Antioxidant benzylidene 2-aminoimidazolones from the Mediterranean sponge Phorbas topsenti

Dat, Nguyen Tien; Nguyen, Xuan Cuong; Longeon, Arlette; Keryhuel, Aline; Le, Minh Ha; Kim, Young Ho; Chau, Van Minh; Bourguet‐Kondracki, Marie‐Lise

doi:10.1016/j.tet.2012.08.074

Cited by 16 publications

(34 citation statements)

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“…Leucettamine B [ 8 ] shares a 2-aminoimidazolone scaffold with various marine natural products such as polyandrocarpamines [ 15 , 16 ], dispacamide [ 17 , 18 , 19 ], aplysinopsine [ 20 , 21 ], clathridine/clathridimine [ 8 , 22 ], hymenialdisine/spongiacidin B [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ] and phorbatopsin [ 31 , 32 ] ( Figure 1 ). A summary of all marine aminoimidazolones described so far, and their natural sources and structures, is presented in Supplementary Table S2 and Supplementary Figure S5 .…”

Section: Resultsmentioning

confidence: 99%

Marine-Derived 2-Aminoimidazolone Alkaloids. Leucettamine B-Related Polyandrocarpamines Inhibit Mammalian and Protozoan DYRK & CLK Kinases

et al. 2017

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A large diversity of 2-aminoimidazolone alkaloids is produced by various marine invertebrates, especially by the marine Calcareous sponges Leucetta and Clathrina. The phylogeny of these sponges and the wide scope of 2-aminoimidazolone alkaloids they produce are reviewed in this article. The origin (invertebrate cells, associated microorganisms, or filtered plankton), physiological functions, and natural molecular targets of these alkaloids are largely unknown. Following the identification of leucettamine B as an inhibitor of selected protein kinases, we synthesized a family of analogues, collectively named leucettines, as potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases) and potential pharmacological leads for the treatment of several diseases, including Alzheimer’s disease and Down syndrome. We assembled a small library of marine sponge- and ascidian-derived 2-aminoimidazolone alkaloids, along with several synthetic analogues, and tested them on a panel of mammalian and protozoan kinases. Polyandrocarpamines A and B were found to be potent and selective inhibitors of DYRKs and CLKs. They inhibited cyclin D1 phosphorylation on a DYRK1A phosphosite in cultured cells. 2-Aminoimidazolones thus represent a promising chemical scaffold for the design of potential therapeutic drug candidates acting as specific inhibitors of disease-relevant kinases, and possibly other disease-relevant targets.

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Section: Resultsmentioning

confidence: 99%

Marine-Derived 2-Aminoimidazolone Alkaloids. Leucettamine B-Related Polyandrocarpamines Inhibit Mammalian and Protozoan DYRK & CLK Kinases

et al. 2017

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“…13). 174 One biological application for these compounds is their antioxidant activity, which was tested using the Oxygen Radical Absorbance Capacity (ORAC) assay. All were shown to have some activity, with phorbatopsin A being most active, having an ORAC value of 0.88 (which is comparable to the positive control Trolox's ORAC value of 1).…”

Section: Spongiacidins a And Bmentioning

confidence: 99%

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

Keel

Tepe

2020

Org. Chem. Front.

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“…Secondary metabolites belonging to the alkaloid class have been also isolated from a sample collected along the coast of Marseille, France, and analyzed by Bouguet's group. With this regard, phorbatopsins are alkaloids with a benzylidene 2-aminoimidazolones structure [26]. Finally, the alkaloid-moiety was also present in the structure of a series of imidazolyl steroids, i.e.…”

Section: Introductionmentioning

confidence: 99%

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Caso¹,

Silva²,

Esposito³

et al. 2021

Preprint

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Porifera, commonly referred to as marine sponges, have stood out as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention along years. They are widespread in all continents, and several structurally unique compounds have been identified from species of this genus. Terpenes, mainly sesterterpenoids, represent the great majority of secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have shown a variety of biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial and anti-inflammatory activities, have been isolated and structurally characterized. This work brings an overview of Phorbas secondary metabolites reported since the first study published in 1993 until 2020, and their biological activities.

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Antioxidant benzylidene 2-aminoimidazolones from the Mediterranean sponge Phorbas topsenti

Cited by 16 publications

References 24 publications

Marine-Derived 2-Aminoimidazolone Alkaloids. Leucettamine B-Related Polyandrocarpamines Inhibit Mammalian and Protozoan DYRK & CLK Kinases

Marine-Derived 2-Aminoimidazolone Alkaloids. Leucettamine B-Related Polyandrocarpamines Inhibit Mammalian and Protozoan DYRK & CLK Kinases

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

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