Title

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

Authors

Xiaojuan Wang, 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.
Jiabao Liu, 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.
Pankaj Pandey
Frank R. Fronczek, Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
Robert J. Doerksen
Jiabao Chen, 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.
Xinzhu Qi, 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.
Peicheng Zhang, 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.
Daneel Ferreira
Frederick A. Valeriote, Department of Internal Medicine, Division of Hematology and Oncology , Henry Ford Health System , Detroit , Michigan 48202 , United States.
Hua Sun, 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.
Shuai Li, 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.
Mark T. Hamann, Department of Drug Discovery and Biomedical Sciences, College of Pharmacy , Medical University of South Carolina , Charleston , South Carolina 29425 , United States.

Document Type

Article

Publication Date

9-21-2018

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.

Publication Source (Journal or Book title)

Organic letters

First Page

5559

Last Page

5563

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