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J Nat Prod. 2014 Jul 25;77(7):1562-71. doi: 10.1021/np400996k. Epub 2014 Jun 18.

Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates.

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1
Faculty of Traditional Thai Medicine, Prince of Songkla University , Hat-Yai, Songkhla 90112, Thailand.

Abstract

Two rare new natural products, the neocaged-xanthone pruniflorone T (1) and the rearranged caged-xanthone pruniflorone U (3), and the known caged-xanthone cochinchinone C (2) were isolated from the roots of Cratoxylum formosum ssp. pruniflorum. The unique structures of 1-3 were determined by analysis of NMR and X-ray diffraction data. The X-ray data of 1-3 revealed that they all exist with both enantiomers in their crystal packing. Separation of 1-3 by chiral HPLC led to the isolation of three pairs of enantiomers, (-)-1/(+)-1, (-)-2/(+)-2, and (-)-3/(+)-3, and their absolute configurations were determined by analysis of single-crystal X-ray diffraction and ECD spectroscopic data. A 1:1 mixture of 1 and 3 showed potent in vitro cytotoxicity against an MCF-7 human breast cancer cell line with an IC50 value of 0.11 μg/mL.

PMID:
24940955
DOI:
10.1021/np400996k
[Indexed for MEDLINE]
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