Production of itaconic acid by Helicobasidium mompa TANAKA.

Araki, Takao; Yamazaki, Yasushi; Suzuki, Naoji

doi:10.3186/jjphytopath.22.83

Cited by 8 publications

(5 citation statements)

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“…IA is industrially produced by the fungus Aspergillus terreus, and is widely used as a building block for synthetic polymers [1][2][3][4][5], food additives [6], and surfactants [7,8]. A. terreus [9,10], Aspergillus itaconicus [11], Helicobasidium mompa [12], Ustilago maydis [13], Ustilago zeae [14], Candida sp. [15], and Pseudozyma antarctica [16] were found to be IA producers in soils, plants, and fermented foods.…”

Section: Introductionmentioning

confidence: 99%

Microbial Screening Based on the Mizoroki–Heck Reaction Permits Exploration of Hydroxyhexylitaconic-Acid-Producing Fungi in Soils

et al. 2020

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Recently, we developed a unique microbial screening method based on the Mizoroki–Heck reaction for itaconic acid (IA)-producing fungi. This method revealed that 37 out of 240 fungal strains isolated from soils produce vinyl compounds, including IA. In this study, we further characterized these compounds in order to verify that the screening method permits the isolation of fungi that produce other vinyl compounds, excluding IA. HPLC analysis showed that 11 out of 37 isolated strains produced IA, similar to Aspergillus terreus S12-1. Surprisingly, the other 8 isolated strains produced two vinyl compounds with HPLC retention times different from that of IA. From these strains, the vinyl compounds of Aspergillus niger S17-5 were characterized. Mass spectrometric and NMR analyses showed that they were identical to 8-hydroxyhexylitaconic acid (8-HHIA) and 9-HHIA. This finding showed that 8-HHIA- and 9-HHIA-producing fungi, as well as IA-producing fungi, are ubiquitously found in soils. Neither 8-HHIA nor 9-HHIA showed antibacterial or anti-inflammatory activities. Interestingly, 8-HHIA and 9-HHIA showed cytotoxicity against the human cervical cancer cell line (HeLa) and human diploid cell line (MRC-5), and MRC-5 only, respectively, compared to IA at the same concentration. This study indicates that the screening method could easily discover fungi producing 8-HHIA and 9-HHIA in soils.

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Section: Introductionmentioning

confidence: 99%

Microbial Screening Based on the Mizoroki–Heck Reaction Permits Exploration of Hydroxyhexylitaconic-Acid-Producing Fungi in Soils

et al. 2020

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“…produced (3S)-hexylitaconic acid (5). 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.…”

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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“…U. zeae),l1) Helicobasidium mompa, 12) and Candida antarctica. 2 ,13) Commercial production has used A. terreus.…”

Section: Discussionmentioning

confidence: 99%

Accumulation of Itaconic, 2-Hydroxyparaconic, Itatartaric, and Malic Acids by Strains of the GenusUstilago

Guevarra

Tabuchi

1990

Agricultural and Biological Chemistry

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Production of itaconic acid by Helicobasidium mompa TANAKA.

Cited by 8 publications

References 0 publications

Microbial Screening Based on the Mizoroki–Heck Reaction Permits Exploration of Hydroxyhexylitaconic-Acid-Producing Fungi in Soils

Microbial Screening Based on the Mizoroki–Heck Reaction Permits Exploration of Hydroxyhexylitaconic-Acid-Producing Fungi in Soils

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

Accumulation of Itaconic, 2-Hydroxyparaconic, Itatartaric, and Malic Acids by Strains of the GenusUstilago

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