Canadensolide - an antifungal metabolite of penicillium canadense

McCorkindale, N.J.; Wright, Jeffrey L. C.; Brian, P. W.; Clarke, Shannon; Hutchinson, S.A.

doi:10.1016/s0040-4039(00)75621-8

Cited by 60 publications

(41 citation statements)

References 4 publications

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“…Our results of the bioactivity of sporothriolide ( 1 ) and dihydrosporothriolide ( 2 ) resemble the study of Krohn et al ( 1994 ) which used an agar plate diffusion assay. The strong antifungal activity of furofurandiones has furthermore previously been described for canadensolide ( 6 ) (McCorkindale et al 1968 ), ethiosolide (Atienza et al 1992 ) and avenaciolide (Brookes et al 1963 ).…”

Section: Resultsmentioning

confidence: 70%

“…The metabolites can retro-biosynthetically be cleaved and they are probably being generated from a fatty acid and a C 3 moiety, which originates from oxaloacetate (Chesters and O´Hagan 1997 ). Those natural products resulting from condensation of the α -position of the fatty acid are referred as type A metabolites and include sporothriolide (Krohn et al 1994 ), canadensolide (McCorkindale et al 1968 ) and xylobovide (Abate et al 1997 ). In contrast, in isomeric type B metabolites like ethisolide (Atienza et al 1992 ) and avenaciolide (Brookes et al 1963 ) the C 3 unit is linked to the β -position of the fatty acid chain.…”

Section: Discussionmentioning

confidence: 99%

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Sporothriolide derivatives as chemotaxonomic markers forHypoxylon monticulosum

et al. 2014

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During the course of a screening for novel anti-infective agents from cultures of tropical Xylariaceae originating from French Guiana and Thailand, pronounced antifungal activity was noted in extracts of cultures of Hypoxylon monticulosum. A bioassay-guided fractionation led to the known metabolite sporothriolide as active principle. In addition, three new derivatives of sporothriolide were isolated, for which we propose the trivial names sporothric acid, isosporothric acid and dihydroisosporothric acid. Their chemical structures were elucidated by high-resolution electrospray mass spectrometry in conjunction with two-dimensional nuclear magnetic resonance (2D-NMR) spectroscopy. From earlier studies on the biogenesis of the chemically similar canadensolides, we postulate that the new compounds were shunt products, rather than biogenetic precursors of sporothriolide. Interestingly, this compound class, as well as strong antifungal activities, was only observed in multiple cultures of H. monticulosum, but not in several hundreds of Hypoxylon cultures studied previously or concurrently. Therefore, sporothriolide production may constitute a species-specific feature with respect to Hypoxylon and the Xylariaceae, although the compound was previously reported from non-related fungal taxa.

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Section: Resultsmentioning

confidence: 70%

Section: Discussionmentioning

confidence: 99%

Sporothriolide derivatives as chemotaxonomic markers forHypoxylon monticulosum

et al. 2014

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“…Canadensolides are formed via condensation of an acetate derived chain with a TCA cycle intermediate (Brookes et al 1963 ; Turner 1971 ; Tanabe et al 1973 ). It was first isolated from “ Penicillium ” canadense (McCorkindale et al 1968 ), but it has been reported once from A. flavus (Sakata et al 1982 ), and the related avenaciolide has been reported from A. avenaceus in Aspergillus section Flavi (Brookes et al 1963 ; Tanabem et al 1973 ; Varga et al 2011b ). The avenaciolides are also present in Aspergillus glaber and A. stramenius from Aspergillus section Fumigati (Ellis et al 1964 ; Samson et al 2007 ), and the avenaciolides are active against methicillin-resistant Staphylococci (Chang et al 2015 ).…”

Section: Secondary Metabolite Potentialmentioning

confidence: 99%

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

Frisvad

Møller

Larsen

et al. 2018

Appl Microbiol Biotechnol

256

269

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This review presents an update on the current knowledge of the secondary metabolite potential of the major fungal species used in industrial biotechnology, i.e., Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei. These species have a long history of safe use for enzyme production. Like most microorganisms that exist in a challenging environment in nature, these fungi can produce a large variety and number of secondary metabolites. Many of these compounds present several properties that make them attractive for different industrial and medical applications. A description of all known secondary metabolites produced by these species is presented here. Mycotoxins are a very limited group of secondary metabolites that can be produced by fungi and that pose health hazards in humans and other vertebrates when ingested in small amounts. Some mycotoxins are species-specific. Here, we present scientific basis for (1) the definition of mycotoxins including an update on their toxicity and (2) the clarity on misclassification of species and their mycotoxin potential reported in literature, e.g., A. oryzae has been wrongly reported as an aflatoxin producer, due to misclassification of Aspergillus flavus strains. It is therefore of paramount importance to accurately describe the mycotoxins that can potentially be produced by a fungal species that is to be used as a production organism and to ensure that production strains are not capable of producing mycotoxins during enzyme production. This review is intended as a reference paper for authorities, companies, and researchers dealing with secondary metabolite assessment, risk evaluation for food or feed enzyme production, or considerations on the use of these species as production hosts.

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“…The syntheses of xylobovide (204), [112] canadensolide (205), [113] sporothriolide (206), [114] and nor-canadensolide (207) by the preceding strategy were achieved by the Fernandes group. On the other hand, as shown in Scheme 40, the synthesis of the other two isomers of phenatic acid B (ent-190a and ent-190b) was accomplished from the chiral diol ent-191.…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

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Canadensolide - an antifungal metabolite of penicillium canadense

Cited by 60 publications

References 4 publications

Sporothriolide derivatives as chemotaxonomic markers forHypoxylon monticulosum

Sporothriolide derivatives as chemotaxonomic markers forHypoxylon monticulosum

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

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