Marin habitats are rich of bioactive compounds with unique structures and biological activities. In this research two fungal strains were isolated from the Red Sea in Egypt coded as Aspergillus sp. SA17 and Aspergillus sp. SA18. Four compounds were structurally elucidated as 2-pentyl tetrahydrofuran (C1), 2-pentyl-3,4-dihydrofuran (C2), (Z)-2-(hepta-1-en-1-yl)tetrahydrofuran (C3), and 2-(3-methyl butane -1-en-1-yl) tetrahydrofuran (C4). The antimicrobial results showed that, the SA17 crude extract has significant efficacy, particularly against S. aureus and Candida albicans, with modest impact on A. niger and limited effectiveness against E. coli. On the other hand, C2 from SA17 demonstrating significant activity against E. coli. The SA18 extract exhibit diminished antibacterial efficacy and a higher degree of selectivity. In addition, the inhibition of acetylcholinesterase (AChE) by crude and purified substances from fungal sources SA17 and SA18 was investigated at various doses. The SA17 crude extract has a moderate inhibition that is dependent on its concentration. However, its purified constituent C2 displays a potent inhibitory action which surpasses that of the crude extract. SA18's crude extract exhibits strong inhibition, whereas its refined component C4 has a moderate but significant impact. Both C1 from SA17 and C3 from SA18 do not contribute to the inhibition of AChE, highlighting the variety in the effectiveness of these compounds obtained from fungi. Furthermore, the most potent compound was selected and studied for its ADME-physicochemical studies. In the light of this study, we can conclude that, endophytic fungi are a potential source for bioactive metabolites with diverse medical applications.