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Molecules 2012, 17(2), 1278-1291;

Synthesis, Characterization and Cytotoxicity of New Rotundic Acid Derivatives

School of Pharmaceutical Sciences, Jilin University, Changchun 130021, China
Jilin Academy of Chinese Medicine Sciences, Changchun 130012, China
Development Center of Traditional Chinese Medicine and Bioengineering, Changchun University of Chinese Medicine, Changchun 130117, China
Norman Bethune College of Medicine, Jilin University, Changchun 130021, China
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. View Full-Text
Keywords: rotundic acid; amino acid derivative; synthesis; characterization; cytotoxicity rotundic acid; amino acid derivative; synthesis; characterization; cytotoxicity

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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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