Three new oleanane-type triterpene saponins from Atractylis flava. (March 2016)

• Record Type: Journal Article
• Authors: Chabani, Sonia; Lavaud, Catherine; Benkhaled, Mohammed; Harakat, Dominique; Long, Christophe; Haba, Hamada
• Is Part Of: Phytochemistry letters. Volume 15(2016:Mar.)
• Page Start: 88
• Page End: 93
• Publication Date: 2016-03
• Subjects: Atractylis flava -- Asteraceae -- Saponins -- Flavonoids -- Triterpenoids -- NMR; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2015.11.017
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Chemical constituents of Atractylis flava were investigated. Three new triterpenoid saponins were isolated from n -BuOH extract. Structures were identified by extensive NMR and HRESIMS experiments. Saponins have been identified for the first time from Atractylis genus. 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 ( 1 H, 13 C, 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.