Avarol and avarone, two new anti-inflammatory agents of marine origin

Ferrándiz, Marı́a Luisa; Sanz, María-Jesús; Bustos, Gloria; Payá, Miguel; Alcaraz, M. J.; Rosa, Salvatore De

doi:10.1016/0014-2999(94)90759-5

Cited by 84 publications

(43 citation statements)

References 29 publications

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“…The redox couple avarol (1) and avarone (2), isolated for the first time from the sponge Dysidea avara by Minale and coworkers [25], has shown strong activity against mouse lymphoma cells [26][27][28], antiviral activity [29][30][31], antiinflammatory activity [32], antipsoriatic properties [33], as well as moderate antifungal and antibacterial activity against Gram-positive strains [34,35]. Intrigued by the wide range of biological activities of these metabolites and the fact that avarol (1) is biosynthesized in large amounts by the sponge, implying an important ecological role [36], we decided to investigate their antifouling activity and prepare a number of lipophilic derivatives that would reduce their solubility in sea water and improve their incorporation in a potential antifouling preparation.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

et al. 2007

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Abstract:The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quinone, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3'-(p-chlorophenyl)avarone (3), 3',4'-ethylenedithioavarone (4), 4'-isopropylthioavarone (5), 4'-tertbutylthioavarone (6), 4'-propylthioavarone (7), 4'-octylthioavarone (8)] were obtained by nucleophilic addition of thiols or p-chloroaniline to avarone. All these compounds wereMolecules 2007, 12 1023 tested, at concentrations ranging from 0.5 to 50 µg/mL, for their effect on the settlement of the cyprid stage of Balanus amphitrite, for toxicity to both nauplii and cyprids and for their growth inhibitory activity on marine bacteria (Cobetia marina, Marinobacterium stanieri, Vibrio fischeri and Pseudoalteromonas haloplanktis) and marine fungi (Halosphaeriopsis mediosetigera, Asteromyces cruciatus, Lulworthia uniseptata and Monodictys pelagica).

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Section: Resultsmentioning

confidence: 99%

Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

et al. 2007

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“…Avarol was found to be a moderate inhibitor of human recombinant synovial phospholipase A 2 and cyclooxygenase and a good inhibitor of lipoxygenase [106,107]. Both avarol and, especially, avarone (2) inhibited the platelet aggregatory process [84].…”

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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“…In addition, bolinaquinone is chemically very close to other molecules, such as avarol and avarone (Ferrá ndiz et al, 1994), which have been reported as potent anti-inflammatory agents. Notably, bolinaquinone, sharing with avarol and avarone a very similar sesquiterpenoid substructure moiety, differs in the benzenoid part attached to the sesquiterpene moiety.…”

Section: Effect Of Bolinaquinone On Acute and Chronic Inflammation DImentioning

confidence: 99%

“…In a previous study (Ferrá ndiz et al, 1994), we reported that avarol, a sesquiterpenoid hydroquinone with weak inhibitory properties against human synovial PLA 2 , and its quinone derivative, avarone, potently inhibited paw edema induced by carrageenan, as well as ear edema induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Bolinaquinone, a sesquiterpenoid derivative sharing both hydroquinone and quinone moieties in its chemical structure ( Fig.…”

mentioning

confidence: 99%

Modulatory Effect of Bolinaquinone, a Marine Sesquiterpenoid, on Acute and Chronic Inflammatory Processes

Lucas¹,

Giannini²,

D’Auria³

et al. 2002

J Pharmacol Exp Ther

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The marine metabolite bolinaquinone is a novel inhibitor of secretory phospholipase A 2 (sPLA 2 ), with a potency on the human synovial enzyme (group II) higher than that of manoalide. This activity on the sPLA 2 was confirmed in vivo in the 8-h zymosan rat air pouch on the secretory enzyme accumulation in the pouch exudate. Additionally, bolinaquinone decreased potently the synthesis and release of leukotriene B 4 (LTB 4 ) in calcimycin (A23187)-stimulated human neutrophils as a consequence of the inhibition of 5-lipoxygenase activity, as well as PGE 2 and NO production on zymosan-stimulated mouse peritoneal macrophages. This compound exerted anti-inflammatory effects by topical and oral routes on the mouse ear edema induced by 12-O-tetradecanoylphorbolacetate, with ID 50 values of 76.7 g/ear and 5.6 mg/kg, respectively, with a significant decrease in PGE 2 , LTB 4 , and tumor necrosis factor-␣ (TNF-␣) levels being more effective than indomethacin. This effect was confirmed in the mouse paw carrageenan edema after oral administration. Moreover, bolinaquinone was able to reduce the inflammatory response of adjuvant arthritis by inhibiting PGE 2 , NO, and TNF-␣ production in paw homogenates without affecting PGE 2 levels in the stomach. Additionally, bolinaquinone inhibited inducible nitric oxide synthase expression and reduced the degree of bone resorption, soft tissue swelling, and osteophyte formation.

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Avarol and avarone, two new anti-inflammatory agents of marine origin

Cited by 84 publications

References 29 publications

Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

Evaluation of the Activity of the Sponge Metabolites Avarol and Avarone and their Synthetic Derivatives Against Fouling Micro- and Macroorganisms

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

Modulatory Effect of Bolinaquinone, a Marine Sesquiterpenoid, on Acute and Chronic Inflammatory Processes

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