Twenty-one aspidosperma−aspidosperma alkaloids, including the new tabernaesines A−J (1−9), were obtained from Tabernaemontana pachysiphon. The structures and absolute configurations were elucidated using HRMS and NMR experiments. Compounds 1−9 possessed a rare spiro heterocycle moiety between the monomeric units, while compounds 4 and 5 were characterized by an indole ring fused with an (N,N-diethyl)methyl amino group. Compounds 1, 5−7, 15, and 16 exhibited moderate cytotoxic potency against various human cancer cell lines at IC 50 2.5−9.8 μM.