Antillatoxin: An Exceptionally Ichthyotoxic Cyclic Lipopeptide from the Tropical Cyanobacterium Lyngbya majuscula

Orjala, Jimmy; Nagle, Dale G.; Hsu, Victor L.; Gerwick, William H.

doi:10.1021/ja00136a031

Cited by 150 publications

(129 citation statements)

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“…The possible existence of temperate cyanophages of Lyngbya majuscula may help explain differences in toxicity previously noted within this species (Orjala et al 1995). Cyanophages have been shown to be important in genetic exchange among prokaryotes (Jiang & Paul 1998), and genes responsible for toxin production may be a result of the inclusion of a temperate cyanophage genome in host DNA, as is observed in other bacteria (Waldor & Mekalanos 1996).…”

Section: Discussionmentioning

confidence: 77%

Virus-like particles associated with Lyngbya majuscula (Cyanophyta; Oscillatoriacea) bloom decline in Moreton Bay, Australia

Hewson¹,

O’Neil²,

Dennison³

2001

Aquat. Microb. Ecol.

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Expansive blooms of the toxic cyanobacterium Lyngbya majuscula were observed in 2 shallow water regions of Moreton Bay, Australia. The rapid bloom decline (8 to <1 km 2 in < 7 d) prompted an investigation of the role of cyanophage viruses in the ecophysiology of L. majuscula. Virus-like particles produced by decaying L. majuscula were observed using electron microscopy. The virus-like particles were similar in morphology to viruses in the genus Cyanostyloviridae. The effect of viruses on L. majuscula photosynthesis was investigated by: (1) creating a virus concentrate using tangential-flow ultrafiltration of seawater surrounding L. majuscula; (2) inoculating L. majuscula with the concentrate; and (3) measuring photosynthetic response using a pulse-amplitude modulated fluorometer. Virus concentrate addition resulted in decreased initial fluorescence, decreased photochemical efficiency and decreased electron transport rate in rapid light curves after 5 d. Viruses present within L. majuscula filaments may play an important role in the bloom dynamics of this ecologically important cyanobacterium. KEY WORDS: Lyngbya majuscula · Cyanophage · Virus · LysogenyResale or republication not permitted without written consent of the publisher

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Section: Discussionmentioning

confidence: 77%

Virus-like particles associated with Lyngbya majuscula (Cyanophyta; Oscillatoriacea) bloom decline in Moreton Bay, Australia

Hewson¹,

O’Neil²,

Dennison³

2001

Aquat. Microb. Ecol.

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“…Quaternary substituted carbon atoms are extremely rare in aliphatic natural products, with the exception of the isoprenoid-based botryococcenes from the alga Botryococcus braunii (27). These rare exceptions also include the tert-butyl lipidic side chains of the feeding deterrents ypaoamide and antillatoxin of the cyanobacterium Lyngbia majuscula (28,29). The latter reports indicate that a biosynthetic pathway for tert-butyl aliphatic structures, although still unclear, is present in the bacterial domain.…”

Section: Resultsmentioning

confidence: 99%

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Kenig

Simons

Crich

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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A pseudohomologous series of branched aliphatic alkanes with a quaternary substituted carbon atom (BAQCs, specifically 2,2-dimethylalkanes and 3,3-and 5,5-diethylalkanes) were identified in warm (65°C) deep-sea hydrothermal waters and Late Cretaceous black shales. 5,5-Diethylalkanes were also observed in modern and Holocene marine shelf sediments and in shales spanning the last 800 million years of the geological record. The carbon number distribution of BAQCs indicates a biological origin. These compounds were observed but not identified in previous studies of 2.0 billion-to 2.2 billion-year-old metasediments and were commonly misidentified in other sediment samples, indicating that BAQCs are widespread in the geological record. The source organisms of BAQCs are unknown, but their paleobiogeographic distribution suggests that they have an affinity for sulfides and might be nonphotosynthetic sulfide oxidizers. P rokaryotes in ancient environments usually are detected by microscopy (1, 2) and geochemical evidence (e.g., stable isotope fractionation of carbon and sulfur; ref.3). The fossil record of bacteria and archaea is meager and controversial because of their poor preservation potential (1, 4). However, some lipids have excellent preservation potential and are used to demonstrate the presence of archaea and bacteria in ancient sedimentary environments (2, 5-9). Here we identify branched aliphatic alkanes with quaternary substituted carbon atoms (BAQCs). These compounds, observed in hydrothermal waters at the Ocean Drilling Project (ODP) site 1026B on the flanks of the Juan de Fuca ridge (Northeast Pacific) are natural products and occur in nonhydrothermal sediments ranging in age from modern to at least 2.0 billion to 2.2 billion years (Ga). MethodsField Sampling. Particulate organic material was retrieved from hydrothermal waters by using a combusted glass-fiber filter (142 mm) affixed to a circulation obviation retrofit kit (10) The Cenomanian and Turonian (Late Cretaceous) samples were collected at outcrops along the Bainbridge river in the Pasquia Hills region of easternmost central Saskatchewan, Canada (12). They are thermally immature based on the dominant 17␤,21␤(H) stereochemical configuration of the hopanes. The descriptions of other sediment samples analyzed can be found in the references listed in the Fig. 3 legend. Laboratory Methods. Extraction, separation, and GC-MS were performed as described (13). The filter and sediment samples were Soxhlet-extracted by using dichloromethane and methanol (7.5:1, vol͞vol). The sediment extracts were further separated by column chromatography to obtain a hydrocarbon fraction. Linear alkanes were removed from the hydrocarbon fraction by adduction on US-Y zeolite to obtain a fraction of branched and cyclic hydrocarbons. The total extract and subfractions, as well as authentic standards, were analyzed by GC-MS on a HewlettPackard 6890 gas chromatograph coupled to a Hewlett-Packard 5973 mass selective detector operated in electron ionization mode at 70 eV, scannin...

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“…Earlier studies showed ATX to be among the most potent ichthyotoxic compounds isolated from a marine alga (1). The ichthyotoxic potency is, in fact, exceeded only by PbTx-1 (1).…”

Section: Discussionmentioning

confidence: 99%

“…M arine cyanobacteria represent a particularly rich source of structurally unique neurotoxic secondary metabolites (1)(2)(3)(4)(5). Lyngbya majuscula is a pantropical marine cyanobacterium that is the source of antillatoxin (ATX), a structurally unusual lipopeptide (1) (Fig.…”

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confidence: 99%

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Antillatoxin is a marine cyanobacterial toxin that potently activates voltage-gated sodium channels

Berman

Okino

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

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M arine cyanobacteria represent a particularly rich source of structurally unique neurotoxic secondary metabolites (1-5). Lyngbya majuscula is a pantropical marine cyanobacterium that is the source of antillatoxin (ATX), a structurally unusual lipopeptide (1) (Fig. 1). Blooms of L. majuscula have been associated with adverse effects on human health. These blooms have been reported to cause respiratory irritation, eye inflammation, and severe contact dermatitis in exposed fishermen and swimmers (6). ATX has been shown to be among the most ichthyotoxic metabolites isolated to date from a marine microalga (1) and, more recently, has been demonstrated to be neurotoxic in primary cultures of rat cerebellar granule cells (4). In the latter study, morphologic evidence of ATX-induced neurotoxicity included swelling of neuronal somata, thinning of neurites, and blebbing of neurite membranes. ATX also induced a concentration-dependent cytotoxicity in cerebellar granule neurons as monitored by lactate dehydrogenase efflux (ATX EC 50 ϭ 20.1 Ϯ 6.4 nM) (4). This neurotoxic response of ATX was prevented by coexposure with noncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptor such as MK-801 and dextrorphan.Voltage-gated sodium channels are responsible for generation of the rising phase of the action potential in membranes of neurons as well as in most other electrically excitable cells. Sodium channels consist of a pore-forming ␣ subunit of 260 kDa associated with auxiliary ␤ subunits of 33-36 kDa (7,8). Voltagegated sodium channels represent the molecular target for an array of natural products including marine neurotoxins. Marine neurotoxins such as tetrodotoxin (TTX), saxitoxin, conotoxins, sea anemone toxins, brevetoxin, and ciguatoxin all bind with high affinity and specificity to at least six distinct receptor sites on sodium channel ␣ subunits (8). Collectively, these toxins have served as important tools to explore the structure and function of voltage-dependent sodium channels. These marine neurotoxins produce characteristic alterations in the two major properties of sodium channels, namely ion permeation and gating (8).The objective of the present study was to test the hypothesis that ATX acts as an activator of voltage-dependent sodium channels. This hypothesis emanated from our previous studies which were consistent with ATX acting as an autocrine excitotoxic agent in cerebellar granule neurons. In this study we have used a combination of neurochemical and pharmacological approaches to show that ATX is a structurally unusual lipopeptide activator of neuronal voltage-gated sodium channels. Materials and MethodsMaterials. Tritiated batrachotoxin A 20-␣-benzoate ([ 3 H]BTX) and 22 Na ϩ were obtained from DuPont͞NEN. Deltamethrin was purchased from Biomol (Plymouth Meeting, PA). Veratridine, brevetoxin-1 (PbTx-1), and ouabain were obtained from Sigma. Sea anemone toxin was purchased from Calbiochem. Fluo-3 AM and pluronic acid were obtained from Molecular Probes. ATX was either authentic natural (Ϫ)-ant...

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Antillatoxin: An Exceptionally Ichthyotoxic Cyclic Lipopeptide from the Tropical Cyanobacterium Lyngbya majuscula

Cited by 150 publications

References 0 publications

Virus-like particles associated with Lyngbya majuscula (Cyanophyta; Oscillatoriacea) bloom decline in Moreton Bay, Australia

Virus-like particles associated with Lyngbya majuscula (Cyanophyta; Oscillatoriacea) bloom decline in Moreton Bay, Australia

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Antillatoxin is a marine cyanobacterial toxin that potently activates voltage-gated sodium channels

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