Characterization of allelopathic compounds from the red tide dinoflagellate Karenia brevis

Harmful Algae - Tập 10 Số 1 - Trang 39-48 - 2010
Emily K. Prince1, Kelsey L. Poulson‐Ellestad1, Tracey L. Myers2, R. Drew Sieg1, Julia Kubanek2
1School of Biology, Georgia Institute of Technology, 310 Ferst Drive, Atlanta, GA 30332-0230, USA
2School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA 30332-0400, USA

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Adolf, 2006, Species specificity and potential roles of Karlodinium micrum toxin, African J. Mar. Sci., 28, 415, 10.2989/18142320609504189

Adolf, 2007, Karlotoxin mediates grazing by Oxyrrhis marina on strains of Karlodinium veneficum, Harmful Algae, 6, 400, 10.1016/j.hal.2006.12.003

Babica, 2006, Exploring the natural role of microcystins—a review of effects on photoautotrophic organisms, J. Phycol., 42, 9, 10.1111/j.1529-8817.2006.00176.x

Baden, 1998, Marine toxins: how they are studied and what they can tell us

Badylak, 2007, Distributions of phytoplankton in Tampa Bay Estuary, USA 2002–2003, Bull. Mar. Sci., 80, 295

Chiang, 2004, Allelochemicals of Botryococcus braunii (Chlorophyceae), J. Phycol., 40, 474, 10.1111/j.1529-8817.2004.03096.x

Cussler, 1997

Deeds, 2006, Sterol-specific membrane interactions with the toxins from Karlodinium micrum (Dinophyceae)—a strategy for self-protection? African, J. Mar. Sci., 28, 421, 10.2989/18142320609504190

Deeds, 2006, Histopathological effects in fish exposed to the toxins from Karlodinium micrum, J. Aquat. Anim. Health, 18, 136, 10.1577/H05-027.1

Dettmer, 2007, Mass spectrometry-based metabolomics, Mass Spectrom. Rev., 26, 51, 10.1002/mas.20108

Figueredo, 2007, Does allelopathy contribute to Cylindrospermopsis raciborskii (cyanobacteria) bloom occurrence and geographic expansion?, J Phycol., 43, 256, 10.1111/j.1529-8817.2007.00333.x

Fistarol, 2003, Allelopathic effect of Prymnesium parvum on a natural plankton community, Mar. Ecol. Prog. Ser., 255, 115, 10.3354/meps255115

Fistarol, 2005, Allelopathic effect on a nutrient-limited phytoplankton species, Aquat. Microb. Ecol., 41, 153, 10.3354/ame041153

Fistarol, 2004, Allelopathy in Alexandrium spp.: effect on a natural plankton community and on algal monocultures, Aquat. Microb. Ecol., 35, 45, 10.3354/ame035045

Ganem, 1978, Shikimate derived metabolites 4. From glucose to aromatics—recent developments in natural products of shikimic acid pathway, Tetrahedron, 34, 3353, 10.1016/0040-4020(78)80222-1

Gross, 2003, Allelopathy of aquatic autotrophs, Crit. Rev. Plant. Sci., 22, 313, 10.1080/713610859

Gross, 1991, Fischerellin, a new allelochemical from the freshwater cyanobacterium Fisherella muscicola, J. Phycol., 27, 686, 10.1111/j.0022-3646.1991.00686.x

Hagmann, 1996, Fischerellin A, a novel photosystem-II-inhibiting allelochemical of the cyanobacterium Fischerella muscicola with antifungal and herbicidal activity, Tetrahedron Lett., 37, 6539, 10.1016/0040-4039(96)01445-1

Hu, 1995, Identification of DTX-4, a new water soluble phosphatase inhibitor from the toxic dinoflagellate Prorocentrum lima, J. Chem. Soc. Chem. Commun., 5, 597, 10.1039/c39950000597

Juttner, 2001, Nostocyclamide M: a cyanobacterial cyclic peptide with allelopathic activity from Nostoc 31, Phytochemistry, 57, 613, 10.1016/S0031-9422(00)00470-2

Kajiwara, 1992, Cell destroying sesquiterpenoid from red tide of Gymnodinium nagasakiense, Phytochemistry, 31, 783, 10.1016/0031-9422(92)80014-6

Keating, 1977, Allelopathic influence on blue-green bloom sequence in a eutrophic lake, Science, 196, 885, 10.1126/science.196.4292.885

Keating, 1978, Blue-green algal inhibition of diatom growth—transition from mesotrophic to eutrophic community structure, Science, 199, 971, 10.1126/science.199.4332.971

Kubanek, 2005, Does the red tide dinoflagellate Karenia brevis use allelopathy to outcompete other phytoplankton?, Limnol. Oceanogr., 50, 883, 10.4319/lo.2005.50.3.0883

Kubanek, 2007, Chemical defense of the red tide dinoflagellate Karenia brevis against rotifer grazing, Limnol. Oceanogr., 52, 1026, 10.4319/lo.2007.52.3.1026

Landsberg, 2002, The effects of harmful algal blooms on aquatic organisms, Rev. Fish Sci., 10, 113, 10.1080/20026491051695

Legrand, 2003, Allelopathy in phytoplankton—biochemical, ecological and evolutionary aspects, Phycologia, 42, 406, 10.2216/i0031-8884-42-4-406.1

Luesch, 2000, Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula, J. Nat. Prod., 63, 1437, 10.1021/np000104n

Lundholm, 2005, Lack of allelopathic effects of the domoic acid-producing marine diatom Pseudo-nitzschia multiseries, Mar. Ecol. Prog. Ser., 288, 21, 10.3354/meps288021

Ma, 2009, Preliminary characterization of extracellular allelochemicals of the toxic marine dinoflagellate Alexandrium tamarense using a Rhodomonas salina bioassay, Mar. Drugs, 7, 497, 10.3390/md7040497

Mason, 1982, Isolation of chlorine-containing antibiotic from the freshwater cyanobacterium Scytonema hofmanni, Science, 215, 400, 10.1126/science.6800032

Milanowski, 2004, Cyclonellin, a new cyclic octapeptide from the marine sponge Axinella carteri, J. Nat. Prod., 67, 441, 10.1021/np030336x

Myers, 2008, Loss of waterborne brevetoxins from exposure to phytoplankton competitors, Harmful Algae, 7, 762, 10.1016/j.hal.2008.03.001

Papke, 1997, Isolation, identification and determination of the absolute configuration of fischerellin B. A new algicide from the freshwater cyanobacterium Fischerella muscicola (Thuret), Tetrahedron Lett., 38, 379, 10.1016/S0040-4039(96)02284-8

Perez, 1997, Identification of allelopathic substances produced by Nannochloris oculata that affect a red tide organism, Gymnodinium breve, Biomed. Lett., 56, 7

Poulson, 2009, Chemical ecology of the marine plankton, Nat. Prod. Rep., 26, 729, 10.1039/b806214p

Prince, 2006, Fitness consequences for copepods feeding on a red tide dinoflagellate: deciphering the effects of nutritional value, toxicity, and feeding behavior, Oecologia, 147, 479, 10.1007/s00442-005-0274-2

Prince, 2008, Effects of harmful algal blooms on competitors: allelopathic mechanisms of the red tide dinoflagellate Karenia brevis, Limnol. Oceanogr., 53, 531, 10.4319/lo.2008.53.2.0531

Prince, 2008, Competing phytoplankton undermines allelopathy of a bloom-forming dinoflagellate, Proc. R. Soc. B: Biol., 275, 2733, 10.1098/rspb.2008.0760

Prince, 2010, Searching for signals in the noise: metabolomics in chemical ecology, Anal. Bioanal. Chem., 396, 193, 10.1007/s00216-009-3162-5

Schlingmann, 2002, Isolation and identification of antifungal polyesters from the marine fungus Hypoxylon oceanicum LL-15G256, Tetrahedron, 58, 6825, 10.1016/S0040-4020(02)00746-9

Schmidt, 2001, Allelopathy in the prymnesiophyte Chrysochromulina polylepis: effect of cell concentration, growth phase and pH, Mar. Ecol. Prog. Ser., 216, 67, 10.3354/meps216067

Shen, 2000

Sheng, 2010, A dinoflagellate exploits toxins to immobilize prey prior to ingestion, Proc. Natl. Acad. Sci. U.S.A., 107, 2082, 10.1073/pnas.0912254107

Silverstein, 2005

Smayda, 1997, Harmful algal blooms: their ecophysiology and general relevance to phytoplankton blooms in the sea, Limnol. Oceanogr., 42, 1137, 10.4319/lo.1997.42.5_part_2.1137

Sugg, 1999, No evidence for an allelopathic role of okadaic acid among ciguatera-associated dinoflagellates, J. Phycol., 35, 93, 10.1046/j.1529-8817.1999.3510093.x

Suikkanen, 2004, Allelopathic effects of the Baltic cyanobacteria Nodularia spumigena, Aphanizomenon flos-aquae and Anabaena lemmermannii on algal monocultures, J Exp. Mar. Biol. Ecol., 308, 85, 10.1016/j.jembe.2004.02.012

Suikkanen, 2006, Allelopathy of Baltic Sea cyanobacteria: no evidence for the role of nodularin, J. Plank. Res., 28, 543, 10.1093/plankt/fbi139

Tameishi, 2009, Allelopathic effects of the dinophyte Prorocentrum minimum on the growth of the bacillariophyte Skeletonema costatum, Harmful Algae, 8, 421, 10.1016/j.hal.2008.09.002

Tillmann, 2009, Allelopathic effects of Alexandrium tamarense on other algae: evidence from mixed growth experiments, Aquat. Microb. Ecol., 57, 101, 10.3354/ame01329

Tillmann, 2002, Toxic effects of Alexandrium spp. on heterotrophic dinoflagellates: an allelochemical defence mechanism independent of PSP-toxin content, Mar. Ecol. Prog. Ser., 230, 47, 10.3354/meps230047

Tillmann, 2007, On the allelochemical potency of the marine dinoflagellate Alexandrium ostenfeldii against heterotrophic and autotrophic protists, J. Plank. Res., 29, 527, 10.1093/plankt/fbm034

Todorova, 1995, Nostocyclamide—a new macrocyclic, thiazole-containing allelochemical from Nostoc sp. 31 (cyanobacteria), J. Org. Chem., 60, 7891, 10.1021/jo00129a032

Van Wagoner, 2008, Isolation and characterization of karlotoxin 1, a new amphipathic toxin from Karlodinium veneficum, Tetrahedron Lett., 49, 6457, 10.1016/j.tetlet.2008.08.103

von Elert, 1997, Phosphorus limitation and not light controls the extracellular release of allelopathic compounds by Trichormus doliolum (cyanobacteria), Limnol. Oceanogr., 42, 1796, 10.4319/lo.1997.42.8.1796

West, 1996, Natural phytoplankton community responses to a bloom of the toxic dinflagellate Gymnodinium breve Davis off the North Carolina coast, Castanea, 61, 356

Wu, 2006, Cytotoxic effects of free fatty acids on phytoplankton algae and cyanobacteria, Aquat. Toxicol., 80, 338, 10.1016/j.aquatox.2006.09.011

Yamasaki, 2007, Allelopathic interactions between the bacillariophyte Skeletonema costatum and the raphidophyte Heterosigma akashiwo, Mar. Ecol. Prog. Ser., 339, 83, 10.3354/meps339083

Yamasaki, 2009, Extracellular polysaccharide-protein complexes of a harmful alga mediate the allelopathic control it exerts within the phytoplankton community, ISME J., 3, 808, 10.1038/ismej.2009.24

Zar, 1999