Aplysinadiene and (r,r) 5 [3,5-dibromo-4-[(2-oxo-5-oxazolidinyl)] methoxyphenyl]-2-oxazolidinone, two novel metabolites from aplysina aerophoba synthes

Norte, Manuel; Rodríguez, Matías L.; Fernández, José J.; Eguren, Liliana; Estrada, Dulce M.

doi:10.1016/s0040-4020(01)86201-3

Cited by 24 publications

(21 citation statements)

References 10 publications

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“…Marine sponges are natural sources of brominated organic compounds (23,24,37) and also support a large amount of microbial biomass (6,13). It is thus conceivable that the abundance of brominated aromatic compounds and other complex secondary metabolites in the sponge tissue would select for bacteria with the ability to metabolize these compounds (6).…”

Section: Discussionmentioning

confidence: 99%

“…The marine environment is also a rich source of naturally occurring halogenated compounds produced by mollusks (3), algae (25), polychaetes (2), jellyfish (43), and sponges (29). A number of sponge species, such as Psammopemma sp., Psammaplysilla purpurea, Aplysina aerophoba, and Dysidea herbacea, have been shown to produce brominated aromatic metabolites, including bromoindoles, bromophenol (BP), polybrominated diphenyl ethers, and dibromodibenzo-p-dioxins (5,7,23,38).…”

mentioning

confidence: 99%

“…Major secondary metabolites of the sponge A. aerophoba are bromophenolic metabolites derived from dibromotyrosine (23,24).…”

mentioning

confidence: 99%

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Reductive Dehalogenation of Brominated Phenolic Compounds by Microorganisms Associated with the Marine Sponge Aplysina aerophoba

Ahn¹,

Rhee

Fennell

et al. 2003

Appl Environ Microbiol

119

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Marine sponges are natural sources of brominated organic compounds, including bromoindoles, bromophenols, and bromopyrroles, that may comprise up to 12% of the sponge dry weight. Aplysina aerophoba sponges harbor large numbers of bacteria that can amount to 40% of the biomass of the animal. We postulated that there might be mechanisms for microbially mediated degradation of these halogenated chemicals within the sponges. The capability of anaerobic microorganisms associated with the marine sponge to transform haloaromatic compounds was tested under different electron-accepting conditions (i.e., denitrifying, sulfidogenic, and methanogenic). We observed dehalogenation activity of sponge-associated microorganisms with various haloaromatics. 2-Bromo-, 3-bromo-, 4-bromo-, 2,6-dibromo-, and 2,4,6-tribromophenol, and 3,5-dibromo-4-hydroxybenzoate were reductively debrominated under methanogenic and sulfidogenic conditions with no activity observed in the presence of nitrate. Monochlorinated phenols were not transformed over a period of 1 year. Debromination of 2,4,6-tribromophenol, and 2,6-dibromophenol to 2-bromophenol was more rapid than the debromination of the monobrominated phenols. Ampicillin and chloramphenicol inhibited activity, suggesting that dehalogenation was mediated by bacteria. Characterization of the debrominating methanogenic consortia by using terminal restriction fragment length polymorphism (TRFLP) and denaturing gradient gel electrophoresis analysis indicated that different 16S ribosomal DNA (rDNA) phylotypes were enriched on the different halogenated substrates. Sponge-associated microorganisms enriched on organobromine compounds had distinct 16S rDNA TRFLP patterns and were most closely related to the ␦ subgroup of the proteobacteria. The presence of homologous reductive dehalogenase gene motifs in the sponge-associated microorganisms suggested that reductive dehalogenation might be coupled to dehalorespiration.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Reductive Dehalogenation of Brominated Phenolic Compounds by Microorganisms Associated with the Marine Sponge Aplysina aerophoba

Ahn¹,

Rhee

Fennell

et al. 2003

Appl Environ Microbiol

119

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“…collected in Cuba (55). Another isomer 67 was identified from the marine sponge Aplysina aerophoba by Norte et al in 1988 and its absolute configuration was determined as R, R by X-ray analysis (21). The optical rotation of 67 ([α] D = −33°) is significantly different from that of 65 and 66, indicating that it is a new diastereomer of 65 and 66.…”

Section: Introductionmentioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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“…The more is the unsaturated side branching at C-7, more deshielded are the signals of the lactone ring, with the increasing order of introducing the compounds 28, 27 and 26 [64,109]. …”

Section: Discussionmentioning

confidence: 99%

Brominated Compounds from Marine Sponges of the Genus Aplysina and a Compilation of Their 13C NMR Spectral Data

et al. 2011

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Aplysina is the best representative genus of the family Aplysinidae. Halogenated substances are its main class of metabolites. These substances contribute greatly to the chemotaxonomy and characterization of the sponges belonging to this genus. Due to their pharmacological activities, these alkaloids are of special interest. The chemistry of halogenated substances and of the alkaloids has long been extensively studied in terrestrial organisms, while the number of marine organisms studied has just started to increase in the last decades. This review describes 101 halogenated substances from 14 species of Aplysina from different parts of the world. These substances can be divided into the following classes: bromotyramines (A), cavernicolins (B), hydroverongiaquinols (C), bromotyrosineketals (D), bromotyrosine lactone derivatives (E), oxazolidones (F), spiroisoxazolines (G), verongiabenzenoids (H), verongiaquinols (I), and dibromocyclohexadienes (J). A compilation of their 13C NMR data is also part of the review. For this purpose 138 references were consulted.

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Aplysinadiene and (r,r) 5 [3,5-dibromo-4-[(2-oxo-5-oxazolidinyl)] methoxyphenyl]-2-oxazolidinone, two novel metabolites from aplysina aerophoba synthes

Cited by 24 publications

References 10 publications

Reductive Dehalogenation of Brominated Phenolic Compounds by Microorganisms Associated with the Marine Sponge Aplysina aerophoba

Reductive Dehalogenation of Brominated Phenolic Compounds by Microorganisms Associated with the Marine Sponge Aplysina aerophoba

The Marine Bromotyrosine Derivatives

Brominated Compounds from Marine Sponges of the Genus Aplysina and a Compilation of Their 13C NMR Spectral Data

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