RESUMEN
Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H-1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-ß-D-galactopyranosyl-(1 â 2)-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-galactopyranosyl-(1 â 3)-α-L-rhamnopyranosyl-(1 â 2)-ß-L-arabinopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-quinovopyranoside; 3-O-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-xylopyranosyl-(1 â 3)-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-quinovopyranoside; 3-O-ß-D-xylopyranosyl-(1 â 3)-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-quinovopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-rhamnopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl quillaic acid 28-O-ß-D-xylopyranosyl-(1 â 3)-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-quinovopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-rhamnopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl quillaic acid 28-O-ß-D-xylopyranosyl-(1 â 3)-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.
Asunto(s)
Saponinas , Triterpenos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ácido Oleanólico/análogos & derivados , Saponinas/farmacología , Triterpenos/farmacologíaRESUMEN
Three undescribed oleanane type triterpenoid saponins (1-3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H-1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-ß-d-glucopyranosyl-(1 â 2)-ß-d-glucuronopyranosyl gypsogenin 28-O-ß-d-galactopyranosyl-(1 â 3)-[ß-d-xylopyranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 2)-ß-l-arabinopyranosyl ester (1), 3-O-ß-d-galactopyranosyl-(1 â 2)-ß-d-glucuronopyranosyl gypsogenin 28-O-α-l-arabinopyranosyl-(1 â 3)-[ß-d-xylopyranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 2)-ß-l-arabinopyranosyl ester (2), 3-O-ß-d-galactopyranosyl-(1 â 2)-ß-d-glucuronopyranosyl gypsogenin 28-O-ß-d-galactopyranosyl-(1 â 3)-[ß-d-xylopyranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 2)-ß-d-galactopyranosyl ester (3), 3-O-ß-d-galactopyranosyl-(1 â 2)-[α-l-arabinopyranosyl-(1 â 3)]-ß-d-glucuronopyranosyl gypsogenin 28-O-ß-d-glucopyranosyl-(1 â 3)-[ß-d-xylopyranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 2)-ß-d-fucopyranosyl ester (4). All saponins possess a partial sequence ß-d-galactopyranosyl-(1 â 2)-ß-d-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 µM, 3.66 ± 1.8 µM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
Asunto(s)
Saponinas , Espectrometría de Masas , Raíces de Plantas/químicaRESUMEN
Six undescribed triterpenoid saponins, named as hylomeconoside C-H, were isolated from the EtOH extract of Hylomecon japonica. On the basis of spectroscopic and chemical evidence, their structures were identified as 3-O-ß-D-galactopyranosyl-(1 â 2)-ß-D-glucuronopyranosyl gypsogenin 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-L-arabinopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-L-arabinopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-glucopyranosyl-(1 â 3)-[ß-D-xylopyranosyl-(1 â 4)]-α-L-rhamnopyranosyl-(1 â 2)-ß-L-arabinopyranoside; 3-O-ß-D-galactopyranosyl-(1 â 2)-ß-D-glucuronopyranosyl gypsogenin 28-O-ß-D-galactopyranosyl-(1 â 3)-[ß-D-xylopyranosyl-(1 â 4)]-α-L-rhamnopyranosyl-(1 â 2)-ß-D-fucopyranoside; 3-O-α-L-rhamnopyranosyl-(1 â 3)-[ß-D-galactopyranosyl-(1 â 4)]-ß-D-glucuronopyranosyl quillaic acid 28-O-ß-D-galactopyranosyl-(1 â 3)-[ß-D-xylopyranosyl-(1 â 4)]-α-L-rhamnopyranosyl-(1 â 2)-ß-D-fucopyranoside; 3-O-α-L-rhamnopyranosyl-(1 â 3)-[ß-D-galactopyranosyl-(1 â 4)]-ß-D-glucuronopyranosyl quillaic acid 28-O-ß-D-xylopyranosyl-(1 â 3)-ß-D-xylopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-quinovopyranoside. The 50% EtOH extract showed moderate inhibitory activity on the human cancer cell line HeLa, HepG-2, MCF-7, A549, K562 and TE-1. And these six compounds were tested for cytotoxicity against K562. Among them, hylomeconoside H was found to be the most active on the K562 cell lines (IC50 6.60 µM).