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

Parthasarathi Panda; Manjuvani Appalashetti; Meenubharathi Natarajan; Chan Park Mary; Subbu S. Venkatraman; Zaher M.A. Judeh

doi:10.1016/j.ejmech.2012.10.034

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

Parthasarathi Panda, Manjuvani Appalashetti, Meenubharathi Natarajan, Chan Park Mary, Subbu S. Venkatraman, Zaher M.A. Judeh^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

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 ₅₀values 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.

Original language	English
Pages (from-to)	418-430
Number of pages	13
Journal	European Journal of Medicinal Chemistry
Volume	58
DOIs	https://doi.org/10.1016/j.ejmech.2012.10.034
Publication status	Published - Dec 2012
Externally published	Yes

ASJC Scopus Subject Areas

Pharmacology
Drug Discovery
Organic Chemistry

Keywords

Antiproliferative activity
HeLa cells
Helonioside A, 3′,4′,6′-tri-O-feruloylsucrose
Isopropylidene acetal
Lapathoside C
Phenylpropanoid sucrose esters
Regioselective acylation
Sucrose esters

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10.1016/j.ejmech.2012.10.034

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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 50values 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.",

keywords = "Antiproliferative activity, HeLa cells, Helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, Isopropylidene acetal, Lapathoside C, Phenylpropanoid sucrose esters, Regioselective acylation, Sucrose esters",

author = "Parthasarathi Panda and Manjuvani Appalashetti and Meenubharathi Natarajan and Mary, {Chan Park} and Venkatraman, {Subbu S.} and Judeh, {Zaher M.A.}",

year = "2012",

month = dec,

doi = "10.1016/j.ejmech.2012.10.034",

language = "English",

volume = "58",

pages = "418--430",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson SAS",

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T1 - Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs

AU - Panda, Parthasarathi

AU - Appalashetti, Manjuvani

AU - Natarajan, Meenubharathi

AU - Mary, Chan Park

AU - Venkatraman, Subbu S.

AU - Judeh, Zaher M.A.

PY - 2012/12

Y1 - 2012/12

N2 - 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 50values 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.

AB - 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 50values 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.

KW - Antiproliferative activity

KW - HeLa cells

KW - Helonioside A, 3′,4′,6′-tri-O-feruloylsucrose

KW - Isopropylidene acetal

KW - Lapathoside C

KW - Phenylpropanoid sucrose esters

KW - Regioselective acylation

KW - Sucrose esters

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M3 - Article

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AN - SCOPUS:84868709604

SN - 0223-5234

VL - 58

SP - 418

EP - 430

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

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

Abstract

ASJC Scopus Subject Areas

Keywords

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