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J Nat Prod. 2017 Jan 27;80(1):53-60. doi: 10.1021/acs.jnatprod.6b00415. Epub 2017 Jan 17.

Semisynthesis of (-)-Rutamarin Derivatives and Their Inhibitory Activity on Epstein-Barr Virus Lytic Replication.

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Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
The Institute of Human Virology, Zhongshan School of Medicine, Sun Yat-sen University , Guangzhou, Guangdong 510080, People's Republic of China.
Guanghua School of Stomatology, Sun Yat-sen University, Guangdong Provincial Key Laboratory of Stomatology , Guangzhou 510080, People's Republic of China.
Department of Microbiology, School of Dental Medicine, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.


(+)-Rutamarin inhibits EBV lytic DNA replication with an IC50 of 7.0 μM. (-)-Chalepin, a (-)-rutamarin derivative, was isolated from the whole plant of Ruta graveolens and used as a precursor of (-)-rutamarin. Altogether, 28 (-)-rutamarin derivatives were synthesized starting from (-)-chalepin. Of these, 16 compounds (2a-e, 3b-e, 3g, 4f, 4k, 4m-p) were found to be more potent against EBV lytic DNA replication than (-)-chalepin. Compounds 4m, 4n, and 4p exhibited IC50 values of 1.5, 0.32, and 0.83 μM and showed selectivity index values (SI) of 801, 211, and >120, respectively. Thus, compounds 4m, 4n, and 4p are considered promising leads for further laboratory investigation.

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