Diketopiperazines from Cultures of the Fungus<i>Colletotrichum gloesporoides</i>

Trigos, Ángel; Reyna, Silvia; Gutierrez, Ma. Luisa; Sanchez, M.I. Torres

doi:10.1080/10575639708043751

Cited by 19 publications

(12 citation statements)

References 3 publications

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“…This findings corroborated with the early study that reported that Colletotrichum gloeosporioides was the prolific producer of 108 plethora of antimicrobial compounds, such as colletotric acid and colletoic acid (Zou et al 2000), diketopiperazines (Trigos et al 1997), artemisinin (Wang et al 2006), phillyrin compounds (Zhang et al 2012) and piperine (Chithra et al 2014).…”

Section: Discussionsupporting

confidence: 81%

Antimicrobial and cytotoxic activities of endophytic fungus Colletotrichum gloeosporioides isolated from endemic tree Cinnamomum malabatrum

Packiaraj¹

2016

SIF

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In a survey of endophytic fungi associated with endemic plant Cinnamomum malabatrum leaves harbored a bioactive endophytic isolate CMS 3 was identified as Colletotrichum gloeosporioides through morphological and phylogenetic analysis based on ITS-rDNA. The ethyl acetate extract of fermentation broth of Colletotrichum gloeosporioides CMS 3 displayed antimicrobial activity against gram positive and gram negative bacteria as well as the fungal pathogen, Candida albicans. The ethyl acetate crude extract showed in vitro cytotoxicity against the HeLa, MCF-7 and MG63 cancer cell lines with the IC 50 values of 94.2µg/ml, 84.3µg/ml and 162µg/ml respectively. Gas chromatography and Mass Spectrophotometry (GC-MS) analysis of crude extract confirmed that CMS 3 was a prolific producer of secondary metabolites, in which nearly 74% of the metabolites not listed in the NIST database. Major compounds were phenol 3, 5-dimethoxy acetate (11.82 %), 4'-isopropylidene-bis-(2-cyclohexyl) phenol, NDidehydrohexacarboxyl-2, 4, 5-trimethylpiperazine and 1, 2, 4-Triazolium ylide. These metabolites may be responsible for its antimicrobial and cytotoxic activities.

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Section: Discussionsupporting

confidence: 81%

Antimicrobial and cytotoxic activities of endophytic fungus Colletotrichum gloeosporioides isolated from endemic tree Cinnamomum malabatrum

Packiaraj¹

2016

SIF

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“…12,16 Some diketopyperazines are wellknown fungal phytotoxins, 17 but the phytotoxic properties of cycloglycylproline are first revealed in the present work.…”

Section: Resultsmentioning

confidence: 63%

Phytotoxic effects of metabolites from Alternaria euphorbiicola against its host plant Euphorbia heterophylla

Vinícius¹,

Varejão²,

Demuner³

et al. 2013

Quím. Nova

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Recebido em 20/11/12; aceito em 15/2/13; publicado na web em 24/5/13A bioassay-guided fractionation of culture filtrates of the fungus Alternaria euphorbiicola, a pathogen of the weed Euphorbia heterophylla, led to the isolation of anhydromevalonolactone (1), tyrosol (2), (R)-(-)-mevalonolactone (3), and cycloglycylproline (4). When tested on the punctured leaves of the host plant, these compounds produced bleached lesions with dark brown margins at concentrations as low as 80 µM. When tested on the leaves of other relevant weeds, only cycloglycylproline showed selective activity against E. heterophylla. This is the first report on the isolation of phytotoxins from A. euphorbiicola and on the phytotoxicity of anhydromevalonolactone, (R)-(-)-mevalonolactone, and cycloglycylproline.Keywords: fungi; phytotoxin; wild poinsettia. INTRODUCTIONSurveys for fungal pathogens of wild poinsettia in Brazil and their evaluation as potential mycoherbicides for the management of this weed were initiated in the late 1980s. Among the fungi collected and studied, preliminary results indicate that Alternaria euphorbiicola Simmons & Engelhard holds great promise for herbicidal control. This fungus was found to cause severe inflorescence necrosis, foliage blight, and stem canker on Euphorbia heterophylla L. 1 Euphorbia heterophylla (wild poinsettia) is regarded as a major weed in many tropical and subtropical countries, being responsible for substantial agricultural losses in important crops, particularly soybeans and corn. 2 During early investigation, when A. euphorbiicola was evaluated as a putative mycoherbicide, it was observed that the application of fungal spore suspensions on the host plant resulted in the production of widespread necrosis at time intervals ranging from few hours to 1-2 days after application. However, this was regarded as too short a period to allow for the occurrence of the whole process of spore germination, fungal penetration of tissues, colonization of plant organs, and development of symptoms due to plant infection. These observations led to the conjecture that A. euphorbiicola might produce phytotoxic metabolites capable of causing the first wave of damage to the host plant.It is well recognized that phytopathogenic fungi commonly produce toxins that may play a role in plant disease development, adversely affecting their infected hosts. 3,4 In this paper, we describe the isolation of anhydromevalonolactone (1), tyrosol (2), (R)-(-)-mevalonolactone (3), and cycloglycylproline (4) from A. euphorbiicola and their phytotoxic activity against the host plant wild poinsettia. EXPERIMENTAL Fungal strain, culture media, and growth conditionsAlternaria euphorbiicola was isolated from naturally infected E. heterophylla plants collected in Viçosa, Minas Gerais State, Brazil. The fungal species was identified by Prof. Robert Weingart Barreto, from the Department of Phytopathology, Universidade Federal de Viçosa (UFV), and stored at 5 °C in the culture collection Octávio de Almeida Drumond of UFV. The fungus was c...

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“…Subsequently, circles were taken (1.2 cm in diameter each) from 8-day cultured fungal plates, and transferred aseptically to 500 mL Erlenmeyer flasks (Â2) that contained 100 mL of papaya flesh (200 g/ L) seed medium, which were maintained in continuous agitation (125 rpm) for 5 days at 25 AE 2 8C. In order to obtain an extensive culture, the resultant mycelium suspension was used to inoculate (1 mL/each) a total of 110 flasks of 500 mL containing 100 mL of papaya medium each, which were maintained under the same conditions for 12 days (Trigos et al, 1997).…”

Section: Fungus Culturementioning

confidence: 99%