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Structure and Cytotoxic Activity of Enzymatic Hydrolysis Products of Secoiridoid Glucosides, Isoligustroside and Isooleuropein
Author(s) -
Kikuchi Masafumi,
Yaoita Yasunori,
Mano Nariyasu,
Kikuchi Masao
Publication year - 2011
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.201000092
Subject(s) - chemistry , stereochemistry , cytotoxic t cell , hydrolysis , enzyme , pyran , enzymatic hydrolysis , carboxylate , cytotoxicity , organic chemistry , biochemistry , in vitro
Hydrolysis of isoligustroside ( 1 ) and isooleuropein ( 2 ), secoiridoid glucosides, in the presence of β ‐glucosidase provided 2‐(4‐hydroxyphenyl)methyl (2 R ,3 S ,4 S )‐3‐formyl‐3,4‐dihydro‐4‐(2‐methoxy‐2‐oxoethyl)‐2‐methyl‐2 H ‐pyran‐5‐carboxylate ( 3 ) and 2‐(3,4‐dihydroxyphenyl)methyl (2 R ,3 S ,4 S )‐3‐formyl‐3,4‐dihydro‐4‐(2‐methoxy‐2‐oxoethyl)‐2‐methyl‐2 H ‐pyran‐5‐carboxylate ( 4 ), respectively. The structures of 3 and 4 were elucidated on the basis of extensive spectral analyses, including 2D‐NMR experiments. Compounds 3 and 4 were found to be new rearrangement products of the aglycones of 1 and 2 . The cytotoxic activities of 3 and 4 were evaluated using a disease‐oriented panel of 39 human cancer cell lines and showed moderate cytotoxic activity for 4 , while 3 exhibited weaker activity compared to that of 4 .