Adamantyl and homoadamantyl derivatives from Garcinia multiflora fruits

Nine undescribed caged polycyclic polyprenylated acylphloroglucinols (PPAPs), including adamantane type PPAPs (1–2), and homoadamantane type PPAPs (3–9), were isolated from the fruits of Garcinia multiflora, along with three known analogues. A new epimeric pair of isohypersampsonone B (5) and epi-isohypersampsonone B (6), featuring an unusual hexahydrofuro[2,3-b]furan-diepoxy ring system fused in a homoadamantane skeleton, was not separated due to the rapid equilibration between the two isomeric forms. All new caged PPAPs (1–9), sharing a common isogeranyl group, were determined on the basis of comprehensive NMR and MS spectroscopic data. Their cytotoxicity against three human tumor cell lines (SGC-7901, HepG2, HCT-116) and the nitric oxide production inhibitory activity of lipopolysaccharides-stimulated RAW 264.7 cells were tested. Compounds 8 and 12 displayed mild cytotoxicity against three human cancer cell lines with IC(50) values of 10–20 μM. Furthermore, compounds 8 and 12 also exhibited NO production inhibitory effect with an IC(50) value of 18.24 and 12.50 μM respectively.