Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity

Hans Wohlmuth; Myrna A. Deseo; Don J. Brushett; Dion R. Thompson; Graham MacFarlane; Lesley M. Stevenson; David N. Leach

doi:10.1021/np900688r

Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity

Hans Wohlmuth, Myrna A. Deseo, Don J. Brushett, Dion R. Thompson, Graham MacFarlane, Lesley M. Stevenson, David N. Leach

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

Abstract

Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E2 production in 3T3 murine fibroblasts (IC50 ≈ 34 μM) and also displayed moderate cytotoxicity against this cell line (IC50 = 52.8 μM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC50 = 117.0 μM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC50 = 44.8 μM), PC3 prostate adenocarcinoma (IC50 = 23.6 μM), HepG2 hepatocyte carcinoma (IC50 = 40.6 μM), and MCF7 mammary adenocarcinoma (IC50 = 56.9 μM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC50 values and dose-response curves.

Original language	English
Pages (from-to)	743-746
Number of pages	4
Journal	Journal of Natural Products
Volume	73
Issue number	4
DOIs	https://doi.org/10.1021/np900688r
Publication status	Published - 2010

Keywords

Zingiberaceae
cell, mediated cytotoxicity
inhibitors
prostaglandins E

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10.1021/np900688r

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title = "Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity",

abstract = "Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E2 production in 3T3 murine fibroblasts (IC50 ≈ 34 μM) and also displayed moderate cytotoxicity against this cell line (IC50 = 52.8 μM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC50 = 117.0 μM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC50 = 44.8 μM), PC3 prostate adenocarcinoma (IC50 = 23.6 μM), HepG2 hepatocyte carcinoma (IC50 = 40.6 μM), and MCF7 mammary adenocarcinoma (IC50 = 56.9 μM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC50 values and dose-response curves.",

keywords = "Zingiberaceae, cell, mediated cytotoxicity, inhibitors, prostaglandins E",

author = "Hans Wohlmuth and Deseo, {Myrna A.} and Brushett, {Don J.} and Thompson, {Dion R.} and Graham MacFarlane and Stevenson, {Lesley M.} and Leach, {David N.}",

year = "2010",

doi = "10.1021/np900688r",

language = "English",

volume = "73",

pages = "743--746",

journal = "Journal of Natural Products",

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T1 - Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity

AU - Wohlmuth, Hans

AU - Deseo, Myrna A.

AU - Brushett, Don J.

AU - Thompson, Dion R.

AU - MacFarlane, Graham

AU - Stevenson, Lesley M.

AU - Leach, David N.

PY - 2010

Y1 - 2010

N2 - Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E2 production in 3T3 murine fibroblasts (IC50 ≈ 34 μM) and also displayed moderate cytotoxicity against this cell line (IC50 = 52.8 μM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC50 = 117.0 μM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC50 = 44.8 μM), PC3 prostate adenocarcinoma (IC50 = 23.6 μM), HepG2 hepatocyte carcinoma (IC50 = 40.6 μM), and MCF7 mammary adenocarcinoma (IC50 = 56.9 μM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC50 values and dose-response curves.

AB - Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E2 production in 3T3 murine fibroblasts (IC50 ≈ 34 μM) and also displayed moderate cytotoxicity against this cell line (IC50 = 52.8 μM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC50 = 117.0 μM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC50 = 44.8 μM), PC3 prostate adenocarcinoma (IC50 = 23.6 μM), HepG2 hepatocyte carcinoma (IC50 = 40.6 μM), and MCF7 mammary adenocarcinoma (IC50 = 56.9 μM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC50 values and dose-response curves.

KW - Zingiberaceae

KW - cell, mediated cytotoxicity

KW - inhibitors

KW - prostaglandins E

UR - http://handle.uws.edu.au:8081/1959.7/uws:31141

U2 - 10.1021/np900688r

DO - 10.1021/np900688r

M3 - Article

SN - 0163-3864

VL - 73

SP - 743

EP - 746

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity

Abstract

Keywords

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