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Molecules 2017, 22(8), 1243; doi:10.3390/molecules22081243

Structural Characterization of Cholestane Rhamnosides from Ornithogalum saundersiae Bulbs and Their Cytotoxic Activity against Cultured Tumor Cells

School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan
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Received: 30 June 2017 / Revised: 14 July 2017 / Accepted: 17 July 2017 / Published: 25 July 2017
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Abstract

Previous phytochemical studies of the bulbs of Ornithogalum saundersiae, an ornamental perennial plant native to South Africa, resulted in the isolation of 29 new cholestane glycosides, some of which were structurally unique and showed potent cytotoxic activity against cultured tumor cell lines. Therefore, we aimed to perform further phytochemical examinations of methanolic extracts obtained from Ornithogalum saundersiae bulbs, isolating 12 new cholestane rhamnosides (112) and seven known compounds (1319). The structures of the new compounds (112) were identified via NMR-based structural characterization methods, and through a sequence of chemical transformations followed by spectroscopic and chromatographic analysis. The cytotoxic activity of the isolated compounds (119) and the derivatives (1a and 6a) against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells was evaluated. Compounds 1012, 16, and 17 showed cytotoxicity against both HL-60 and A549 cells. Compound 11 showed potent cytotoxicity with an IC50 value of 0.16 µM against HL-60 cells and induced apoptotic cell death via a mitochondrion-independent pathway. View Full-Text
Keywords: Ornithogalum saundersiae; Asparagaceae; Liliaceae; cholestane rhamnoside; cytotoxicity; HL-60 cells; A549 cells; apoptosis Ornithogalum saundersiae; Asparagaceae; Liliaceae; cholestane rhamnoside; cytotoxicity; HL-60 cells; A549 cells; apoptosis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Iguchi, T.; Kuroda, M.; Naito, R.; Watanabe, T.; Matsuo, Y.; Yokosuka, A.; Mimaki, Y. Structural Characterization of Cholestane Rhamnosides from Ornithogalum saundersiae Bulbs and Their Cytotoxic Activity against Cultured Tumor Cells. Molecules 2017, 22, 1243.

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