Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification.
Jing-Shuai WuXiao-Hui ShiYa-Hui ZhangChang-Lun ShaoXiu-Mei FuXin LiGuang-Shan YaoChang-Yun WangPublished in: Molecules (Basel, Switzerland) (2020)
Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (-)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (-)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.
Keyphrases
- candida albicans
- histone deacetylase
- high resolution
- biofilm formation
- pseudomonas aeruginosa
- dna methylation
- gene expression
- rheumatoid arthritis
- magnetic resonance
- cystic fibrosis
- molecular docking
- electronic health record
- big data
- escherichia coli
- magnetic resonance imaging
- computed tomography
- cell wall
- ankylosing spondylitis
- staphylococcus aureus
- machine learning
- idiopathic pulmonary fibrosis