ChemInform Abstract: Omphalotins E—I, Five Oxidatively Modified Nematicidal Cyclopeptides from Omphalotus olearius.

Liermann, Johannes C.; Opatz, Till; Kolshorn, Heinz; Antelo, Luís T.; Hof, Carolin; Anke, Heidrun

doi:10.1002/chin.200925186

Cited by 8 publications

(10 citation statements)

References 1 publication

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“…Non-terpenoid secondary metabolites of O. olearius include the nematicidal omphalotins (A-F) (Liermann et al, 2009) and the siderophore ferrichrome A (Welzel et al, 2005). Omphalotins are cyclopeptides that are likely made by a non-ribosomal peptide synthase (NRPS).…”

Section: Resultsmentioning

confidence: 99%

Draft Genome of Omphalotus olearius Provides a Predictive Framework for Sesquiterpenoid Natural Product Biosynthesis in Basidiomycota

Wawrzyn

Quin

Choudhary

et al. 2012

Chemistry & Biology

151

272

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SUMMARY The secondary metabolome of Basidiomycota represents a largely uncharacterized source of pharmaceutically relevant natural products. Terpenoids are the primary class of bioactive compounds isolated from mushrooms. The Jack O’Lantern mushroom Omphalotus olearius was identified 50 years ago as a prolific producer of anticancer illudin sesquiterpenoids, however to date there have been exceptionally few studies into the biosynthesis of these important compounds. Here we report the draft genome sequence of O. olearius, which reveals a diverse network of sesquiterpene synthases and two metabolic gene clusters associated with illudin biosynthesis. Their biochemical characterization enabled a comprehensive survey of all currently available Basidiomycota genomes, thereby creating a predictive resource for terpenoid natural product biosynthesis in these organisms. Our results will facilitate discovery and biosynthetic production of unique pharmaceutically relevant bioactive compounds from Basidiomycota.

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Section: Resultsmentioning

confidence: 99%

Draft Genome of Omphalotus olearius Provides a Predictive Framework for Sesquiterpenoid Natural Product Biosynthesis in Basidiomycota

Wawrzyn

Quin

Choudhary

et al. 2012

Chemistry & Biology

151

272

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“…Their distributions, biological activities and structures are shown in Table 10 and Figure 10 , respectively. Nine cyclic dodecapeptides omphalotins A–I ( 264 – 272 ) with nematicidal activity were identified in the mushroom O. olearius [ 191 , 192 ]. They have been considered as the potent nematicidal agents that seemed to be highly selective for Meloidogyne incognita [ 193 ].…”

Section: Cyclic Dodecapeptidesmentioning

confidence: 99%

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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“…Compounds 62a , 62b , 62c and 62d exhibited strong and selective nematicidal activity against the plant pathogen Meloidogyne incognita , with LD 50 values of 2, 1, 0.5-1 and 1 μg/mL respectively, while the positive control ivermectin possessed a comparable LD 50 value of 2 μg/mL. None of these compounds showed antibacterial or antifungal activities, neither cytotoxic effects towards mouse leukaemia cells or human colon adenocarcinoma cells at concentrations up to 50 μg/mL [111]. Notamide A 63 (Fig.…”

Section: N-hydroxy-substituted Fused Five-membered Ring Systemsmentioning

confidence: 99%

Bioactive heterocycles containing endocyclic N-hydroxy groups

Rani

Granchi

2015

European Journal of Medicinal Chemistry

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Drug-likeness rules consider N-O single bonds as “structural alerts” which should not be present in a perspective drug candidate. In most cases this concern is correct, since it is known that N-hydroxy metabolites of branded drugs produce reactive species that cause serious side effects. However, this dangerous reactivity of the N-OH species generally takes place when the nitrogen atom is not comprised in a cyclic moiety. In fact, the same type of metabolic behavior should not be expected when the nitrogen atom is included in the ring of an aromatic heterocyclic scaffold. Nevertheless, heterocycles bearing endocyclic N-hydroxy portions have so far been poorly studied as chemical classes that may provide new therapeutic agents. This review provides an overview of N-OH-containing heterocycles with reported bioactivities that may be considered as therapeutically relevant and, therefore, may extend the chemical space available for the future development of novel pharmaceuticals. A systematic treatment of the various chemical classes belonging to this particular family of molecules is described along with a discussion of the biological activities associated to the most important examples.

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ChemInform Abstract: Omphalotins E—I, Five Oxidatively Modified Nematicidal Cyclopeptides from Omphalotus olearius.

Abstract: Peptides U 0400 Omphalotins E-I, Five Oxidatively Modified Nematicidal Cyclopeptides from Omphalotus olearius. -(LIERMANN, J. C.; OPATZ*, T.; KOLSHORN, H.; ANTELO, L.; HOF, C.; ANKE, H.; Eur.

Cited by 8 publications

References 1 publication

Draft Genome of Omphalotus olearius Provides a Predictive Framework for Sesquiterpenoid Natural Product Biosynthesis in Basidiomycota

Draft Genome of Omphalotus olearius Provides a Predictive Framework for Sesquiterpenoid Natural Product Biosynthesis in Basidiomycota

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

Bioactive heterocycles containing endocyclic N-hydroxy groups

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