Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10

Abstract

Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1–6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new cyclic pentapeptolide, aselacin D (9); together with a known compound, aselacin C (10), were isolated and characterized from the sponge-derived fungus Acremonium persicinum F10. In addition, two new siderophore analogues chelating gallium ions (Ga3+), Ga (Ⅲ)-acremonpeptide E (7) and Ga (Ⅲ)-acremonpeptide F (8), using isolated acremonpeptides E and F, were prepared. The planar structures of 1–10 were elucidated by HRESIMS and (1D and 2D) NMR. The absolute configurations of amino acids were determined by means of the advanced Marfey’s method and X-ray single-crystal diffraction analysis. X-ray fluorescence (XRF) spectrometer was performed to disclose the elements of compound 1, indicating the existence of aluminum (Al). Al (Ⅲ)-acremonpeptides E (1), Ga (Ⅲ)-acremonpeptides E (5), Al (Ⅲ)-acremonpeptide F (7), and Ga (Ⅲ)-acremonpeptide F (8) displayed high in vitro anti-fungal activities, which are comparable to amphotericin B, against Aspergillus fumigatus and Aspergillus niger.

Marine natural products

“…The aluminium complexes, Al( iii )-acremonpeptide E 254 and Al( iii )-acremonpeptide F 258 exhibited moderate to potent inhibition of two fungal strains. 132 Acremopeptaibols A–F 261–266 were obtained from a further strain of Acremonium , 133 and an Acrostalgamus strain was the source of N -methoxyindolediketopiperazines, acrozines D–G 267–270 . 134 A molecular networking guided strategy was utilised in the isolation of amaurones A–I 271–279 , polyketide pyrones from Amauroascus sp.…”

Recent Advances in Chemistry and Bioactivities of Secondary Metabolites from the Genus Acremonium

“…Six new hydroxamate siderophore cyclohexapeptides, Al (III)-acremonpeptide E (76), acremonpeptide E (77), Fe (III)-acremonpeptide E (78), acremonpeptide F (79), Al (III)acremonpeptide F (80), and Fe (III)-acremonpeptide F (81), and one new cyclic pentapeptolide, aselacin D (82), together with a known compound, aselacin C, were isolated from the sponge-derived fungus A. persicinum F10. Compounds 76 and 80 showed pronounced antifungal activity against Aspergillus fumigatus and A. niger with a shared MIC value of 1 µg/mL, and both showed no cytotoxicity against human embryonic lung fibroblasts (MRC-5) at a concentration of 30 µM [35].…”