Apoptotic Activity of New Oxisterigmatocystin Derivatives from the Marine-Derived Fungus Aspergillus nomius NC06

Abstract

Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, K, and L (1, 2, and 3), and one known compound, aspergillicin A (4). Structures of the compounds were elucidated by 1D and 2D NMR spectroscopy and by high-resolution mass spectrometry. The isolated compounds were tested for cytotoxic activity against HT 29 colon cancer cells, where compounds 1, 2, and 4 exhibited IC50 values of 6.28, 15.14, and 1.63 µM, respectively. Under the fluorescence microscope by using a double staining method, HT 29 cells were observed to be viable, apoptotic, and necrotic after treatment with the cytotoxic compounds 1, 2, and 4. The result shows that compounds 1 and 2 were able to induce apoptosis and cell death in HT 29 cells.

Marine natural products

“…144 Other Aspergillus strains were the source of viomellein derivatives 308 and 309 , 145 polyketides 310 and 311 (the latter a known synthetic derivative but new NP), 146 prenylated phenylbutyrolactones 312–315 , 147 phomaligol derivatives 316–319 , 148 320 and 321 , 149 and highly rearranged ergostanes 322 and 323 . 150 Benzophenone 324 , 151 pinophilin B epimer 325 , 152 alkaloid 326 , 153 and dihydrofuranone derivative 327 153 were obtained from A. fumigatus strains, whilst other Aspergillus strains were the source of phenol derivatives 328 , 329 , 154 oxisterigmatocystins 330–332 , 155 a sulfonated diphenylether-aminol-amino acid ester guanidinium salt 333 and its diphenyl ether sulfate component 334 , 156 and sesquiterpenoid lactone 335 . 157…”

Cytotoxic Compounds from Marine Fungi: Sources, Structures, and Bioactivity

“…The deep-sea-derived fungus Engyodontium album DFFSCS021 yielded a new chromone, engyodontiumone H (132), demonstrating cytotoxic activity against human histiocytic lymphoma U937, with an IC 50 value of 4.9 µM, whereas doxorubicin as the positive control inhibited U937, with the IC 50 value of 0.06 µM [81]. Aspergillus nomius NC06, isolated from the marine sponge Neopetrosia chaliniformis, produced two new oxisterigmatocystins, J (133) and K (134), which exhibited cytotoxic activity against HT 29 colon cancer cells, with IC 50 values of 6.28 and 15.14 µM, while taxol, as the positive control, inhibited HT29, with the IC 50 value of 0.48 µM [82]. Aspergillus niger, isolated from the Mediterranean sponge Axinella damicornis, yielded 3,3'-bicoumarin bicoumanigrin (135), inhibiting the activity of human tumor cells at concentrations ranging from 1 to 20 µg/mL [44].…”

The Biosynthesis, Structure Diversity and Bioactivity of Sterigmatocystins and Aflatoxins: A Review

“…Two new compounds, Aspertenol A (14), B (15), were isolated from the secondary metabolites 5) were discovered [25]. Three new compounds, including sterigmatocystin-hemiacetal (5), sterigmatocystin-ethoxyacetal (6) and O-methylsterigmatocystinhemiacetal (7), were isolated from the Aspergillus sp. [26].…”

“…Five new compounds, sterigmatocystin B (21), C (22) and oxisterigmatocystin A-C (23)(24)(25), were isolated from Aspergillus versicolor 15XS43ZD-1 [33]. Three new compounds, oxisterigmatocystin J-L (26-28), were isolated from the marine-derived fungus Aspergillus nomius NC06 [7,34]. One new compound, acyl-hemiacetal sterigmatocystin B (29), was isolated from Aspergillus nidulans of Nyctanthes arbor-tristis [35].…”