title: Structure and cytotoxic activity of enzymatic hydrolysis products of secoiridoid glucosides, isoligustroside and isooleuropein.
abstract: Hydrolysis of isoligustroside (1) and isooleuropein (2), secoiridoid glucosides, in the presence of β-glucosidase provided 2-(4-hydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (3) and 2-(3,4-dihydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-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.
authors.affiliation: Department of Pharmaceutical Sciences, Tohoku University Hospital, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi, 980-8547, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Kikuchi
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Yaoita
authors.forename: Nariyasu
authors.initials: N
authors.lastname: Mano
authors.forename: Masao
authors.initials: M
authors.lastname: Kikuchi
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006868:Hydrolysis; D057888:Iridoid Glucosides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy*; D018515:Plant Leaves / Q000737:chemistry; D031662:Syringa / Q000737:chemistry*; D001617:beta-Glucosidase / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D057888:Iridoid Glucosides; D001617:beta-Glucosidase