Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid QuinonesReport as inadecuate




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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.



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 A2PLA2, 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. View Full-Text

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.





Author: Cherie A Motti 1,* , Marie-Lise Bourguet-Kondracki 2, Arlette Longeon 2, Jason R Doyle 1, Lyndon E Llewellyn 1, Dianne M Tapiolas 1 and Ping Yin 3

Source: http://mdpi.com/



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