The isolation, structure determination and cytotoxicity of the new fungal metabolite, trichodermamide C

Davis, Rohan A.; Longden, James; Avery, Vicky M.; Healy, Peter Conrad

doi:10.1016/j.bmcl.2008.03.090

Cited by 47 publications

(55 citation statements)

References 14 publications

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“…in the outer bark of the rainforest tree Glochidion ferdinandi (family Euphorbiaceae). Epichlicin shows inhibitory activity toward the spore germination of fungi at 22 nm of IC 50 value (Seto et al 2007), and trichodermamide C displays cytotoxicity toward the human colorectal carcinoma HCT116 and human lung carcinoma A549 with IC 50 values of 0.68 and 4.28 μg/ml, respectively (Davis et al 2008). In this study, pentapeptide SBNP1, which, to our knowledge, is the first reported peptide in P. oxalicum, was a new compound, suggesting that endophytic fungi are a rich resource for novel natural products discovery.…”

Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

“…A plethora of natural products especially diverse novel peptides have been discovered from endophytic microorganisms (Seto et al 2007;Davis et al 2008;Chomcheon et al 2010;Koulman et al 2012). Recent examples include epichlicin (Seto et al 2007), a novel cyclic peptide isolated from Epichloe typhina, an endophytic fungus of the timothy plant (Phleum pretense L.), and trichodermamide C (Davis et al 2008), a new dipeptide discovered from the malt extract broth of an endophytic fungus Eupenicillium sp.…”

Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

“…Recent examples include epichlicin (Seto et al 2007), a novel cyclic peptide isolated from Epichloe typhina, an endophytic fungus of the timothy plant (Phleum pretense L.), and trichodermamide C (Davis et al 2008), a new dipeptide discovered from the malt extract broth of an endophytic fungus Eupenicillium sp. in the outer bark of the rainforest tree Glochidion ferdinandi (family Euphorbiaceae).…”

Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

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Endophytes in the plant Huperzia serrata: fungal diversity and discovery of a new pentapeptide

et al. 2014

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Endophytic fungi are an underexploited resource of natural products and have a capacity to produce diverse classes of plant-derived secondary metabolites. Here, we investigated the diversity of endophytic fungi from Huperzia serrata and the potential for discovering novel fungal natural products. One hundred and fifty-five endophytic fungi isolates obtained from H. serrata, belonging to four classes Dothideomycetes (47.3 %), Sordariomycetes (36.8 %), Eurotiomycetes (10.6 %) and an undefined class (5.3 %, Mucoraceae), were grouped into nine genera based on morphological and molecular identification. Colletotrichum, Cladosporium, Sordariomycetes and Guignardia were the dominant genera, whereas the remaining genera were infrequent groups. To our knowledge, the fungal genera Mucor and Neurospora were first reported in Huperzia plant. Among these endophytic fungi isolates, strain B14, belonging to Penicillium oxalicum, gave a gray precipitate with Dragendorff's reagent. A new pentapeptide was isolated from the culture of strain B14, and its chemical structure was elucidated on the basis of spectroscopic data from (1)H NMR, (13)C NMR and ESI-MS/MS. Taken together, H. serrata has a significant diversity of endophytic fungi that could be a rich resource for the discovery of new natural products.

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Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

Section: Identification Of a Novel Pentapeptide From Endophytic Fungimentioning

confidence: 99%

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Endophytes in the plant Huperzia serrata: fungal diversity and discovery of a new pentapeptide

et al. 2014

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“…These tests used lung (A-549), breast (MDA-MB-231 and MCF-7), and In previous studies, some anti-cancer drugs have been found in endophyte cultures (Jiao et al 2006;Davis et al 2008). Many cytotoxic constituents were isolated from extracts of the endophytic fungi, Fusarium sp.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

Evaluation of the bioactivities of extracts of endophytes isolated from Taiwanese herbal plants

Hsieh

Hsu

Lai

et al. 2009

World J Microbiol Biotechnol

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The endophytic extracts from 19 endophytes, isolated from 13 species of Taiwanese plants, were evaluated for biological activity, including cytotoxicity, anti-platelet aggregation, and anti-inflammatory activity. The extracts of 12 endophytes exhibited inhibitory effects on collageninduced platelet aggregation with IC 50 values of 19.85-87.64 lg/ml. Four strains, Rahnella aquatilis, Pantoea agglomerans, Rhodotorula sp., and Penicillium paxilli, also showed inhibitory effects on thrombin-induced platelet aggregation with IC 50 values of 42.80-61.54 lg/ml. Additionally 12 extracts of endophytes exhibited cytotoxicities with IC 50 values of 0.12-19.83 lg/ml. However, eight extracts revealed inhibitory effects on superoxide anion generation induced by fMLP (N-formyl-L-methionyl-L-leucyl-L-phenylalanine) in human neutrophils. The extract of Rahnella aquatilis showed anti-platelet aggregation activity, and bioassay-directed fractionation led to the isolation of six compounds, including one isoalloxazine: lumichrome (1); two isoflavones: genistein (2) and daidzein (3); two cyclic peptides: cyclo-Pro-Val (4) and cyclo-Pro-Phe (5); and one benzenoid: methyl 2,4,5-trimethoxybenzoate (6). These results indicated that endophytes from Taiwanese herbal plants could be useful sources for research and development of bioactive lead compounds from nature.

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“…As rarely discovered fungal secondary metabolites, only a few analogues, namely, trichodermamides A-C, aspergillazines A-E and dithioaspergillazine A have been reported from Trichoderma sp., 1,2 Eupenicillium sp. 3 and Aspergillus sp. 4 The structural diversity of reported trichodermamides is mainly represented by the variety of substitutions on the cyclohexane ring of the 1,2-oxazadecaline moiety (rings A and B).…”

Section: Introductionmentioning

confidence: 99%

Trichodermamides D–F, heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core isolated from the endophytic fungus Penicillium janthinellum HDN13-309

et al. 2017

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Three new heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core, named trichodermamides D-F (1-3), together with the known trichodermamides A-C (4-6), were isolated from the broth of the mangrove-derived endophytic fungus Penicillium janthinellum HDN13-309. The structures were elucidated through extensive NMR spectroscopic and physical data. The absolute configurations of compounds 1-3 were determined by ECD calculations and single-crystal X-ray diffraction experiments. The cytoprotective activities were evaluated on different phase II detoxifying enzymes (SOD2, AKR1C1, HO-1 and NQO1), and compounds 4 and 6 showed potent inducing effects at the concentration of 10 mM.

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The isolation, structure determination and cytotoxicity of the new fungal metabolite, trichodermamide C

Cited by 47 publications

References 14 publications

Endophytes in the plant Huperzia serrata: fungal diversity and discovery of a new pentapeptide

Endophytes in the plant Huperzia serrata: fungal diversity and discovery of a new pentapeptide

Evaluation of the bioactivities of extracts of endophytes isolated from Taiwanese herbal plants

Trichodermamides D–F, heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core isolated from the endophytic fungus Penicillium janthinellum HDN13-309

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