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Synthesis and Cytotoxicity of a Novel Iridoid Glucoside Derived from Aucubin
Author(s) -
Mouriès Christine,
Rakotondramasy Vokatsoa C.,
Libot Francine,
Koch Michel,
Tillequin François,
Deguin Brigitte
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590046
Subject(s) - chemistry , aucubin , iridoid , stereochemistry , pharmacophore , glucoside , glycoside , cytotoxicity , salidroside , in vitro , biochemistry , medicine , alternative medicine , pathology , chromatography
The novel iridoid glycoside 2 was prepared in six steps (15% overall yield) from natural aucubin ( 1 ) and fully characterized. Compound 2 , which comprises the same conjugated cyclopentenone pharmacophore as known antitumor oxylipins and prostaglandins, displayed significant antiproliferative in vitro activity towards leukemia L1210 cells. The Michael addition of nucleophilic thiols to compound 2 occurred on a different position compared to classical Δ 7 ‐prostaglandin A 1 methyl ester. The resulting adducts 7a and 7b were fully characterized, and their MS fragmentation patterns were elucidated.