Chevalinulins A (1)andB(2), two indolediketopiperazine alkaloids containing an unprecedented spiro-[bicyclo[2.2.2]octane-diketopiperazine] skeleton, together with aknown analogue neoechinulin B (3), were isolated from the deep-sea cold-seep-derived fungusAspergillus chevalieriCS-122. Theirstructures were determined by spectroscopic analysis, single-crystalX-ray diffraction, specific rotation (SR), and NMR calculations.Compounds1and2exhibited significantin vivoproangiogenicactivity in transgenic zebrafish.