New Cyclohexadepsipeptides from an Entomogenous Fungus <i>Fusarium proliferatum</i> and Their Cytotoxicity and Autophagy‐Inducing Activity

Tian, Jin; Han, Junjie; Zhang, Xue; He, Liming; Zhang, Yongjie; Li, Bao; Liu, Hongwei

doi:10.1002/cbdv.201500262

Cited by 8 publications

(5 citation statements)

References 13 publications

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“…The above NMR data suggested that compound 4 possessed three N Me amino acid and three 2-hydroxycarboxylic acid units. Comparison of the NMR data of 4 with those reported suggested that 4 belonged to a group of enniatins . In addition, the molecular weight of 4 is 14 mass units higher than MK1688 ( 9 ), indicating one additional methyl group in 4 .…”

Section: Resultsmentioning

confidence: 61%

Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus Fusarium sp.

et al. 2022

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In this work, four new cyclodepsipeptides, fusarihexins C–E (1–3) and enniatin Q (4), four new cyclopentane derivatives, fusarilins A–D (5–8), together with eight known compounds (9–16), were isolated from cultures of the endophytic fungus Fusarium sp. The structures of the isolated compounds were elucidated by analysis of HRMS and NMR spectroscopic data. The absolute configurations were determined using Marfey’s method, a modified Mosher’s method, single-crystal X-ray diffraction analysis, and ECD analysis. The antitumor activities of the isolated compounds in vitro were evaluated. Cyclodepsipeptides displayed cytotoxicities against the Huh-7, MRMT-1, and HepG-2 cell lines. Compounds 4, 9, 10, and 12 with IC50 values of 1.0–9.1 μM exhibited the most potent cytotoxicities against the three cell lines as compared to the positive control-5-fluorouracil. Compounds 1–3 and 11 exhibited moderate cytotoxic activities (IC50 values of 10.7–20.1 μM).

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Section: Resultsmentioning

confidence: 61%

Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus Fusarium sp.

et al. 2022

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“…Beauvenniatin F ( 105 ) was isolated from an entomogenous fungus Fusarium proliferatum from the cadaver of an unidentified insect collected in Tibet, and exhibited strong cytotoxicity against K562/A (adriamycin-resistant K562) cells with IC 50 value of 3.78 μM, and autophagy-inducing activity at the concentration of 20 μM in GFP-LC3 stable HeLa cells [ 86 ]. Beauvenniatins F ( 105 ), G 1 ( 106 ), G 2 ( 107 ), G 3 ( 108 ), H 1 ( 109 ), H 2 ( 110 ), and H 3 ( 111 ) from the fungus Acremonium sp.…”

Section: Cyclic Hexadepsipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi

et al. 2018

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Cyclic depsipeptides (CDPs) are cyclopeptides in which amide groups are replaced by corresponding lactone bonds due to the presence of a hydroxylated carboxylic acid in the peptide structure. These peptides sometimes display additional chemical modifications, including unusual amino acid residues in their structures. This review highlights the occurrence, structures and biological activities of the fungal CDPs reported until October 2017. About 352 fungal CDPs belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, and tridecadepsipeptides have been isolated from fungi. These metabolites are mainly reported from the genera Acremonium, Alternaria, Aspergillus, Beauveria, Fusarium, Isaria, Metarhizium, Penicillium, and Rosellina. They are known to exhibit various biological activities such as cytotoxic, phytotoxic, antimicrobial, antiviral, anthelmintic, insecticidal, antimalarial, antitumoral and enzyme-inhibitory activities. Some CDPs (i.e., PF1022A, enniatins and destruxins) have been applied as pharmaceuticals and agrochemicals.

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“…Beauvenniatin F has exhibited strong cytotoxicity against adriamycin-resistant myelogenous leukemia cells (K-562), with an IC 50 of 2.78 μM, and autophagy-inducing activity at a concentration of 20 μM in green fluorescent protein-light chain 3-stable HeLa cells [ 94 ]. These depsipeptides also displayed cytotoxicity against epithelial carcinoma (KB), lymphoma (BC), and lung carcinoma cells (NCI-H187), with IC 50 values ranging from 1.00 to 2.29 μM as well as against kidney epithelial cells (Vero) at 1.9–5.5 μM [ 95 ].…”

Section: Depsipeptides With a Recognized Mechanism Of Targeting Cance...mentioning

confidence: 99%

Depsipeptides Targeting Tumor Cells: Milestones from In Vitro to Clinical Trials

2023

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Cancer is currently considered one of the most threatening diseases worldwide. Diet could be one of the factors that can be enhanced to comprehensively address a cancer patient’s condition. Unfortunately, most molecules capable of targeting cancer cells are found in uncommon food sources. Among them, depsipeptides have emerged as one of the most reliable choices for cancer treatment. These cyclic amino acid oligomers, with one or more subunits replaced by a hydroxylated carboxylic acid resulting in one lactone bond in a core ring, have broadly proven their cancer-targeting efficacy, some even reaching clinical trials and being commercialized as “anticancer” drugs. This review aimed to describe these depsipeptides, their reported amino acid sequences, determined structure, and the specific mechanism by which they target tumor cells including apoptosis, oncosis, and elastase inhibition, among others. Furthermore, we have delved into state-of-the-art in vivo and clinical trials, current methods for purification and synthesis, and the recognized disadvantages of these molecules. The information collated in this review can help researchers decide whether these molecules should be incorporated into functional foods in the near future.

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New Cyclohexadepsipeptides from an Entomogenous Fungus Fusarium proliferatum and Their Cytotoxicity and Autophagy‐Inducing Activity

Cited by 8 publications

References 13 publications

Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus Fusarium sp.

Cytotoxic Cyclodepsipeptides and Cyclopentane Derivatives from a Plant-Associated Fungus Fusarium sp.

Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi

Depsipeptides Targeting Tumor Cells: Milestones from In Vitro to Clinical Trials

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