Flavonoid glycosides from Adina racemosa and their inhibitory activities on eukaryotic protein synthesis.
From the dried leaves, flowers, and twigs of Adina racemosa, five new flavonoid glycosides, quercetin 3-O-alpha-l-rhamnopyranosyl(1-->6)-(3-O-trans-p-coumaroyl)-beta-d-galactopyranoside (1), quercetin 3-O-alpha-l-rhamnopyranosyl(1-->6)-[(4-O-trans-p-coumaroyl)-alpha-l-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-d-galactopyranoside (2), kaempferol 3-O-alpha-l-rhamnopyranosyl(1-->6)-[(4-O-trans-p-coumaroyl)-alpha-l-rhamnopyranosyl(1--> 2)]-(4-O-trans-p-coumaroyl)-beta-d-galactopyranoside (3), quercetin 3-O-alpha-l-rhamnopyranosyl(1-->6)-[(4-O-trans-p-coumaroyl)-alpha-l-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-d-galactopyranoside (4), and quercetin 3-O-alpha-l-rhamnopyranosyl(1-->6)-[(4-O-trans-caffeoyl)-alpha-l-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-d-galactopyranoside (5), and eight known compounds were isolated. The structures of the new compounds were determined by spectroscopic and chemical means. Their inhibitory activities on protein synthesis were assessed. The new glycosides were found to be inhibitors of eukayrotic, but not prokaryotic, protein synthesis.
Itoh
Atsuko
A
Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan.
Tanahashi
Takao
T
Nagakura
Naotaka
N
Takenaka
Yukiko
Y
Chen
Cheng-Chang
CC
Pelletier
Jerry
J
D005057:Eukaryotic Cells / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D035264:Flowers / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D011387:Prokaryotic Cells / Q000187:drug effects; D011500:Protein Synthesis Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012270:Ribosomes / Q000187:drug effects / Q000502:physiology; D019666:Rubiaceae / Q000737:chemistry*; D013237:Stereoisomerism; D013624:Taiwan
D005419:Flavonoids; D006027:Glycosides; D011500:Protein Synthesis Inhibitors