Acylated oleanane-type saponins from Ganophyllum giganteum

• Published in: Phytochemistry (Oxford) Vol. 98; pp. 236 - 242
• Main Authors: Montes, Elier Galarraga, Mitaine-Offer, Anne-Claire, Amaro-Luis, Juan Manuel, Paululat, Thomas, Delaude, Clément, Pouységu, Laurent, Quideau, Stéphane, Rojas, Luis B., Delemasure, Stéphanie, Dutartre, Patrick, Lacaille-Dubois, Marie-Aleth
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-02-2014
• Subjects: Acylation; Animals; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Biological Products - chemical synthesis; Biological Products - chemistry; Biological Products - pharmacology; Cell Line, Tumor; Cell Proliferation - drug effects; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Ganophyllum giganteum; Humans; Hydrolysis; Inflammation - drug therapy; Medicagenic acid; Mice; Molecular Conformation; Oleanolic Acid - analogs & derivatives; Oleanolic Acid - chemistry; Plant Roots - chemistry; Sapindaceae; Sapindaceae - chemistry; Saponins; Saponins - chemical synthesis; Saponins - chemistry; Saponins - pharmacology; Structure-Activity Relationship; Zanhic acid; Saponins; Zanhic acid; Medicagenic acid; Ganophyllum giganteum; Sapindaceae
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2013.11.003

Five oleanane-type saponins (1–5) were isolated from the barks of Ganophyllum giganteum. The fucopyranosyl moiety of the oligosaccharidic chain of two saponins possessed an unusual substitution of the C-4 position by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.
•Five oleanane-type glycosides were isolated from the barks.•Structures were determined by 2D NMR and by mass spectrometry.•Two saponins possessed an unusual substitution of the Fuc-4 position by an ester group formed by two symmetrical C5 nilic acid.•Chemotaxonomic conclusions were discussed.•Cytotoxicity and anti-iflammatory activity of the isolated compounds were evaluated.
Five oleanane-type saponins, 3-O-β-D-glucuronopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (1), 3-O-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (2), zanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (3), zanhic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (4), medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the β-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.