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Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones

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dc.contributor Macquarie Univ
dc.contributor Museum National D'histoire Naturelle (mnhn)
dc.contributor Macquarie University
dc.contributor Sorbonne Universites (comue)
dc.contributor French National Museum Of Natural History
dc.contributor Australian Inst Marine Sci
dc.contributor Australian Institute Of Marine Science
dc.contributor Nufarm Australi Ltd
dc.contributor Museum Natl Hist Nat
dc.contributor Lab Chim & Biochim Substances Nat
dc.contributor Dept Chem
dc.contributor Australian Institute Of Marine Science (aims) en YIN, PING BOURGUET-KONDRACKI, MARIE-LISE LONGEON, ARLETTE LLEWELLYN, LYNDON E. TAPIOLAS, DIANNE M. MOTTI, CHERIE A. DOYLE, JASON R. 2017-03-21T00:47:29Z 2017-03-21T00:47:29Z 2013-02-28T06:41:23Z 2019-07-08T02:22:41Z 2013-02-28T06:41:23Z 2013-02-28T06:41:23Z 2017-03-21T00:47:29Z 2019-07-08T02:22:41Z 2007-07-01
dc.identifier 7561 en
dc.identifier.citation Motti CA, Bourguet-Kondracki M-L, Longeon A, Doyle JR, Llewellyn LE, Tapiolas DM and Yin P (2007) Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones. Molecules. 12: 1376-1388. en
dc.identifier.issn 1420-3049
dc.description.abstract Eight naturally occurring marine-sponge derived sesquiterpenoid quinones were evaluated as potential inhibitors of pyruvate phosphate dikinase (PPDK), a C-4 Plant regulatory enzyme. Of these, the hydroxyquinones ilimaquinone, ethylsmenoquinone and smenoquinone inhibited PPDK activity with IC50's (reported with 95% confidence intervals) of 285.4 (256.4 - 317.7), 316.2 (279.2 - 358.1) and 556.0 (505.9 - 611.0) gm, respectively, as well as being phytotoxic to the C4 plant Digitaria ciliaris. The potential anti-inflammatory activity of these compounds, using bee venom phospholipase A(2) (PLA(2)), was also evaluated. Ethylsmenoquinone, smenospongiarine, smenospongidine and ilimaquinone inhibited PLA2 activity (% inhibition of 73.2 +/- 4.8 at 269 mu M, 61.5 +/- 6.1 at 242 mu M, 41.0 +/- 0.6 at 224 mu M and 36.4 +/- 8.2 at 279 mu M, respectively). SAR analyses indicate that a hydroxyquinone functionality and a short, hydroxide/alkoxide side-chain at C-20 is preferred for inhibition of PPDK activity, and that a larger amine side-chain at C20 is tolerated for PLA(2) inhibitory activity.
dc.language English
dc.language en en
dc.relation.ispartof Molecules - pages: 12: 1376-1388 en
dc.relation.ispartof Null
dc.subject Inhibition
dc.subject Transport
dc.subject C-4 Plant
dc.subject Vesiculation
dc.subject Agents
dc.subject Chemistry
dc.subject Chemistry, Organic
dc.subject Sesquiterpene Hydroxyquinones/hydroquinones/amino-quinones
dc.subject Phospholipase A(2) (pla(2))
dc.subject Ilimaquinone
dc.subject Natural-products
dc.subject Pyruvate Phosphate Dikinase (ppdk)
dc.subject Chemistry, Multidisciplinary
dc.subject Avarol
dc.subject Antiinflammatory Activity
dc.subject Metabolite
dc.subject Biochemistry & Molecular Biology
dc.subject Golgi Membranes
dc.subject Dikinase
dc.title Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones
dc.type journal article en
dc.identifier.wos WOS:000250488100012

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