Halogenated Compounds from Marine Algae

Marine algae produce a cocktail of halogenated metabolites with potential commercial value. Structures exhibited by these compounds go from acyclic entities with a linear chain to complex polycyclic molecules. Their medical and pharmaceutical application has been investigated for a few decades, however other properties, such as antifouling, are not to be discarded. Many compounds were discovered in the last years, although the need for new drugs keeps this field open as many algal species are poorly screened. The ecological role of marine algal halogenated metabolites has somehow been overlooked. This new research field will provide valuable and novel insight into the marine ecosystem dynamics as well as a new approach to comprehending biodiversity. Furthermore, understanding interactions between halogenated compound production by algae and the environment, including anthropogenic or global climate changes, is a challenging target for the coming years. Research of halogenated metabolites has been more focused on macroalgae than on phytoplankton. However, phytoplankton could be a very promising material since it is the base of the marine food chain with quick adaptation to environmental changes, which undoubtedly has consequences on secondary metabolism. This paper reviews recent progress on this field and presents trends on the role of marine algae as producers of halogenated compounds.

[1]  Y. Shimasaki,et al.  Allelopathic effects of the dinophyte Prorocentrum minimum on the growth of the bacillariophyte Skeletonema costatum , 2009 .

[2]  R. Cannell.  How to Approach the Isolation of a Natural Product , 1998 .

[3]  M. Hay.  Marine chemical ecology: chemical signals and cues structure marine populations, communities, and ecosystems. , 2009, Annual review of marine science.

[4]  Á. Mombrú,et al.  New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity. , 2001, Journal of natural products.

[5]  P. Harrison,et al.  Seaweed Ecology and Physiology. , 1995 .

[6]  Alison Butler,et al.  Mechanistic considerations of halogenating enzymes , 2009, Nature.

[7]  E. P. Stout,et al.  Desorption electrospray ionization mass spectrometry reveals surface-mediated antifungal chemical defense of a tropical seaweed , 2009, Proceedings of the National Academy of Sciences.

[8]  P. Scheuer.  Marine Natural Products: Chemical and Biological Perspectives , 1977 .

[9]  H. Paerl,et al.  Climate change: a catalyst for global expansion of harmful cyanobacterial blooms. , 2009, Environmental microbiology reports.

[10]  Lijun Han,et al.  Sesquiterpenes from the Marine Red Alga Laurencia saitoi , 2009 .

[11]  D. Faulkner.  Marine natural products. , 2000, Natural product reports.

[12]  B. Baker,et al.  Introduction to the Chemical Ecology of Marine Natural Products , 2001 .

[13]  J. Kubanek,et al.  Chemical ecology of the marine plankton. , 2009, Natural product reports.

[14]  A. Wright,et al.  Laurencia rigida: chemical investigations of its antifouling dichloromethane extract. , 1997, Journal of natural products.

[15]  William Fenical,et al.  CHEMICAL ECOLOGY AND MARINE BIODIVERSITY: INSIGHTS AND PRODUCTS FROM THE SEA , 1996 .

[16]  Xiao‐Ming Li,et al.  Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae) , 2009 .

[17]  Phillip C. Wright,et al.  Marine cyanobacteria—a prolific source of natural products , 2001 .

[18]  B. Kloareg,et al.  Iodine uptake in Laminariales involves extracellular, haloperoxidase-mediated oxidation of iodide , 1998, Planta.

[19]  V. Paul,et al.  Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula. , 2001, Journal of the American Chemical Society.

[20]  C. Amsler.  Algal Sensory Chemical Ecology , 2008 .

[21]  V. Paul,et al.  Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp. , 2008, Journal of the American Chemical Society.

[22]  A. Wright,et al.  Three new sesquiterpenes from the red alga Laurencia perforata. , 2003, Journal of natural products.

[23]  M. Harlin,et al.  Allelochemistry in marine macroalgae , 1987 .

[24]  P. Colepicolo,et al.  Metabolites from algae with economical impact. , 2007, Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.

[25]  M. Guyot,et al.  New bromoditerpenes from the red alga Sphaerococcus coronopifolius. , 2001, Journal of natural products.

[26]  C. Vairappan.  Potent antibacterial activity of halogenated metabolites from Malaysian red algae, Laurencia majuscula (Rhodomelaceae, Ceramiales). , 2003, Biomolecular engineering.

[27]  G. Pohnert,et al.  Metabolic profiling reveals growth stage variability in diatom exudates , 2009 .

[28]  W. Fenical,et al.  Chemical Defense Against Diverse Coral-Reef Herbivores. , 1987, Ecology.

[29]  R. Contreras,et al.  An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: studies by NMR spectroscopic and computational methods. , 2009, Phytochemistry.

[30]  E. Ibáñez,et al.  Screening for bioactive compounds from algae. , 2010, Journal of pharmaceutical and biomedical analysis.

[31]  Peter J. Smith,et al.  Antiplasmodial halogenated monoterpenes from the marine red alga Plocamium cornutum. , 2009, Phytochemistry.

[32]  Phang Siew-Moi.  Biologically active polybrominated indoles in the red alga Laurencia similis from the coastal waters of Sabah (Rhodomelaceae, Ceramiales). , 2004 .

[33]  Minoru Suzuki,et al.  Diterpenoid feeding-deterrents from Laurencia saitoi , 1998 .

[34]  G. Pohnert,et al.  Searching for signals in the noise: metabolomics in chemical ecology , 2010, Analytical and bioanalytical chemistry.

[35]  P. Jensen,et al.  Neomangicols: Structures and Absolute Stereochemistries of Unprecedented Halogenated Sesterterpenes from a Marine Fungus of the Genus Fusarium. , 1999 .

[36]  P. Scheuer,et al.  Two new chamigranes from an hawaiian red alga, Laurencia cartilaginea , 1997 .

[37]  C. Walsh,et al.  Halogenation strategies in natural product biosynthesis. , 2008, Chemistry & biology.

[38]  C. Amsler,et al.  Defenses of polar macroalgae against herbivores and biofoulers , 2009 .

[39]  G. Chlipala,et al.  Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua. , 2009, Journal of natural products.

[40]  Lijun Han,et al.  Sesquiterpenes from the red alga Laurencia tristicha. , 2005, Journal of natural products.

[41]  E. P. Stout,et al.  Antimalarial bromophycolides J-Q from the Fijian red alga Callophycus serratus. , 2009, The Journal of organic chemistry.

[42]  P. Horta,et al.  Isolation of elatol from Laurencia microcladia and its palatability to the sea urchin Echinometra lucunter , 2009 .

[43]  Oliver Fiehn,et al.  Combining Genomics, Metabolome Analysis, and Biochemical Modelling to Understand Metabolic Networks , 2001, Comparative and functional genomics.

[44]  Michael A. Borowitzka,et al.  Microalgae as sources of pharmaceuticals and other biologically active compounds , 1995, Journal of Applied Phycology.

[45]  M. Allen,et al.  The isolation and structure of aplysistatin. , 1977, Journal of the American Chemical Society.

[46]  Karen L. Erickson.  Chapter 4 – Constituents of Laurencia , 1983 .

[47]  H. Laatsch,et al.  Bromoanaindolone, a novel antimicrobial exometabolite from the cyanobacterium Anabaena constricta , 2009, Natural product research.

[48]  M. Hay,et al.  Are Tropical Plants Better Defended? Palatability and Defenses of Temperate vs. Tropical Seaweeds , 1996 .

[49]  M. Satake,et al.  Gambieric acids, new potent antifungal substances with unprecedented polyether structures from a marine dinoflagellate Gambierdiscus toxicus , 1992 .

[50]  P. Pandey.  Endangered Medicinal Species of the Indian Ocean: Radical Need for Conservation , 2009, Chemistry & biodiversity.

[51]  Mark R. Viant,et al.  Environmental metabolomics: a critical review and future perspectives , 2009, Metabolomics.

[52]  R. Tollrian,et al.  Chemical cues, defence metabolites and the shaping of pelagic interspecific interactions. , 2007, Trends in ecology & evolution.

[53]  W. Fenical,et al.  CHEMOTAXONOMY IN MARINE ALGAE: CHEMICAL SEPARATION OF SOME LAURENCIA SPECIES (RHODOPHYTA) FROM THE GULF OF CALIFORNIA 1 , 1975 .

[54]  P. Potin,et al.  New trends in marine chemical ecology , 2006 .

[55]  J. Wiseman,et al.  Desorption Electrospray Ionization ( DESI ) Mass Spectrometry : A brief introduction and overview , 2022 .

[56]  M. Ghiselin,et al.  Marine Natural Products Chemistry as an Evolutionary Narrative , 2001 .

[57]  V. Paul,et al.  Lyngbyastatins 8–10, Elastase Inhibitors with Cyclic Depsipeptide Scaffolds Isolated from the Marine Cyanobacterium Lyngbya semiplena , 2009, Marine drugs.

[58]  Zheng Ouyang,et al.  Ambient Mass Spectrometry , 2006, Science.

[59]  G. Bernardinelli,et al.  Venustatriol. A new, anti-viral, triterpene tetracyclic ether from Laurencia venusta , 1986 .

[60]  Simone Brogi,et al.  Tetrahydrofuran acetogenins from Laurencia glandulifera. , 2009, Journal of natural products.

[61]  D. Faulkner.  Marine natural products (1999) , 2001 .

[62]  P. Reddy,et al.  Meroditerpenoids from the southern Australian marine brown alga Sargassum fallax. , 2009, Phytochemistry.

[63]  J. Pezzuto,et al.  Brominated sesquiterpenes from the red alga Laurencia obtusa. , 2003, Journal of natural products.

[64]  V. Roussis,et al.  C15 acetogenins with antistaphylococcal activity from the red alga Laurencia glandulifera , 2008 .

[65]  V. Paul,et al.  Chemical Defenses: From Compounds to Communities , 2007, The Biological Bulletin.

[66]  J. Kubanek,et al.  Competing phytoplankton undermines allelopathy of a bloom-forming dinoflagellate , 2008, Proceedings of the Royal Society B: Biological Sciences.

[67]  Lik Tong Tan,et al.  Bioactive natural products from marine cyanobacteria for drug discovery. , 2007, Phytochemistry.

[68]  Lijun Han,et al.  [Studies on chemical constituents of Laurencia saitoi]. , 2009, Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.

[69]  R. Nys,et al.  Seaweed-herbivore interactions at a small scale: direct tests of feeding deterrence by filamentous algae , 2006 .

[70]  Xiao‐Ming Li,et al.  Brominated Selinane Sesquiterpenes from the Marine Brown Alga Dictyopteris divaricata , 2009, Marine drugs.

[71]  Amy L. Lane,et al.  Reactive desorption electrospray ionization mass spectrometry (DESI-MS) of natural products of a marine alga , 2009, Analytical and bioanalytical chemistry.