Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-xylopyranosyl-(1 → 6)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid and 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.

Saponins are bioactive compounds occurring in many plant species having a wide range of biological activities such as immunoadjuvant, cytotoxic, analgesic, antimicrobial and anti-inflammatory activities, just to mention a few. The aim of our researches concerns the isolation, structural elucidation and biological investigation of saponins from various plant species [1]. In this context, the study of the roots and leaves of Weigela stelzneri(Caprifoliaceae) led to isolation of four new and two known oleanane-type saponins mainly by medium pressure- and vacuum-liquid chromatography on silica gel (normal and reversed-phase RP-18) [1]. The new compounds were elucidated by a combination of spectroscopic techniques including 1D-, 2D-NMR, and mass spectrometry as glycosides of oleanolic acid, three of them being monodesmosides at C-3 with a branched oligosaccharidic chain made of six sugar units, whereas the known ones were hederagenin derivatives. The six compounds were evaluated for their cytotoxicity against a human cancer cell line (colorectal SW480) and a mouse cancer cell line (mammary EMT6), and for their anti-inflammatory activity. The results show that two new compounds differing only by the first sugar unit of the hexasaccharidic chain at C-3 (arabinopyranosyl instead of xylopyranosyl) exhibited the strongest cytotoxicity on both cell lines (IC50 5.41 µM and 1.54 µM, respectively), which was better than those of the positive controls etoposide and methotrexate. Furthermore, they revealed a significant modulatory effect of the IL-1β production on human lymphocytes stimulated with endotoxins, showing therefore a strong anti-inflammatory potential.

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. "Yellow Coast", and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

Three new spirostane-type glycosides (1-3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside (1), (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside (2), and (20S,25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480).

Steroidal saponins are a class of glycosides occurring in many plant species. The aglycon part of these glycosides is constituted by a furostane or spirostane-type skeleton, rarely cholestane. These saponins are known for their interesting pharmacological activities such as antifungal, anti-ischemia, antispasmodic, cytotoxic, haemolytic [1 – 3], and anti-inflammatory properties [4]. The aim of our researches was the isolation and structural elucidation of the steroidal saponins from the biodiversity. In this context, the study of three plants species, Dracaena marginata, D. fragrans (Asparagaceae) and Allium flavum (Amaryllidaceae) led to isolation of twenty-one natural glycosides by column chromatography on Sephadex LH-20, medium pressure liquid chromatography and vacuum liquid chromatography on silica gel and reversed-phase RP-18 silica gel. The structures were elucidated by a detailed spectral analysis by 600 MHz 2D-NMR (COSY, TOCSY, ROESY/NOESY, HSQC, HMBC/HMQC), and mass spectrometry. Six new compounds were characterized as spirostane and furostane- type glycosides from D. marginata (1 – 3) and from A. flavum (4 – 6). The presence of a 4-O-sulfated arabinopyranosyl moiety in the oligosaccharide chain at C-1 of the steroid skeleton underlined the originality of the compounds of the two Dracaena species, and might represent a chemotaxonomic marker of the genus Dracena. The isolation and structure elucidation of the six new compounds will be presented.

Three new steroidal saponins and ten known ones were isolated from the bark of Dracaena marginata, along with two known steroidal saponins from the roots. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments and mass spectrometry as (25R)-26-(beta-D-glucopyranosyloxy)3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 –> 2)-[alpha-L-rhamnopyranosyl-(1 –> 4)]-beta-D-glucopyranoside (1), (25R)-26-(beta-D-glucopyranosyloxy)-3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 –> 2)-4-O-sulfo-alpha-L-arabinopyranoside (2), and (25S)-3beta-hydroxyspirost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 –> 2)-4-O-sulfo-alpha-L-arabinopyranoside (3).