Abstract

Twelve new polymethylated phloroglucinol meroterpenoids (PPMs), baeckfrutones A–L (1–12), were isolated from the twigs and leaves of Baeckea frutescens. Their structures and absolute configurations were unambiguously established by extensive spectroscopic methods (HRESIMS, NMR, and ECD) and single crystal X-ray diffraction. PPM 1 is a rare PPM comprising enone-type phloroglucinol and α-phellandrene units, whereas 2–4, 6, and 7, are the first hybrids of enone-type phloroglucinol and sabinene moieties with different stereochemistry. (−)-2 and 11 showed remarkable cytotoxicities against DU145 and HCT116 cells with IC50 values of 1.33 and 12.89 μM, respectively. 6, 7, (+)-9, and 10 displayed significant anti-inflammatory activity with inhibitory rates of 74.64, 75.37, 55.13, and 75.01% at the concentration of 50 μM, respectively.

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