Effects of marine 2-polyprenyl-1,4-hydroquinones on phospholipase A2 activity and some inflammatory responses

Gil, Blanca; Sanz, María-Jesús; Terencio, María Carmen; Giulio, A. De; Rosa, Salvatore De; Alcaraz, M. J.; Payá, Miguel

doi:10.1016/0014-2999(95)00419-l

Cited by 32 publications

(22 citation statements)

References 30 publications

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“…It behaves as a redox inhibitor, reducing the iron site. Good inhibitory potency and notable selectivity were exhibited by the nonreducing inhibitor dimethoxypuupehenol (50, Figure 16) Prenyl hydroquinones of the type 51 ( Figure 16) isolated from the sponge Ircinia spinosula showed an antiinflammatory activity which was at least in part a consequence of phospholipase A 2 inhibition [112]. v) Golgi-disturbing activity…”

Section: Iv) Antiinflammatory Activitymentioning

confidence: 99%

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Sladić

Gašić

2006

Molecules

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A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedorearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo-and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.

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Section: Iv) Antiinflammatory Activitymentioning

confidence: 99%

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Sladić

Gašić

2006

Molecules

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“…[8,9] Numerous marine natural products (MNPs) featuring a quinone and/or hydroxyquinone nucleus elicited sPLA 2 inactivation with good potency. [10,11] Among MNPs, bolinaquinone (BLQ, 1) is one of the most active and shows the ability to strongly inhibit human synovial PLA 2 (hsPLA 2 ), bee venom PLA 2 (bvPLA 2 ), and porcine pancreatic group I PLA 2 , with IC 50 values of 0.2, 0.1, and 0.4 mm, respectively. Remarkably, this product also exerted no effects on cPLA 2 .…”

Section: Introductionmentioning

confidence: 99%

The Molecular Mechanism of Bee Venom Phospholipase A₂ Inactivation by Bolinaquinone

et al. 2006

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The molecular basis of the inactivation of bee venom PLA2 by the marine natural product bolinaquinone (BLQ) was studied by several spectral techniques (CD, fluorescence, and NMR spectroscopy, mass spectrometry), biomimetic reactions, and molecular modeling. Our data suggest competitive inhibition based on a BLQ-PLA2 noncovalent molecular recognition. However, BLQ is also able to react selectively with Lys133 through conjugate addition followed by a beta elimination. The biological implications of both the covalent and noncovalent molecular events are discussed.

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“…In this field, the marine environment offers a rich source of molecules endowed with anti-PLA 2 properties, a number of which have shown a potent and selective in vitro and in vivo anti-sPLA 2 activity (Potts et al, 1992a,b;Terracciano et al, 2006;Gomez-Paloma et al, 2005). One of the most widespread groups of constituents found in sessile organisms, including sponges, with a typical selective profile against secretory PLA 2 's are terpenoidic quinones (Gil et al, 1995;Coop et al, 1991). Bolinaquinone (BLQ;De Guzman et al, 1998), one of the most active metabolites of this class, inactivates human synovial sPLA 2 -IIA, bee venom PLA 2 and porcine pancreatic group I PLA 2 , with IC 50 values in the mM range, demonstrating its higher activity with respect to other known PLA 2 natural inhibitors, such as manoalide (Soriente et al, 1999;Glaser and Jacobs, 1987;Glaser et al, 1989;Jacobson et al, 1990) and petrosaspongiolide M (Dal Piaz et al, 2002;Monti et al, 2004a,b;Monti et al, 2009).…”

mentioning

confidence: 98%

The molecular mechanism of human group IIA phospholipase A2 inactivation by bolinaquinone

Monti

Chini

Margarucci

et al. 2009

J of Molecular Recognition

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The molecular basis of the human group IIA secretory phospholipase A(2) inactivation by bolinaquinone (BLQ), a hydroxyquinone marine terpenoid, has been investigated for the comprehension of its relevant antiinflammatory properties, through the combination of spectroscopic techniques, biosensors analysis, mass spectrometry (MS) and molecular docking. Indeed, sPLA(2)s are well known to be implicated in the pathogenesis of inflammation such as rheumatoid arthritis, septic shock, psoriasis and asthma. Our results suggest a mechanism of competitive inhibition guided by a non-covalent molecular recognition event, disclosing the key role of the BLQ hydroxyl-quinone moiety in the chelation of the catalytic Ca(2+) ion inside the enzyme active site.The understanding of the sPLA(2)-IIA inactivation mechanism by BLQ could be useful for the development of a new chemical class of PLA(2) inhibitors, able to specifically target the enzyme active site.

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Effects of marine 2-polyprenyl-1,4-hydroquinones on phospholipase A2 activity and some inflammatory responses

Cited by 32 publications

References 30 publications

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

The Molecular Mechanism of Bee Venom Phospholipase A₂ Inactivation by Bolinaquinone

The molecular mechanism of human group IIA phospholipase A2 inactivation by bolinaquinone

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Effects of marine 2-polyprenyl-1,4-hydroquinones on phospholipase A2 activity and some inflammatory responses

Cited by 32 publications

References 30 publications

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

The Molecular Mechanism of Bee Venom Phospholipase A2 Inactivation by Bolinaquinone

The molecular mechanism of human group IIA phospholipase A2 inactivation by bolinaquinone

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The Molecular Mechanism of Bee Venom Phospholipase A₂ Inactivation by Bolinaquinone