Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs

• Main Authors: Panda, Parthasarathi, Appalashetti, Manjuvani, Natarajan, Meenubharathi, Mary, Chan-Park, Venkatraman, Subbu S., Judeh, Zaher M. A.
• Other Authors: School of Chemical and Biomedical Engineering
• Format: Article
• Language: English
• Published: 2013
• Subjects: DRNTU::Engineering::Chemical engineering; DRNTU::Engineering::Materials
• Online Access: https://hdl.handle.net/10356/99846; http://hdl.handle.net/10220/13751
• Institution: Nanyang Technological University

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 IC50values 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.