Abstract
Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2–4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 µM, respectively.
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References
Yokosuka A, Mimaki Y (2008) Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity. Phytochemistry 69:2724–2730
Yokosuka A, Sato K, Yamori T, Mimaki Y (2010) Triterpene glycosides from Curculigo orchioides and their cytotoxic activity. J Nat Prod 73:1102–1106
Yokosuka A, Sato K, Mimaki Y (2010) Cycloartane glycosides from the rhizomes of Curculigo orchioides. Phytochemistry 71:2174–2181
Jitsuno M, Mimaki Y (2010) Triterpene glycosides from the aerial parts of Larrea tridentata. Phytochemistry 71:2157–2167
Yokosuka A, Matsuo Y, Jitsuno M, Adachi K, Mimaki Y (2011) Larrealignans A and B, novel lignan glycosides from the aerial parts of Larrea tridentata. Chem Pharm Bull (Tokyo) 59:1467–1470
Matovic NJ, Stuthe JMU, Challinor VL, Bernhardt PV, Lehmann RP, Kitching W, De Voss JJ (2011) The truth about false unicorn (Chamaelirium luteum): total synthesis of 23R,24S-chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb. Chemistry 17:7578–7591
Challinor VL, Stuthe JMU, Bernhardt PV, Lehmann RP, Kitching W, De Voss JJ (2011) Structure and absolute configuration of helosides A and B, new saponins from Chamaelirium luteum. J Nat Prod 74:1557–1560
Challinor VL, Hayes PY, Bernhardt PV, Kitching W, Lehmann RP, De Voss JJ (2011) Revision of the absolute configurations of bethosides B and C and their aglycone. J Org Chem 76:7275–7280
Takeda K, Minato H, Shimaoka A (1968) Structures of chiograsterol A and B. Chem Commun 2:104–106
Challinor VL, Stuthe JMU, Parsons PG, Lambert LK, Lehmann RP, Kitching W, De Voss JJ (2012) Structure and bioactivity of steroidal saponins isolated from the roots of Chamaelirium luteum (False Unicorn). J Nat Prod 75:1469–1479
Iorizzi M, Bryan P, McClintock J, Minale L, Palagiano E, Maurelli S, Riccio R, Zollo F (1995) Chemical and biological investigation of the polar constituents of the starfish Luidia clathrata, collected in the gulf of Mexico. J Nat Prod 58:653–671
Sargent JM, Taylor CG (1989) Appraisal of the MTT assay as a rapid test of chemosensitivity in acute myeloid leukaemia. Br J Cancer 60:206–210
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Yokosuka, A., Takagi, K. & Mimaki, Y. New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity. J Nat Med 67, 590–598 (2013). https://doi.org/10.1007/s11418-012-0718-z
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DOI: https://doi.org/10.1007/s11418-012-0718-z