title: Synthesis and antiproliferative activity of helonioside A, 3',4',6'-tri-O-feruloylsucrose, lapathoside C and their analogs.
abstract: The first total synthesis of natural phenylpropanoid sucrose esters (PSEs) helonioside A 1, 3',4',6'-tri-O-feruloylsucrose 2 and lapathoside C 3 along with 17 unnatural PSE analogs has been successfully accomplished in a short and simple synthetic route. A selected set of 17 synthesized PSEs were evaluated for the antiproliferative activity against human cervical epithelioid carcinoma (HeLa) cell lines using MTS assay method. Eleven (11) compounds showed significant antiproliferative activity with their IC(50)values ranging from 0.16 to 6.01 μM. The structure-activity-relationship studies revealed that the antiproliferative activity is influenced by the lipophilicity and number of feruloyl substituents on these compounds. The preliminary screening indicated that these compounds are potentially very valuable source for new lead chemotherapeutics.
authors.affiliation: School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Singapore.
authors.forename: Parthasarathi
authors.initials: P
authors.lastname: Panda
authors.forename: Manjuvani
authors.initials: M
authors.lastname: Appalashetti
authors.forename: Meenubharathi
authors.initials: M
authors.lastname: Natarajan
authors.forename: Chan-Park
authors.initials: CP
authors.lastname: Mary
authors.forename: Subbu S
authors.initials: SS
authors.lastname: Venkatraman
authors.forename: Zaher M A
authors.initials: ZM
authors.lastname: Judeh
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002934:Cinnamates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003373:Coumaric Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C581085:3',4',6'-tri-O-feruloylsucrose; C581084:3',6'-di-O-feruloylsucrose; D000970:Antineoplastic Agents; D002934:Cinnamates; D003373:Coumaric Acids; C440670:lapathoside C; D013395:Sucrose