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Molecules 2012, 17(2), 1278-1291; doi:10.3390/molecules17021278

Synthesis, Characterization and Cytotoxicity of New Rotundic Acid Derivatives

1,*  and 5,*
1 School of Pharmaceutical Sciences, Jilin University, Changchun 130021, China 2 Jilin Academy of Chinese Medicine Sciences, Changchun 130012, China 3 Development Center of Traditional Chinese Medicine and Bioengineering, Changchun University of Chinese Medicine, Changchun 130117, China 4 Norman Bethune College of Medicine, Jilin University, Changchun 130021, China 5 China-Japan Union Hospital, Jilin University, Changchun 130033, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 5 December 2011 / Revised: 17 January 2012 / Accepted: 20 January 2012 / Published: 31 January 2012
(This article belongs to the Section Medicinal Chemistry)
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Rotundic acid (RA, 1), a natural compound, exhibits potent tumor cell growth inhibiting properties. To date there are no reports on derivatives of RA. Furthermore, the 28-COOH position of RA might make it unstable and induced serious gastrointestinal side effects when it was applied in vivo. Therefore, in order to explore and make use of this compound, eight new amino acid derivatives of RA at the 28-COOH position were synthesized and evaluated for their cytotoxicities in vitro on three tumor cell lines including A375, HepG2 and NCI-H446. As a result, a few of these new amino acid derivatives showed stronger cytotoxicity. Compound 5a was found to have the best inhibition activity on the three tested human tumor cell lines with IC50 values of less than 10 μM compared with RA treatment. Meanwhile, the cytotoxicity of compound 6b was significantly higher than that of RA on the A375 cell line and almost the same as RA on the HepG2 and NCI-H446 cell lines. Hence, compounds 5a and 6b may serve as potential lead compounds for the development of new anti-tumor drugs.
Keywords: rotundic acid; amino acid derivative; synthesis; characterization; cytotoxicity rotundic acid; amino acid derivative; synthesis; characterization; cytotoxicity
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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He, Y.-F.; Nan, M.-L.; Sun, J.-M.; Meng, Z.-J.; Yue, F.-G.; Zhao, Q.-C.; Yang, X.-H.; Wang, H. Synthesis, Characterization and Cytotoxicity of New Rotundic Acid Derivatives. Molecules 2012, 17, 1278-1291.

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