies.
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Institute of Chemical Kinetics and Combustion, Novosibirsk, 630090, Russian Federation.
We describe the challenging solid-phase synthesis of the medium-length (14 amino-acid residues) peptaibiotic ampullosporin A, originally extracted from the fungus Sepedonium ampullosporum, and an analog doubly spin labeled (at positions 3 and 13) with the stable nitroxyl free-radical 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-4-carboxylic acid (TOAC). The results of a circular dichrosim investigation in methanol strongly support the view that both peptides are essentially right-handed helical, in particular endowed with a large population of α-helical conformers. We also observed a significant quenching effect from the TOAC(3) nitroxyl radical on the fluorescence of Trp(1), compatible with that expected when both residues are closely located on the same helix segment.
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