Abstract
Eleven undescribed monoterpenoid bisindole alkaloids, alstomaphyines A−K (1−11), along with three known analogues were isolated from the leaves and stem bark of the Alstonia macrophylla. Compounds 1−3 were unprecedented dimerization alkaloids incorporating a macroline-type motif with an ajmaline-type motif via a C−C linkage. Their structures and absolute configurations were elucidated by extensive spectroscopic analysis, electronic circular dichroism (ECD) calculation, and CD exciton chirality method. Compounds 1−3 displayed potential inhibitory bioactivity against AChE with IC50 values of 4.44 ± 0.35, 3.59 ± 0.18, and 3.71 ± 0.23 μM, respectively. Enzyme kinetic study revealed compounds 1−3 as mixed competitive AChE inhibitors. Besides, compounds 8 and 12−14 exhibited better cytotoxicity against human cancer cell line HT-29 than cisplatin. Flow cytometry data revealed that compounds 8, 13, and 14 significantly induced the HT-29 cells arrest in G0/G1 phase in a concentration-dependent manner.
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