Eight new linear peptides, simplicilliumtides AeH (1e8) were isolated from a culture broth of the deepsea-derived fungal strain Simplicillium obclavatum EIODSF 020. Their structures were elucidated by spectroscopic analysis, and their absolute configurations were determined by Marfey's method. Compounds 1e2 are linear tetrapeptides possessing a 2-aminobenzoic acid residue. Compounds 3e8 are acetylated linear tri- or di-peptides. Their antifouling, antibacterial, cytotoxic, and acetylcholinesterase inhibiting activities were evaluated. Compound 4 showed strong antifouling activity against Bugula neritina larvae settlement. And 1, 5, 7 and 8 showed weak cytotoxicity towards human leukemia HL-60 or K562 cell line.