Flufuran, an Antifungal 3,5‐Disubstituted Furan Produced by <i>Aspergillus flavus</i><scp>Link</scp>

Evidente, Antonio; Cristinzio, Gennaro; Punzo, Biancavaleria; Andolfi, Anna; Testa, Antonino; Melck, Dominique

doi:10.1002/cbdv.200800292

Cited by 36 publications

(27 citation statements)

References 11 publications

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“…15,29 Recently, tyrosol was also identified as a phytotoxic metabolite produced by N. parvum. 17 This fungus was isolated together with four other Botryosphaeriaceae from declining grapevines in Spain. 16 From the organic extract of N. australe isolated from juniper, metabolites 5 and 6 were obtained.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Cyclobotryoxide, a Phytotoxic Metabolite Produced by the Plurivorous Pathogen Neofusicoccum australe

et al. 2012

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Two isolates of Neofusicoccum australe belonging to ITS haplotypes H4 and H1 and associated with grapevine cordon dieback and branch dieback of Phoenicean juniper, respectively, have been shown to produce in vitro structurally different secondary metabolites. From the strain BOT48 of N. australe (haplotype H4) a new cyclohexenone oxide, namely, cyclobotryoxide, was isolated together with 3-methylcatechol and tyrosol. Cyclobotryoxide was characterized as (1S,5R,6S)-5-hydroxy-3-methoxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one by spectroscopic, optical, and chemical methods. The strain BL24 (haplotype H1) produced tyrosol along with botryosphaerone D and (3S,4S)-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-1(2H)-naphthalenone. The metabolites obtained from both strains were tested at four concentrations on leaves of grapevine cv. Cannonau, holm oak, and cork oak by the leaf puncture assay. Cyclobotryoxide proved to be the most phytotoxic compound. Tyrosol and cyclobotryoxide were also tested on detached grapevine leaves at concentrations of 0.25 and 0.5 mg/mL. Only cyclobotryoxide was found to be active in this bioassay.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…11 −15 In particular, Botryosphaeriaceae species associated with declining grapevine are able to produce hydrophilic and lipophilic bioactive metabolites in liquid culture. 16 So far, phytotoxins have been isolated from Neof usicoccum parvum 17 and Diplodia seriata, 18 although their role on symptom disease expression needs to be fully elucidated.…”

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Cyclobotryoxide, a Phytotoxic Metabolite Produced by the Plurivorous Pathogen Neofusicoccum australe

et al. 2012

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“…Tyrosol (2) is a known metabolite produced by various phytopathogenic fungi, and its phytotoxicity is well documented. 11,13 (R)-(-)-mevalonolactone (3) is a terpenoid corresponding to the cyclic form of mevalonic acid, the starting building block of the major biosynthetic route for the synthesis of steroids and terpenes in fungi. 14 Although this compound has also been isolated from soil and phytopathogenic fungi, 15 the present paper is the first report of its phytotoxic properties.…”

Section: Resultsmentioning

confidence: 99%

“…The red-brown residue (186 mg) thus obtained exhibited phytotoxic activity when assayed on E. heterophylla leaves and was fractionated by CC. The column was eluted with a gradient of hexane-ethyl 13 …”

Section: Chemical Analysismentioning

confidence: 99%

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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“…The furan ring is an important structural motif that is present in many naturally occurring and synthetic compounds, many of which show interesting biological activities Among polysubstituted furans, compounds bearing a carboxylate group at the 3‐position are particularly widespread, and a variety of natural products, pharmaceticals, and agrochemicals have structures of this type. Flufuran, Tournefolins B and C, Wortmannin, Pukalide, Pseudopteroide, and Angelone (Figure ) are representative examples of natural products built on this framework.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Functional‐Group‐Tolerant Synthesis of Substituted Furans through the Pd‐Catalyzed 5‐exo‐dig Cyclization/Coupling of γ‐Acetylenic β‐Keto Esters with (Hetero)Aryl Bromides

Kołodziejczyk

Chaładaj

2018

Eur J Org Chem

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We report an efficient protocol for the synthesis of 2,3,5‐trisubstituted furans through the reaction of readily available γ‐acetylenic β‐keto esters with aryl and heteroaryl bromides. The reaction, which involves a 5‐exo‐dig cyclization, coupling, and isomerization of a double bond, proceeds smoothly with very low catalyst loading (0.1 mol‐%), and shows excellent functional‐group tolerance.

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Flufuran, an Antifungal 3,5‐Disubstituted Furan Produced by Aspergillus flavusLink

Cited by 36 publications

References 11 publications

Cyclobotryoxide, a Phytotoxic Metabolite Produced by the Plurivorous Pathogen Neofusicoccum australe

Cyclobotryoxide, a Phytotoxic Metabolite Produced by the Plurivorous Pathogen Neofusicoccum australe

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

Efficient and Functional‐Group‐Tolerant Synthesis of Substituted Furans through the Pd‐Catalyzed 5‐exo‐dig Cyclization/Coupling of γ‐Acetylenic β‐Keto Esters with (Hetero)Aryl Bromides

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