Nodupetide, a potent insecticide and antimicrobial from Nodulisporium sp. associated with Riptortus pedestris

Wu, Hui; Lin, Liang‐Hung; Xu, Qin; Han, Wen Bo; Zhang, Song; Liu, Ze Wen; Mei, Ya; Yao, Zhisheng; Tan, Ren Xiang

doi:10.1016/j.tetlet.2017.01.009

Cited by 17 publications

(14 citation statements)

References 22 publications

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“…CNL-878 co-cultured with the marine sediment-derived actinomycete Salinispora arenicola CNH-665 [7]; emericellamides C–F from the non-marine Aspergillus nidulans [8]; nodupetide from the insect-derived fungus Nodulisporum sp. IFB-A163 [9]; as well as numerous isariins and iso-isariins from Isaria spp. and Beauveria felina [10,11,12,13,14,15,16,17].…”

Section: Resultsmentioning

confidence: 99%

Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi

et al. 2019

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Chemical analysis of a cultivation of an Australian Mugil mullet gastrointestinal tract (GIT) derived fungus, Scopulariopsis sp. CMB-F458, yielded the known lipodepsipeptides scopularides A (1) and B (2). A comparative global natural product social (GNPS) molecular networking analysis of ×63 co-isolated fungi, detected two additional fungi producing new scopularides, with Beauveria sp. CMB-F585 yielding scopularides C–G (3–7) and Scopulariopsis sp. CMB-F115 yielding scopularide H (8). Structures inclusive of absolute configurations were assigned by detailed spectroscopic and C3 Marfey’s analysis, together with X-ray analyses of 3 and 8, and biosynthetic considerations. Scopularides A–H (1–8) did not exhibit significant growth inhibitory activity against a selection of Gram positive (+ve) and negative (−ve) bacteria, a fungus, or a panel of three human carcinoma cell lines.

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Section: Resultsmentioning

confidence: 99%

Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi

et al. 2019

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“…Nodupeptide ( 242 ) was isolated from the gut of the insect Riptortus pedestris . This compound displayed insecticidal activity against rice brown planthopper ( Nilaparvata lugens ) with an LD 50 value of 70 ng/larva, and inhibitory activity towards the drug-resistant human pathogenic bacterium Pseudomonas aeruginosa with the MIC value (5.0 μM) comparable to that (3.2 μM) of the positive control ciprofloxacin [ 100 ].…”

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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“…Cyclodepsipeptides are heterodetic cyclic peptides that have an ester bond (depsi) in their backbone structure, with one or more hydroxylated carboxylic acid that substitutes an amino acid in the peptide backbone [1] . Cyclodepsipeptides were originally isolated from bacteria, [2,3] fungi, [4–6] and other marine organisms [7–10] and display a wide range of biological activities, such as antifungal, [6,11] antibacterial, [12,13] antitumor, [14] antimalarial, [6,15] anticancer [16] and insecticidal properties [17] . The presence of unique constituents in cyclodepsipeptide backbones, including α‐hydroxy acid in aureobasidin [11] and β‐hydroxy acid residues in nodupetide [17] are the main attraction for cyclodepsipeptides.…”

Section: Introductionmentioning

confidence: 99%

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

et al. 2022

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Cyclodepsipeptide are a class of natural cyclic peptides that have a wide range of biological activities, hence the potential to be developed as new drug candidates. Cyclodpesipeptides comprise a backbone of amide bonds and at least one ester moiety, thus are complex and challenging to synthesis. Generally, cyclodepsipeptides are synthesised via solid‐phase peptide synthesis, solution‐phase or a combination of solid and solution‐phase. Currently, solid‐phase peptide synthesis is more in demand, but it also has several challenges in its application especially for the cyclodepsipeptide that contains N‐methylated residues, as well as solution‐phase peptide synthesis tends to have a longer reaction step. Therefore, the combination of solid and solution‐phase peptide synthesis is a better alternative. This review discusses the synthetic strategies for cyclodepsipeptides including the preparation of precursor and macrocyclization.

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Nodupetide, a potent insecticide and antimicrobial from Nodulisporium sp. associated with Riptortus pedestris

Cited by 17 publications

References 22 publications

Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi

Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi

Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

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