TY - JOUR
T1 - A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica
AU - Othman, Ahmed
AU - Amen, Yhiya
AU - Shimizu, Kuniyoshi
N1 - Funding Information:
First author (A. O.) would like to express his deepest gratitude for the Egyptian cultural affairs and Missions' sector, Ministry of Higher Education, Egypt for the scholarship and financial support.
Publisher Copyright:
© 2021 Elsevier B.V.
PY - 2021/7
Y1 - 2021/7
N2 - 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.
AB - 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.
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U2 - 10.1016/j.fitote.2021.104907
DO - 10.1016/j.fitote.2021.104907
M3 - Article
C2 - 33892125
AN - SCOPUS:85105545683
VL - 152
JO - Fitoterapia
JF - Fitoterapia
SN - 0367-326X
M1 - 104907
ER -