Itaconic Acid Fermentation by a Yeast Belonging to the Genus<i>Candida</i>

Tabuchi, Takeshi; Sugisawa, Teruhide; Ishidori, Tsuguo; Nakahara, Tadaatsu; Sugiyama, Junta

doi:10.1080/00021369.1981.10864534

Cited by 21 publications

(13 citation statements)

References 5 publications

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“…4,12) Itaconic acid has been found as a metabolite of filamentous fungi such as Aspergillus itaconicus, 13) Helicobasidium mompa, 14) Ustilago zeae, 15) and U. maydis 16) and some yeast belonging to the genus Candida. 17) Whilst alkylated derivatives (alkylitaconic acids) have been isolated from lichens and several fungi. The other analogues of alkylitaconic acid are alkylcitraconic acids, called chaetomellic acids (Fig.…”

Section: Resultsmentioning

confidence: 99%

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Zhang

Lee

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Although dicarboxylic acids do not occur in appreciable amount as components of animal or vegetal lipids, generally they are important metabolic products of fatty acids. Especially the a,b-dicarboxylic acid and its derivatives, such as itaconic acid 1,2) and citraconic acid derivatives, 3) have been of much interest for their biosynthesis, stereochemistry, and chemical relationship. Furthermore, some of them were reported to exhibit various interesting bioactivities, such as plant growth-stimulation, 4) production of a cellulolytic active oxygen species, inhibition of the iron redox reaction, 5) inhibition of p53-HDM2 interaction which can induce apoptosis in human cancer cells, 6) and anti-trypanosomal activity. 7)In the course of search for bioactive metabolites from marine organisms, five hexylitaconic acid derivatives including four new ones (1-4) were isolated from a sponge-derived fungus Penicillium sp. Herein we describe the structure elucidation and the biological evaluation of the compounds. Results and DiscussionAccurate mass measurement (high resolution (HR)-FAB-MS) of compound 1 (m/z 259.1549 [MϩH] ϩ , Dϩ0.4 mmu) revealed the molecular formula to be C 13 H 22 O 5 with three degrees of unsaturation. Thirteen carbon signals were evident in the 13 C-NMR spectrum (Table 1) and deduced to be three methyl, five methylene, two methine, and three quaternary carbons from the distortionless enhancement by polarization transfer (DEPT)135 spectrum. According to 1 H-and In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as a a,b b-dicarboxylic acid derivatives, such as hexylitaconic acid and tensyuic acids which were previously reported as metabolite of Aspergillus niger, Penicillium striatisporum, or Apiospora montagnei. The isolated compounds were evaluated for cytotoxicity against a panel of five human solid tumor cell lines, and for anti-inflammatory activity gauged by their inhibitory effects on the production of major pro-inflammatory mediators (nitric oxide (NO), interleukin (IL)-6, tumor necrosis factor (TNF)-a a, and IL-1b b) in murine macrophage cells. Compounds 1 and 4 showed weak inhibition of IL-1b b production at the concentration of 200 m mM.

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Section: Resultsmentioning

confidence: 99%

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Zhang

Lee

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The main advantage of itaconic acid today is that its production does not depend on petrochemical sources. Itaconic acid can be produced from a variety of agricultural products, for example, through the fermentation of molasses by Aspergillus itaconicus 1, Aspergillus terreus ,2 some strains of Candida ,3 and Ustilago 4 through the direct enzymatic conversion of citric acid,5 or even from starch 6. Its use is relatively widespread, and reviews by Tate7 and, more recently, Willke and Vorlop8 covered this topic in great detail.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of itaconic acid initiated by a potassium persulfate/N,N‐dimethylethanolamine system

Veličković

Džunuzović

Griffiths

et al. 2008

J of Applied Polymer Sci

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ABSTRACT:The synthesis and characterization of poly (itaconic acid) (PIA) with a novel initiator/activator system is presented. The initiator in this system was potassium persulfate, whereas the activator was N,Ndimethylethanolamine (DMEA). PIA was synthesized in distilled water and in 0.1M HCl at 40 C with reaction times of 72 and 96 h. PIA was investigated with differential scanning calorimetry, gel permeation chromatography, and pulse gradient spin echo-NMR and compared to the same polymer synthesized in dioxane with 2,2 0 -azobisisobutyronitrile as the initiator. It was shown that, despite the fact that some residual DMEA remained in the system, the properties of the PIA polymerized in the aqueous phase were very similar to the dioxane-synthesized polymer, which will enable a faster, cheaper, and environmentally more acceptable polymerization of itaconic acid.

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“…Strain SB-2 was isolated from the exudate of a tree at Ishigaki Island near Taiwan and selected by the screening method described in the preceding paper 1 ) as the yeast producing an unknown acid. Candida sorbosa CBS 1910, the type strain of the species,Z) Abbreviations: HMG and HMG-CoA, 3-hydroxy-3-methylglutaric acid and its CoA ester.…”

Section: Methodsmentioning

confidence: 99%