Previous phytochemical investigations reported that Calophyllum spp have biosynthesized a wide range of bioactive phenolics such as xanthones and coumarins. The phytochemical study conducted on the stem bark of C. canum has led to the isolation of eight trioxygenated xanthones namely: 5-methoxytrapezifolixanthone (1), 5-methoxyananixanthone (2), caloxanthone C (3), 1,5-dihydroxy-3-methoxy-4-isoprenylxanthone (4), 6-deoxyisojacareubin (5), euxanthone (6), trapezifolixanthone (7), ananixanthone (8), together with three common triterpenoids, β-sitosterol (9), friedelin (10), and stigmasterol (11). Furthermore, xanthones 1 and 2 were isolated for the first time as naturally occurring xanthones from the plant extract. The structures of these compounds were identified and elucidated using advanced spectroscopic techniques such as 1D & 2D NMR, MS, and FTIR. The neuroprotective property of selected compounds were tested through in vitro stroke model. Among all tested compounds, 1 µm of compounds 8, 9 and 10 showed significant neuroprotective activity via reduction of apoptosis by ~ 50%.
The title compound (trivial name brasixanthone B), C23H22O5, isolated from Calophyllum gracilentum, is characterized by a xanthone skeleton of three fused six-membered rings plus an additional fused pyrano ring and one 3-methylbut-2-enyl side chain. The core xanthone moiety is almost planar, with a maximum deviation 0.057 (4) Å from the mean plane. In the molecule, an intramolecular O—H...O hydrogen bond forms an S(6) ring motif. The crystal structure features intermolecular O—H...O and C—H...O interactions.
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