Secondary Metabolites from the Culture of the Marine Sponge-Associated Fungi Talaromyces tratensis and Sporidesmium circinophorum

Abstract

Wortmin (1), meso-1,4-bis(4-methoxybenzyl)-2,3-butanediol (2), and a new isocoumarin derivative tratenopyrone (3) were isolated from the marine sponge-associated fungus Talaromyces tratensis KUFA 0091. A new diphenyl ether derivative, circinophoric acid (4), was isolated, together with the previously reported anthraquinones catenarin and physcion, the benzophenone monomethylsoluchrin, and β-ergosterol-5,8-endoperoxide, from the marine sponge-associated fungus Sporidesmium circinophorum KUFA 0043. The structures of the new compounds were established based on an extensive analysis of 1D and 2D NMR spectra, and, in the case of compounds 2-4, also by X-ray analysis. All of the isolated compounds were tested for their antibacterial activity against Gram-positive and Gram-negative bacteria, and multidrug-resistant isolates from the environment, as well as for their anti-quorum sensing based on the pigment production of Chromobacterium violaceum ATCC 31523. None of the compounds exhibited either antibacterial (MIC > 256 µg/mL) or anti-quorum sensing activities. The compounds were also inactive in the antifungal (MIC > 512 µg/mL) and cancer cell line (GI50 > 150 µM) assays.

Genome-Inspired Chemical Exploration of Marine Fungus Aspergillus fumigatus MF071

“…Other known compounds were identified as 18-oxotryprostatin A ( 3 ) [ 22 ], sulochrin ( 5 ) [ 26 ], monomethylsulochrin ( 6 ) [ 23 ], 6-methoxyspirotryprostatin B ( 7 ) [ 22 ], spirotryprostatin A ( 8 ) [ 27 ], spirotryprostatin C ( 9 ) [ 28 ], pseurotin A ( 11 ) [ 25 ], azaspirofuran A ( 12 ) [ 29 ], demethoxyfumitremorgin C ( 13 ) [ 30 ], fumitremorgin C ( 14 ) [ 28 ], 13-oxofumitremorgin B ( 15 ) [ 31 ], fumitremorgin B ( 16 ) [ 28 ], verruculogen ( 17 ) [ 28 ], helvolinic acid ( 18 ) [ 32 ], helvolic acid ( 19 ) [ 33 ], fumiquinazolines J ( 20 ) [ 34 ], chaetominine ( 21 ) [ 35 ], fumigaclavine C ( 22 ) [ 36 ], 9-deacetylfumigaclavine C ( 23 ) [ 36 ], fumagiringillin ( 24 ) [ 37 ], asterric acid ( 25 ), circinophoric acid ( 26 ) [ 38 ], dimethyl 2,3′-dimethylosoate ( 27 ) [ 23 ], methylated asterric acid ( 28 ) [ 39 ], endocrocin ( 29 ) [ 40 ], and questin ( 30 ) [ 41 ]. Their 1 H and 13 C NMR data were identical to those reported in the literature.…”

Antibiotics Development and the Potentials of Marine-Derived Compounds to Stem the Tide of Multidrug-Resistant Pathogenic Bacteria, Fungi, and Protozoa

“…)-associated fungi, Talaromyces tratensis and Sporidesmium circinophorum (Gulf of Thailand), wortmin (1), meso-1,4-bis(4-methoxybenzyl)-2,3-butanediol (2), and isocoumarin derivative tratenopyrone (3) were synthesized by the former, while the latter produced diphenyl ether derivative, circinophoric acid (4), and other known compounds, catenarin, physcion, mono-methylsoluchrin, and β-ergosterol-5,8-endoperoxide. None of the compounds inhibited C. albicans ATCC 10232 (> 512 µg/mL) [102].…”

Biological activity of sponge-associated fungi from Karimunjawa Islands, Indonesia against pathogenic Streptococcus pneumoniae

“…Evidence has emerged, demonstrating that many natural products extracted from marine animals and algae are the products of associated microorganisms, mostly bacteria, and fungi (Raghukumar 2008). Spongeassociated fungi have the potential to produce new chemical entities (Volgraf et al 2008;Blunt et al 2010;Vasanthabharathi 2012;Vicente et al 2013;Bolanos et al 2015;Imhoff 2016;Indraningrat et al 2016) that actively inhibited the growths of various pathogenic microorganisms (Khoeri et al 2011;Mayer et al 2013;Radjasa et al 2013;Buttachon et al 2016;Corral et al 2018). Our previous research also showed that spongeassociated fungi have several bioactivities such as anti-S. aureus and E. coli (Wittriansyah et al 2016), antibacterial produced by sponge Agelas sp.…”