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

Authors
  • Othman, Ahmed1
  • Amen, Yhiya2
  • Shimizu, Kuniyoshi3
  • 1 Department of Agro-environmental Sciences, Graduate School of Bioresources and Bioenvironmental Sciences, Kyushu University, Fukuoka 819-0395, Japan; Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, Egypt. , (Egypt)
  • 2 Department of Agro-environmental Sciences, Graduate School of Bioresources and Bioenvironmental Sciences, Kyushu University, Fukuoka 819-0395, Japan; Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. , (Egypt)
  • 3 Department of Agro-environmental Sciences, Graduate School of Bioresources and Bioenvironmental Sciences, Kyushu University, Fukuoka 819-0395, Japan. Electronic address: [email protected] , (Japan)
Type
Published Article
Journal
Fitoterapia
Publication Date
Jul 01, 2021
Volume
152
Pages
104907–104907
Identifiers
DOI: 10.1016/j.fitote.2021.104907
PMID: 33892125
Source
Medline
Keywords
Language
English
License
Unknown

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. Copyright © 2021 Elsevier B.V. All rights reserved.

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