Computationally Assisted Assignment of the Kadsuraols, a Class of Chemopreventive Agents for the Control of Liver Cancer
Wang X, Liu J, Pandey P, Fronczek FR, Doerksen RJ, Chen J, Qi X, Zhang P, Ferreira D, Valeriote FA, Sun H, Li S, Hamann MT. Computationally Assisted Assignment of the Kadsuraols, a Class of Chemopreventive Agents for the Control of Liver Cancer. Org Lett. 2018 Sep 21;20(18):5559-5563.
Kadsuraols A-C (1-3), which are tetrahydrocyclobutaphenanthrofuranone-type lignans with a new carbon skeleton comprising a four-membered ring across C-1'-C-8, have been isolated from the roots of Kadsura longipedunculata. Their structures and absolute configurations were unambiguously determined using nuclear magnetic resonance, X-ray diffraction crystallography, DP4+ calculations, and computed and experimental electronic circular dichroism spectra. Kadsuraol C (3) exhibited hepatoprotective activity against N-acetyl- p-aminophenol (APAP)-induced toxicity. The compounds showed no cytotoxicity at 10 μM in a zone assay.
Medical Subject Headings
Antineoplastic Agents, Phytogenic; Cell Proliferation; Chemoprevention; Crystallography, X-Ray; Drug Screening Assays, Antitumor; Hep G2 Cells; Humans; Kadsura; Liver Neoplasms; Models, Molecular; Plant Roots; Quantum Theory