A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207

Abstract

A new ergosterol analog, talarosterone (1) and a new bis-anthraquinone derivative (3) were isolated, together with ten known compounds including palmitic acid, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol-5,8-endoperoxide, cyathisterone (2), emodin (4a), questinol (4b), citreorosein (4c), fallacinol (4d), rheoemodin (4e) and secalonic acid A (5), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis, and in the case of talarosterone (1), the absolute configurations of its stereogenic carbons were determined by X-ray crystallographic analysis. The structure and stereochemistry of cyathisterone (2) was also confirmed by X-ray analysis. The anthraquinones 4a–e and secalonic acid A (5) were tested for their anti-obesity activity using the zebrafish Nile red assay. Only citreorosein (4c) and questinol (4b) exhibited significant anti-obesity activity, while emodin (4a) and secalonic acid A (5) caused toxicity (death) for all exposed zebrafish larvae after 24 h.

A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213

“…The structures of byssochlamic acid [ 7 ], hopan-3β,22-diol ( 5 ) [ 15 ], chevalone B [ 12 ], chevalone C [ 16 ], sartorypyrone B [ 5 ], helvolic acid [ 5 ], lumichrome ( 6 ) [ 21 ], harmane ( 7 ) [ 20 ], β-sitostenone [ 8 ], ergosta-4,6,8 [ 14 ] 22-tetraen-3-one [ 19 ], cyathisterone [ 10 ], dehydromevalonic acid lactone [ 6 ], aszonalenin [ 13 ], secalonic acid A [ 14 ] and fellutanine A [ 13 ] ( Figure 1 and Supplementary Materials, Figure S1 ) were elucidated by analysis of their 1 H, 13 C NMR spectra and HRMS data, as well as by comparison of their spectral data to those reported in the literature ( Supplementary Materials, Figures S2–S31 ).…”

“…Chromatographic fractionation and further purification of the ethyl acetate extract of N. fennelliae KUFA 0811, yielded a previously undescribed 2,3-dihydro-4 H -chromen-4-one dimer which we have named paecilin E ( 1 ), in addition to the previously described dehydromevalonic acid lactone [ 6 ], byssochlamic acid [ 7 ], β-sitostenone [ 8 ], ergosta-4,6,8 (14), 22-tetraen-3-one [ 9 ], cyathisterone [ 10 ], dankasterone A ( 2 ) [ 11 ], chevalone B [ 12 ], helvolic acid [ 5 ], aszonalenin [ 13 ], secalonic acid A [ 14 ] and fellutanine A [ 13 ]. The ethyl acetate extract of N. tsunodae KUFC 9213 furnished, besides sartorypyrone B and helvolic acid which were previous isolated in our first study [ 5 ], byssochlamic acid [ 7 ], hopan-3β,22-diol ( 5 ) [ 15 ], chevalone C [ 16 ], a chromanol derivative ( 3 ) [ 17 , 18 ], (3β,5α,22 E )-3,5-dihydroxyergosta-7,22-dien-6-one ( 4 ) [ 19 ], the alkaloid harmane ( 7 ) [ 20 ], and lumichrome ( 6 ) [ 21 ].…”

Antibacterial Activity of Indonesian Sponge Associated Fungi Against Clinical Pathogenic Multidrug Resistant Bacteria

“…This fungus had 100% similarity to Trichoderma reesei KU377472.1. Fungi from genus Trichoderma are commonly isolated as spongeassociated fungi (Sibero et al, 2016;Mohamed-Benkada et al, 2016;Pang et al, 2017). T. reesei MPS 14.5/MT 04 was also found as fungal associate in Cinachyrella sp.…”

“…In addition, several discoveries were successfully isolate new compounds from sponge-associated fungi with biological activities (Zin et al, 2016;Noinart et al, 2017). Furthermore, Liu et al (2017) isolated 11 compounds from sponge-derived fungus Aspergillus sydowii J05B-7F-4.…”

Sponge-associated fungi from a mangrove habitat in Indonesia: species composition, antimicrobial activity, enzyme screening and bioactive profiling

“…Exploration of fungal metabolites is significantly increased after the scientists figured out that marine fungi, especially sponge-associated fungi, produce structurally unique bioactive compounds (Hasan et al 2015;Imhoff 2016). This fungal group produced certain potential bioactive compounds for pharmaceutical application such as citreorosein (anti-obesity activity, IC 50 = 0.17 lM), truncateol M (antiviral activity, IC 50 = 8.8 lM), misszrtine A (cytotoxic, IC 50 = 3.1 lM), and aspergillusene A (antibacterial activity, MIC = 4.3 lM) (Wang et al 2014;Zhao et al 2015;Noinart et al 2017;Zhou et al 2018). Nevertheless, it is noted that most of the bioactive compounds and their producer were isolated from sponges collected from seagrass or coral reef ecosystems.…”