TY - JOUR
T1 - Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and ligustroside
AU - Kikuchi, Masao
AU - Kikuchi, Masafumi
AU - Mano, Nariyasu
AU - Uehara, Yoshimasa
AU - MacHida, Koichi
N1 - Funding Information:
Acknowledgments We are grateful to the Screening Committee of Anticancer Drugs supported by Grant-in-Aid for Scientific Research on Priority Area ‘‘Cancer’’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan, for the evaluation of biological activity. We are also grateful to Mr. Shin-ichi Satoh and Mr. Tomoyuki Matsuki of Tohoku Pharmaceutical University for NMR and MS measurements.
PY - 2011/1
Y1 - 2011/1
N2 - 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.
AB - 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.
KW - Aglycone
KW - Cytotoxic activity
KW - EGFR tyrosine kinase inhibitory activity
KW - Enzymatic hydrolysis
KW - Oleoside-type secoiridoid glucoside
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U2 - 10.1007/s11418-010-0476-8
DO - 10.1007/s11418-010-0476-8
M3 - Article
C2 - 21042869
AN - SCOPUS:78651398235
SN - 1340-3443
VL - 65
SP - 237
EP - 240
JO - Journal of Natural Medicines
JF - Journal of Natural Medicines
IS - 1
ER -
