Steroidal saponins from the leaves of Yucca de - smetiana and their in vitro antitumor activity: structure activity rela
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Med Chem Res (2013) 22:4877–4885 DOI 10.1007/s00044-013-0497-4
ORIGINAL RESEARCH
Steroidal saponins from the leaves of Yucca de-smetiana and their in vitro antitumor activity: structure activity relationships through a molecular modeling approach Jacqueline Eskander • Ola K. Sakka • Dominique Harakat • Catherine Lavaud
Received: 2 October 2012 / Accepted: 15 January 2013 / Published online: 30 January 2013 Ó Springer Science+Business Media New York 2013
Abstract Four steroidal saponins were isolated from the leaves of Yucca de-smetiana Baker. Their structures were established using one- and two- dimensional NMR spectroscopy and mass spectrometry. The structure of the new steroidal saponin was identified as: (25R)-3b-hydroxy-5 a-spirostan-3-O-b-D-xylopyranosyl-(1 ? 2)-b-D-galactopyranosyl-(1 ? 2)-O-[b-D-glucopyranosyl-(1 ? 3)]-b-D-glucopyranosyl-(1 ? 4)-b-D-galactopyranoside (desmettianoside C) along with three known spirostanol and furostanol saponins. The isolated saponins were evaluated for their antitumor activity against HCT116, MCF7, HepG2, and A549 cell lines. Saponins 3 and 4 showed potent activity against HCT116, MCF7, and HepG2 cell lines in comparison with the positive control doxorubicin. A molecular modeling approach was performed to establish conformational criteria that could affect the biological activity of the isolated saponins.
J. Eskander (&) C. Lavaud Laboratoire de Pharmacognosie, Institut de Chimie Mole´culaire de Reims (ICMR), UMR-CNRS 7312, Baˆtiment 18, BP 1039, 51687 Reims Cedex 2, France e-mail: [email protected] O. K. Sakka Department of Chemistry, American University in Cairo, P.O. Box 74, New Cairo 11835, Egypt D. Harakat Service d’analyse, Institut de Chimie Mole´culaire de Reims (ICMR), UMR-CNRS 7312, Baˆtiment 18, BP 1039, 51687 Reims Cedex 2, France Present Address: J. Eskander Pharmacognosy Department, Faculty of Pharmacy, Helwan University, POB 11795, Ain-Helwan, Cairo, Egypt
Keywords Yucca de-smetiana Steroidal saponins Desmettianoside C Antitumor activity Molecular modeling
Introduction Yucca genus (Agavaceae) is widely distributed in central and northern America; many of them are cultivated in the tropical gardens of the world as ornamental plants. The main application of Yucca products is in animal nutrition as a food additive to reduce ammonia and fecal odors in animal excreta (Cheeke, 2000) and improve the growth and productivity of livestock and poultry (Anthony et al., 1994; Balog et al., 1994). Another important application for Yucca extracts is as a foaming agent in soft drink, pharmaceutical, cosmetic, and food industries, which is attributed to the very high steroidal saponins content in Yucca species (Piacente et al., 2005; Oleszek et al., 2001; Hostettmann and Marston, 1995; Mahato et al., 1982). Studies of steroidal saponins from Yucca genus have mainly focused on Y. schidigera (Oleszek et al., 2001), Y. gloriosa (Skhirtladze et al., 2006), Y. filamentosa (Dragalin and Kintia, 1975), Y. elephantipes (Zhang et al., 2008), Y. aloifolia
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