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Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
Tbilisi State Medical University, Departement of Pharmacognosy, 33, Vazha Pshavela Ave., Tbilisi, 0177, Georgia
Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université de la Méditerranée; 27 Boul. Jean Moulin, 13385 Marseille, cedex 5, France
Laboratoire LASEVE, Université du Québec à Chicoutimi, 555 Boul. de l’Université, Département des Sciences Fondamentales, Chicoutimi, Québec, Canada
* Author to whom correspondence should be addressed.
Received: 1 October 2008; in revised form: 17 November 2008 / Accepted: 24 November 2008 / Published: 26 November 2008
Abstract: Allium leucanthum C. Koch is an endemic Caucasian species that grows in Georgia. The flowers are used in traditional medicine. Phytochemical investigation allowed the isolation of seven spirostanol type saponins from the flowers. Their structures were elucidated on the base of NMR and HRESIMS spectrometry data. A new compound, which we have named leucospiroside A (5), has been identified as (25R)-5α-spirostane-2α,3β,6β-triol 3-O-β-glucopyranosyl-(1→3)-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranosyl-(1→4)-β-galactopyranoside. The six others were known substances, but are described in this plant for the first time. The crude extract, spirostanol and furostanol fractions, as well as isolated compounds, were evaluated for their in vitro cytotoxic activity. Compounds 1-3 and 5 were found to be the most active, with relatively similar IC50 values ranging from 3.7 to 5.8 μM for a lung cancer cell line (A549) and 5.6 to 8.2 μM for a colon cancer cell line (DLD-1).
Keywords: Allium leucathum; Spirostane saponins; Structure determination; Cytotoxic activity
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Mskhiladze, L.; Legault, J.; Lavoie, S.; Mshvildadze, V.; Kuchukhidze, J.; Elias, R.; Pichette, A. Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum. Molecules 2008, 13, 2925-2934.
Mskhiladze L, Legault J, Lavoie S, Mshvildadze V, Kuchukhidze J, Elias R, Pichette A. Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum. Molecules. 2008; 13(12):2925-2934.
Mskhiladze, Lasha; Legault, Jean; Lavoie, Serge; Mshvildadze, Vakhtang; Kuchukhidze, Jumber; Elias, Riad; Pichette, André. 2008. "Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum." Molecules 13, no. 12: 2925-2934.