Biotransformation of the Brominated Compounds in the Marine Sponge<i>Verongia aerophoba</i>: Evidence for an Induced Chemical Defense?

Teeyapant, R.; Woerdenbag, H. J.; Groß, H.; Proksch, Peter

doi:10.1055/s-2006-959888

Cited by 17 publications

(18 citation statements)

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“…Other roles, such as antibacterial activities, are far less investigated but could also explain the observed variation in secondary chemistry (6). The natural products found in A. aerophoba can be rapidly converted into aeroplysinin-1 and dienone, which show stronger antibiotic activity than their precursors and may protect this sponge from invasion by bacterial pathogens (27,68,73). The predominant bacterial community in A. aerophoba seemed to be fairly constant between and within individuals, although some bacteria significantly varied their relative abundance between the ectosome and choanosome tissues of the sponge.…”

Section: Discussionmentioning

confidence: 99%

Exploring the Links between Natural Products and Bacterial Assemblages in the SpongeAplysina aerophoba

Sacristán-Soriano

Banaigs

Casamayor

et al. 2011

Appl Environ Microbiol

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The sponge Aplysina aerophoba produces a large diversity of brominated alkaloids (BAs) and hosts a complex microbial assemblage. Although BAs are located within sponge cells, the enzymes that bind halogen elements to organic compounds have been exclusively described in algae, fungi, and bacteria. Bacterial communities within A. aerophoba could therefore be involved in the biosynthesis of these compounds. This study investigates whether changes in both the concentration of BAs and the bacterial assemblages are correlated in A. aerophoba. To do so, we quantified major natural products using high-performance liquid chromatography and analyzed bacterial assemblages using denaturing gradient gel electrophoresis on the 16S rRNA gene. We identified multiple associations between bacteria and natural products, including a strong relationship between a Chloroflexi phylotype and aplysinamisin-1 and between an unidentified bacterium and aerophobin-2 and isofistularin-3. Our results suggest that these bacteria could either be involved in the production of BAs or be directly affected by them. To our knowledge, this is one of the first reports that find a significant correlation between natural products and bacterial populations in any benthic organism. Further investigating these associations will shed light on the organization and functioning of host-endobiont systems such as Aplysina aerophoba.

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Section: Discussionmentioning

confidence: 99%

Exploring the Links between Natural Products and Bacterial Assemblages in the SpongeAplysina aerophoba

Sacristán-Soriano

Banaigs

Casamayor

et al. 2011

Appl Environ Microbiol

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“…The causes and consequences of this variation are receiving much attention from marine researchers due to the important biological, ecological and evolutionary implications (Chanas et al 1996, Cronin & Hay 1996a,b, Hay 1996, Becerro et al 1998, Sarà et al 1998, Paul & Puglisi 2004. Some marine organisms modify their levels of secondary metabolites according to the predation level (Paul & Van Alstyne 1992, Teeyapant & Proksch 1993, Cronin & Hay 1996b; however, other factors that may influence this plasticity need investigation. Physical or environmental factors play a major role in determining levels of secondary chemical compounds in marine algae (Yates & Peckol 1993, Cronin & Hay 1996a, and may be equally important for invertebrates (Thompson et al 1985, Becerro et al 1995.…”

Section: Discussionmentioning

confidence: 99%

Effects of depth and light on secondary metabolites and cyanobacterial symbionts of the sponge Dysidea granulosa

Becerro¹,

Paul²

2004

Mar. Ecol. Prog. Ser.

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The tropical sponge Dysidea granulosa contains a number of symbiotic heterotrophic bacteria and large quantities of the photosynthetic cyanobacterium Oscillatoria spongeliae, which are reported to be responsible for the production of ecologically active polybrominated diphenyl ethers (BDEs) in Dysidea spp. In order to better understand the relationship between these symbionts and the production of BDEs, we looked at the variation in secondary chemistry in 3 populations of D. granulosa and the relationship between cyanobacteria and secondary chemistry in the sponge, and experimentally assessed the role that depth and light play in this relationship by transplanting sponges in the field. At a population scale, the concentration of BDEs is positively correlated with the concentration of chlorophyll a (chl a), both varying significantly between populations. Yet, in sponges experimentally transplanted to a deeper site, the concentration of chl a decreased significantly while BDE concentration remained stable. We specifically tested the importance of light in determining levels of symbionts and BDEs by placing sponges under transparent, UV-opaque, and black Plexiglas plates. After 5 wk, levels of BDEs and chl a had decreased significantly, although these trends differed between light treatment, suggesting a lack of direct correlation between BDEs and cyanobacterial populations. This was also supported by a within-sponge analysis of chl a and BDEs, since high levels of compounds were found in the choanosome of the sponge, whereas chl a and cyanobacterial contents were minimal. Our data suggest that the relationship between the levels of BDEs in D. granulosa and its photosynthetic symbionts is more complex than expected. Variation in the levels of secondary metabolites and symbionts seems to be related at a population scale, but unrelated at an individual scale.

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“…Based on the results of the present study, probably not. Experiments performed with A. aerophoba were not done with living sponge, but with freeze-dried tissue samples and cell-free extracts (Teeyapant & Proksch 1993, Teeyapant et al 1993a,b, Weiss et al 1996, Ebel et al 1997. Identical incubation experiments performed with purified substrates and cell-free extracts of A. archeri and A. cauliformis did yield 3 to 30% conversion of high molecular weight metabolites to dibromocyclohexadienone and aeroplysinin-1, but only after 20 min at 50°C (< 2% conversion after 20 min at 20°C), and conversion occurred only with cell-free extracts of A. cauliformis at this physiologically unrealistic temperature (Puyana 2001).…”

Section: Discussionmentioning

confidence: 99%

“…Recent studies with the Mediterranean and Eastern Atlantic sponge Aplysina aerophoba have been interpreted to suggest that a series of high molecular weight, brominated secondary metabolites undergo rapid, enzyme-mediated transformation in response to tissue damage (Teeyapant & Proksch 1993, Teeyapant et al 1993a. The putative final products of this biotransformation (dibromocyclohexadienone and aeroplysinin-1; see Fig.…”

Section: Introductionmentioning

confidence: 99%

Are there activated chemical defenses in sponges of the genus Aplysina from the Caribbean?

Puyana¹,

Fenical²,

Pawlik³

2003

Mar. Ecol. Prog. Ser.

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The Mediterranean sponge Aplysina aerophoba has been proposed to rely on damageinduced activation of chemical defenses against pathogens and fish predators. High molecular weight brominated tyrosine derivatives have been suggested to undergo rapid, enzyme-mediated transformations into the metabolites aeroplysinin-1 and dibromocyclohexadienone following tissue damage, a process also called 'biotransformation'. These putative end-products were found to exhibit greater defensive activity compared to their precursors. Because sponges of the genus Aplysina possess similar chemical components worldwide, it has been suggested that the activation of chemical defenses is a common feature in this group. Herein, we report in situ and laboratory experiments conducted with living specimens of 2 species from the Caribbean, Aplysina insularis and A. archeri. Changes in sponge tissue secondary metabolites during time-course experiments were determined using diode-array high performance liquid chromatography coupled with mass spectrometry (LC-MS) analyses of extracts of flash frozen samples. We obtained no evidence of chemical transformation after tissue damage. In short (150 s) and long (30 and 120 min) time-course experiments, conversion of the major high molecular weight brominated constituents into the low molecular weight aeroplysinin-1 or dibromocyclohexadienone was not apparent: there was neither a reduction in the concentration of putative precursor metabolites, nor an increase in end products. Past observations of transformation may be the result of differential tissue extraction efficiency, hydrolysis from insoluble precursors or the heterogeneous distribution of metabolites in sponge tissue.

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Biotransformation of the Brominated Compounds in the Marine SpongeVerongia aerophoba: Evidence for an Induced Chemical Defense?

Cited by 17 publications

References 0 publications

Exploring the Links between Natural Products and Bacterial Assemblages in the SpongeAplysina aerophoba

Exploring the Links between Natural Products and Bacterial Assemblages in the SpongeAplysina aerophoba

Effects of depth and light on secondary metabolites and cyanobacterial symbionts of the sponge Dysidea granulosa

Are there activated chemical defenses in sponges of the genus Aplysina from the Caribbean?

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