A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica

Ahmed Othman, Yhiya Amen, Kuniyoshi Shimizu

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Abstract

In recent years, the scientific interest and particularly the economic significance of halophytic plants has been highly demanding due to the medicinal and nutraceutical potential of its bioactive compounds. A xero-halophyte Bassia indica is deemed to be a very cheap source of natural entities without chemical or biological investigation. In this context, a new acylated flavonol tetraglycoside, kaempferol-3-O-β-D-glucopyranosyl-(1→6)-O-[β-D-galactopyranosyl-(1→3)-2-O-trans-feruloyl-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (14), together with rare occurring flavonol triglycoside, isorhamnetin-3-O-β-D-glucopyranosyl-(1→6)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (15), were isolated from the aqueous methanol extract of the aerial parts of B. indica. The study also reported an optimal separation and characterization of a new seco-glycosidic oleanane saponin with 2′R,3′S stereocenters, identified as (2′R,3′S)-3-O-[2′-hydroxy-3′-(2"-O-glycolyl)-oxo-propionic acid-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl-olean-12-en-3β-ol-28-oic acid (17), in addition to its derivative, 3-O-[2′-(2"-O-glycolyl)-glyoxylyl-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl-olean-12-en-3β-ol-28-oic acid (16). The structures of all isolated compounds were elucidated based on 1D, 2D NMR, and HR-MS analysis, as well as comparing with similar derivatives published in the literature. Furthermore, thirteen known compounds were isolated and identified as β-sitosterol (1), vanillic acid (2), o-hydroxybenzoic acid (3), р-hydroxybenzoic acid (4), 6,7-dihydroxycoumarin (5), methyl caffeate (6), caffeic acid (7), quercetin (8), uracil (9), thymidine (10), tachioside (11), isorhamnetin-3-O-β-D-glucopyranoside (12), kaempferol-3-O-rutinoside (13). The anticholinesterase activity of all isolated compounds was evaluated.

Original languageEnglish
Article number104907
JournalFitoterapia
Volume152
DOIs
Publication statusPublished - Jul 2021

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery

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