New Bromopyrrole Alkaloids from the Indopacific Sponge <i>Agelas nakamurai</i>

Eder, C.; Proksch, Peter; Wray,; Rw, van Soest; Ferdinandus, E; La, Pattisina; Sudarsono, Sudarsono

doi:10.1021/np990071f

Cited by 56 publications

(49 citation statements)

References 10 publications

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“…All compounds inhibited the growth of several Grampositive and Gram-negative bacteria in the agar plate diffusion assay [224]. Six dimeric bromopyrrole alkaloids were isolated from a Florida Keys specimen of A. conifera.…”

Section: Cyclobutane-containing Alkaloids From Marine Sourcesmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

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Section: Cyclobutane-containing Alkaloids From Marine Sourcesmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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“…26 When 1a and 3a were isolated from the same sponges, 1a is always by far the major constituent. 1b,2b,14 …”

Section: Resultsmentioning

confidence: 99%

“…Guided by this biosynthetic hypothesis, we have developed an asymmetric approach to accomplish the syntheses of 1a and 3 , and revised their absolute stereochemistries recently. 8e We report herein the syntheses of all members of sceptrins ( 1 ) and the pseudo-symmetric [2+2] dimer nakamuric acid ( 2 ) 5b,14 . Additionally, we provide a mechanistic understanding of the pathway selectivity of the cycloaddition of 4 •+ / 4 .…”

Section: Introductionmentioning

confidence: 99%

Syntheses of sceptrins and nakamuric acid and insights into the biosyntheses of pyrrole–imidazole dimers

Wang

Gao

et al. 2015

Org. Chem. Front.

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Sceptrins and nakamuric acid are structurally unique antibiotics isolated from marine sponges. Recent studies suggest that the biosynthesis of these dimeric pyrrole–imidazole alkaloids involves a single-electron transfer (SET)-promoted [2+2] cycloaddition to form their cyclobutane core skeletons. We describe herein the biomimetic syntheses of racemic sceptrin and nakamuric acid. We also report the asymmetric syntheses of sceptrin, bromosceptrin, and dibromosceptrin in their natural enantiomeric form. We further provide mechanistic insights into the pathway selectivity of the SET-promoted [2+2] and [4+2] cycloadditions that lead to the divergent formation of the sceptrin and ageliferin core skeletons. Both the [2+2] and [4+2] cycloadditions are stepwise reactions, with the [2+2] pathway kinetically and thermodynamically favored over the [4+2] pathway. For the [2+2] cycloaddition, the dimerization of pyrrole–imidazole monomers is rate-limiting, whereas for the [4+2] cycloaddition, the cyclization is the slowest step.

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“…Murray et al 2013) focuses on Agelas species as producers of interesting molecules e.g. Agelas clathrodes , Agelas linnaei , Agelas mauritiana , Agelas nakamurai , Agelas oroides , and Agelas sceptrum (Walker et al 1981, Fathi-Afshar et al 1989, Keifer et al 1991, Braekman et al 1992, Bernan et al 1993, König and Wright 1993, Chanas et al 1996, König et al 1998, Eder et al 1999, Assmann et al 2000, 2001, 2004, Fattorusso and Taglialatela-Scafati 2000, Assmann and Köck 2002, Fujita et al 2003, Bickmeyer et al 2004, 2005, 2008, Bickmeyer 2005, Costantino et al 2006, Meketa and Weinreb 2006, Ferretti 2006, Vik et al 2006, Ding et al 2007, Ferretti et al 2007, 2009, Vergne et al 2008, Hertiani et al 2010, Said et al 2010, Regalado et al 2011, Mordhorst et al 2015). In this scenario of intensive bioprospecting, research knowledge of systematics and taxonomy in depth is a key tool to identify and define the status of specimens/biomaterial to be processed.…”

Section: Introductionmentioning

confidence: 99%

A new species of Agelas from the Zanzibar Archipelago, western Indian Ocean (Porifera, Demospongiae)

Manconi

Pronzato²,

Perino³

2016

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A new sponge species (Demospongiae: Agelasida: Agelasidae) is described from the eastern coast of Unguja Island in the Zanzibar Archipelago. Agelas sansibarica sp. n. is compared to all other Agelas species described so far. The new species differs from its congeners mainly in its three categories of verticillate spicules (acanthostyles, acanthostrongyles, and acanthoxeas) and their sizes. Acanthostrongyles, well represented in the spicular complement, are an exclusive trait of the new species widening the morphological range of the genus. Summarizing on spicular complement and spicular morphotraits of 36 species belonging to the genus Agelas: i) 32 species show only acanthostyles from Indo-Pacific (n = 14), Atlantic (n = 17), and Mediterranean (n = 1); ii) three Indo-Pacific species show acanthostyles and acanthoxeas; iii) one species Agelas sansibarica sp. n. from the western Indian Ocean is characterised by the unique trait of three categories of verticillate spicules (acanthostyles, acanthostrongyles and acanthoxeas). A key for the Indo-Pacific species is supplied together with short descriptions, illustrations, and geographic range; literature on chemical bioprospecting of the genus Agelas is also provided.

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New Bromopyrrole Alkaloids from the Indopacific Sponge Agelas nakamurai

Cited by 56 publications

References 10 publications

Bioactive cyclobutane-containing alkaloids

Bioactive cyclobutane-containing alkaloids

Syntheses of sceptrins and nakamuric acid and insights into the biosyntheses of pyrrole–imidazole dimers

A new species of Agelas from the Zanzibar Archipelago, western Indian Ocean (Porifera, Demospongiae)

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