A New Citrinin Derivative from the Indonesian Marine Sponge-Associated Fungus Penicillium citrinum

Abstract

Sponge-associated fungi are attractive targets for the isolation of bioactive natural products with different pharmaceutical purposes. In this investigation, 20 fungi were isolated from 10 different sponge specimens. One isolate, the fungus Penicillium citrinum strain WK-P9, showed activity against Bacillus subtilis JH642 when cultivated in malt extract medium. One new and three known citrinin derivatives were isolated from the extract of this fungus. The structures were elucidated by 1D and 2D NMR spectroscopy, as well as LC-HRMS. Their antibacterial activity against a set of common human pathogenic bacteria and fungi was tested. Compound 2 showed moderate activity against Mycobacterium smegmatis ATCC607 with a minimum inhibitory concentration (MIC) of 32 µg/mL. Compound 4 exhibited moderate growth inhibition against Bacillus subtilis JH642, B. megaterium DSM32, and M. smegmatis ATCC607 with MICs of 16, 16, and 32 µg/mL, respectively. Furthermore, weak activities of 64 µg/mL against B. subtilis DSM10 and S. aureus ATCC25923 were observed for compound 4.

Recent Findings in Azaphilone Pigments

“…Monascus pilosus BCRC 38072, a citrinin-free strain, was able to produce several azaphilone pigments including three new Monascus red pigments without citrinin presence: monapilonitrile A (51), monapilosine (52), and N-ethanolic monapilosine (53) [49] (Figure 5). Metabolites (52) and (53) are nitrogenated azaphilones lacking or bearing the N-hydroxyethyl group, respectively.…”

“…Penicillium citrinum WK-P9 was isolated as an associated fungus from the sponge Suberea sp., displaying antibacterial activity. The bio-guided chemical investigation of its ethyl acetate extract led to the isolation of a new citrinin derivative called penicitrinone G ( 57 ) [ 52 ]. Genome mining, epigenetic regulation, optimization of culture conditions, and one-strain-many-compounds (OSMAC) were investigated as a possible way to prioritize the production of other polyketide metabolites different than the rubratoxins in Penicillium dangeardii [ 53 ].…”

Draft Genome Sequence of the Type Strain Bacillus subtilis subsp. subtilis DSM10

“…subtilis type strain DSM10 is a generally accessible Bacillus strain from the German Collection of Microorganisms and Cultures GmbH (DSMZ). It has been used as a reference strain for applied biotechnological research ( 1 – 4 ). For instance, the DSM10 T strain produces notable amounts of surfactin ( 2 , 5 , 6 ) and secretes proteases (data not shown).…”

Rare Chromone Derivatives from the Marine-Derived Penicillium citrinum with Anti-Cancer and Anti-Inflammatory Activities

“…These compounds are important source of biologically effective secondary metabolites, which are very interesting and important for drug discovery. In particular, a large number of natural products with biological activities are found in the genus Penicillium , which has diverse biological activities such as antibacterial, antifungal, antitumor, and antiviral activities [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. Diverse dihydroisocoumarins [ 4 ], citrinin [ 15 ], benzopyrans [ 17 ], benzophenones [ 18 ] and their derivatives were isolated from Penicillium citrinum in the past studies.…”