Muqubilin, a new c24-isoprenoid from a marine sponge

Kashman, Yoel; Rotem, Michal

doi:10.1016/s0040-4039(01)93630-5

Cited by 58 publications

(57 citation statements)

References 3 publications

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“…A series of peroxyterpenes was isolated from the sponges Diacarnus bismarckensis , the most active of which, (+)-muqubilone B ( 112 ) and sigmosceptrellin B ( 113 ) showed high activity against Trypanosoma brucei [ 94 ]. (+)-Muqubilone B ( 112 ) and muqubilin ( 114 ) (isolated from the sponges Prianos [ 95 ]) were in vitro effective against herpes virus (HSV-1), muqubilin ( 114 ) and (−)-sigmosceptrellin B ( 113 ) exhibited in vitro activity against Toxoplasma gondii ( Scheme 19 ) [ 96 ]. Muqubilin ( 114 ) possesses herbicidal activity against tobacco Nicotiana tabacum [ 97 ], as well as epimuqubilin ( 115 ) showed NO inhibitory activity [ 98 ].…”

Section: 12-dioxanesmentioning

confidence: 99%

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

et al. 2017

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The biological activity of organic peroxides is usually associated with the antimalarial properties of artemisinin and its derivatives. However, the analysis of published data indicates that organic peroxides exhibit a variety of biological activity, which is still being given insufficient attention. In the present review, we deal with natural, semi-synthetic and synthetic peroxides exhibiting anthelmintic, antiprotozoal, fungicidal, antiviral and other activities that have not been described in detail earlier. The review is mainly concerned with the development of methods for the synthesis of biologically active natural peroxides, as well as its isolation from natural sources and the modification of natural peroxides. In addition, much attention is paid to the substantially cheaper biologically active synthetic peroxides. The present review summarizes 217 publications mainly from 2000 onwards.

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Section: 12-dioxanesmentioning

confidence: 99%

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

et al. 2017

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“…With this aim, we used a ligand-based approach [ 19 ] to screen and identify possible candidates in our in house-developed database StOrMoDB (Structurally Oriented Molecular DataBase) of marine natural compounds and found (−)-Muqubilin A (Muq) as a potential hit. Muq is a norterpene cyclic peroxide described from distinct Red Sea sponges [ 20 , 21 ] and recently isolated in our institute from the sponge Diacarnus erythraeanus [ 22 ]. Norterpene cyclic peroxides are active metabolites endowed with cytoxic activity against a variety of cancer cell lines [ 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

In Silico Identification and Experimental Validation of (−)-Muqubilin A, a Marine Norterpene Peroxide, as PPARα/γ-RXRα Agonist and RARα Positive Allosteric Modulator

et al. 2019

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The nuclear receptors (NRs) RARα, RXRα, PPARα, and PPARγ represent promising pharmacological targets for the treatment of neurodegenerative diseases. In the search for molecules able to simultaneously target all the above-mentioned NRs, we screened an in-house developed molecular database using a ligand-based approach, identifying (−)-Muqubilin (Muq), a cyclic peroxide norterpene from a marine sponge, as a potential hit. The ability of this compound to stably and effectively bind these NRs was assessed by molecular docking and molecular dynamics simulations. Muq recapitulated all the main interactions of a canonical full agonist for RXRα and both PPARα and PPARγ, whereas the binding mode toward RARα showed peculiar features potentially impairing its activity as full agonist. Luciferase assays confirmed that Muq acts as a full agonist for RXRα, PPARα, and PPARγ with an activity in the low- to sub-micromolar range. On the other hand, in the case of RAR, a very weak agonist activity was observed in the micromolar range. Quite surprisingly, we found that Muq is a positive allosteric modulator for RARα, as both luciferase assays and in vivo analysis using a zebrafish transgenic retinoic acid (RA) reporter line showed that co-administration of Muq with RA produced a potent synergistic enhancement of RARα activation and RA signaling.

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“…Isolated compounds were found to be inhibitors of cytochrome P450-1A activity as well as inducers of glutathione Stransferases (GST), quinone reductase (QR), and epoxide hydrolase (mEH) establishing chemopreventive and tumor anti-initiating activity for these characterized metabolites. 36 Hurghaperoxide A (98), norsesterterpene cyclic peroxide, was isolated from an undescribed Red Sea sponge. 37 In 1999, (-)-Wistarin (99), an enantiomeric sesterterpene, was isolated from the Red Sea sponge of Ircinia sp.…”

Section: Diterpenesmentioning

confidence: 99%

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2017

IJPSR

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Muqubilin, a new c24-isoprenoid from a marine sponge

Cited by 58 publications

References 3 publications

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

In Silico Identification and Experimental Validation of (−)-Muqubilin A, a Marine Norterpene Peroxide, as PPARα/γ-RXRα Agonist and RARα Positive Allosteric Modulator

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