Five new alkaloids from the stem bark of Daphniphyllum macropodum.

Five new alkaloids, daphnicyclidins M and N (compounds 1 and 2) and calyciphyllines Q-S (compounds 3-5), along with four known ones, paxiphylline C (6), macropodumine B (7), macropodumine C (8) and daphnicyclidin A (9) were isolated from the stem bark of Daphniphyllum macropodum. Calyciphylline Q (3) is the first calyciphylline A derivative possessing a double bond between C-18 and C-19. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. Compounds 1, 2, 8 and 9 exhibited cytotoxic activity against P-388 cells with IC₅₀ values of 5.7, 6.5, 10.3 and 13.8 µM, respectively. Compounds 1 and 2 also showed cytotoxic activity against SGC-7901 cells with IC₅₀ values of 22.4 and 25.6 µM.