Terretonin O: a new meroterpenoid from Aspergillus terreus

Abstract

Terretonin O (1), a new meroterpenoid, was isolated individually from both methanolic extracts of thermophilic Aspergillus terreus TM8 and marine Aspergillus terreus LGO13. The recently reported terretonins M (2) and N (3) were further isolated from the fungus LGO13 along with nine known compounds, terrelumamide A (4), terrein (5), methyl-3,4,5-trimethoxyl-2-[2-(nicotinamide)benzamido]benzoate (6), butyrolactones I-III (7-9), aspulvinone O (10), ergosterol, ergost-4-ene-3-one and methyl linoleate. Structure of terretonin O (1) was established on the bases of HRESIMS, 1D and 2D NMR spectra and comparison with its analogues in literatures. The relative stereochemistry of 1 was assigned on the basis of NOESY spectra and comparison with reported configuration of its congener compounds 2 and 3. The antimicrobial and cytotoxic activities of the fungal extracts and obtained compounds were assayed using a set of microorganisms, and cervix carcinoma cell line (KB-3-1), respectively. Isolation and taxonomical characterization of the producing strains are reported.

Bioactive secondary metabolites from new endophytic fungus Curvularia. sp isolated from Rauwolfia macrophylla

“…The concentrations of the compounds were finally in the range of 250 mg mL -1 to 0.01 mg mL -1 . Microtiter plates containing Escherichia coli and Staphylococcus warneri were incubated at 37°C and those containing Micrococcus luteus and Pseudomonas agarici were incubated at 30 °C for 24 h. The minimum inhibition concentration (MIC) was calculated according to our previous work [19].…”

Antibiotics from Extremophilic Micromycetes

“…As before [286], terretonin (444), demonstrated weak antibacterial activity [284]. Later, new terpenoid, terretonin O (442), was isolated from thermophilic Aspergillus terreus TM8 and marine Aspergillus terreus LGO13 [287]. Presumably, compound (442) is a biosynthetic precursor of the recently isolated terretonins M (441) [288] and N (443) [289].…”

“…The marine strain of Aspergillus terreus LGO13 [287] produces the terpenoids described above and several known metabolites with the antibiotic activity, i.e., butyrolactones I-III (490-492) [316] and aspulvinone O (498) [317]. A deep-sea micromycete of the same species, Aspergillus terreus SCSIO FZQ028 [318], became the source of several structurally similar butenolides including a new compound, (±)-asperteretal F (494), and its recently described close analog asperteretal E (493) [319] that contained 2-benzyl-3phenyl-substituted lactone.…”

Production of Terretonin N and Butyrolactone I by Thermophilic Aspergillus terreus TM8 Promoted Apoptosis and Cell Death in Human Prostate and Ovarian Cancer Cells

“…In the course of this work, two interesting compounds, terretonin N (1) [ 10 ] and butyrolactone I (2) [ 11 ], obtained recently from our investigation into thermophilic fungus Aspergillus terreus TM8 [ 12 ], were examined as anticancer agents against prostate adenocarcinoma (PC-3) and ovary adenocarcinoma (SKOV3) human cell lines. The chemical structures of the two compounds were fully identified and characterized in our recently published data [ 11 , 12 , 13 ]. In addition, our team reported the full taxonomy of the producing thermophilic Aspergillus terreus TM8 previously [ 10 , 11 , 12 , 13 ].…”

“…The chemical structures of the two compounds were fully identified and characterized in our recently published data [ 11 , 12 , 13 ]. In addition, our team reported the full taxonomy of the producing thermophilic Aspergillus terreus TM8 previously [ 10 , 11 , 12 , 13 ]. The structure of the isolated metabolites, shown in Figure 1 , were assigned by comparison of their 1D and 2D NMR spectroscopy and ESI HR mass measurements with our recently published data [ 10 , 11 , 12 , 13 ].…”