Trichodermamides A and B, Cytotoxic Modified Dipeptides from the Marine-Derived Fungus <i>Trichoderma virens</i>

Garo, Eliane; Starks, Courtney M.; Jensen, Paul R.; Fenical, William; Lobkovsky, Emil; Clardy, Jon

doi:10.1021/np0204390

Cited by 174 publications

(120 citation statements)

References 20 publications

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“…The structure of 28 was established by X-ray diffraction analysis while the structure assignment of 27 and the determination of the absolute stereochemistry was accomplished by means of spectral and chemical methods. Compound 28 displayed significant in vitro cytotoxicity against HCT-116 human colon carcinoma with an IC 50 (inhibitor concentration yielding 50% inhibition) of 0.32 lg/ml while 27 was found to have a weak cytotoxic effect on three cancer cell lines P388, A-549, and HL-60 (Garo et al 2003;Liu et al 2005a). …”

Section: Trichodermamidesmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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Trichoderma species are free-living fungi that are highly interactive in root, soil and foliar environments and have been used successfully in field trials to control many crop pathogens. Structural and biological studies of the metabolites isolated from Trichoderma species are reviewed. This review, encompassing all the literature in this field up to the present and in which 269 references are cited, also includes a detailed study of the biological activity of the metabolites, especially the role of these metabolites in biological control mechanisms. Some aspects of the biosynthesis of these metabolites and related compounds are likewise discussed.

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Section: Trichodermamidesmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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“…7 Considering the small amount isolated of both esculetin-4-carboxylic acid methyl ester and ethyl ester, it is reasonable to suggest a microbial origin for such compounds, although the occurrence of coumarin derivatives in fungi and bacteria has not been frequently observed. 8 Metabolites bearing a coumarin moiety have been isolated from the marine fungus Trichoderma virens 9 and from the marine ascomycete Leptosphaeria oraemaris. 10 The isolation of plant-related metabolites from sponges is rare.…”

Section: Resultsmentioning

confidence: 99%

A SARS-coronovirus 3CL protease inhibitor isolated from the marine sponge Axinella cf. corrugata: structure elucidation and synthesis

Lira¹,

Seleghim²,

Williams³

et al. 2007

J. Braz. Chem. Soc.

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Dois derivados cumarínicos, o ester metílico do ácido 4-esculetinocarboxílico (1) e o éster etílico do ácido 4-esculetinocarboxílico (2), foram isolados da esponja marinha Axinella cf. corrugata. A determinação estrutural dos compostos isolados foi realizada pela análise de seus dados espectroscópicos e pela síntese do composto 2. Estes são os primeiros derivados cumarínicos isolados de uma esponja marinha. O éster etílico 2 apresentou atividade in vitro contra a SARS 3Cl-protease e de inibição de células Vero infectadas com o SARS coronavírus, em concentrações que não provocaram citotoxicidade.Two coumarin derivatives, esculetin-4-carboxylic acid methyl ester (1) and esculetin-4-carboxylic acid ethyl ester (2), have been isolated from the marine sponge Axinella cf. corrugata. Structure determination included analysis of spectroscopic data and total synthesis of compound 2. These are the first coumarin derivatives isolated from a marine sponge. The ethyl ester 2 was found to be an in vitro inhibitor of SARS 3CL-protease and an effective inhibitor of SARS-CoV replication in Vero cells at non-cytotoxic concentrations.Keywords: esculetin, marine sponge, Axinella cf. corrugata, SARS, anti-viral IntroductionIn 2002 and 2003, several cases of a life-threatening respiratory disease that was ultimately named "severe acute respiratory syndrome" (SARS) were reported from Guangdong Province in mainland China, Hong Kong, Canada, and Vietnam.1 The etiological agent responsible for SARS was quickly found to be a novel coronavirus (SARS-CoV). Among the viral gene products are several large polyproteins that must be proteolytically processed to generate the individual proteins required for viral replication to occur. Two viral proteases, PL2 pro and 3CL pro , are involved in degrading the large polyproteins. 2The viral protease 3CL pro is considered the most important of the two because it is responsible for the release of the key replicative proteins of the vírus, including the viral RNA polymerase and helicase proteins. The central role of 3CL pro in SARS-CoV replication has made it a high profile target for developing antiviral drugs to treat SARS.2 Recently, a novel fluorescence resonance energy transfer (FRET)-based assay to screen for 3CL pro inhibitors has been developed in one of our laboratories.3 As part of a screening of crude marine sponge extracts and pure compounds isolated from the marine sponges using this assay, we have found that the new natural product esculetin-4-carboxylic acid ethyl ester (2) isolated from Axinella cf. corrugata collected in Brazil is a an effective inhibitor of 3CL pro in vitro. 441 Lira et al. Vol. 18, No. 2, 2007 In our current search for new biologically active marine natural products, 4,5 we decided to investigate the MeOH crude extract of the sponge Axinella cf. corrugata, which displayed cytotoxic activity against breast MCF-7 and colon B16 cancer cell lines. Although the cytotoxic activity was lost during the crude extract fractionation, photodiode array detection-HPLC analysi...

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“…JBIR-81 (239) and JBIR-82 (240) showed protective activity against L -glutamate toxicity in N18-RE-105 cells with EC 50 values of 0.7 and 1.5 μM, respectively, which are much more effective than a representative antioxidant, α-tocopherol (Izumikawa et al 2010). Trichodermamide B (241) appeared cytotoxic to HCT116 cells with an IC 50 value of 0.32 μg/mL (0.71 μM) (Garo et al 2003).…”

Section: Peptidesmentioning

confidence: 99%

Mycochemistry of marine algicolous fungi

Wang

2016

Fungal Diversity

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Marine algicolous fungi refer to the fungi inhabiting or associated with marine algae, which have attracted a great attention for natural product researchers due to their chemical diversity and biological activity during the past two decades. Up to the end of 2014, a total of 366 new natural products, including polyketides, terpenoids, polyketide-terpenoids, peptides, alkaloids, and shikimate derivatives, have been characterized from them. Among these metabolites, 240 compounds feature cytotoxic, antibacterial, antifungal, antimicroalgal, zooplankton-toxic, antiprotozoal, antioxidative, enzyme-modulatory, and/or some other activities. This review gives a comprehensive coverage of both chemical and biological aspects of the secondary metabolites from marine algicolous fungi.

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Trichodermamides A and B, Cytotoxic Modified Dipeptides from the Marine-Derived Fungus Trichoderma virens

Cited by 174 publications

References 20 publications

Secondary metabolites from species of the biocontrol agent Trichoderma

Secondary metabolites from species of the biocontrol agent Trichoderma

A SARS-coronovirus 3CL protease inhibitor isolated from the marine sponge Axinella cf. corrugata: structure elucidation and synthesis

Mycochemistry of marine algicolous fungi

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