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Molecules ; 20(9): 17627-44, 2015 Sep 23.
Article de Anglais | MEDLINE | ID: mdl-26404231

RÉSUMÉ

UHPLC-DAD-HRMS based dereplication guided the detection of new halogenated alkaloids co-produced by Talaromyces wortmannii. From the fungal growth in large scale, the epimers 2,8-dichlororugulovasines A and B were purified and further identified by means of a HPLC-SPE/NMR hyphenated system. Brominated rugulovasines were also detected when the microbial incubation medium was supplemented with bromine sources. Studies from 1D/2D NMR and HRMS spectroscopy data allowed the structural elucidation of the dichlorinated compounds, while tandem MS/HRMS data analysis supported the rationalization of brominated congeners. Preliminary genetic studies revealed evidence that FADH2 dependent halogenase can be involved in the biosynthesis of the produced halocompounds.


Sujet(s)
Indoles/isolement et purification , Talaromyces/composition chimique , Talaromyces/croissance et développement , Produits biologiques/composition chimique , Produits biologiques/isolement et purification , Chromatographie en phase liquide à haute performance , Alcaloïdes de l'ergot/biosynthèse , Flavine adénine dinucléotide/analogues et dérivés , Flavine adénine dinucléotide/métabolisme , Protéines fongiques/métabolisme , Halogénation , Indoles/composition chimique , Structure moléculaire , Talaromyces/enzymologie
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