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Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus

Polyesters containing 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate and 3-hydroxybutyrate moieties have been isolated from many fungal species. Talaromyces stipitatus was previously reported to produce a similar polyester, talapolyester G. The complete genome sequence and the development of bioinformati...

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Autor principal: al Fahad, Ahmed J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9318984/
https://www.ncbi.nlm.nih.gov/pubmed/35889347
http://dx.doi.org/10.3390/molecules27144473
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author al Fahad, Ahmed J.
author_facet al Fahad, Ahmed J.
author_sort al Fahad, Ahmed J.
collection PubMed
description Polyesters containing 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate and 3-hydroxybutyrate moieties have been isolated from many fungal species. Talaromyces stipitatus was previously reported to produce a similar polyester, talapolyester G. The complete genome sequence and the development of bioinformatics tools have enabled the discovery of the biosynthetic potential of this microorganism. Here, a putative biosynthetic gene cluster (BGC) of the polyesters encoding a highly reducing polyketide synthase (HR-PKS) and nonreducing polyketide synthase (NR-PKS), a cytochrome P450 and a regulator, was identified. Although talapolyester G does not require an oxidative step for its biosynthesis, further investigation into the secondary metabolite production of T. stipitatus resulted in isolating two new metabolites called talarodioxadione and talarooxime, in addition to three known compounds, namely 6-hydroxymellein, 15G256α and transtorine that have never been reported from this organism. Interestingly, the biosynthesis of the cyclic polyester 15G256α requires hydroxylation of an inactive methyl group and thus could be a product of the identified gene cluster. The two compounds, talarooxime and transtorine, are probably the catabolic metabolites of tryptophan through the kynurenine pathway. Tryptophan metabolism exists in almost all organisms and has been of interest to many researchers. The biosynthesis of the new oxime is proposed to involve two subsequent N-hydroxylation of 2-aminoacetophenone.
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spelling pubmed-93189842022-07-27 Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus al Fahad, Ahmed J. Molecules Article Polyesters containing 2,4-dihydroxy-6-(2-hydroxypropyl)benzoate and 3-hydroxybutyrate moieties have been isolated from many fungal species. Talaromyces stipitatus was previously reported to produce a similar polyester, talapolyester G. The complete genome sequence and the development of bioinformatics tools have enabled the discovery of the biosynthetic potential of this microorganism. Here, a putative biosynthetic gene cluster (BGC) of the polyesters encoding a highly reducing polyketide synthase (HR-PKS) and nonreducing polyketide synthase (NR-PKS), a cytochrome P450 and a regulator, was identified. Although talapolyester G does not require an oxidative step for its biosynthesis, further investigation into the secondary metabolite production of T. stipitatus resulted in isolating two new metabolites called talarodioxadione and talarooxime, in addition to three known compounds, namely 6-hydroxymellein, 15G256α and transtorine that have never been reported from this organism. Interestingly, the biosynthesis of the cyclic polyester 15G256α requires hydroxylation of an inactive methyl group and thus could be a product of the identified gene cluster. The two compounds, talarooxime and transtorine, are probably the catabolic metabolites of tryptophan through the kynurenine pathway. Tryptophan metabolism exists in almost all organisms and has been of interest to many researchers. The biosynthesis of the new oxime is proposed to involve two subsequent N-hydroxylation of 2-aminoacetophenone. MDPI 2022-07-13 /pmc/articles/PMC9318984/ /pubmed/35889347 http://dx.doi.org/10.3390/molecules27144473 Text en © 2022 by the author. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
al Fahad, Ahmed J.
Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title_full Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title_fullStr Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title_full_unstemmed Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title_short Putative Biosynthesis of Talarodioxadione & Talarooxime from Talaromyces stipitatus
title_sort putative biosynthesis of talarodioxadione & talarooxime from talaromyces stipitatus
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9318984/
https://www.ncbi.nlm.nih.gov/pubmed/35889347
http://dx.doi.org/10.3390/molecules27144473
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