Computationally Assisted Assignment of the Kadsuraols, a Class of Chemopreventive Agents for the Control of Liver Cancer.

Xiaojuan Wang, Jiabao Liu, Pankaj Pandey, Frank R Fronczek, Robert J Doerksen, Jiabao Chen, Xinzhu Qi, Peicheng Zhang, Daneel Ferreira, Frederick A Valeriote, Hua Sun, Shuai Li, Mark T Hamann

Journal: Organic letters 2019;20(18):5559-5563

PMID: 30192555

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Abstract

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.

Address: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.; Department of Drug Discovery and Biomedical Sciences, College of Pharmacy , Medical University of South Carolina , Charleston , South Carolina 29425 , United States.; State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.; Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.; Department of Internal Medicine, Division of Hematology and Oncology , Henry Ford Health System , Detroit , Michigan 48202 , United States.; Department of Drug Discovery and Biomedical Sciences, College of Pharmacy , Medical University of South Carolina , Charleston , South Carolina 29425 , United States.

DOI: 10.1021/acs.orglett.8b02207

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MeSH Terms: 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