New Trichobrachins, 11-residue peptaibols from a marine strain of Trichoderma longibrachiatum

Ruiz, Nicolás; Wielgosz‐Collin, Gaëtane; Poirier, Laurence; Grovel, Olivier; Petit, Karina; Mohamed-Benkada, Mustapha; Pont, Thibaut Robiou du; Bissett, John; Vérité, Philippe; Barnathan, Gilles; Pouchus, Yves François

doi:10.1016/j.peptides.2007.05.012

Cited by 59 publications

(51 citation statements)

References 39 publications

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“…They belong to the same peptide family based on the sequence model Ac-XXX-XXX-XXX-XXX-Aib-Pro-XXX-XXX-Aib-Pro-XXXol, where Ac is acetyl-, Aib is ␣-aminoisobutyric acid, ol indicates reduction to the amino-alcohol, and XXX corresponds to variable amino acids. Seventeen sequences were new and the eighteen others were similar to already known 11-residue peptaibols such as trichobrachins (Trichoderma longibrachiatum) (20,41), trichofumins (Trichoderma sp. HKI 0276) (42), trichorovins (T. harzianum) (43), trichorozins (T. harzianum) (44), and hypomurocins, formerly originated from Hypocrea muroiana (45), which was recently demonstrated to be H. atroviridis (46).…”

Section: Resultsmentioning

confidence: 95%

“…Methanol of HPLC quality grade was purchased from Baker (Deventer, Holland). Microheterogenous mixtures of peptaibols were sequenced using consecutive fragmentation in ESI-MS n , according to the method described previously (20,23).…”

Section: Methodsmentioning

confidence: 99%

“…An extensive survey of 28 Trichoderma/Hypocrea species for peptaibol production by intact-cell MALDI-TOF mass spectrometry (ICMS) revealed that peptaibols are produced by all strains with some producing up to five peptide families of different sizes (19). In addition to terrestrial strains, peptaibols have also been isolated from marine strains of Trichoderma (7,20,22,23).…”

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Two Classes of New Peptaibols Are Synthesized by a Single Non-ribosomal Peptide Synthetase of Trichoderma virens

Mukherjee

Wiest

Ruiz

et al. 2011

Journal of Biological Chemistry

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107

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Peptaibols are a group of small peptides having a high ␣-aminoisobutyric acid (Aib) content and produced by filamentous fungi, especially by the members of the genus Trichoderma (anamorph Hypocrea). These antibiotics are economically important for their anti-microbial and anti-cancer properties as well as ability to induce systemic resistance in plants against microbial invasion. In this study we present sequences of two classes (11-residue and 14-residue) of peptaibols produced by the biocontrol fungus Trichoderma virens. Of the 35 11-residue peptaibols sequenced, 18 are hitherto not described, and all the 53 14-residue sequences described by us here are new. We have also identified a peptaibol synthetase (non-ribosomal peptide synthetase, NRPS) with 14 complete modules in the genome of this fungus and disruption of this single gene (designated as tex2) resulted in the loss of both the classes of peptaibols. We, thus present here an unprecedented case where a single NRPS encodes for two classes of peptaibols. The new peptaibols identified here could have applications as therapeutic agents for the management of human and plant health.

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Section: Resultsmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Two Classes of New Peptaibols Are Synthesized by a Single Non-ribosomal Peptide Synthetase of Trichoderma virens

Mukherjee

Wiest

Ruiz

et al. 2011

Journal of Biological Chemistry

Self Cite

107

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“…Also, some marine Hypocrea strains from hosts, seawater or sediments are reported to possess larvicidal or antitumor activities, including T. koningii against blowfly larvae and strains which inhibit different cancer cell lines, e.g., a Trichoderma sp., T. reesei, T. longibrachiatum and T. virens [26][27][28][29][30]. Their diverse cytotoxic products are reported to include α-aminoisobutyric acid, dipeptides, cyclotetrapeptide, peptides, peptaibols, cyclopentenone and polyketide derivatives.…”

Section: Relationship Between Systematics and Biological Potentialmentioning

confidence: 99%

Biological and chemical diversity of cytotoxin-producing symbiotic marine fungi in intertidal zone of Dalian

Zhang

Feng

et al. 2012

Chin. Sci. Bull.

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In this study, the biological and chemical diversity of 8 symbiotic marine fungal strains, with strong cytotoxicity against brine shrimp larvae, were investigated by nucleotide sequencing, morphology and cluster analysis of HPTLC fingerprint. These strains were identified by ITS rDNA sequencing, phylogenic analysis, and morphology to be Hypocrea lixii, Chaetomium globosum, Aspergillus fumigatus, Asp. clavatus and Alternaria sp. Their differences in secondary metabolites were shown by cluster analysis of digitalized colors of HPTLC spots, a newly developed method, which produced a similar dendrogram with that of ITS cluster analysis. Furthermore, this method can fully display intraspecific differences and even the remarkable difference in Aspergillus strains which goes beyond the boundary between genera. Their biological-chemical diversity may be the basis of their potent cytotoxicity and implies their potential in producing diversified antitumor or pesticidal constituents. Symbiotic fungi live on the surface or in the inner tissue of their hosts. Some terrestrial symbiotic fungi have been found to produce toxins or anti-feedants to protect their hosts from predators and grazers [1]. Some of these compounds can be used as antitumor or pesticidal agents. Symbiotic marine fungi have been isolated from seaweeds, sponges, corals, mangroves and sea grasses, also showing taxonomicall diversity and producing numerous active compounds [2]. The intertidal coastline of Dalian possesses diversified natural and artificial habitats and also high biodiversity of marine plants, invertebrates, and microorganisms. In our screening for useful cytotoxins from local symbiotic marine fungi using brine shrimp lethality test, a widely used bifunctional preliminary screening model to discover antitumor drugs and pesticides from the sea [3][4][5], eight strains with potent activities were discovered. Herein, we report the study on the biological and chemical diversity of these bioactive strains by ITS rDNA sequence analysis, morphology, and metabolite fingerprinting using a new cluster method.

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“…2 At the same time, many structurally novel and biologically active secondary metabolites have been reported from the species. For example, peptibols, 3 which are linear peptides characterized by an acetylated N-terminus, showed cytotoxic, membraneperturbing and antibiotic activities. Trichocaranes 4 A-D, isolated from Trichoderma virens, significantly inhibited the growth of etiolated wheat coleoptiles.…”

Section: Introductionmentioning

confidence: 99%

Two acid sorbicillin analogues from saline lands-derived fungus Trichoderma sp.

Liu

Huang

et al. 2011

J Antibiot

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Two new acid sorbicillin analogues, (E)-6-(2,4-dihydroxyl-5-methylphenyl)-6-oxo-2-hexenoic acid (1) and 6-(2,4-dihydroxyl-5-methylphenyl)-6-oxohexanoic acid (2), together with 12 known compounds, were isolated from a saline lands-derived fungus Trichoderma sp. The structures of the new compounds were established by interpretation of their spectroscopic data. Their cytotoxic effects on P388 and HL-60 cell lines were preliminarily evaluated by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide (MTT) method. Furthermore, the new compounds exhibited weak radical scavenging activity against DPPH (1,1-diphenyl-2-picrylhydrazyl). The Journal of Antibiotics (2011) 64, 645-647; doi:10.1038/ja.2011; published online 20 July 2011Keywords: cytotoxicity; fungus; sorbicillinoids; Trichoderma sp. INTRODUCTIONFungi of the genus Trichoderma are ubiquitous in the environment. In recent years, more and more attention has been paid to them because of a wide range of prospective utility 1 as biological control agents to suppress different fungal plant pathogens and to promote plant growth and for producing commercial enzymes, such as cellulases, hemicellulases, proteases and b-1,3-glucanase. 2 At the same time, many structurally novel and biologically active secondary metabolites have been reported from the species. For example, peptibols, 3 which are linear peptides characterized by an acetylated N-terminus, showed cytotoxic, membraneperturbing and antibiotic activities. Trichocaranes 4 A-D, isolated from Trichoderma virens, significantly inhibited the growth of etiolated wheat coleoptiles. In addition, a series of sorbicillin-related compounds 5-7 from Trichoderma showed moderate radical scavenging activity.In our search for cytotoxic compounds from fungi, a Trichoderma sp. was isolated from the saline lands soil collected along the coast of Bohai Bay in Zhanhua, Shandong Province, China. Its extract showed moderate activity to brine shrimp. The isolation work led to the finding of two new compounds (E)-6-(2,4-dihydroxyl-5-methylphenyl)-6-oxo-2-hexenoic acid (1) and 6-(2,4-dihydroxyl-5-methylphenyl)-6-oxohexanoic acid (2), along with 12 known ones, which were trichodimerol, bisvertinolone, adenosine, ergosterol, ergosterol peroxide, cerevisterol, 3b,5a-dihydroxy-6b-methoxyergosta-7,22-diene, (22E,24R)-5a,6a-epoxyergosta-8,22-diene-3b,7a-respectively. The known compounds were identified by comparison with previously reported physical and spectral data. In this paper, we reported the new compounds' isolation, structure elucidation, cytotoxic activities to P388 and HL-60 cell lines and radical scavenging activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) (Figure 1).

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New Trichobrachins, 11-residue peptaibols from a marine strain of Trichoderma longibrachiatum

Cited by 59 publications

References 39 publications

Two Classes of New Peptaibols Are Synthesized by a Single Non-ribosomal Peptide Synthetase of Trichoderma virens

Two Classes of New Peptaibols Are Synthesized by a Single Non-ribosomal Peptide Synthetase of Trichoderma virens

Biological and chemical diversity of cytotoxin-producing symbiotic marine fungi in intertidal zone of Dalian

Two acid sorbicillin analogues from saline lands-derived fungus Trichoderma sp.

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