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Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones
Australian Institute of Marine Science, Townsville, Queensland, 4810, Australia
Laboratoire de Chimie et Biochimie des Substances Naturelles, Muséum National d’Histoire Naturelle, 57 rue Cuvier (CP 54), Paris, 75005, France
Nufarm Australia Limited, Department of Chemistry, Macquarie University, North Ryde, NSW, 2109, Australia
* Author to whom correspondence should be addressed.
Received: 18 June 2007; in revised form: 6 July 2007 / Accepted: 9 July 2007 / Published: 11 July 2007
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.
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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.
Motti CA, Bourguet-Kondracki M-L, Longeon A, Doyle JR, Llewellyn LE, Tapiolas DM, Yin P. Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones. Molecules. 2007; 12(7):1376-1388.
Motti, Cherie A.; Bourguet-Kondracki, Marie-Lise; Longeon, Arlette; Doyle, Jason R.; Llewellyn, Lyndon E.; Tapiolas, Dianne M.; Yin, Ping. 2007. "Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones." Molecules 12, no. 7: 1376-1388.