Alternative Extraction and Characterization of Nitrogen-Containing Azaphilone Red Pigments and Ergosterol Derivatives from the Marine-Derived Fungal Talaromyces sp. 30570 Strain with Industrial Relevance

Abstract

Many species of Talaromyces of marine origin could be considered as non-toxigenic fungal cell factory. Some strains could produce water-soluble active biopigments in submerged cultures. These fungal pigments are of interest due to their applications in the design of new pharmaceutical products. In this study, the azaphilone red pigments and ergosterol derivatives produced by a wild type of Talaromyces sp. 30570 (CBS 206.89 B) marine-derived fungal strain with industrial relevance were described. The strain was isolated from the coral reef of the Réunion island. An alternative extraction of the fungal pigments using high pressure with eco-friendly solvents was studied. Twelve different red pigments were detected, including two pigmented ergosterol derivatives. Nine metabolites were identified using HPLC-PDA-ESI/MS as Monascus-like azaphilone pigments. In particular, derivatives of nitrogen-containing azaphilone red pigment, like PP-R, 6-[(Z)-2-Carboxyvinyl]-N-GABA-PP-V, N-threonine-monascorubramin, N-glutaryl-rubropunctamin, monascorubramin, and presumed N-threonyl-rubropunctamin (or acid form of the pigment PP-R) were the major pigmented compounds produced. Interestingly, the bioproduction of these red pigments occurred only when complex organic nitrogen sources were present in the culture medium. These findings are important for the field of the selective production of Monascus-like azaphilone red pigments for the industries.

Biosynthesis of Novel Naphthoquinone Derivatives in the Commonly-used Chassis Cells Saccharomyces cerevisiae and Escherichia coli

“…30570 marine-derived fungal strain, 6 among which were occurred only when complex organic nitrogen sources were present in the culture medium. These structures contained an amino acid residues [ 35 ]. Sun et al also demonstrated the influences of exogenous glucose and pyruvate on the polyketide product flaviolin in an engineered E. coli BL21(DE3) [ 19 ].…”

Chemical Profiling, Bioactivity Evaluation and the Discovery of a Novel Biopigment Produced by Penicillium purpurogenum CBS 113139

“…The pigments produced in Pigment Complex A were first analyzed by UV/Vis diode array chromatography. Using the same chromatographic conditions, we proceeded to the determination of these compounds using HR-MS. For the identification of the compounds, we searched the current literature for the known metabolites of Penicillium purpurogenum [ 18 , 19 , 20 ], collected all the reported compounds and created an in-house library containing their chemical structures. We used this library in conjunction with Bruker’s MetaboBASE Plant Library to annotate the compounds being reported in Table S3 .…”

Recent Findings in Azaphilone Pigments

“…The third pigment (sassafrinamine A) (3) is purple and displays a nitrogen into the isochromene system substituted with ethyl-1-ol group (Figure 2). The fungus Aspergillus cavenicola afforded the nitrogenated azaphilones trans-cavernamine (4), ciscavernamine (5), amino acid derivatives of cis-cavernamines (6-10), hydroxy-cavernamine (11), amino acid derivatives of hydroxy-cavernamines (12)(13)(14)(15)(16), and two oxygenated derivatives cis and trans-cavernines (17)(18) [34]. The marine-derived fungus Aspergillus falconensis yielded five mitorubrins derivative azaphilones with different benzoyl moieties: two new chlorinated azaphilones, falconensins O and P (19 and 20) when the fungus was cultivated in a solid rice medium containing 3.5% NaCl and three additional new azaphilone derivatives (21)(22)(23) when NaCl was replaced by 3.5% NaBr [35].…”

“…Eco-friendly solvents were chosen for the extraction (90 °C and 10 MPa) as water, methanol and/or ethanol. At the end, twelve nitrogen-containing azaphilone red pigments were identified while known mycotoxins were not produced [ 13 ]. Two-phase aqueous extraction [ 107 ] was successfully tested for the extraction of pigments from T. albobiverticillius .…”

“…Fungal bio-pigments have the advantage of being produced using inexpensive sources of carbon and nitrogen, that can even be obtained from food by-products or from agro-industrial residues [12]. One of the most promising classes of fungal pigments in research as industrial pigments are azaphilones, compounds that stand out for their yellow, orange and red colors [13]. This class of fungal secondary metabolites encompasses a large number of compounds of polyketide origin, containing a pyrone-quinone core, a chiral quaternary center and hydroxyl groups as substituents.…”