Bile acids from a Marine Sponge-Associated Fungus Penicillium sp.

Abstract

Chemical investigation of a marine-derived fungus, Penicillium sp. 108YD020, resulted in the discovery of six bile acid derivatives, glycocholic acid (1), glycocholic acid methyl ester (2), cholic acid (3), glycochenodeoxycholic acid (4), glycodeoxycholic acid methyl ester (5), and cholic acid methyl ester (6). The structures of six bile acid derivatives 1-6 were determined by the detailed analysis of 1D, 2D NMR and LC-MS data, along with chemical methods and literature data analysis.

Secondary Metabolites from the Culture of the Marine-derived Fungus Paradendryphiella salina PC 362H and Evaluation of the Anticancer Activity of Its Metabolite Hyalodendrin

“…The relative stereochemistry of 1 was also deduced from the NOESY correlations from H 3 In addition to 1, the previously described glycocholic acid methyl ester (2, Figure 2) [24], (-)-(3R, 6R) hyalodendrin (3, Figure 2) [25] and (-)-(3R, 6R) bisdethiodi(methylthio)hyalodendrin (4, Figure 2), also known as gliovictin [26], were isolated from the crude extract of P. salina PC 362H strain. The absolute configuration of 3 was deduced from its optical rotation sign and from structural consideration.…”

“…Mobile phases were (A): 95% milliQ water (0.05% trifluoroacetic acid), 5% acetonitrile and (B): 5% milliQ water (0.05% TFA), 95% acetonitrile. The separation was achieved at a flow rate of 10 mL/min with the following gradients: 95%-65% A; 5%-35% B in 6 min, 65%-60% A; 35%-40% B in 30 min, 60%-5% A; 40%-95% B in 3 min, 5% A; 95% B during 3 min and 5%-95% A; 95%-5% B in 6 min to yield 1 (7 mg, 23 min, 36% ACN in H 2 O) and 2 (34 min, 38% ACN in H 2 O) [24]. (Tables S2 and S3) [24][25][26].…”

“…We here report the isolation and structural characterization of the previously unreported pentanorlanostane, dendryphiellide A (1), together with the previously described glycocholic acid methyl ester (2) [24], (3R, 6R) hyalodendrin (3), an epidithiodioxopiperazine previously isolated from Penicillium species [25] and (3R, 6R) bisdethiodi(methylthio)hyalodendrin (4) [26]. Further biological characterization allowed the identification of 3 as the active compound responsible for the cytotoxic activity of the crude extract on MCF7 and MCF7-Sh-WISP2 cells.…”

Draft Genome Sequence of the Yeast Strain Hormonema macrosporum POB-4, which Produces the Biosurfactant Glycocholic Acid

“…Microbial production of bile acid conjugates such as glycocholic acid has been documented previously. Two studies have shown the production of glycocholic acid by fungus Penicillum sp., which belongs to subdivision Pezizomycotina of Ascomycota same as strain POB-4 [8,9]. Moreover, bacterial strains with marine origin as well as gut bacteria have been reported to produce bile acid conjugates [10−12].…”