Eudesmane-type sesquiterpenoids with cytotoxic and anti-inflammatory activities from the fruits of Magnolia grandiflora.

Eight new eudesmane-type sesquiterpenoids, designated as magnogranols A-H (1-8), along with four known analogs, were isolated from the fruits of Magnolia grandiflora. Their structures and absolute configurations were comprehensively elucidated by a combination of modern spectroscopic and computational techniques, including HRMS, IR, NMR spectroscopy, NMR calculations, single-crystal X-ray diffraction, and electronic circular dichroism calculations. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines (K562, A549, HepG2, MDA-MB-231, and SW480), and their anti-inflammatory activities were determined by measuring the inhibitory effect on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. The results showed that 9 exhibited potential cytotoxicity against all tested cancer cell lines, with IC50 values ranging from 16.49 to 20.32 μM. Compound 10 displayed moderate cytotoxicity against K562, A549, MDA-MB-231, and SW480 cell lines, with IC50 values of 15.44 ± 0.28, 18.16 ± 0.59, 22.18 ± 0.27, and 16.62 ± 0.32 μM, respectively. Compound 11 showed moderate cytotoxicity specifically against the K562 cell line, with an IC50 value of 14.43 ± 0.50 μM. Additionally, compounds 10 and 11 exerted significant inhibitory effects on LPS-induced NO production in RAW 264.7 macrophages, with IC50 values of 9.91 ± 0.66 and 34.12 ± 0.30 μM, respectively. These findings highlight the potential of M. grandiflora fruits as a promising source of bioactive natural products for pharmaceutical research.