Halogen chemistry of the red alga Asparagopsis

McConnell, Oliver J.; Fenical, William

doi:10.1016/0031-9422(77)80067-8

Cited by 154 publications

(106 citation statements)

References 18 publications

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“…Production of CHBr 3, CHBr2C1, CHzBr2C1, CH2Br 2, CHBrC12, CCI4, CHCI 3 and CH3I, which has been demonstrated in E. denticulatum, has also been reported for other red algae, such as Asparagopsis sp. (Bonnemaisoniaceae) (McConnell & Fenical, 1977) and Mastocarpus stellatus(.Stackhouse):Guiry (Gigartinaceae) (as Gigartina stellata in Gschwend et al, 1985), brown algae, such as Ascophyllum nodosum (Linnaeus) Le Jolis (Fucaceae), Fucus vesiculosus Linnaeus (Fucaceae) (Gschwend et al, 1985), Sargassum sp. (Sargassaceae) and Laminaria sp.…”

Section: Discussionmentioning

confidence: 99%

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Mtolera

Collén

Pedersén

et al. 1996

European Journal of Phycology

101

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Eucheuma denticulatum has been shown to release bromoform, diiodomethane, dibromochloromethane, perchloroethylene, chloroiodomethane, chloroform, sec-butyl iodide, methyl iodide, methylchloroform, carbon tetrachloride, trichloroethylene and butyl iodide into its growth media, with bromoform (310 4-25 #g kg DW -~ h -1) and diiodomethane (182 q-9 #g kg DW -~ h -I) being the dominant volatile hatocarbons (VHCs). The production of VHCs was always higher at a photon flux density of 1500 than at 400 #tool photon m -2 s -1. The influence of pH was minimal at 400 #tool photon m -2 s -1. The addition of azide decreased mean VHC production at pH 8"2 4-0"2 and 8"8. Algae kept in media where extracellular hydrogen peroxide was decomposed by addition of manganese dioxide showed a decrease in VHC production at pH 8"2 q-0"2 and an increase at pH 8"8. We suggest that high light intensity and carbon dioxide deficiency caused by high pH in E. denticulatum promote VHC production through induction of hydrogen peroxide synthesis.Key words: bromoform, Eucheuma denticulatum, halocarbons, hydrogen peroxide, red algae, sodium azide. IntroductionRecent Arctic field studies, especially during spring, have established that there are changes in the ozone composition of the lower Arctic atmosphere (0-2 km) resulting from an increased tropospheric halogen content, notably of bromine, with algal volatile halocarbons (VHCs) being suspected to be a contributory source (Barrie et al., 1988;Sturges et al., 1992). Depending upon the atmospheric lifetime of a particular VHC released into the troposphere, photolysis can produce halogen atoms which catalyse stratospheric ozone removal (Molina & Rowland, 1974). Bromine is considered to be a more efficient catalyst than chlorine in destroying ozone (Prather et al., 1984), and consequently the marine organisms contributing to the production of bromo-compounds are thought to have an important potential influence on the composition of the stratosphere.Halo-peroxidases are known to catalyse the synthesis of halogenated compounds (Krenn et al., 1989; Wever et al., 1991). The synthesis occurs in the presence of hydrogen peroxide (HzO2), the respective halide ion and a suitable acceptor (for example, fl-keto acids, cyclic fldiketones and substituted phenols: Hager et al., 1966 that VHCs are cleavage products of halogenated C3 or C4 ketones. Such polyhaloketones are widely accepted to be toxic, and their presence has also been reported in some prolific VHC producers (Fenical, 1974). The bromoperoxidase from the red alga Bonnemaisonia hamifera Harlot (Bonnemaisoniaceae) can, for instance, produce dibromomethane, bromoform and pentylbromide in vitro from bromide ions, H20 2 and 3-oxooctanoic acid (Theiler et aL, 1978).For a metabolite system to be effective for defence purposes or in an allelopathic interaction, the distribution of producer enzymes, metabolite precursors or the metabolites themselves should ensure that metabolites can easily reach the grazers, parasites or competitors. From the literature on alg...

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Section: Discussionmentioning

confidence: 99%

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Mtolera

Collén

Pedersén

et al. 1996

European Journal of Phycology

101

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“…Among the diverse varieties of seaweeds, the red algae, Asparagopsis taxiformis constitutes the most abundant biomass on the coast. A. taxiformis releases a variety of bioactive compounds during its growth cycle, several chemical compounds, possessing various biologically relevant activities, having been isolated from FENICAL, 1977;WOOLARD et al, 1979;LATURNUS et al, 1996;EL-BAROTY et al, 2007;GENOVESE, 2009). However, very little is known about the functions of these metabolites in their natural environment.…”

Section: Introductionmentioning

confidence: 99%

Bioactivity of the red algae Asparagopsis taxiformis collected from the Southwestern coast of India

et al. 2010

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A B S T R A C TAmong the diverse variety of red algae, Asparagopsis taxiformis constitutes one of the abundant biomass in the Kollam coast (Southwest coast of India). Therefore, in the present study, A. taxiformis was collected, extracted and fractionated using column chromatography. The individual fractions were evaluated in vitro for their antifouling, anticyanobacterial, piscicidal and crustaceans toxicity assays. The fraction eluted with 2:8, petroleum ether and ethyl acetate exhibited strong and broad spectrum of bioactivity. In antifouling assay against Limnea truncatula, the active algal fraction produced 80% of foot repellency at 150 mg/L whereas in anticyanobacterial assay, the active fraction inhibited 100% growth of Trichodesmium sp. at 320 mg/L. The algal fraction showed higher piscicidal effect at the level of 60 mg/L. The crustacean toxicity of the active fraction was also evaluated to find compounds without toxicity in non target organisms, Penaeus monodon and Macrobrachium rosenbergii. It was found that column fraction showed less toxicity against the non target organisms. The chemical constituents of the active fraction were identified by means of chromatographic systems such as TLC, reverse phase HPLC and GC-MS. The overall activity profile envisages that the active column fraction of A. taxiformis might contain synergistic bioactive metabolites that could be utilized for the control of fouling organisms, algal bloom and herbivorous/predaceous fishes in aquaculture ponds. R E S U M OEntre as diversas variedades de algas vermelhas, Asparogopsis taxiformis constitui uma das que apresentam alta biomassa na costa de Kollam (Sudoeste da Índia). No presente estudo A. taxiformis foi coletada, seca e reduzida a pó, após o que foi realizada sua extração e feito o fracionamento usando-se cromatografia por coluna. As frações individuais foram avaliadas in vitro em ensaios para testar sua capacidade anti-incrustante, anticianobacteria e toxicidade para peixes e crustáceos. A fração extraída com eter de petróleo e etil acetato (2:8) apresentou o espectro de bioatividade mais forte e amplo. No ensaio anti-incrustação efetuado com com o molusco pulmonado Limnea truncatula, a fração algal ativa produziu 80% de repelência do pé em 150 mg/l, enquanto que no ensaio anticianobacteria a fração ativa inibiu 100% do crescimento de Trichodesmium sp., em 320 mg/l. A fração algal mostrou o efeito mais intenso contra peixes no nível de 60 mg/l. Em relação aos crustáceos, a toxicidade da fração ativa foi avaliada também visando encontrar compostos não tóxicos para organismos não alvo, tais como Penaeus monodon e Macrobrachium rosembergii. Foi visto que a fração ativa da coluna mostrou menor toxicidade para estas espécies. Os componentes químicos da fração ativa foram identificados por meio dos sistemas cromatográficos, tais como TLC, fase reversa do HPLC e GC-MS. O perfil geral de atividade aponta que a fração ativa da coluna para A. taxiformis pode conter metabolitos bioativos sinérgicos que podem ser utilizados para o c...

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“…Although structural and nutritional differences may have influenced the outcome of this experiment, the storage of chemical defences in these specialised structures provides an alternative explanation. A. armata produces numerous bioactive halogenated metabolites that are stored in refractile inclusions (McConnell & Fenical 1977, Paul et al 2006. While there have been no reports on the natural product chemistry of either B. amphiglanda or A. tenue (Marinlit 2005), the widespread occurrence of similar storage structures, in particular in the red algae of the Ceramiaceae (Young & West 1979), suggests that chemical defence may be more common in filamentous algae than predicted by functional form models (Littler & Littler 1980, Steneck & Dethier 1994.…”

Section: Discussionmentioning

confidence: 99%

Seaweedherbivore interactions at a small scale: direct tests of feeding deterrence by filamentous algae

Paul

Nys²,

Steinberg³

2006

Mar. Ecol. Prog. Ser.

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High growth rates and temporal or spatial opportunism are considered central to the success of filamentous algae, in particular for escaping or minimising the effects of herbivory. However, the role of chemical defences in filamentous algae has received far less attention. We investigated possible chemical feeding deterrence by filamentous red algae that have conspicuous cellular inclusions (Asparagopsis armata, Anotrichium tenue and Balliella amphiglanda) and 2 others without inclusions (Callithamnion korfense and Ulva sp.). The 3 algae with cellular inclusions were consumed at lower rates by a generalist amphipod, Hyale nigra, than the other 2 algae. To determine the potential role of chemical defences for A. armata, we conducted tests against herbivores using algae in which the production of halogenated metabolites was manipulated. This manipulation had no effect on carbon and nitrogen values of the algae, and allowed us to directly test the role of algal secondary metabolites in defence against herbivores without using artificial diets. Bromide (+) algae (with halogenated metabolites) deterred grazing by 2 mesograzers (Hyale nigra and juvenile abalone Haliotis rubra), which consumed up to 4 times more bromide (-) (metabolite-free) algae than bromide (+) algae. Juveniles of the sea hare Aplysia parvula were not deterred by the chemical defences in bromide (+) A. armata. In field assays, artificial diets containing a crude extract of A. armata were also active against herbivores. Although functional form models typically predict that tolerance -not resistance -should be the key defensive strategy for marine algae with simple architecture, this study demonstrates that resistance traits may also be important and more broadly utilised in filamentous species.

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Halogen chemistry of the red alga Asparagopsis

Cited by 154 publications

References 18 publications

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Bioactivity of the red algae Asparagopsis taxiformis collected from the Southwestern coast of India

Seaweedherbivore interactions at a small scale: direct tests of feeding deterrence by filamentous algae

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Halogen chemistry of the red alga Asparagopsis

Cited by 154 publications

References 18 publications

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Stress-induced production of volatile halogenated organic compounds inEucheuma denticulatum(Rhodophyta) caused by elevated pH and high light intensities

Bioactivity of the red algae Asparagopsis taxiformis collected from the Southwestern coast of India

Seaweedherbivore interactions at a small scale: direct tests of feeding deterrence by filamentous algae

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Seaweedherbivore interactions at a small scale: direct tests of feeding deterrence by filamentous algae