Three new oleanane-type triterpene saponins from Atractylis flava

Abstract

Three new bidesmosidic saponins (1–3), along with thirteen known metabolites consisting of two flavonoids and eleven triterpenoids were identified in dichloromethane and n-butanol extracts of the whole plant Atractylis flava Desf. The saponins were characterized as 3-O-[β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl]-16α-hydroxygypsogenic acid (1), 3-O-[β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-16α-hydroxygypsogenic acid (2), and 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-28-O-[((3-O-acetyl)-β-d-xylopyranosyl)-(1 → 4)-((2-O-acetyl)-α-l-rhamnopyranosyl)-(1 → 2)-β-d-xylopyranosyl]-quillaic acid (3). Structures of all isolated compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, TOCSY, HSQC-TOCSY, HMBC, ROESY and NOESY), high-resolution electrospray ionization mass spectrometry (HRESIMS), acid hydrolysis, measurement of optical rotation and comparison with literature data.