Antibacterial anthranilic acid derivatives from Geijera parviflora

Qingyao Shou; Linda K Banbury; Alan T Maccarone; Dane E Renshaw; Htwe Mon; Stefani Griesser; Hans J Griesser; Stephen J Blanksby; Joshua E Smith; Hans Wohlmuth

doi:10.1016/j.fitote.2013.12.008

Antibacterial anthranilic acid derivatives from Geijera parviflora

Fitoterapia. 2014 Mar:93:62-6. doi: 10.1016/j.fitote.2013.12.008. Epub 2013 Dec 25.

Authors

Affiliations

¹ Southern Cross Plant Science, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia. Electronic address: qingyao.shou@scu.edu.au.
² Southern Cross Plant Science, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia. Electronic address: linda.banbury@scu.edu.au.
³ School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia. Electronic address: alan_maccarone@uow.edu.au.
⁴ Southern Cross Plant Science, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia. Electronic address: dane.renshaw@scu.edu.au.
⁵ Ian Wark Research Institute, University of South Australia, Mawson Lakes, SA 5095, Australia. Electronic address: htwe.mon@mymail.unisa.edu.au.
⁶ Ian Wark Research Institute, University of South Australia, Mawson Lakes, SA 5095, Australia. Electronic address: stefani.griesser@unisa.edu.au.
⁷ Ian Wark Research Institute, University of South Australia, Mawson Lakes, SA 5095, Australia. Electronic address: hans.griesser@unisa.edu.au.
⁸ School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia. Electronic address: blanksby@uow.edu.au.
⁹ Southern Cross Plant Science, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia. Electronic address: joshua.smith@scu.edu.au.
¹⁰ Division of Research, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia. Electronic address: hans.wohlmuth@scu.edu.au.

PMID: 24370663
DOI: 10.1016/j.fitote.2013.12.008

Abstract

Five anthranilic acid derivatives, a mixture I of three new compounds 11'-hexadecenoylanthranilic acid (1), 9'-hexadecenoylanthranilic acid (2), and 7'-hexadecenoylanthranilic acid (3), as well as a new compound 9,12,15-octadecatrienoylanthranilic acid (4) together with a new natural product, hexadecanoylanthranilic acid (5), were isolated from Geijera parviflora Lindl. (Rutaceae). Their structures were elucidated by extensive spectroscopic measurements, and the positions of the double bonds in compounds 1-3 of the mixture I were determined by tandem mass spectrometry employing ozone-induced dissociation. The mixture I and compound 5 showed good antibacterial activity against several Gram-positive strains.

Keywords: Anthranilic acid derivative; Antibacterial activity; Geijera parviflora; Rutaceae.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification*
Microbial Sensitivity Tests
Rutaceae / chemistry*
ortho-Aminobenzoates / chemistry*

Substances

Anti-Bacterial Agents
ortho-Aminobenzoates
anthranilic acid