Detection of a Toxic Methylated Derivative of Phomopsin A Produced by the Legume-Infesting Fungus <i>Diaporthe toxica</i>

Schloß, Svenja; Hackl, Thomas; Herz, Corinna; Lamy, Evelyn; Koch, Matthias; Rohn, Sascha; Maul, Ronald

doi:10.1021/acs.jnatprod.6b00662

Cited by 19 publications

(12 citation statements)

References 14 publications

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“…Phomopsins A ( 283 ), B ( 284 ) and F ( 285 ) were isolated from Phomopsis leptostromiformis [ 205 , 206 ] and Diaporthe toxica [ 207 ]. They have a structure similar to HV-toxin M ( 282 ).…”

Section: Cyclic Peptides Containing Ether Bonds In the Core Ringmentioning

confidence: 99%

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Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals.

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Section: Cyclic Peptides Containing Ether Bonds In the Core Ringmentioning

confidence: 99%

“…They have a structure similar to HV-toxin M ( 282 ). Phomopsins are mycotoxins known to be responsible for fatal liver disease of lupin-fed sheep, and displayed phytotoxic and cytotoxic activities [ 206 , 207 ].…”

Section: Cyclic Peptides Containing Ether Bonds In the Core Ringmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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“…Toxicity is caused by the secondary metabolites of the fungus, phomopsins A through E, which are a group of hexapeptide macrocyclic mycotoxins [79,82]. Phomopsin A is the most toxic and abundant metabolite and is often accompanied by small quantities of phomopsin B, which has potential toxicity two to five times less than phomopsin A [79,82,83]. The occurrence of phomopsins C, D and E have been reported but are less common [82].…”

Section: Phomopsinsmentioning

confidence: 99%

“…Phomopsin A is the most toxic and abundant metabolite and is often accompanied by small quantities of phomopsin B, which has potential toxicity two to five times less than phomopsin A [79,82,83]. The occurrence of phomopsins C, D and E have been reported but are less common [82]. Unlike pyrrolizidine alkaloids, no bioactivation is required to exert toxicity; in fact, phomopsins are rapidly metabolized to less toxic components in the liver [81].…”

Section: Phomopsinsmentioning

confidence: 99%

Plant and Fungal Hepatotoxicities of Cattle in Australia, with a Focus on Minimally Understood Toxins

Manthorpe

Jerrett

Rawlin

et al. 2020

Toxins

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Plant- and fungus-derived hepatotoxins are a major cause of disease and production losses in ruminants in Australia and around the world. Many are well studied and described in the literature; however, this is not the case for a number of hepatotoxicities with economic and animal welfare impacts, such as acute bovine liver disease (ABLD), brassica-associated liver disease (BALD) and Trema tomentosa, Argentipallium blandowskianum and Lythrum hyssopifolia toxicity. Additionally, significant overlap in the clinical presentation and pathology of these conditions can present a diagnostic challenge for veterinarians. This review summarizes the current and most recently published knowledge of common plant- and fungus-associated hepatotoxins affecting cattle in Australia, with a focus on the mechanisms of toxicity and distinguishing diagnostic features. Consolidation of the current understanding of hepatotoxic mechanisms in cattle provides insight into the potential mechanisms of lesser-known toxins, including cellular and subcellular targets and potential metabolic pathways. In the absence of specific etiological investigations, the study of epidemiological, clinical and pathological features of hepatotoxicity provides valuable insights into potential toxic mechanisms and is integral for the successful diagnosis and management of these conditions.

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“…K. obovate (L.) Druce (Family Rhizophoraceae) is a common mangrove in East Asia and is known to possess several entophytic fungi such as Botryosphaeria sp., Cladosporium sp., Meyerozyma guilliermondii , Penicillium sp., Talaromyces sp., and Diaporthe sp . Among the endophytes, fungus of the genus Diaporthe was reported to produce alkaloids, benzofurans, depsidones, diterpenoids, peptides,sesquiterpenes, and triterpenes . Besides, the foregoing natural products isolated from Diaporthe were found to exhibit diverse pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

Natural Products from Diaporthe arecae with Anti‐Angiogenic Activity

Chang

Wang

et al. 2019

Israel Journal of Chemistry

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A new indoleglycerol, designated as arecine (1), and twenty‐three known diketopiperazines 2–24 were isolated from the endophytic fungus Diaporthe arecae associated with mangrove Kandelia obovate. Structures of all secondary metabolites 1–24 were identified on the basis of their spectrometric data, especially the nuclear magnetic resonance, optical rotation, and mass data. The absolute stereochemistry of compound 1 was determined by comparing its experimental electronic circular dichroism spectrum to those of in silico generated. Moreover, the 1H and 13C NMR spectroscopic data of isolated diketopiperazines 3–24 were measured in dimethyl sulfoxide‐d6 and presented in Table 2 for a convenient comparison. Pharmacological study showed cordysinin A (2) possessed mild anti‐angiogenic activity, which suppressed tube formation with an IC50 value of 15.1±0.2 μg/mL.

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Detection of a Toxic Methylated Derivative of Phomopsin A Produced by the Legume-Infesting Fungus Diaporthe toxica

Cited by 19 publications

References 14 publications

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Plant and Fungal Hepatotoxicities of Cattle in Australia, with a Focus on Minimally Understood Toxins

Natural Products from Diaporthe arecae with Anti‐Angiogenic Activity

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