02310naa a2200325 a 450000100080000000500110000800800410001902400560006010000170011624501580013326000090029152012770030065300160157765300250159365300260161870000170164470000170166170000230167870000180170170000230171970000170174270000230175970000170178270000230179970000180182270000200184070000230186070000210188377300800190421536042023-09-01       2023    bl uuuu     u00u1 u    #d7 ahttps://dx.doi.org/10.21577/0103-5053.202300272DOI1 aPERES, E. G.  aDereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.h[electronic resource]  c2023  aPenicillium meliponae, a recently described and rare species, was isolated as an endophytic fungus from the Amazonian plant Duguetia sthelechantha, and has been proven to be a pigment producer. Considering the high productivity of this species and the lack of data on its chemical composition, the present study aimed to characterize the chemical profile of P. meliponae and evaluate the influence of agitation and the use of different culture media. For this purpose, liquid chromatography coupled with mass spectrometry (LC-MS/MS) and molecular networking were used, allowing the identification of 17 azaphilone molecules with sclerotiorin-like skeletons, becoming the first chemical report of this species. In addition, the different production patterns in the tested culture media were indicative that this species is sensitive to changes in the composition of the carbon source and to the presence of agitation. Furthermore, this work contributes to the fragmentation mechanisms of the different possible structural arrangements for azaphilones of the sclerotiorin type and serves as a repository of information on the gas-phase behavior of this type of metabolite in mass spectrometry experiments and will assist future studies aimed at the discovery of azaphilones.  aAzaphilones  aMolecular networking  aPenicillium meliponae1 aSOUZA, M. P.1 aSOUSA, T. F.1 aSILVA, C. V. A. da1 aBARROS, A. L.1 aSILVA, F. M. A. da1 aCOSTA, E. V.1 aMEDEIROS, L. S. de1 aFORIM, M. R.1 aSOUZA, A. D. L. de1 aPAZ, W. H. P.1 aSILVA, G. F. da1 aSOUZA, A. Q. L. de1 aKOOLEN, H. H. F.  tJournal of the Brazilian Chemical Societygv. 34, n. 8, p. 1139-1153, 2023.