Miliseol A–D: new lanostane triterpenoids from <i>Miliusa sessilis</i> and their wound-healing activity

Investigation of the <i>Miliusa sessilis</i> hexane extract led to four novel lanostane triterpenoids, miliseol A-D (<b>1-4</b>) and five known compounds (<b>5-9</b>). Through extensive spectroscopic analyses, the new compounds were identified as (3<i>β</i>,23<i>S</i>)-23-methoxy-24-methylene-29-nor-5<i>α</i>-lanost-9(11)-en-3-ol (<b>1</b>), (3<i>β</i>,23<i>S</i>)-23-methoxy-24-methylene-5<i>α</i>-lanost-9(11)-en-3-ol (<b>2</b>), (3<i>β</i>,16<i>β</i>)-24-methylene-5<i>α</i>-lanost-9(11)-ene-3,16-diol (<b>3</b>), and (3<i>β</i>,24<i>S</i>)-24,24¹-epoxy-5<i>α</i>-lanost-9(11)-en-3-ol (<b>4</b>). The density functional theory (DFT) computations combined with a statistical procedure (DP4+) were used to identify the stereochemistry of compound <b>4</b>. The X-ray crystallographic data was utilised to confirm the absolute configurations of compounds <b>1</b> and <b>3</b>. The known compounds were isolated and elucidated as (+)-spathulenol (<b>5</b>), phytol (<b>6</b>), T-muurolol (<b>7</b>), <i>β</i>-sitosterol (<b>8</b>), and <i>β</i>-sitosterol-3-<i>O</i>-<i>β</i>-d-glucopyranoside (<b>9</b>) through spectroscopic analyses and comparison with the literature. Biological activity screening indicated that compound <b>1</b> promoted cell migration in the HaCaT cell line, with minimal cytotoxicity at the tested concentrations. This finding suggests its potential as an enhancing agent for skin wound healing.