Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and ligustroside.
Hydrolysis of oleoside-type secoiridoid glucosides, oleuropein (1) and ligustroside (2), in the presence of β-glucosidase provided their aglycones, named (5S,8R,9S)-7-3,4-dihydroxyphenethyl elenolate (3) and (5S,8R,9S)-7-4-hydroxyphenethyl elenolate (4), respectively. The structures of 3 and 4 were identified by spectroscopic means and optical rotation measurements. Evaluation of the cytotoxic and epidermal growth factor receptor (EGFR) tyrosine kinase inhibitory activities of compounds 1-4 showed that compounds 3 and 4 exhibited moderate cytotoxicity against a disease-oriented panel of 39 human cancer cell lines in vitro, whereas compound 3 inhibited the enzyme.
Department of Pharmaceutical Sciences, Tohoku University Hospital, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574, Japan.
Masafumi
M
Kikuchi
Nariyasu
N
Mano
Yoshimasa
Y
Uehara
Koichi
K
Machida
Masao
M
Kikuchi
D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D066246:ErbB Receptors / Q000037:antagonists & inhibitors*; D006801:Humans; D057888:Iridoid Glucosides / Q000737:chemistry / Q000378:metabolism*; D039823:Iridoids; D011714:Pyrans / Q000737:chemistry / Q000378:metabolism*; D001617:beta-Glucosidase / Q000378:metabolism*
D004791:Enzyme Inhibitors; D057888:Iridoid Glucosides; D039823:Iridoids; D011714:Pyrans; C002769:oleuropein; D066246:ErbB Receptors; D001617:beta-Glucosidase