Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus Trichoderma harzianum D13.

A new polyketide derivative, nafuredin C (1), a novel heterocyclic dipeptide, trichodermamide G (3), together with four known biogenetically related compounds nafuredin A (2), trichodermamide A (4), aspergillazin A (5), and peniisocoumarin H (6), were isolated from the mangrove-derived fungus Trichoderma harzianum D13. Their structures, including their absolute configurations, were determined by spectroscopic analysis and time-dependent density functional theory-electronic circular dichroism (ECD) calculations. Trichodermamide G was found to be a novel epithiodiketopiperazine derivative with an unprecedented cyclic system containing a sulfur bridge, and nafuredin C represented the third nafuredin derivative of these homologous compounds. The new compound nafuredin C exhibited obvious antifungal activity against Magnaporthe oryzae with a minimum inhibitory concentration (MIC) of 8.63 µM, which is on the same order of magnitude as the positive control carbendazim (MIC = 3.27 µM).

Variation in Chemical Composition and Biological Activities of Flos Chrysanthemi indici Essential Oil under Different Extraction Methods.

Flos Chrysanthemi indici, an important medicinal and aromatic plant in China, is considered to have many different preservative and pharmacological properties. Considering the capability of essential oils (EOs), the present study is conducted to compare different extraction methods in order to improve yield and biological activities. Hydro-distillation (HD), steam-distillation (SD), solvent-free microwave extraction (SFME), and supercritical fluid extraction (SFE) are employed to prepare EOs from Flos Chrysanthemi indici. A total of 71 compounds are assigned by gas chromatography/mass spectrometry (GC-MS) in comparison with retention indices. These include 32 (HD), 16 (SD), 31 (SFME) and 38 (SFE) compounds. Major constituents of EOs differ according to the extraction methods were heptenol, tricosane, camphor, borneol, and eucalyptol. EOs extracted by SFME exhibit higher antioxidant activity. All EOs show varying degrees of antimicrobial activity, with minimum inhibitory concentration (MIC) ranging from 0.0625 to 0.125 mg/mL and SFME and SFE prove to be efficient extraction methods. EOs alter the hyphal morphology of Alternaria alternata, with visible bumps forming on the mycelium. Overall, these results indicate that the extraction method can significantly influence the composition and biological activity of EOs and SFME and SFE are outstanding methods to extract EOs with high yield and antimicrobial activity.

Phytotoxicity and anti-phytopathogenic activities of marine-derived fungi and their secondary metabolites.

To find new pesticides for agricultural use, 133 fungal strains were isolated from coastal marine habitats, from which 37 independent isolates were identified, belonging to 20 genera in nine orders, and the diversity of the isolated fungi were discussed. The phytotoxicity and anti-phytopathogenic fungal and bacterial activities of these 37 extracts, and two previously isolated fungal extracts were evaluated, displaying different levels of bioactivity. Based on the bioactive and chemical screening, an Alternaria sp. (P8) strain, which showed prominent bioactivity and contained abundant secondary metabolites was selected for further chemical investigation; one new compound, a benzopyranone (1), and seven known compounds (2-8) were obtained. Their structures were determined by analysing extensive NMR spectroscopic data and ECD comparisons. Compounds 1, 2, and 6-8 showed obvious phytotoxicity, especially against amaranth, and compound 1 also showed potent antifungal activity toward Alternaria brassicicola. To the best of our knowledge, this is the first report of the phytotoxicity of marine-derived fungi and their secondary metabolites. These studies should provide the foundation for future research into the use of such fungal extracts to combat weeds and diseases in agriculture.