Miliseol A-D: new lanostane triterpenoids from Miliusa sessilis and their wound-healing activity

Investigation of the Miliusa sessilis hexane extract led to four novel lanostane triterpenoids, miliseol A-D (1-4) and five known compounds (5-9). Through extensive spectroscopic analyses, the new compounds were identified as (3β,23S)-23-methoxy-24-methylene-29-nor-5α-lanost-9(11)-en-3-ol (1), (3β,23S)-23-methoxy-24-methylene-5α-lanost-9(11)-en-3-ol (2), (3β,16β)-24-methylene-5α-lanost-9(11)-ene-3,16-diol (3), and (3β,24S)-24,24¹-epoxy-5α-lanost-9(11)-en-3-ol (4). The density functional theory (DFT) computations combined with a statistical procedure (DP4+) were used to identify the stereochemistry of compound 4. The X-ray crystallographic data was utilised to confirm the absolute configurations of compounds 1 and 3. The known compounds were isolated and elucidated as (+)-spathulenol (5), phytol (6), T-muurolol (7), β-sitosterol (8), and β-sitosterol-3-O-β-d-glucopyranoside (9) through spectroscopic analyses and comparison with the literature. Biological activity screening indicated that compound 1 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.