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.

Exploring the Xylariaceae and its relatives.

The Xylariaceae and its relatives rank as one of the best-known members of the Ascomycota. They are now well recognized for their diversity, global distribution, ecological activities and their outstanding novel metabolites with wide ranging bioactivity.

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.

New furan derivatives from Annulohypoxylon spougei fungus.

Two new furan derivatives, annulofurans A-B (1-2), together with six known compounds were isolated from Annulohypoxylon spougei fungus. The structures were determined based on NMR and mass spectrometry data. The absolute configurations of annulofurans A-B were determined by Electronic Circular Dichroism (ECD) experiment and comparisons with the experimental ECD spectra of synthesized stereoisomers. The evaluation of the effects on radish and ruzi grass radicle elongation by the isolated compounds showed that annulofuran A affected radicle elongation of ruzi grass. The known 2-hydroxyphenylacetic acid methyl ester (7) had significant effects against both radish and ruzi grass radicle elongation, which were comparable to the commercial herbicide, glyphosate.

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.

A new α-pyrone derivative from Annulohypoxylon stygium SWUF09-030.

A new α-pyrone derivative, namely annulopyronoate (1), together with the known isobenzofuranone, diphenyl ether, sesquiterpene, phenolic and diketopiperazine derivatives (2-12) were isolated from a filamentous fungus Annulohypoxylon stygium SWUF09-030. The structures were determined by analysis of spectroscopic and MS data. The absolute configuration of 1 was determined by comparison of experimental and calculated Electronic Circular Dichroism (ECD) spectra. Compounds 3-5 and 7 exhibited both anti-proliferative effects against HeLa, HT29, HCT116, MCF-7 and Vero cell lines and inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.

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).

Chemical constituents and cytotoxic activity from the wood-decaying fungus Xylaria sp. SWUF08-37.

A new cyclic pentapeptide, pentaminolarin (1), and a new cytochalasin, xylochalasin (2), along with thirteen known compounds (3-15) were isolated from the wood-decaying fungus Xylaria sp. SWUF08-37. The absolute configurations of 1 were determined by a combination of Marfey's method and TDDFT ECD calculation and the absolute configurations of 2 were established by TDDFT ECD calculation. Compound 12 showed moderate cytotoxicity against HeLa (IC50 = 19.60 µg/mL), HT29 (IC50 = 17.31 µg/mL), HCT116 (IC50 = 14.28 µg/mL), MCF-7 (IC50 = 15.38 µg/mL), and Vero (IC50 = 24.97 µg/mL) cell lines by MTT assay. Compounds 1 and 2 showed slight cytotoxicity against all tested cancer cell lines.

A new amino amidine derivative from the wood-decaying fungus Xylaria cf. cubensis SWUF08-86.

The secondary metabolites of Xylaria cf. cubensis SWUF08-86 fungus were investigated, and the chromatographic separation of the crude extracts yielded seventeen compounds. The structure elucidation by spectroscopic analysis including 1D and 2D NMR and the comparison of these data with literature, along with HREIMS spectrometry, revealed one new amino amidine derivative (1), together with five known simple cyclic dipeptide analogs, diketopiperazines (2-6) and eleven other known compounds, including one hemi-cycline (10), three aromatic derivatives (11-13), one sesquiterpene (14) and three sterols (15-17). The isolated compounds were screened for anticancer and anti-pathogenic bacterial and fungal activities. Based on this work, Xylaria cf. cubensis SWUF08-86 has proven to be a diverse secondary metabolites producer.

A new cerebroside and the cytotoxic constituents isolated from Xylaria allantoidea SWUF76.

A new cerebroside, namely allantoside (1), and 10 known compounds (2-11) were isolated from Xylaria allantoidea SWUF76. The structure of compound 1 was determined by comprehensive spectroscopic analysis including 1D and 2D nuclear magnetic resonance (NMR) as well as high-resolution electron ionisation mass spectrometry (HREIMS) and electrospray ionisation mass spectrometry (ESIMS). Compounds 1, 4, 5, 6, 7, 8 and 11 were evaluated for cytotoxic activities against cancer cell lines (Hela, HT29, HCT116 and MCF-7) and normal Vero cell lines by MTT assay. Compounds 6 and 7 exhibited anticancer activity after 24 h of treatment. Compound 7 showed significant cytotoxicity against Hela (IC50 = 2.24 µg/mL), HT29 (IC50 = 2.51 µg/mL), HCT116 (IC50 = 3.50 µg/mL) and MCF-7 (IC50 = 3.77 µg/mL) and Vero (IC50:3.65 µg/mL) cells. Compound 6 showed slight cytotoxicity against all tested cancer cell lines.