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Molecules 2007, 12(7), 1376-1388; doi:10.3390/12071376
Article

Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones

1,* , 2, 2, 1, 1, 1 and 3
1 Australian Institute of Marine Science, Townsville, Queensland, 4810, Australia 2 Laboratoire de Chimie et Biochimie des Substances Naturelles, Muséum National d’Histoire Naturelle, 57 rue Cuvier (CP 54), Paris, 75005, France 3 Nufarm Australia Limited, Department of Chemistry, Macquarie University, North Ryde, NSW, 2109, Australia
* Author to whom correspondence should be addressed.
Received: 18 June 2007 / Revised: 6 July 2007 / Accepted: 9 July 2007 / Published: 11 July 2007
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Abstract

Eight naturally occurring marine-sponge derived sesquiterpenoid quinones wereevaluated as potential inhibitors of pyruvate phosphate dikinase (PPDK), a C4 plantregulatory enzyme. Of these, the hydroxyquinones ilimaquinone, ethylsmenoquinone andsmenoquinone inhibited PPDK activity with IC50’s (reported with 95% confidenceintervals) of 285.4 (256.4 – 317.7), 316.2 (279.2 – 358.1) and 556.0 (505.9 – 611.0) μM,respectively, as well as being phytotoxic to the C4 plant Digitaria ciliaris. The potentialanti-inflammatory activity of these compounds, using bee venom phospholipase A2(PLA2), was also evaluated. Ethylsmenoquinone, smenospongiarine, smenospongidine andilimaquinone inhibited PLA2 activity (% inhibition of 73.2 + 4.8 at 269 μM, 61.5 + 6.1 at242 μM, 41.0 + 0.6 at 224 μM and 36.4 + 8.2 at 279 μM, respectively). SAR analysesindicate that a hydroxyquinone functionality and a short, hydroxide/alkoxide side-chain atC-20 is preferred for inhibition of PPDK activity, and that a larger amine side-chain at C-20 is tolerated for PLA2 inhibitory activity.
Keywords: Pyruvate phosphate dikinase (PPDK);C4 plant;phospholipase A2 (PLA2);anti-inflammatory activity;sesquiterpene hydroxyquinones/hydroquinones/amino-quinones;ilimaquinone. Pyruvate phosphate dikinase (PPDK); C4 plant; phospholipase A2 (PLA2); anti-inflammatory activity; sesquiterpene hydroxyquinones/hydroquinones/amino-quinones; ilimaquinone.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Motti, C.A.; Bourguet-Kondracki, M.-L.; Longeon, A.; Doyle, J.R.; Llewellyn, L.E.; Tapiolas, D.M.; Yin, P. Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones. Molecules 2007, 12, 1376-1388.

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