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RESEARCH ARTICLE (Open Access)

Arsenosugar phospholipids and arsenic hydrocarbons in two species of brown macroalgae

Sara García-Salgado A , Georg Raber B D , Reingard Raml C , Christoph Magnes C and Kevin A. Francesconi B
+ Author Affiliations
- Author Affiliations

A School of Civil Engineering, Department of Hydraulic and Energy Technology, University College for the Technical Engineering of Public Works, Polytechnic University of Madrid, E-28014 Madrid, Spain.

B Institute of Chemistry – Analytical Chemistry, Karl-Franzens University Graz, A-8010 Graz, Austria.

C HEALTH – Institute for Biomedicine and Health Sciences, Joanneum Research, A-8036 Graz, Austria.

D Corresponding author. Email: georg.raber@uni-graz.at

Environmental Chemistry 9(1) 63-66 https://doi.org/10.1071/EN11164
Submitted: 20 December 2011  Accepted: 17 January 2012   Published: 14 February 2012

Journal Compilation © CSIRO Publishing JYEAR Open Access CC BY-NC-ND

Environmental context. Although organoarsenic compounds occur in marine organisms at high concentrations, the origin and role of these compounds is unknown. Arsenic-containing lipids (arsenolipids) are newly discovered compounds in fish. We identify a range of arsenolipids in algae and propose that algae are the origin of these unusual arsenic compounds in marine ecosystems.

Abstract. Fourteen arsenolipids, including 11 new compounds, were identified and quantified in two species of brown algae, Wakame (Undaria pinnatifida) and Hijiki (Hizikia fusiformis), by high resolution mass spectrometry, high performance liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry. Both algal species contained arsenosugar-phospholipids as the major type of arsenolipid, and arsenic-hydrocarbons were also significant components, particularly in Hijiki. The origin of the various arsenolipids, and the possible significance of their relative quantities, is briefly discussed.


References

[1]  K. A. Francesconi, J. S. Edmonds, Arsenic and marine organisms. Adv. Inorg. Chem. 1997, 44, 147.
| 1:CAS:528:DyaK2sXhsVajtbs%3D&md5=d94bd17c5ae977ea49c0ef689ca97d1eCAS |

[2]  G. Lunde, The synthesis of fat and water soluble arseno organic compounds in marine and limnetic algae. Acta Chem. Scand. 1973, 27, 1586.
The synthesis of fat and water soluble arseno organic compounds in marine and limnetic algae.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXltlCitbY%3D&md5=9c0809c72eb7cd3334de3cf0beb4e343CAS |

[3]  R. V. Cooney, R. O. Mumma, A. A. Benson, Arsoniumphospholipid in algae. Proc. Natl. Acad. Sci. USA 1978, 75, 4262.
Arsoniumphospholipid in algae.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXhvFShtQ%3D%3D&md5=0f71fc9f2c9a87c3149032d0fc1f5a30CAS |

[4]  J. J. Wrench, R. F. Addison, Reduction, methylation, and incorporation of arsenic into lipids by the marine-phytoplankton Dunaliella tertiolecta. Can. J. Fish. Aquat. Sci. 1981, 38, 518.
Reduction, methylation, and incorporation of arsenic into lipids by the marine-phytoplankton Dunaliella tertiolecta.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXksFGkt74%3D&md5=27d6839c715f100d37e9448d8a12ec0aCAS |

[5]  M. Morita, Y. Shibata, Isolation and identification of arseno-lipid from a brown alga, Undaria pinnatifida (Wakame). Chemosphere 1988, 17, 1147.
Isolation and identification of arseno-lipid from a brown alga, Undaria pinnatifida (Wakame).Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXkvVOlt78%3D&md5=cd17541ee1fd9c0b7f3ecbad743a2e69CAS |

[6]  A. Rumpler, J. S. Edmonds, M. Katsu, K. B. Jensen, W. Goessler, G. Raber, H. Gunnlaugsdottir, K. A. Francesconi, Arsenic-containing long-chain fatty acids in cod liver oil: a result of biosynthetic infidelity. Angew. Chem. Int. Ed. 2008, 47, 2665.
Arsenic-containing long-chain fatty acids in cod liver oil: a result of biosynthetic infidelity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXkvFejsL4%3D&md5=d28e6f01dd610ac43a22cc186ab76f07CAS |

[7]  M. S. Taleshi, K. B. Jensen, G. Raber, J. S. Edmonds, H. Gunnlaugsdottir, K. A. Francesconi, Arsenic-containing hydrocarbons: Natural compounds in oil from the fish capelin, Mallotus villosus. Chem. Commun. 2008, 39, 4706.
Arsenic-containing hydrocarbons: Natural compounds in oil from the fish capelin, Mallotus villosus.Crossref | GoogleScholarGoogle Scholar |

[8]  U. Arroyo-Abad, J. Mattusch, S. Mothes, M. Moeder, R. Wennrich, M. P. Elizalde-Gonzalez, F. M. Matysik, Detection of arsenic-containing hydrocarbons in canned cod liver tissue. Talanta 2010, 82, 38.
Detection of arsenic-containing hydrocarbons in canned cod liver tissue.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntVyktbo%3D&md5=9f0f1132bab9829fcf02cf1670e5d3f4CAS |

[9]  M. S. Taleshi, J. S. Edmonds, W. Goessler, M. J. Ruiz-Chancho, G. Raber, K. B. Jenson, K. A. Francesconi, Arsenic-containing lipids are natural constituents of sashimi tuna. Environ. Sci. Technol. 2010, 44, 1478.
Arsenic-containing lipids are natural constituents of sashimi tuna.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptlymtg%3D%3D&md5=62e81b7eae7f468593e1c7eb8d089359CAS |

[10]  K. O. Amayo, A. Petursdottir, C. Newcombe, H. Gunnlaugsdottir, A. Raab, E. M. Krupp, J. Feldmann, Identification and quantification of arsenolipids using reversed-phase HPLC coupled simultaneously to High-Resolution ICPMS and High-Resolution Electrospray MS without Species-Specific Standards. Anal. Chem. 2011, 83, 3589.
| 1:CAS:528:DC%2BC3MXksFaktL4%3D&md5=416d9d52be689503f7dcb2996b5ee2d6CAS |

[11]  E. G. Bligh, W. J. Dyer, A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 1959, 37, 911.
A rapid method of total lipid extraction and purification.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXhtVSgt70%3D&md5=1787b0c250b0b5bc032e6143e23adf51CAS |

[12]  G. Raber, S. Khoomrung, M. S. Taleshi, J. S. Edmonds, K. A. Francesconi, Identification of arsenolipids with GC/MS. Talanta 2009, 78, 1215.
Identification of arsenolipids with GC/MS.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjtVSnsL8%3D&md5=62321dda92c7528f428cc6960fd07dc3CAS |

[13]  G. Raber, R. Raml, W. Goessler, K. A. Francesconi, Quantitative speciation of arsenic compounds when using organic solvent gradients in HPLC-ICPMS. J. Anal. At. Spectrom. 2010, 25, 570.
Quantitative speciation of arsenic compounds when using organic solvent gradients in HPLC-ICPMS.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjslWisL4%3D&md5=4409bb12de54221f8639395e137257cdCAS |

[14]  M. J. Ruiz-Chancho, M. S. Taleshi, W. Goessler, K. A. Francesconi, A method for screening arsenolipids in fish oils by HPLC-ICPMS. J. Anal. At. Spectrom. 2011, [Published online ahead of print 13 December 2011]
A method for screening arsenolipids in fish oils by HPLC-ICPMS.Crossref | GoogleScholarGoogle Scholar |

[15]  A. Benson, Arsonium compounds in algae. Proc. Natl. Acad. Sci. USA 1989, 86, 6131.
Arsonium compounds in algae.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXmtFWmu74%3D&md5=77a9746596fe273a04dc8f73e37d3edbCAS |

[16]  J. S. Edmonds, Y. Shibata, K. A. Francesconi, J. Yoshinaga, M. Morita, Arsenic lipids in the digestive gland of the western rock lobster Panulirus cygnus: an investigation by HPLC ICP-MS. Sci. Total Environ. 1992, 122, 321.
Arsenic lipids in the digestive gland of the western rock lobster Panulirus cygnus: an investigation by HPLC ICP-MS.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XmtV2itL4%3D&md5=57446df7fc7377bd9be8a4a54eee4dbfCAS |

[17]  S. Devalla, J. Feldmann, Determination of lipid-soluble arsenic species in seaweed-eating sheep from Orkney. Appl. Organomet. Chem. 2003, 17, 906.
Determination of lipid-soluble arsenic species in seaweed-eating sheep from Orkney.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpvV2hs7k%3D&md5=ed883f7d0a1003daa663bc8f326b1c2bCAS |

[18]  B. A. S. Van Mooy, H. F. Fredricks, B. E. Pedler, S. T. Dyhrman, D. M. Karl, M. Koblizek, M. W. Lomas, T. J. Mincer, L. R. Moore, T. Moutin, M. S. Rappe, E. A. Webb, Phytoplankton in the ocean use non-phosphorus lipids in response to phosphorus scarcity. Nature 2009, 458, 69.
Phytoplankton in the ocean use non-phosphorus lipids in response to phosphorus scarcity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1ehtbY%3D&md5=32db6bf5d2a56fd088d3080cb06469e6CAS |