Abstract
The genus Penicillium is among the most promising alkaloid-producing fungal and therefore plays an important role in terms of producing molecules with biotechnological potential. Thus, in order to identify alkaloid-producing fungi, 25 endophytic Penicillium strains previously isolated from Amazon medicinal plants were subject to an integrative approach based on direct infusion positive electrospray ionization mass spectrometry (ESI-MS) and principal component analysis (PCA). The multivariate analysis pointed paxiline (1), glandicoline B (2), roquefortine C (3), and oxaline (5) as responsible for the segregation of three promising alkaloid-producing groups, been these groups constituted for P. chrysogenum, P. oxalicum, P. paxilli, and P. rubens strains. These alkaloids and the glandicoline A (4) were tentatively identified by multiple-stage mass spectrometry. In addition, compounds 1 and 2 were isolated and confirmed by using 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Overall, the chemical profile analysis by ESI-MS along with PCA provided a simple and effective approach to screening alkaloid-producing Penicillium strains for biotechnological applications.
Highlights
Fungi are widely distributed throughout the planet integrating the biogeological cycles of all ecosystems.1 They comprise a wide variety of species, around 3.8 million, distributed mainly on environments such as in soil, water, and associated with plants and othersVol 32, No 9, 2021 da Silva-Filho et al. are sources of new metabolites with diverse biological activities.5 Among these endophytes, some genus as Aspergillus, Trichoderma, Fusarium, and Penicillium stand out in terms of producing molecules with several biotechnological potentials, such as antibiotics, antioxidants, and antitumoral agents.6-9Since the discovery of the penicillin in 1929, the genus Penicillium, which is composed by approximately 354 known species,10 has been described as a promising source of bioactive compounds, such as polyphenols, polyketides, and alkaloids.11-13 Alkaloids produced by Penicillium has been showed potential to biotechnological applications, been their antimicrobial, antiviral, and anticancer activities previously described.14-18The prospection of bioactive compounds or new molecules from microorganisms is an important and complex task, which usually demands modern analytical techniques with high sensitivity and selectivity, such as that based on mass spectrometry (MS).19,20 In the recent years, these mass spectrometry-based approaches has been proved to be a powerful strategy for the screening and identification of bioactive compounds in plant and microorganism species as well as to chemotaxonomic approaches, when combined with chemometric tools.21-23 in this study, 25 endophytic Penicillium strains previously isolated from Amazon medicinal plants were screened for alkaloid-producing by an integrative approach based on direct infusion positive electrospray ionization mass spectrometry (ESI-MS) and principal component analysis (PCA)
This proposal was based on previous studies with fungal alkaloids containing an odd number of nitrogen atoms, such as indole alkaloids, where protonation process provides products with even m/z values
In the first principal component analysis (PCA) score plot (Figure 1a), based on the relative intensity of m/z 150 to 1000 (850 variables), five main groups were observed, being group I formed by three strains, group II by eight strains, group III by three strains, group IV by four strains and group V by seven strains
Summary
Fungi are widely distributed throughout the planet integrating the biogeological cycles of all ecosystems.1 They comprise a wide variety of species, around 3.8 million, distributed mainly on environments such as in soil, water, and associated with plants and othersVol 32, No 9, 2021 da Silva-Filho et al. are sources of new metabolites with diverse biological activities.5 Among these endophytes, some genus as Aspergillus, Trichoderma, Fusarium, and Penicillium stand out in terms of producing molecules with several biotechnological potentials, such as antibiotics, antioxidants, and antitumoral agents.6-9Since the discovery of the penicillin in 1929, the genus Penicillium, which is composed by approximately 354 known species,10 has been described as a promising source of bioactive compounds, such as polyphenols, polyketides, and alkaloids.11-13 Alkaloids produced by Penicillium has been showed potential to biotechnological applications, been their antimicrobial, antiviral, and anticancer activities previously described.14-18The prospection of bioactive compounds or new molecules from microorganisms is an important and complex task, which usually demands modern analytical techniques with high sensitivity and selectivity, such as that based on mass spectrometry (MS).19,20 In the recent years, these mass spectrometry-based approaches has been proved to be a powerful strategy for the screening and identification of bioactive compounds in plant and microorganism species as well as to chemotaxonomic approaches, when combined with chemometric tools.21-23 in this study, 25 endophytic Penicillium strains previously isolated from Amazon medicinal plants were screened for alkaloid-producing by an integrative approach based on direct infusion positive electrospray ionization mass spectrometry (ESI-MS) and principal component analysis (PCA). For the fungal metabolic production, two strains with even peaks in their mass-spectra profiles, P. paxilli (O) and P. rubens (V), were cultivated in preparative scale, using 60 Erlenmeyer flasks of 1 L containing 300 mL of ISP2 liquid medium each.
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