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Chemical epigenetic modifiers could optimize the compound biosynthesis of endophytes by activating the silent genes. Treatment of procaine, an epigenetic modifier, on endophytic fungus Talaromyces wortmannii isolated from Morus Cathayana Hemsl., was evaluated with NMR spectroscopy analysis combined with multivariate data analysis and antibacterial assay. In total, 29 compounds were successfully annotated in the T. wortmannii extracts and most of them are primary metabolites. Semi-quantitative 1H NMR analysis revealed that the concentrations of some annotated compounds increased in the treated endophyte, including wortmin, mannitol, and choline. Meanwhile, the contents of glucose and skyrin decreased in the treated T. wortmannii. Multivariate data analysis successfully distinguished the metabolite profile of the treated T. wortmannii from that of the control endophyte. This analysis revealed that procaine treatment on T. wortmannii possibly induced the biosynthesis of mannitol, choline, lactic acid, and phosphocholine and repressed the contents of fatty acids, including palmitic, stearic, linoleic, and oleic acids. The antibacterial assay revealed chloroform extracts of the treated endophyte, and its control possessed potent antibacterial activity against the tested pathogenic bacteria. Meanwhile, the antibacterial activity of water-methanol extract of the treated T. wortmannii increased against Enterococcus faecalis and Salmonella enterica. In this report, the procaine treatment altered the metabolite profiles of the endophytic fungus T. wortmannii. Here we also demonstrated that 1H NMR-based metabolomics was the effective method to study the effect of the epigenetic modifier on endophytic fungi. [Display omitted] • Procaine treatment modified the metabolite profiles of Talaromyces wortmannii. • Wortmin biosynthesis was induced by the procaine treatment. • Mannitol concentration increased significantly on the treated T. wortmannii. [ABSTRACT FROM AUTHOR]

Caffeine is a naturally occurring central nervous system (CNS) stimulant found in many drinks and foods. Many interesting biological activities of caffeine, and some of its derivatives, have been reported. Therefore, this study aims to conduct chemical transformations of caffeine. The method used is direct fluorination of caffeine using Selectfluor® in acetonitrile at room temperature, followed by purification to obtain 8‐fluorocaffeine. This reaction can be done on a multigram scale. Subsequently, 8‐fluorocaffeine was further modified by a nucleophilic substitution reaction with amines and alcohols as the nucleophiles under reflux conditions in an appropriate solvent to form fifteen 8‐substituted caffeine derivatives, with yields ranging from moderate to high. Of these derivatives, four are novel compounds, which are 8‐(3‐chloro‐4‐fluorophenyl)aminocaffeine, 8‐(3‐aminophenyl)amino‐caffeine, 8‐(azetidin‐1‐yl)‐caffeine, and 8‐(tetrahydrofuran‐3‐yl)oxycaffeine. [ABSTRACT FROM AUTHOR]

Morus is one of the main genera of the Moraceae family and widely cultivated in Southeast Asia for silkworm feeding. This genus also produces valuable bioactive phenolic compounds such as flavonoids, stilbenes, 2-arylbenzofurans, and Diels-Alder adducts. Previous phytochemical investigation of Morus shalun reported the Diels-Alder adducts as the mayor phenolic compounds isolated from root cultures. The Diels-Alder adduct is considered formed by the intermolecular [4+2]- cycloaddition between a diene of dehydroprenyl phenol with a dienophile of the α, β-unsaturated carbonyl group of a chalcone. This reaction in plant tissues is naturally catalyzed by the enzyme Diels-Alderase. The experiment was designed to determine the existence of Diels-Alderase isolated from a root culture of M. shalun by evaluating its activity in the biotransformation process of morachalcone A to produce kuwanon J. Biotransformation was detected using HPLC and LCMS. Kuwanon J showed significantly higher cytotoxic activities against the three human cancer cell lines HeLa, A459, and MCF7 compared with morachalcone A. [ABSTRACT FROM AUTHOR]

A new quinone derivative, named epoxyquinophomopsin (1), was isolated from the EtOAc extract of the fermentation broth culture of an endophytic fungus Phomopsis sp. from Morus cathayana. Structure of compound 1 was determined mainly by NMR and mass spectral data. Biogenetically compound 1 can be regarded as a degradative product of the previously reported anthraquinone found in the fungus. [ABSTRACT FROM AUTHOR]

A new phenolic sesquiterpene, dysoxyphenol (1), and the known sesquiterpene, 7R,10S-2-hydroxycalamenene (2), were isolated from the acetone extract of Dysoxylum densiflorum seeds. The structures of these compounds were determined based on physical, Nuclear Magnetic Resonance, and mass spectral data. Both compounds were evaluated for their antibacterial and antifungal properties against seven pathogenic bacteria and two wood-rotting fungi, respectively. The results showed that both compounds have significant antibacterial properties only against Bacillus subtilis (Minimum Inhibitory Concentration 28 μM), while in the antifungal evaluation compound 1 was found to be more active than compound 2. Therefore, compound 1 has promising antifungal properties that can be developed further for finding new antifungal agents.