Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities.

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Bioorg Med Chem Lett. 2011 Feb 1;21(3):1027-31. Epub 2010 Dec 10.

Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities.

Zhao JM, Li N, Zhang H, Wu CF, Piao HR, Zhao YQ.

Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules, Ministry of Education, Yanbian University College of Pharmacy, Gongyuan Road, Yanji 133000, People's Republic of China; Liaoning Xinzhong Modern Medicine Co., Ltd, Shenyang 110041, People's Republic of China.

Abstract

Three new dammarane-type sapogenins (1, 3, and 5) together with two known ones (2 and 4) were isolated from the total hydrolyzed saponins extracted from Panax ginseng berry. Their structures were elucidated using a combination of 1D and 2D (1)H and (13)C NMR spectra and mass spectroscopy as 20(R)-25-methoxyl-dammarane-3?,12?,20-triol (1), 20(R)-25-methoxyl-dammarane-3?,6?,12?,20-tetrol (2), 20(R)-20-methoxyl-dammarane-3?,12?,25-triol (3), 20(R)-20,25-dimethoxyl-dammarane-3?,12?-diol (4), and (12R,20S,24S)-20,24-; 12,24-diepoxy-dammarane-3?-ol (5). Their antitumor activities were evaluated in six human cancer cell lines. The novel compounds 1 and 3 showed significant cytotoxic activity against the six cell lines. The IC(50) values of 3 against HepG2, Colon205, and HL-60 were the lowest (8.78, 8.64, and 3.98?M, respectively). Compounds 1 and 20(S)-25-OCH(3)-PPD, which are a pair of configuration isomers, showed a 10- to 100-fold greater growth inhibition than ginsenoside-Rg(3) (an anti-cancer clinical agent in China). The data presented here may be useful for the development of novel anti-cancer agents.

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