Bioactive oleanane-type saponins from Hylomecon Japonica.

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.

Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities.

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.

Triterpenoid saponins from the herb Hylomecon japonica.

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).