Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and ligustroside

Journal of Natural Medicines

Volumn 65, Issue 1, 2011, Pages 237-240

  Kikuchi, Masao ^c   Kikuchi, Masafumi ^a   Mano, Nariyasu ^a   Uehara, Yoshimasa ^b   MacHida, Koichi ^c  

^a TOHOKU UNIVERSITY HOSPITAL   (Japan)

^b IWATE MEDICAL UNIVERSITY   (Japan)

^c TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Aglycone; Cytotoxic activity; EGFR tyrosine kinase inhibitory activity; Enzymatic hydrolysis; Oleoside type secoiridoid glucoside

Indexed keywords

7 3,4 DIHYDROXYPHENETHYL ELENOLATE; 7 4 HYDROXYPHENETHYL ELENOLATE; AGLYCONE; ANTINEOPLASTIC AGENT; BETA GLUCOSIDASE; CYTOTOXIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; LIGUSTROSIDE; OLEUROPEIN; SECOIRIDOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG IDENTIFICATION; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; PLANT LEAF;

BETA-GLUCOSIDASE; CELL LINE, TUMOR; CELL SURVIVAL; ENZYME INHIBITORS; HUMANS; IRIDOID GLUCOSIDES; PYRANS; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 78651398235     PISSN: 13403443     EISSN: 18610293     Source Type: Journal    
DOI: 10.1007/s11418-010-0476-8     Document Type: Article

References (13)

1. Kikuchi M, Yaoita Y, Mano N, Kikuchi M (2010) Structure and cytotoxic activity of aglycones obtained by enzymatic hydrolysis of secoiridoid glucosides, isoligustroside and isooleuropein. Chem Biodivers (in press)
2. H Babich F Visioli 2003 In vitro cytotoxicity to human cells in culture of some phenolics from olive oil Farmaco 58 403 407 1:CAS:528: DC%2BD3sXjt1Knsrk%3D 12729835 10.1016/S0014-827X(03)00048-X (Pubitemid 36506948)
3. R Fabiani A De Bartolomeo P Rosignoli M Servili R Selvaggini GF Montedoro C Di Saverio G Morozzi 2006 Virgin olive oil phenols inhibit proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiation J Nutr 136 614 619 1:CAS:528:DC%2BD28XitVOrtr4%3D 16484533
4. JA Menendez A Vazquez-Martin R Garcia-Villalba A Carrasco-Pancorbo C Oliveras-Ferraros A Fernandez-Gutierrez A Segura-Carretero 2008 tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial extra-virgin olive oil (EVOO) BMC Cancer 8 377 19094209 10.1186/1471-2407-8-377
5. M Kikuchi Y Yamauchi 1987 Studies on the constituents of Syringa Species. I. Isolation and structures of iridoids and secoiridoids from the leaves of Syringa reticulata (Blume) Hara Yakugaku Zasshi 107 23 27 1:CAS:528: DyaL2sXhslaqtrw%3D
6. S Christophoridou P Dais LH Tseng M Spraul 2005 Separation and identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with postcolumn solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR) J Agric Food Chem 53 4667 4679 1:CAS:528:DC%2BD2MXktVWqtbc%3D 15941298 10.1021/jf040466r (Pubitemid 40937580)
7. P Gariboldi G Jommi L Verotta 1986 Secoiridoids from Olea europaea Phytochemistry 25 865 869 1:CAS:528:DyaL28Xkt1Wltr8%3D 10.1016/0031-9422(86) 80018-8
8. G Montedoro M Servili M Baldioli R Selvaggini E Miniati A Macchioni 1993 Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives J Agric Food Chem 41 2228 2234 1:CAS:528:DyaK3sXmsVynurk%3D 10.1021/jf00035a076
9. T Yamori A Matsunaga S Sato K Yamazaki A Komi K Ishizu I Mita H Edatsugi Y Matsuba K Takezawa O Nakanishi H Kohno Y Nakajima H Komatsu T Andoh T Tsuruo 1999 Potent antitumor activity of MS-247, a novel DNA minor groove binder, evaluated by an in vitro and in vivo human cancer cell line panel Cancer Res 59 4042 4049 1:CAS:528:DyaK1MXlsVOltbg%3D 10463605
10. Yamori T, Uehara Y, Yoshida M, Inoue M, Seimiya H, Mizugaki T, Kawada M, Osada H, Matsuura M (2010) Gan To Kagaku Ryoho 37 Suppl. I. Cancer and Chemotherapy Publishers Co., Japan, pp 72-73
11. M Guiso C Marra 2005 Highlights in oleuropein aglycone structure Nat Prod Res 19 105 109 1:CAS:528:DC%2BD2MXhtlaqtr4%3D 15715252 10.1080/ 14786410410001696147 (Pubitemid 40185876)
12. N Normanno MR Maiello A De Luca 2003 Epidermal growth factor receptor tyrosine kinase inhibitors (EGFR-TKIs): simple drugs with a complex mechanism of action? J Cell Physiol 194 13 19 1:CAS:528:DC%2BD38XptlGqs7g%3D 12447985 10.1002/jcp.10194 (Pubitemid 35424223)
13. S Dan M Okamura M Seki K Yamazaki H Sugita M Okui Y Mukai H Nishimura R Asaka K Nomura Y Ishikawa T Yamori 2010 Correlating phosphatidylinositol 3-kinase inhibitor efficacy with signaling pathway status: in silico and biological evaluations Cancer Res 70 4982 4994 1:CAS:528:DC%2BC3cXntlKltLw%3D 20530683 10.1158/0008-5472.CAN-09-4172