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Medicinal plants belonging to the genus  Ardisia  are traditionally used to cure various human diseases including inflammation and cancer. This study aimed to purify and characterize cytotoxic and anti-inflammatory compounds from  Ardisia sieboldii  leaves. Bioassay-guided chromatographic analyses yielded three compounds, 2-methyl-5-(8 Z -heptadecenyl) resorcinol ( 1 ), 5-(8 Z -heptadecenyl) resorcinol ( 2 ), and ardisiaquinone A ( 3 ), whereas liquid chromatography–electrospray ionisation–mass spectrometry chemical profiling revealed the presence of diverse resorcinol and alkylbenzoquinone derivatives in cytotoxic 70% methanol extracts. Chemical structures of  1  –  3  were confirmed by spectroscopic methods including  1 H NMR (nuclear magnetic resonance),  13 C NMR, and electrospray ionisation–mass spectrometry. Compounds  1  and  2  were purified from  A. sieboldii  for the first time, and all three compounds showed cytotoxicity against a panel of cancer cell lines and brine shrimps in a dose-response manner. Among them, compound  2  exhibited the highest cytotoxicity on cancer cells (IC 50  values of 8.8–25.7 μM) as well as on brine shrimps (IC 50  value of 5.1 μM). Compounds  1  –  3  exhibited anti-inflammatory effects through inhibiting protein denaturation (IC 50  values of 5.8–9.6 μM), cyclooxygenase-2 activity (IC 50  values of 34.5–60.1 μM), and nitrite formation in RAW 264.7 cells. Cytotoxic and anti-inflammatory activities of  1  –  3  demonstrated in this study deserve further investigation for considering their suitability as candidates or leads to develop anticancer and anti-inflammatory drugs.

Cytotoxic and anti-inflammatory resorcinol and alkylbenzoquinone derivatives from the leaves of Ardisia sieboldii