Iridoid-monoterpenoid indole alkaloid hybrids (IMIAHs)represent a rare class of natural products reported from only several plants of Rubiaceae and Dipsacaceae families, while their structural assignments remain a very challenging work due to complexity and flexibility. In the current study, a new IMIAH (1)was isolated from the roots of Dipsacus asper and its structure with absolute configuration was unambiguously established by a combination of spectroscopic analyses, chemical degradation and ECD calculation. A new oleanane-type triterpenoid saponin (2)and 15 known co-metabolites were also obtained and structurally characterized. Our biological evaluations showed that compound 2 exhibited moderate inhibition against acetylcholine esterase (AChE)with an IC 50 value of 15.8 ± 0.56 μM, and compound 15 displayed potent cytotoxicity selectively against human A549 and H157 lung cancer cells with IC 50 values of 6.94 ± 0.24 and 9.06 ± 0.12 μM, respectively. © 2019 Elsevier B.V.