Identification of a novel series of alkylitaconic acids in wood cultures of <i>Ceriporiopsis subvermispora</i> by gas chromatography/mass spectrometry

Río, José C. del; Gutiérrez, Ana; Martı́nez, Marı́a Jesús; Martı́nez, Ángel T.

doi:10.1002/rcm.547

Cited by 10 publications

(3 citation statements)

References 32 publications

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“…An m/z 257 fragment should be obtained from hydroxylation and silylation of cis-4-hexadecenylitaconic acid, which was not observed. As discussed by del Río et al (16), this conclusion is also supported by the 13 C NMR spectrum of this compound (19) that shows a shift difference between the two olefinic carbons of the alkyl chain (0.3 ppm) that is smaller than expected if the double bond was located at C-4, closer to the carboxylates. Similar differences have been reported between olefinic carbon signals in the 13 C NMR spectra of oleic (18:1 9c ) and petroselinic (18:1 6c ) acids (38).…”

Section: Fig 3 Lipids and Fungal Biomass During 7-week Decay Of Eucsupporting

confidence: 74%

“…Trimethylsilyldiazomethane methylation and bis(trimethylsilyl)trifluoroacetamide (BSTFA) silylation, alone or subsequently applied, were used to elucidate the molecular structure of new fungal metabolites. Doublebond position in the alkyl chain of alkylitaconic acids was determined by hydroxylation with osmium tetroxide followed by silylation of the diol derivative using BSTFA (16). Compounds were identified by comparing their mass spectra with mass spectra in the Wiley and Nist libraries, by mass "fragmentography" and, when possible, by comparison with standards.…”

Section: Methodsmentioning

confidence: 99%

“…The two other alkylitaconic acids (peaks I and III) have not been previously reported. We deduced their chemical structures, and those of the four minor compounds (dodecylitaconic, tetradecenylitaconic, octadecenylitaconic, and octadecylitaconic acids), from the mass spectra of underivatized, methylated, and silylated derivatives (16). The three dominant alkylitaconic acids also were found in cultures of C. subvermispora CZ-3 and FP90031.…”

Section: Fig 3 Lipids and Fungal Biomass During 7-week Decay Of Eucmentioning

confidence: 99%

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Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

Gutiérrez

Río

Martinez-Inigo

et al. 2002

Appl Environ Microbiol

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Lipids were analyzed by gas chromatography-mass spectrometry for a 7-week in vitro decay of eucalypt wood by four ligninolytic basidiomycetes. The sound wood contained up to 75 mg of lipophilic compounds per 100 g of wood. Hydrolysis of sterol esters, which represented 38% of total wood lipids, occurred during the fungal decay. The initial increase of linoleic and other free unsaturated fatty acids paralleled the decrease of sterol esters. Moreover, new lipid compounds were found at advanced stages of wood decay that were identified from their mass spectra as unsaturated dicarboxylic acids consisting of a long aliphatic chain attached to the C-3 position of itaconic acid. These dicarboxylic acids were especially abundant in the wood treated with Ceriporiopsis subvermispora (up to 24 mg per 100 g of wood) but also were produced by Phlebia radiata, Pleurotus pulmonarius, and Bjerkandera adusta. We hypothesize that three main alkylitaconic acids (tetradecylitaconic, cis-7-hexadecenylitaconic, and hexadecylitaconic acids) are synthesized by fungi in condensation reactions involving palmitic, oleic, and stearic acids. We suggest that both wood unsaturated fatty acids (present in free form or released from esters during natural decay) and unsaturated metabolites synthesized by fungi could serve as a source for peroxidizable lipids in lignin degradation by white rot basidiomycetes.Fungi produce a variety of lipids including fatty acids in free or esterified form, e.g., glycerides, phospholipids, glycolipids, sterol esters, sphingolipids, or simple esters, as well as other lipids, e.g., free sterols, sterol glycosides, and hydrocarbons (46,54,56). Vegetative mycelium (from pure cultures) and fruit bodies of basidiomycetes differ in both lipid content and fatty acid profiles. Linoleic (18:2 9c,12c ), oleic (18:1 9c ), and palmitic (16:0) acids are the main fatty acids in most cases. Linoleic acid is very abundant in fruit bodies and may account for as much as 70 to 80% of the lipids present (1,42,48,49). Other saturated and unsaturated fatty acids are present in basidiomycetes at lower levels. As reported for other filamentous fungi, unsaturated fatty acids could help basidiomycetes adapt to low growth temperatures (11,12). These fatty acids also may have a role in lignin degradation.Lipid peroxidation reactions could be a part of the lignin degradation process by white rot basidiomycetes. When unsaturated fatty acids are oxidized in the presence of manganese peroxidase (MnP), a ligninolytic peroxidase that oxidizes Mn 2ϩ to Mn 3ϩ , lipid hydroperoxides and free radicals are formed. This reaction is considered to be sufficient for lignin degradation by some ligninolytic fungi, e.g., Ceriporiopsis (syn. Poria) subvermispora, that lack lignin peroxidase (LiP) (4, 31-33). LiP, which has a high redox potential that enables direct oxidation of nonphenolic lignin units, was described in the white rot fungus Phanerochaete chrysosporium together with MnP (37). However, LiP has not been detected in some efficient lignin-degrading...

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Section: Fig 3 Lipids and Fungal Biomass During 7-week Decay Of Eucsupporting

confidence: 74%

Section: Methodsmentioning

confidence: 99%

Section: Fig 3 Lipids and Fungal Biomass During 7-week Decay Of Eucmentioning

confidence: 99%

See 1 more Smart Citation

Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

Gutiérrez

Río

Martinez-Inigo

et al. 2002

Appl Environ Microbiol

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Current literature in mass spectrometry

2002

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 20th. Feb. 2002)

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Ligninolytic ability and potential biotechnology applications of the South American FungusPleurotus laciniatocrenatus

Saparrat

Guillén

2005

Folia Microbiol

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The extracellular ligninolytic enzyme system of Pleurotus laciniatocrenatus, grown under different culture conditions, was characterized and the ability of this strain to degrade different components of Eucalyptus globulus wood was determined. In shaken liquid cultures grown on a C-limited medium supplemented with yeast extract (0.1%) and peptone (0.5%), the fungus produced extracellular aryl-alcohol oxidase (Aao), laccase (Lac), manganese-dependent peroxidase (MnP) and manganese-independent peroxidase (MiP) activities, their maximum levels being, respectively, about 600, 50, 1360, and 920 pkat/mL. The supplementation of 1 mmol/L vanillic acid and 150 micromol/L CuSO4 produced an increase of Lac activity levels up to 4-fold and 68.3-fold, respectively. No significant differences were found in the levels of the other ligninolytic enzyme activities when compared to the basal medium. Solid-state fermentation cultures on E. globulus wood chips revealed Lac and MiP activities. These cultures showed degradative activity on lignin and lipophilic wood extractives.

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Identification of a novel series of alkylitaconic acids in wood cultures of Ceriporiopsis subvermispora by gas chromatography/mass spectrometry

Cited by 10 publications

References 32 publications

Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

Current literature in mass spectrometry

Ligninolytic ability and potential biotechnology applications of the South American FungusPleurotus laciniatocrenatus

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