Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs
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 ev...
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2013
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/99846 http://hdl.handle.net/10220/13751 |
| _version_ | 1826128021727215616 |
|---|---|
| author | Panda, Parthasarathi Appalashetti, Manjuvani Natarajan, Meenubharathi Mary, Chan-Park Venkatraman, Subbu S. Judeh, Zaher M. A. |
| author2 | School of Chemical and Biomedical Engineering |
| author_facet | School of Chemical and Biomedical Engineering Panda, Parthasarathi Appalashetti, Manjuvani Natarajan, Meenubharathi Mary, Chan-Park Venkatraman, Subbu S. Judeh, Zaher M. A. |
| author_sort | Panda, Parthasarathi |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T07:18:04Z |
| format | Journal Article |
| id | ntu-10356/99846 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:18:04Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/998462020-06-01T10:26:35Z Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs Panda, Parthasarathi Appalashetti, Manjuvani Natarajan, Meenubharathi Mary, Chan-Park Venkatraman, Subbu S. Judeh, Zaher M. A. School of Chemical and Biomedical Engineering School of Materials Science & Engineering DRNTU::Engineering::Chemical engineering DRNTU::Engineering::Materials 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. 2013-09-30T08:53:39Z 2019-12-06T20:12:17Z 2013-09-30T08:53:39Z 2019-12-06T20:12:17Z 2012 2012 Journal Article Panda, P., Appalashetti, M., Natarajan, M., Mary, C. P., Venkatraman, S. S., & Judeh, Z. M. A. (2012). Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs. European journal of medicinal chemistry, 58, 418-430. https://hdl.handle.net/10356/99846 http://hdl.handle.net/10220/13751 10.1016/j.ejmech.2012.10.034 en European journal of medicinal chemistry |
| spellingShingle | DRNTU::Engineering::Chemical engineering DRNTU::Engineering::Materials Panda, Parthasarathi Appalashetti, Manjuvani Natarajan, Meenubharathi Mary, Chan-Park Venkatraman, Subbu S. Judeh, Zaher M. A. Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title | Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title_full | Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title_fullStr | Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title_full_unstemmed | Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title_short | Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs |
| title_sort | synthesis and antiproliferative activity of helonioside a 3 4 6 tri o feruloylsucrose lapathoside c and their analogs |
| topic | DRNTU::Engineering::Chemical engineering DRNTU::Engineering::Materials |
| url | https://hdl.handle.net/10356/99846 http://hdl.handle.net/10220/13751 |
| work_keys_str_mv | AT pandaparthasarathi synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs AT appalashettimanjuvani synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs AT natarajanmeenubharathi synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs AT marychanpark synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs AT venkatramansubbus synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs AT judehzaherma synthesisandantiproliferativeactivityofheloniosidea346trioferuloylsucroselapathosidecandtheiranalogs |