Planta Med 2008; 74 - PB24
DOI: 10.1055/s-0028-1084369

Steroidal saponins from the roots of Smilax aspera subsp. mauritanica

Z Belhouchet 1, M Sautour 1, T Miyamoto 2, MA Lacaille-Dubois 1
  • 1Laboratoire de Pharmacognosie, Unité de Molécules d'Intérêt Biologique, UMIB UPRES- EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France
  • 2Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812–8582, Japan

The genus Smilax contains 350 species, which are widely distributed in tropical regions of east Asia, and South and North America. Several Smilax species have already been studied chemically and found to contain steroidal saponins and from a biological point of view, some species were documented to exhibit antiinflammatory [1], NO-modulating [2], and antileprosic activity [3]. Recently, antifungal steroidal saponins were isolated from the rhizome of S. medica [4–5]. As part of our ongoing search for new antifungal steroid saponins [4–7], a phytochemical investigation of the roots of S. medica subsp. mauritanica has led to the isolation by several chromatographic steps on normal and reversed phase silica gel of two new steroidal saponins, (25S)-5β-spirostane-3β-ol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (1), (25S)-3β,5β,22α-furostane-3,22,26-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 26-O-β-D-glucopyranoside (2), along with four known saponins, curillin G (3), asparagoside E (4), asparoside A (5) and asparoside B (6). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR (COSY, TOCSY, HSQC and HMBC). In addition, the antifungal activity of these compounds was tested against three human pathogenic yeasts (Candida albicans, C. glabrata and C. tropicalis). Curillin G (3) exhibited antifungal activity against the human pathogenic yeasts C. albicans, C. glabrata and C. tropicalis (MICs of 25, 25 and 50µg/ml, respectively) whereas the other compounds were inactive. The reference compound ketoconazole was used as positive control.

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