Halogenated acetic and acrylic acids from the red alga Asparagopsis taxiformis

Woolard, Frank X.; Moore, Richard E.; Roller, Peter P.

doi:10.1016/s0031-9422(00)84271-5

Cited by 64 publications

(43 citation statements)

References 9 publications

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“…These structures were confirmed using commercial standards, except for dibromoacrylic acid (methyl ester). The mass spectrum of dibromoacrylic acid (methyl ester) matched the spectrum previously described for methyl 3, 3 dibromoacrylate (Woolard et al 1979).…”

Section: Natural Product Chemistry Of Asparagopsis Armatasupporting

confidence: 65%

“…DBA). No iodinated acids were detected, despite being the major acid products of Asparagopsis taxiformis (Woolard et al 1979). Haloacetones and halobutanones, previously described for A. armata (McConnell & Fenical 1977), were not found.…”

Section: Discussionmentioning

confidence: 57%

“…A. armata is a member of the Bonnemaisoniaceae, a family with well characterised chemistry (Fenical 1975). Over 100 halogenated compounds are found in the genus Asparagopsis alone, including haloforms, haloacids and haloketones (McConnell & Fenical 1977, Woolard et al 1979). The natural products of A. armata have been proposed to act in bacterial antifouling (Hornsey & Hide 1974, McConnell & Fenical 1979, although ecological tests against relevant bacteria have not been performed.…”

Section: Introductionmentioning

confidence: 99%

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Chemical defence against bacteria in the red alga Asparagopsis armata: linking structure with function

Paul¹,

Nys²,

Steinberg³

2006

Mar. Ecol. Prog. Ser.

235

226

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Although numerous algal products have antimicrobial activity, limited knowledge of metabolite localisation and presentation in algae has meant that ecological roles of algal natural products are not well understood. In this study, extracts of Asparagopsis armata had antibacterial activity against marine (Vibrio spp.) and biomedical (Escherichia coli, Pseudomonas aeruginosa and Staphylococcus spp.) strains. The major natural products in both life-history stages of A. armata (as determined by gas chromatography-mass spectrometry analysis [GC-MS]) were bromoform (0.58 to 4.3% of dry weight [DW]) and dibromoacetic acid [DBA] (0.02 to 2.6% DW), and each compound was active against these same bacteria. To resolve whether this antibiotic activity was ecologically relevant, we examined the localisation of metabolites in the specialised cells of A. armata and observed a delivery mechanism for the release of metabolites to the surface. Bromoform and DBA were subsequently quantified in the surrounding medium of laboratory cultures, establishing their release from the alga. In a novel ecological test of algal natural products, halogenated metabolites in A. armata were manipulated by omitting bromine from an artificial seawater medium. Significantly higher densities of epiphytic bacteria occurred on algae that no longer produced halogenated metabolites. Both bromoform and DBA were more active against bacteria isolated from algae lacking brominated metabolites than algae producing normal amounts of these compounds. Taken together, these results indicate that halogenated metabolites of A. armata may be important in reducing epiphytic bacterial densities.KEY WORDS: Chemical defence · Antifouling · Algae · Bacteria · Gland cell · Bromoform · Dibromoacetic acid · Gas chromatography-mass spectrometry Resale or republication not permitted without written consent of the publisher

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Section: Natural Product Chemistry Of Asparagopsis Armatasupporting

confidence: 65%

Section: Discussionmentioning

confidence: 57%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Chemical defence against bacteria in the red alga Asparagopsis armata: linking structure with function

Paul¹,

Nys²,

Steinberg³

2006

Mar. Ecol. Prog. Ser.

235

226

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“…Both the extract and isolated metabolite were non-deterrent (Table 3). Asparagopsis taxiformis produces halogenated ketones and acetones and halomethanes (Burreson et al 1975a, McConnell & Fenical 1977, Woolard et al 1979. The extract did not deter Zebrasoma flavescens.…”

Section: Halogenated Monoterpenes Have Been Isolated Frommentioning

confidence: 99%

Feeding preferences of the surgeonfish Zebrasoma flavescens in relation to chemical defenses of tropical algae

Wylie¹,

Paul²

1988

Mar. Ecol. Prog. Ser.

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Seaweed preferences of the tropical herbivorous surgeonfish Zebrasorna flavescens were examined in aquarium assays on Guam, in order to examine the role of secondary metabolites in determining its preferences. Of 55 species of macrophytes examined (49 algae, 5 cyanobactena, l seagrass), only 7 species were highly preferred. Seaweed extracts were examined by thin-layer chromatography (TLC) and proton nuclear magnetic resonance (NMR) spectroscopy to determine the presence or absence of secondary metabolites. Extracts from the non-preferred seaweeds and several pure major metabolites from these seaweeds were tested as feeding deterrents by applying them to the surface of Enterornorpha clathrata, a preferred alga. Extracts that contained secondary metabolites and were the most deterrent were from Bryopsis pennata, Chlorodesmis fastigiata, Desmia hornernanni, Microcoleus lyngbyaceus, Liagora farinosa, and Dictyota bartayresii. The deterrent pure metabolites were malygamide A (from M. lyngbyaceus), chlorodesmin (from C. fastigiata), pachydictyol A (from D. bartayresii), ochtodene (from D. hornernanni), and a fatty acid metabolite isolated from L. farinosa. Several extracts which did not contain metabolites based on our chemical analyses were also significantly deterrent including those from Codiurn geppii, Padina tenuis, Galaxaura oblongata, and Halyrnenia durvlllaei. Extracts from Caulerpa racernosa, Avrainvillea obscura, and Asparagopsis taxiformis contained secondary metabolites yet were non-deterrent. The pure metabolites caulerpin, caulerpenyne, and avrainvilleol from C, racernosa and A. obscura were also non-deterrent. Secondary metabolites appear to account for the low palatabhty of many of the seaweeds examined. However, not all secondary metabolites were effective deterrents toward this herbivore.

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“…Rats excrete 2-chloroacrylate when they are treated orally with herbicides containing a haloallyl substituent (20). In addition, various halogenated acrylic acids are produced by red algae (21). However, no enzyme catalyzing the conversion of 2-chloroacrylate has been identified.…”

mentioning

confidence: 99%

2-Haloacrylate Reductase, a Novel Enzyme of the Medium Chain Dehydrogenase/Reductase Superfamily That Catalyzes the Reduction of a Carbon-Carbon Double Bond of Unsaturated Organohalogen Compounds

Kurata

Kurihara

Kamachi

et al. 2005

Journal of Biological Chemistry

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A soil bacterium, Burkholderia sp. WS, grows on 2-chloroacrylate as the sole carbon source. To identify the enzymes metabolizing 2-chloroacrylate, we carried out comparative two-dimensional gel electrophoresis of the proteins from 2-chloroacrylate-and lactate-grown bacterial cells. As a result, we found that a protein named CAA43 was inducibly synthesized when the cells were grown on 2-chloroacrylate. The CAA43 gene was cloned and shown to encode a protein of 333 amino acid residues (M r 35,788) that shared a significant sequence similarity with NADPH-dependent quinone oxidoreductase from Escherichia coli (38.2% identity). CAA43 was overproduced in E. coli and purified to homogeneity. The purified protein catalyzed the NADPH-dependent reduction of the carbon-carbon double bond of 2-chloroacrylate to produce (S)-2-chloropropionate, which is probably further metabolized to (R)-lactate by (S)-2-haloacid dehalogenase in Burkholderia sp. WS. NADH did not serve as a reductant. Despite the sequence similarity to quinone oxidoreductases, CAA43 did not act on 1,4-benzoquinone and 1,4-naphthoquinone. 2-Chloroacrylate analogs, such as acrylate and methacrylate, were also inert as the substrates. In contrast, 2-bromoacrylate served as the substrate. Thus, we named this novel enzyme 2-haloacrylate reductase. This study revealed a new pathway for the degradation of unsaturated organohalogen compounds. It is also notable that the enzyme is useful for the production of (S)-2-chloropropionate, which is used for the industrial production of aryloxyphenoxypropionic acid herbicides.

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Halogenated acetic and acrylic acids from the red alga Asparagopsis taxiformis

Cited by 64 publications

References 9 publications

Chemical defence against bacteria in the red alga Asparagopsis armata: linking structure with function

Chemical defence against bacteria in the red alga Asparagopsis armata: linking structure with function

Feeding preferences of the surgeonfish Zebrasoma flavescens in relation to chemical defenses of tropical algae

2-Haloacrylate Reductase, a Novel Enzyme of the Medium Chain Dehydrogenase/Reductase Superfamily That Catalyzes the Reduction of a Carbon-Carbon Double Bond of Unsaturated Organohalogen Compounds

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