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New Triterpenoidal Saponins Acylated with Monoterpenic Acid from Albizia adianthifolia
Author(s) -
Haddad Mohamed,
Miyamoto Tomofumi,
LacailleDubois MarieAleth
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - Portuguese
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490112
Subject(s) - chemistry , stereochemistry , hydroxymethyl
Four new triterpenoidal saponins acylated with monoterpenic acid, i.e. , adianthifoliosides C, D, E, and F ( 1 – 4 ), besides the two known julibroside III and the monodesmonoterpenyl elliptoside A, were isolated from the roots of Albizia adianthifolia. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies and mass spectrometry as 3‐ O ‐{ O ‐ α ‐ L ‐arabinopyranosyl‐(1→2)‐ O ‐ β ‐ d‐ fucopyranosyl‐(1→6)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→2)]‐ β ‐ d‐ glucopyranosyl}‐21‐ O ‐{(2 E ,6 S )‐6‐{{4‐ O ‐[(2 E ,6 S )‐2,6‐dimethyl‐6‐( β ‐ D ‐quinovopyranosyloxy)octa‐2,7‐dienoyl]‐ β ‐ d‐ quinovopyranosyl}oxy}‐2‐(hydroxymethyl)‐6‐methylocta‐2,7‐dienoyl}acacic acid 28‐{ O ‐ α ‐ L ‐arabinofuranosyl‐(1→4)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→3)]‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ β ‐ d‐ glucopyranosyl} ester ( 1 ), 21‐ O ‐{(2 E ,6 S )‐6‐{{4‐ O ‐[(2 E ,6 S )‐2,6‐dimethyl‐6‐( β ‐ d‐ quinovopyranosyloxy)octa‐2,7‐dienoyl]‐ β ‐ d‐ quinovopyranosyl}oxy}‐2‐(hydroxymethyl)‐6‐methylocta‐2,7‐dienoyl}‐3‐ O ‐{ O ‐ β ‐ D ‐xylopyranosyl‐(1→2)‐ O ‐ β ‐ d‐ fucopyranosyl‐(1→6)‐2‐(acetylamino)‐2‐deoxy‐ β ‐ d‐ glucopyranosyl}acacic acid 28‐{ O ‐ α ‐ L ‐arabinofuranosyl‐(1→4)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→3)]‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ β ‐ d‐ glucopyranosyl} ester ( 2 ), 21‐ O ‐{(2 E ,6 S )‐6‐{{3‐ O ‐[(2 E ,6 S )‐2,6‐dimethyl‐6‐( β ‐ d‐ quinovopyranosyloxy)octa‐2,7‐dienoyl]‐ β ‐ d‐ quinovopyranosyl}oxy}‐2,6‐dimethylocta‐2,7‐dienoyl}‐3‐ O ‐{ O ‐ β ‐ D ‐xylopyranosyl‐(1→2)‐ O ‐ β ‐ d‐ fucopyranosyl‐(1→6)‐2‐(acetylamino)‐2‐deoxy‐ β ‐ d‐ glucopyranosyl}acacic acid 28‐{ O ‐ α ‐ L ‐arabinofuranosyl‐(1→4)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→3)]‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ β ‐ d‐ glucopyranosyl} ester ( 3 ), and 3‐ O ‐{ O ‐ α ‐ L ‐arabinopyranosyl‐(1→2)‐ O ‐ β ‐ d‐ fucopyranosyl‐(1→6)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→2)]‐ β ‐ d‐ glucopyranosyl}‐21‐ O ‐{(2 E ,6 S )‐2,6‐dimethyl‐6‐( β ‐ d‐ quinovopyranosyloxy)octa‐2,7‐dienoyl}acacic acid 28‐{ O ‐ α ‐ L ‐arabinofuranosyl‐(1→4)‐ O ‐[ β ‐ d‐ glucopyranosyl‐(1→3)]‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ β ‐ d‐ glucopyranosyl} ester ( 4 ).