Premium
Acylated Triterpene Saponins from Atroxima liberica Stapf
Author(s) -
Tabopda Turibio Kuiate,
MitaineOffer AnneClaire,
Miyamoto Tomofumi,
Tanaka Chiaki,
Mirjolet JeanFrançois,
Duchamp Olivier,
Ngadjui Bonaventure Tchaleu,
LacailleDubois MarieAleth
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100147
Subject(s) - chemistry , triterpene , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , trisaccharide , saponin , medicine , alternative medicine , pathology
The four new acylated triterpene saponins 1 – 4 , isolated as two pairs of isomers and named libericosides A 1 /A 2 and B 1 /B 2 , one pair of isomers 5 / 6 , the ( Z )‐isomer libericoside C 2 ( 5 ) being new, one new sucrose ester, atroximoside ( 7 ), and eight known compounds were isolated from the roots of Atroxima liberica by repeated MPLC and VLC on normal and reversed‐phase silica gel. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies ( 1 H‐ and 13 C‐NMR, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3‐ O ‐ β ‐ D ‐glucopyranosylpresenegenin 28‐{ O ‐ α ‐ L ‐arabinopyranosyl‐(1→3)‐ O ‐ β ‐ D ‐xylopyranosyl‐(1→4)‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐4‐ O ‐[( E )‐3,4‐dimethoxycinnamoyl]‐ β ‐ D ‐fucopyranosyl} ester ( 1 ) and its ( Z )‐isomer 2 , 3‐ O ‐ β ‐ D ‐glucopyranosylpresenegenin 28‐{ O ‐ α ‐ L ‐arabinopyranosyl‐(1→4)‐ O ‐ β ‐ D ‐xylopyranosyl‐(1→4)‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ O ‐[ O‐β ‐ D ‐xylopyranosyl‐(1→3)‐ β ‐ D ‐glucopyranosyl‐(1→3)]‐4‐ O ‐[( E )‐3,4‐dimethoxycinnamoyl]‐ β ‐ D ‐fucopyranosyl} ester ( 3 ) and its ( Z )‐isomer 4 , 3‐ O ‐ β ‐ D ‐glucopyranosylpresenegenin 28‐{ O ‐ β ‐ D ‐xylopyranosyl‐(1→4)‐ O ‐ α ‐ L ‐rhamnopyranosyl‐(1→2)‐ O ‐[6‐ O ‐acetyl‐ β ‐ D ‐glucopyranosyl‐(1→3)]‐4‐ O ‐[( Z )‐3,4‐dimethoxycinnamoyl]‐ β ‐ D ‐fucopyranosyl} ester ( 5 ), and 3‐ O ‐[( Z )‐feruloyl]‐ β ‐ D ‐fructofuranosyl α ‐ D ‐glucopyranoside ( 7 ). Compounds 1 – 6 and the known saponins 8 / 9 were evaluated against the human colon cancer cells HCT 116 and HT‐29 and showed moderate to weak cytotoxicity.