Engleromophilane, a new broad spectrum bioactive eremophilane-type sesquiterpene from Engleromyces sinensis fungus.

A new eremophilane sesquiterpene, named engleromophilane (1) together with known eremoxylarin E (2) and steroids (3-7) were isolated from the fungus Engleromyces sinensis culture. The structures were deduced by the analysis of spectroscopic and MS data, together with the comparison of calculated 13C NMR chemical shifts and Electronic Circular Dichroism (ECD) spectra. Compound 1 showed cytotoxic effects against Hela, PC-3, HT29 and A549 cell lines with IC50 in the ranges of 4.84-9.48 µg/mL. Compounds 1 and 2 exhibited substantial antimicrobial activity against E. coli, S. aureus, and B. subtilis. Moreover, compounds 1-3 showed α-glucosidase inhibitory activity, in which 2 displayed a strong inhibitory effect with an IC50 value of 0.13 ± 0.01 µg/mL. This work has given additional value to the E. sinensis fungus as a remarkable bioactive compound producer, together with the possibility of increasing cultivation to industrial scales.

Antiproliferative polyketides from fungus Xylaria cf. Longipes SWUF08-81 in different culture media.

Bioactive compounds from the wood-decay fungus Xylaria cf. longipes SWUF08-81, cultivated in three different culture media (GM, YM and PDB), were isolated. Their structures and stereochemistry were deduced from spectroscopic and MS data analysis, together with quantum chemical calculations of 13C NMR chemical shifts and electronic circular dichroism (ECD) spectra. Five undescribed polyketides including dibenzofuran (1), mellein (2), dihydroisocoumarin (15), and two pyrans (16, 17), together with twenty-three compounds were determined. Compounds 18 and 20 were significantly toxic against cancer cell lines (HCT116, HT29, MCF-7 and HeLa) based on the MTT assay. Quantification by HPLC showed that 18 was produced three-fold higher in the broth of PDB than YM. These studies showed that the production of different compounds were primarily dependent on nutrition sources and it has given a starting point for the growth optimization conditions for the scaling up of bioactive compounds production.

Hypoxylonone, a new oxa-bridged seven-membered ring analog from fungus Hypoxylon cf. subgilvum SWUF15-004.

A new oxa-bridged seven-membered ring analog, hypoxylonone (1), and thirteen known compounds (2-14) were isolated from fungus Hypoxylon cf. subgilvum SWUF15-004. The structures were elucidated by the analysis of spectroscopic (IR, 1 D and 2 D NMR), HRESIMS and X-ray diffraction (MoKα) data. Several isolated compounds were evaluated for cytotoxicity against four human cancer cell lines (HeLa, HT29, MCF-7, A549). Compound 1 exhibited weak inhibitory effects of the nitric oxide production in RAW264.7 cells. Compounds 8 and 9 exhibited slight cytotoxicity.

Anti-inflammatory and anti-proliferative activities of chemical constituents from fungus Biscogniauxia whalleyi SWUF13-085.

The fungus Biscogniauxia whalleyi SWUF13-085 from the Graphostomataceae family was studied for potential anti-inflammatory and anticancer agents. A diverse array of natural products was identified. Six of which were undescribed compounds, including xylariterpenoids L-N, (1R,2S,6R,7S)-1,2-dihydroxy-α-bisabolol, 6-[(1R)-1-hydroxy-1-methyl-2-propenyl]-4-methoxy-3-methyl-2H-pyran-2-one and (1R*,4S*,5S*,7S*,10R*)-guaia-11 (12)-en-7,10-diol. Several of the isolated compounds such as bergamotene, guaiane and phthalide derivatives showed activity in both the inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC50 values in the range of 2.48-10.82 µg/mL and anti-proliferation against HeLa cells with IC50 values in the range of 8.64-31.16 µg/mL. While compounds such as cerebrosides A and C only exhibited inhibitory effects on NO production with IC50 values in the range of 4.45-10.28 µg/mL.

Anti-inflammatory and cytotoxic agents from Xylaria sp. SWUF09-62 fungus.

The ongoing search for anti-cancer agents from microorganisms led to the isolation of four new compounds including 6-ethyl-8-hydroxy-4H-chromen-4-one (1), 6-ethyl-7,8-dihydroxy-4H-chromen-4-one (2), (3S)-3,4-dihydro-8-hydroxy-7-methoxy-3-methylisocoumarin (3) and (3S)-3,4-dihydro-5,7,8-trihydroxy-3-methylisocoumarin (4), together with eleven known compounds (5-15) from Xylaria sp. SWUF09-62 fungus. The chemical structures were deduced from IR, 1D and 2D NMR, and MS data. The absolute configurations of 3 and 4 were determined by ECD experiment. Compounds 2 and 4 indicated possible chemo-prevention and chemo-therapeutic properties, exhibited anti-inflammatory properties by reducing nitric oxide production in LPS-stimulated RAW264.7 cells (IC50 = 1.57 ± 0.25 and 3.02 ± 0.27 µg/mL) and cytotoxicity against HT29 cells (IC50 = 16.46 ± 0.48 and 97.78 ± 7.14 µg/mL).