cinnamosmolide and drimane

Phytochemical investigation of the ethyl acetate and methanol extracts of the bark of Madagascan endemic and medicinal plant Cinnamosma fragrans led to the isolation of two drimane sesquiterpene derivatives: cinnafragroside A (1) and cinnafragrin E (2), two aromatic glycosides: 3,4,5-trimethoxyphenol 1-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (3) and 3,4-dimethoxyphenyl-1-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (4), together with 12 known compounds identified as: helicide (6), 1-(α-l-rhamnosyl(1→6)-β-d-glucopyranosyloxy)-3,4,5-trimethoxybenzene (7), vanilloloside (8), cinnamadin (9), ugandensolide (10), cinnamosmolide (11), cinnamolide (12), polygodial (13), cinnamodial (14), bemadienolide (15), 4-isopropyl-6-methyl-α-tetralone (16), and capsicodendrin (17). Another new compound, 11-norcinnafragrolide-9-one (5), was obtained during chemical derivatization of capsicodendrin and gave a hint to understanding the structure required for the antiproliferative activity of 17. The structures of the new compounds were elucidated based on the interpretation of their spectroscopic data including one and two dimensional nuclear magnetic resonance (1D- and 2D-NMR) and mass spectroscopic data. All isolated compounds were evaluated against the hormone dependent breast cancer cell line MCF-7. Compound 17 exhibited the most potent activity with an IC

Topics: Antineoplastic Agents, Phytogenic; Breast Neoplasms; Cell Proliferation; Female; Glycosides; Humans; Magnoliopsida; MCF-7 Cells; Models, Molecular; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes

Two new drimane-type sesquiterpenes, cinnamadin (1) and cinnamodial 11alpha,12beta-dimethyl acetal (2), together with pereniporin B (3), ugandensolide (4), polygodial (5), capsicodendrin, cinnamodial (6), sitosterol, stigmasterol, lignoceric acid, cinnamosmolide (7), D-mannitol, and delta-tocotrienol were isolated from Cinnamosma madagascariensis. The structures of the new compounds were determined by physical, chemical, and spectroscopic evidence. Compound 7 and D-mannitol were isolated in high yield (5% and 1.36%, respectively). Evaluation of the alpha-glucosidase inhibitory properties of the isolated metabolites demonstrated that compounds 1 and 4 show moderate effects, while cinnamodial (6) exhibited the most potent activity. The chemosystematics of Cinnamosma species are also discussed.

Topics: Crystallography, X-Ray; Glycoside Hydrolase Inhibitors; Madagascar; Magnoliopsida; Molecular Conformation; Molecular Structure; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes