Fusacandins A and B; Novel Antifungal Antibiotics of the Papulacandin Class from Fusarium sambucinum. II. Isolation and Structural Elucidation.

Hochlowski, Jill E.; Whittern, David N.; Buko, Alexander M.; Alder, L.; McAlpine, James B.

doi:10.7164/antibiotics.48.614

Cited by 16 publications

(4 citation statements)

References 14 publications

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“…Fusarium sambucinum was reported to be active against a wide range of both Candida species and filamentous fungi, such as Aspergillus niger , in addition to its activity against C. albicans and C. tropicalis (Hochlowski et al . ). We also examined the phylogenetic relationship of F. sambucinum to MS‐R1 strain, but its ITS sequence, retrieved from NCBI, was very different from the present isolate (data not shown).…”

Section: Discussionmentioning

confidence: 97%

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A novel echinocandin MIG0310 with anticandida activity from newly isolated Fusarium sp. strain MS-R1

Masaphy

2014

J Appl Microbiol

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Aim: To isolate and identify an anticandida compound from newly isolated Fusarium strain MS-R1 and characterization of its activity against standard and clinical strains of Candida. Methods and Results: The fungal strain, Fusarium strain MS-R1, was isolated from soil. Molecular identification according to the internal transcribed spacer region of the rRNA gene sequence showed the strain to be strongly related to Fusarium brachygibbosum complex. Successive extractions of the active compound showed activity against Candida albicans, including clinical strains. Inhibition of a clinical strain of Candida tropicalis, but not Candida krusei and Candida glabrata, was also shown as tested by the broth microdilution assay. The compound was purified by liquid chromatography coupled with thin-layer chromatography and bioautography and characterized by nuclear magnetic resonance spectroscopy. It was confirmed to have the molecular formula C 48 H 66 O 18 and was identified as an echinocandin with a novel structure. Conclusion: A novel echinocandin-type antifungal metabolite, MIG0310, was isolated and characterized. This is a second echinocandin reported from a Fusarium species, indicating this genus to have wider range of echinocandin compounds. Significance and Impact of the Study: The new compound may lead to new anticandidal drugs, broadening the treatment opportunities for Candida species, including those that are resistant to the current antifungal drugs.

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Section: Discussionmentioning

confidence: 97%

“…Only one case of echinocandin production by a Fusarium species was previously reported. The echinocandin fusacandin, produced by Fusarium sambucinum , is also related to the papulacandins, although it differs in its molecular structures (Hochlowski et al …”

Section: Discussionmentioning

confidence: 99%

A novel echinocandin MIG0310 with anticandida activity from newly isolated Fusarium sp. strain MS-R1

Masaphy

2014

J Appl Microbiol

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“…To this group of secondary metabolites belong F-10748 A2 63, B2 64, C2 65, and D2 66, also from Papularia sphaerosperma, chaetiacandin 67 from Monochaetia dimorphospora [100,101], and corynecandin 68 from Coryneum modonium [102]. Fusacandin A 69 and B 70 have also such a reduced spiroketal, but they are unique due to the attachment of an additional galactose to the galactose unit [103,104] (Figure 7). Chaetiacandin 67 and corynecandin 68 are the only papulacandins with a shortened fatty acid at the glucose unit.…”

Section: From Papulacandins and Echinocandins To Drugs Against Fungalmentioning

confidence: 99%

Fungal Metabolites for the Control of Biofilm Infections

Estrela

Abraham

2016

Agriculture

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Many microbes attach to surfaces and produce a complex matrix of polymers surrounding their cells, forming a biofilm. In biofilms, microbes are much better protected against hostile environments, impairing the action of most antibiotics. A pressing demand exists for novel therapeutic strategies against biofilm infections, which are a grave health wise on mucosal surfaces and medical devices. From fungi, a large number of secondary metabolites with antimicrobial activity have been characterized. This review discusses natural compounds from fungi which are effective against fungal and bacterial biofilms. Some molecules are able to block the cell communication process essential for biofilm formation (known as quorum sensing), others can penetrate and kill cells within the structure. Several targets have been identified, ranging from the inhibition of quorum sensing receptors and virulence factors, to cell wall synthesizing enzymes. Only one group of these fungal metabolites has been optimized and made it to the market, but more preclinical studies are ongoing to expand the biofilm-fighting arsenal. The broad diversity of bioactive compounds from fungi, their activities against various pathogens, and the multi-target trait of some molecules are promising aspects of fungal secondary metabolites. Future screenings for biofilm-controlling compounds will contribute to several novel clinical applications.

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“…Recently, in a direct comparison, papulacandin B was shown to be superior in some aspects compared to the drug caspofungin and a few drug candidates [15]. Its interesting biological activity has stimulated the search for new members of the papulacandin family, and several new compounds that are structurally related have been isolated, such as chaetiacandein [16–17], L-687,781 [18–19], Mer-WF3010 [20–21], BU-4794F [22], fusacandins [23–24], saricandin and PF-1042 [25], corynecandin [26–27] and the F-10748 series [28]. These structures vary mostly with respect to the two partially unsaturated acyl chains on the sugars.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal properties of papulacandin derivatives

Kaaden

Breukink²,

Pieters

2012

Beilstein J. Org. Chem.

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SummaryDerivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid.

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Fusacandins A and B; Novel Antifungal Antibiotics of the Papulacandin Class from Fusarium sambucinum. II. Isolation and Structural Elucidation.

Cited by 16 publications

References 14 publications

A novel echinocandin MIG0310 with anticandida activity from newly isolated Fusarium sp. strain MS-R1

A novel echinocandin MIG0310 with anticandida activity from newly isolated Fusarium sp. strain MS-R1

Fungal Metabolites for the Control of Biofilm Infections

Synthesis and antifungal properties of papulacandin derivatives

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