Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)

Ritesh Raju; Dhanushka Gunawardena; Most Afia Ahktar; Mitchell Low; Paul Reddell; Gerald Munch

Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)

Ritesh Raju, Dhanushka Gunawardena, Most Afia Ahktar, Mitchell Low, Paul Reddell, Gerald Munch

Western Sydney University

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

27 Citations (Scopus)

Abstract

Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei led to the isolation of the known plant sterols emmolic acid (1), alphitolic acid (2), trans- and cis-coumaroyl esters of alphitolic acid (3 and 4) and betulinic acid (5). A detailed spectroscopic analysis led to the structure elucidation of the alphitolic acid derivatives (1-5), and the semi-synthetic emmolic acid acetate (6). When tested in LPS (Lipopolysaccharides) + IFN-Î³ (Interferon gamma) activated RAW 264.7 macrophages, all compounds except (1) exhibited potent anti-inflammatory activity (IC50 values as low as 1.7 Î¼M) in terms of downregulation of NO and TNF-Î± production, but also demonstrated some considerable cytotoxicity.

Original language	English
Article number	1521
Number of pages	7
Journal	Molecules
Volume	21
Issue number	11
Publication status	Published - 1 Nov 2016

Bibliographical note

Publisher Copyright:
© 2016 by the authors; licensee MDPI.

Open Access - Access Right Statement

© 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).

Keywords

Australia
anti-inflammatory agents
inflammation
materia medica, vegetable
nitric oxide
rain forests

Cite this

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title = "Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)",

abstract = "Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei led to the isolation of the known plant sterols emmolic acid (1), alphitolic acid (2), trans- and cis-coumaroyl esters of alphitolic acid (3 and 4) and betulinic acid (5). A detailed spectroscopic analysis led to the structure elucidation of the alphitolic acid derivatives (1-5), and the semi-synthetic emmolic acid acetate (6). When tested in LPS (Lipopolysaccharides) + IFN-{\^I}³ (Interferon gamma) activated RAW 264.7 macrophages, all compounds except (1) exhibited potent anti-inflammatory activity (IC50 values as low as 1.7 {\^I}¼M) in terms of downregulation of NO and TNF-{\^I}± production, but also demonstrated some considerable cytotoxicity.",

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author = "Ritesh Raju and Dhanushka Gunawardena and Ahktar, {Most Afia} and Mitchell Low and Paul Reddell and Gerald Munch",

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T1 - Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)

AU - Raju, Ritesh

AU - Gunawardena, Dhanushka

AU - Ahktar, Most Afia

AU - Low, Mitchell

AU - Reddell, Paul

AU - Munch, Gerald

PY - 2016/11/1

Y1 - 2016/11/1

N2 - Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei led to the isolation of the known plant sterols emmolic acid (1), alphitolic acid (2), trans- and cis-coumaroyl esters of alphitolic acid (3 and 4) and betulinic acid (5). A detailed spectroscopic analysis led to the structure elucidation of the alphitolic acid derivatives (1-5), and the semi-synthetic emmolic acid acetate (6). When tested in LPS (Lipopolysaccharides) + IFN-Î³ (Interferon gamma) activated RAW 264.7 macrophages, all compounds except (1) exhibited potent anti-inflammatory activity (IC50 values as low as 1.7 Î¼M) in terms of downregulation of NO and TNF-Î± production, but also demonstrated some considerable cytotoxicity.

AB - Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei led to the isolation of the known plant sterols emmolic acid (1), alphitolic acid (2), trans- and cis-coumaroyl esters of alphitolic acid (3 and 4) and betulinic acid (5). A detailed spectroscopic analysis led to the structure elucidation of the alphitolic acid derivatives (1-5), and the semi-synthetic emmolic acid acetate (6). When tested in LPS (Lipopolysaccharides) + IFN-Î³ (Interferon gamma) activated RAW 264.7 macrophages, all compounds except (1) exhibited potent anti-inflammatory activity (IC50 values as low as 1.7 Î¼M) in terms of downregulation of NO and TNF-Î± production, but also demonstrated some considerable cytotoxicity.

KW - Australia

KW - anti-inflammatory agents

KW - inflammation

KW - materia medica, vegetable

KW - nitric oxide

KW - rain forests

UR - http://handle.uws.edu.au:8081/1959.7/uws:37726

M3 - Article

SN - 1420-3049

VL - 21

JO - Molecules

JF - Molecules

IS - 11

M1 - 1521

ER -

Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)

Abstract

Bibliographical note

Open Access - Access Right Statement

Keywords

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