α-(15-Hydroxyhexadecyl)itaconic acid from Usnea aliphatica

Keogh, Myles F.; Zurita, Marta E.

doi:10.1016/0031-9422(77)83032-x

Cited by 12 publications

(8 citation statements)

References 5 publications

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“…The amount of hexadecenylitaconic acid we obtained from eucalypt wood (approximately 7 mg 100 g of wood Ϫ1 ) was similar to that reported on beech wood preextracted with benzene-ethanol (2:1) and supplemented with glucose and ammonium (19). An itaconic acid-type microbial metabolite with a long alkyl chain, 15-hydroxyhexadecylitaconic acid (a hydroxylated form of compound III), also has been isolated from the lichen Usnea aliphatica (35).…”

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

confidence: 80%

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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: 80%

“…The fragment at m/z 171 was formed in a similar manner from the citraconic isomer. A McLafferty rearrangement of the methyl ester produced the fragment at m/z 158 (35). The fragment at m/z 126 may arise from a loss of methoxyl from the fragment at m/z 157.…”

Section: Resultsmentioning

confidence: 99%

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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“…However, apart from the above noted papers,1–3 there have not to our knowledge been other reports of itaconic acid derivatives linked to a long aliphatic chain. In the present paper, we extend the range of the alkylitaconic acids identified in cultures of the basidiomycete C. subvermispora .…”

mentioning

confidence: 89%

“…Other metabolites with related structures have also been reported in the literature to occur in microorganisms. For example, 15‐hydroxyhexadecyl itaconic acid has been identified in the lichen Usnea aliphatica ,2 and butylhydroxyitaconic acid has been reported to occur in the conidial fungus Penicillium decumbens 3. Another natural product of related structure is itaconic acid, which is known to be produced by several fungi, such as those from the genus Aspergillus 4,.…”

mentioning

confidence: 99%

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

Río

Gutiérrez

Martı́nez

et al. 2001

Rapid Comm Mass Spectrometry

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A novel series of long-chain unsaturated dicarboxylic acids consisting of a long aliphatic chain attached to the C-3 position of itaconic acid has been identified by gas chromatography/mass spectrometry during in vitro decay of eucalypt wood by the white-rot basidiomycete Ceriporiopsis subvermispora. The major compounds were identified as tetradecyl-, 7-hexadecenyl- and hexadecylitaconic acids by their mass fragmentation patterns. Other members of the same compound series, identified as dodecanyl-, tridecanyl-, tetradecenyl-, pentadecanyl-, octadecenyl- and octadecanylitaconic acids, were present in very minor amounts or traces. Whereas hexadecenylitaconic acid has already been reported in cultures of C. subvermispora, to our knowledge this is the first report of the presence of the other alkylitaconic acids in fungal cultures. These new alkylitaconic-type metabolites may constitute a source for peroxidizable lipids involved in lignin degradation during wood decay by C. subvermispora and other white-rot basidiomycetes.

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“…(-)-2-methylene-3R-carboxy-18R-hydroxynonadecanoic acid) has been reported previously from Parmotrema xanthinum (Müll.Arg.) Hale and Usnea aliphatica Hale (Keogh and Zurita 1977;Huneck and Snatzke 1980;van den Boom et al 2007). In a recent review of lichen chemistry in southeast Alaska and British Columbia, one of us (T.S.)…”

Section: Hypogymnia Wilfianamentioning

confidence: 94%

Hypogymnia recurvaandHypogymnia wilfianaspp. nov., two new lichens from western North AmericaThis paper is one of a selection of papers published as part of the special Schofield Gedenkschrift.

Goward

Ahtı

Elix

et al. 2010

Botany

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Hypogymnia metaphysodes was first described from Japan and Sakhalin, and later reported from western North America. Here we show that the North American material currently referred to H. metaphysodes differs from that species not only morphologically and chemically, but also in ascospore size and shape. We also show that the North American material is in fact heterogeneous, and can be assigned to two well-defined species here described as new: Hypogymnia recurva sp. nov. and H. wilfiana sp. nov. Both of these lichens contain distinctive secondary metabolites: vittatolic acid in the case of H. recurva, and 2-methylene-3-carboxy-18-hydroxynonadecanoic acid (''apinnatic acid''), reported here for the first time from Hypogymnia, in H. wilfiana. Both of our new species are so far known only from western North America, where they occur primarily as epiphytes on the branches of conifers. Hypogymnia metaphysodes s. str. has not yet been reliably reported from this region and should be excluded from the North American lichen flora.Résumé : On a décrit l'Hypogymnia metaphysodes pour la première fois au Japon et Sakhalin puis par la suite on l'a rapporté dans l'ouest de l'Amérique du Nord. Les auteurs montrent que le matériel nord-américain habituellement considéré comme appartenant au H. metaphysodes diffère de cette espèce non seulement morphologiquement et chimiquement, mais aussi par la forme et la dimension de ses spores. Les auteurs montrent également que le matériel nord-américain est en fait hétérogène, et constitue deux entités bien définies ici décrites comme nouvelles espèces : Hypogymnia recurva sp. nov. et H. wilfiana sp. nov. Ces deux espèces de lichens contiennent des métabolites secondaires distinctifs; l'acide vittatolique, dans le cas du H. recurva et l'acide 2-méthylène-3-carboxy-18-hydroxynonadécanoïque (acide 'apinnatique), rapporté ici pour la première fois chez les Hypogymnia, soit l'H. wilfiana. Jusqu'ici, ces deux nouvelles espèces ne sont connues que pour l'ouest de l'Amérique du Nord, où on les retrouve surtout comme épiphyte sur les branches des conifères. Il n'y a aucune mention fiable de la présence de l'Hypogymnia metaphysodes s. str. dans cette ré-gion et l'on devrait l'exclure de la flore lichénique nord-américaine.Mots-clés : Colombie-Brittanique, Parmeliaceae, systématique, chromatographie sur couche mince, acide apinnatique, acide vittatolique.

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α-(15-Hydroxyhexadecyl)itaconic acid from Usnea aliphatica

Cited by 12 publications

References 5 publications

Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

Production of New Unsaturated Lipids during Wood Decay by Ligninolytic Basidiomycetes

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

Hypogymnia recurvaandHypogymnia wilfianaspp. nov., two new lichens from western North AmericaThis paper is one of a selection of papers published as part of the special Schofield Gedenkschrift.

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