1. Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates.
- Author
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Boonnak N, Chantrapromma S, Fun HK, Yuenyongsawad S, Patrick BO, Maneerat W, Williams DE, and Andersen RJ
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Camptothecin pharmacology, Chromatography, High Pressure Liquid, Crystallography, X-Ray, Drug Screening Assays, Antitumor, Female, Humans, Inhibitory Concentration 50, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Stereoisomerism, Thailand, Xanthones chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Clusiaceae chemistry, Xanthones isolation & purification, Xanthones pharmacology
- 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.
- Published
- 2014
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