Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora

Amirta, Rudianto; Fujimori, Kunio; Shirai, Nobuyuki; Honda, Yoshio; Watanabe, Takashi

doi:10.1016/s0009-3084(03)00098-7

Cited by 24 publications

(16 citation statements)

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“…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.…”

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“…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)(2)(3)(4) were isolated from a sponge-derived fungus Penicillium sp. Herein we describe the structure elucidation and the biological evaluation of the compounds.…”

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

Zhang

Lee

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[22][23][24] Particular acids involved in lignin degradation produced by this fungus are ceriporic acids, which are acids with an itaconic core and different lengths of the alkyl side chains. 25,26 Hermann et al 27 reported a similar pH change for the growth of L. edodes on sawdust. Although no in depth analyses of the acid production have been conducted for L. edodes as far as we know, this fungus is known to produce oxalic acids.…”

Section: Resultsmentioning

confidence: 85%

Preservation of Ceriporiopsis subvermispora and Lentinula edodes treated wheat straw under anaerobic conditions

et al. 2017

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BACKGROUNDNo attention has been paid so far to the preservation of fungal‐treated lignocellulose for longer periods. In the present study, we treated wheat straw (WS) with the white‐rot fungi Ceriporiopsis subvermispora and Lentinula edodes for 8 weeks and assessed changes in pH, chemical composition and in vitro gas production (IVGP) weekly. Fungal‐treated WS was also stored for 64 days ‘as is’, with the addition of lactic acid bacteria (LAB) or with a combination of LAB and molasses in airtight glass jars mimicking ensiling conditions.RESULTSBoth fungi significantly reduced the lignin and hemicellulose content of WS, and increased the cellulose content. The IVGP increased with increasing time of incubation, indicating the increase in digestibility. Both fungi lowered the pH of WS under 4.3, which guarantees an initial and stable low pH during anaerobic storage. Minor changes in fibre composition and IVGP were observed for stored L. edodes treated WS, whereas no change occurred for C. subvermispora.CONCLUSIONIt is possible to conserve C. subvermispora and L. edodes treated straw under anaerobic condition without additives up to 64 days. This finding is important for practical application to supply fungi‐treated feed to ruminant animals for a prolonged period. © 2017 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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“…74,75 Esse grupo propõe que os ácidos alquilitacônicos podem participar na supressão da reação de Fenton por meio da interação e indisponibilização de íons ferro, além de evitar também a repolimerização de fenóis derivados de lignina, oxidados pela ação enzimática. 74 As hipóteses mencionadas anteriormente são corroboradas pela grande seletividade de algumas espécies de fungos causadores de podridão branca em degradar lignina, mantendo os polissacarídeos de certa forma preservados.…”

Section: Sistema Fentonunclassified

Mecanismos envolvidos na biodegradação de materiais lignocelulósicos e aplicações tecnológicas correlatas

Aguiar¹,

Ferraz²

2011

Quím. Nova

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Recebido em 9/11/10; aceito em 21/6/11; publicado na web em 8/8/11MECHANISMS INVOLVED IN THE BIODEGRADATION OF LIGNOCELLULOSIC MATERIALS AND RELATED TECHNOLOGICAL APPLICATIONS. The biodegradation of lignocellulosic materials is an important natural process because it is responsible for the carbon recycling. When induced under controlled conditions, this process can be used for technological applications such as biopulping, biobleaching of cellulosic pulps, pre-treatment for subsequent saccharification and cellulosic-ethanol production, and increase of the digestibility in agroindustrial residues used for animal feed. In the present work, the enzymatic and non-enzymatic mechanisms involved in the biodegradation of lignocellulosic materials by fungi were reviewed. Furthermore, the technological applications of these extracellular metabolites are presented and discussed.Keywords: wood biodegradation; oxidative enzymes; Fenton reaction. INTRODUÇÃOA biodegradação dos materiais lignocelulósicos tem sido objeto de muitos estudos, pois, além de corresponder a uma importante etapa do ciclo do carbono na natureza, também pode ser aplicada em processos tecnológicos. As aplicações em questão são variadas e incluem desde a ação direta de fungos sobre a madeira, desenhada como uma etapa de pré-tratamento aos processos de fabricação de celulose e papel, 1,2 até processos que usam os fungos decompositores de materiais lignocelulósicos como agentes indutores da degradação de compostos xenobióticos, quer em solos contaminados 3 ou em efluentes industriais. 4 O pré-tratamento de materiais lignocelulósicos com fungos também tem sido apontado como uma forma de facilitar processos subsequentes de conversão da celulose em açúcares fermentescíveis destinados à bioconversão em etanol e outros produtos de interesse comercial. 5,6 Também na área de nutrição animal, a aplicação de fungos decompositores de materiais lignocelulósicos tem sido descrita. Nesse caso, o pré-tratamento biológico é usado para aumentar a digestibilidade de resíduos agroindustriais utilizados na alimentação de ruminantes e não ruminantes. Os fungos, principalmente os causadores de podridão branca seletivos na degradação de lignina, desestruturam a parede celular vegetal, promovendo a conversão dos polissacarídeos em açúcares de fácil assimilação. Além disso, a biomassa fúngica que se desenvolve sobre o lignocelulósico pode servir como fonte de proteína. 7 A aplicação de enzimas produzidas pelos fungos decompositores de materiais lignocelulósicos também tem ganhado muito interesse na atualidade. O uso de xilanases 8 e lacases 9,10 em processos de branqueamento de polpas celulósicas e a aplicação de celulases na hidrólise enzimática de celulose nos processos de produção de etanol de segunda geração, 11 são exemplos de como o avanço no entendimento da biodegradação dos lignocelulósicos tem permitido explorar aplicações tecnológicas de grande relevância para o mundo moderno.O desenvolvimento das aplicações mencionadas anteriormente tem ocorrido de forma simultânea à ger...

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Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora

Cited by 24 publications

References 24 publications

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

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

Preservation of Ceriporiopsis subvermispora and Lentinula edodes treated wheat straw under anaerobic conditions

Mecanismos envolvidos na biodegradação de materiais lignocelulósicos e aplicações tecnológicas correlatas

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