Two new 1,2,3,4-tetrahydroanthraquinones, auxarthrol A (compound 1) and auxarthrol B (2), along with three known pyrrolyloctatetraenyl-alpha-pyrone pigments, auxarconjugatin A (3), auxarconjugatin B (4) and rumbrin (5), were isolated from the fungus Auxarthron umbrinum. Structure elucidation of new compounds 1 and 2 was accomplished by spectroscopic data analysis while identification of the known pigments (3-5) was achieved by LC-MS-photodiode array detection.
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http://dx.doi.org/10.1007/s10295-003-0106-5 | DOI Listing |
Acta Pharm Sin B
November 2022
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
Investigation on how nature produces natural compounds with chemical and biological diversity at the genetic level offers inspiration for the discovery of new natural products and even their biological targets. The polyketide rumbrin () is a lipid peroxide production and calcium accumulation inhibitor, which contains a chlorinated pyrrole moiety that is a rare chemical feature in fungal natural products. Here, we identify the biosynthetic gene cluster (BGC) of and its isomer 12-rumbrin () from DSM3193, and elucidate their biosynthetic pathway based on heterologous expression, chemical complementation, and isotopic labeling.
View Article and Find Full Text PDFJ Mycol Med
December 2014
Department of Natural Products, Piramal Enterprises Limited, 1, Nirlon Complex, Off Western Express Highway, Near NSE Complex, Goregaon (East), Mumbai 400 063, India.
One hundred and twenty-five samples were collected from eight different sites in the vicinity of Sanjay Gandhi National Park (SGNP) and screened for the presence of keratinophilic fungi using hair baiting technique for isolation. Seventy-three isolates were recovered and identified. The cultures were identified using macro- and micro-morphological features.
View Article and Find Full Text PDFMed Mycol
August 2013
Department of Botany, Faculty of Science, Charles University in Prague, Prague, Czech Republic.
Auxarthron is a genus within the Onygenales encompassing keratinophilic species with typical ascomata (gymnothecia) consisting of anastomosing network of thick-walled hyphae and small globose or oblate ascospores. No association of this genus with clinically relevant cases of human or animal infection has been reported. This paper describes the isolation of an undescribed Auxarthron species as an agent of proven onychomycosis affecting almost all fingernails in a man with psoriasis.
View Article and Find Full Text PDFOrg Biomol Chem
September 2011
School of Biomolecular and Biomedical Sciences, Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin, Republic of Ireland.
The biosynthesis of the pyrrolyl moiety of the fungal metabolite rumbrin originates from pyrrole-2-carboxylic acid. In an effort to produce novel derivatives with enhanced biological activity a series of substituted pyrrole-2-carboxylates were synthesised and incubated with the producing organism, Auxarthron umbrinum. Several 4-halo-pyrrole-2-carboxylic acids were incorporated into the metabolite yielding three new derivatives: 3-fluoro-, 3-chloro- and 3-bromo-isorumbrin, which were generated in milligram quantities enabling cytotoxicity assays to be conducted.
View Article and Find Full Text PDFOrg Biomol Chem
January 2009
School of Biomolecular and Biomedical Sciences, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin, Belfield, Dublin 4, Republic of Ireland.
The biosynthesis of the pyrrolylpolyene rumbrin (1) in the fungus Auxarthron umbrinum was elucidated using feeding studies with labelled precursors. Incorporation of stable isotopes from [(15)N]-proline, [(13)C]-methionine and [(13)C]-acetate confirmed that these were the precursors of the pyrrole moiety, methyl groups, and backbone of rumbrin, respectively. Label-dilution experiments with pyrrole-2-carboxylate confirmed it was a direct precursor in the biosynthesis of rumbrin.
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