Isolation, identification and bioactivities of abietane diterpenoids from Premna szemaoensis

Investigation of the leaves and stems of Premna szemaoensis resulted in the isolation of twelve new abietane diterpenoids, szemaoenoids A–L (1–12), together with four known abietane diterpenoids (13–16). The structures involved two rearranged-abietane skeletons: 17(15 → 16)-abeo-abietane (7, 10–12, 14 and 15) and 17(15 → 16),18(4 → 3)-diabeo-abietane (1–6, 13 and 16). The structures of the new compounds were established mainly by analyzing NMR and HRESIMS data. The absolute configurations of 1, 3 and 10 were confirmed by single crystal X-ray diffraction analysis. In bioactivity assays, compounds 11, 12, 14 and 15 were active against two human colon cancer cell lines (HCT-116 and HT-29) with IC(50) values ranging from 8.8 to 34.3 μM, and compounds 10, 13 and 14 exhibited effective free radical scavenging activity with IC(50) values ranging from 35.6 to 41.5 μM by DPPH experiment.