Itaconic acid derivatives and diketopiperazine from the marine-derived fungus Aspergillus aculeatus CRI322-03

Antia, Bassey S.; Aree, Thammarat; Kasettrathat, Chairut; Wiyakrutta, Suthep; Ekpa, Okon D.; Ekpe, Udofot J.; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat

doi:10.1016/j.phytochem.2011.02.013

Cited by 38 publications

(21 citation statements)

References 21 publications

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“…In addition, two compounds corresponding to the molecular formulae C 11 H 18 O 5 (RT 4.62 min) and C H 16 O 6 (RT 4.70 min) were detected. They could be attributed to itaconic acid derivatives, the same or similar to those previously isolated from a seawater isolate of A. aculeatus, namely 9-hydroxylitaconic acid and 9-hydroxylitaconic acid-4-methyl ester [42]. Apart from citric acid, the AP contained considerably lower amounts of all acids in comparison to the CCF (Fig.…”

Section: Chemical Characterization Of Extracellular Metabolitessupporting

confidence: 68%

Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum

Jovičić-Petrović

Jeremić

Vučković

et al. 2016

Arch biol sci (Beogr)

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Adding compost to soil can result in plant disease suppression through the mechanisms of antagonistic action of compost microflora against plant pathogens. The aim of the study was to select effective antagonists of Pythium aphanidermatum from compost, to assess the effect of its extracellular metabolites on the plant pathogen, and to characterize antifungal metabolites. The fungal isolate selected by a confrontation test was identified as Aspergillus piperis A/5 on the basis of morphological features and the internal transcribed spacer (ITS) region, ?-tubulin and calmodulin partial sequences. Liquid chromatography-mass spectroscopy (LC-MS) analysis showed that gluconic and citric acid were the most abundant in the organic culture extract. However, the main antifungal activity was contained in the aqueous phase remaining after the organic solvent extraction. The presence of considerable amounts of proteins in both the crude culture extract as well as the aqueous phase remaining after solvent extraction was confirmed by SDS-PAGE. Isolated Aspergillus piperis A/5 exhibits strong antifungal activity against the phytopathogen Pythium aphanidermatum. It secretes a complex mixture of metabolites consisting of small molecules, including gluconic acid, citric acid and itaconic acid derivatives, but the most potent antifungal activity was associated with proteins resistant to heat and organic solvents. Our findings about the activity and characterization of antagonistic strain metabolites contribute to the understanding of the mechanism of interaction of antifungal metabolites as well as fungal-fungal interaction. The obtained results provide a basis for further application development in agriculture and food processing. [Projekat Ministarstva nauke Republike Srbije, br. TR31080 i br. ON173048, i EU Commission project AREA, br.316004]

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Section: Chemical Characterization Of Extracellular Metabolitessupporting

confidence: 68%

Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum

Jovičić-Petrović

Jeremić

Vučković

et al. 2016

Arch biol sci (Beogr)

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“…The chemical diversity of natural diketopiperazines is high and there are also several recent reports on novel diketopiperazines of unknown functions and activities which widens the diversity of this class of compounds. Recently, the diketopiperazines pre-aurantiamine 86 and aurantiamine 87 have been reported from a marine Aspergillus aculeatus isolate [127] ( Figure 6). However, no antimicrobial activities have been reported.…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial and Biofilm Inhibiting Diketopiperazines

Carvalho

Abraham²

2012

CMC

144

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“…Chemical investigation of the extract obtained from this strain led to the isolation of three new metabolites: ethyl 8-hydroxyhexylitaconate (5), methyl 8-hydroxyhexylitaconate (2) and ethyl 9-hydroxyhexylitaconate (4) along with nine known compounds: three hexylitaconic acid derivatives 1, 3 and 6 [29][30][31], four diketopiperazines 7-10 [32,33], 2-phenylethyl alcohol 11 and one isocoumarin 12 [34] (Figure 4a).…”

Section: Fungal Metabolites Isolation and Structure Elucidationmentioning

confidence: 99%

A Novel High-Throughput Screening Platform Identifies Itaconate Derivatives from Marine Penicillium antarcticum as Inhibitors of Mesenchymal Stem Cell Differentiation

et al. 2020

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Worldwide diffused diseases such as osteoarthritis, atherosclerosis or chronic kidney disease are associated with a tissue calcification process which may involve unexpected local stem cell differentiation. Current pharmacological treatments for such musculoskeletal conditions are weakly effective, sometimes extremely expensive and often absent. The potential to develop new therapies is represented by the discovery of small molecules modulating resident progenitor cell differentiation to prevent aberrant tissue calcification. The marine environment is a rich reserve of compounds with pharmaceutical potential and many novel molecules are isolated from macro and microorganisms annually. The potential of small molecules synthetized by marine filamentous fungi to influence the osteogenic and chondrogenic differentiation of human mesenchymal stem/stromal cells (hMSCs) was investigated using a novel, high-throughput automated screening platform. Metabolites synthetized by the marine-derived fungus Penicillium antarcticum were evaluated on the platform. Itaconic acid derivatives were identified as inhibitors of calcium elaboration into the matrix of osteogenically differentiated hMSCs and also inhibited hMSC chondrogenic differentiation, highlighting their capacity to impair ectopic calcification. Bioactive small molecule discovery is critical to address ectopic tissue calcification and the use of biologically relevant assays to identify naturally occurring metabolites from marine sources represents a strategy that can contribute to this effort.

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Itaconic acid derivatives and diketopiperazine from the marine-derived fungus Aspergillus aculeatus CRI322-03

Cited by 38 publications

References 21 publications

Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum

Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum

Antimicrobial and Biofilm Inhibiting Diketopiperazines

A Novel High-Throughput Screening Platform Identifies Itaconate Derivatives from Marine Penicillium antarcticum as Inhibitors of Mesenchymal Stem Cell Differentiation

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