Synthesis and Characterization of Arsenolipids: Naturally Occurring Arsenic Compounds in Fish and Algae

作者: Mojtaba S. Taleshi , Rune K. Seidler-Egdal , Kenneth B. Jensen , Tanja Schwerdtle , Kevin A. Francesconi

DOI: 10.1021/OM4011092

关键词: Fish <Actinopterygii>BiotransformationLong chainOrganic chemistrySodiumAlgaeArsenicChemistrySpectral properties

摘要: Arsenic-containing lipids (arsenolipids) are natural products present in fish and algae. Because these compounds occur foods, there is considerable interest their human toxicology. We report the synthesis characterization of seven arsenic-containing lipids, including six products. The comprise dimethylarsinyl groups attached to saturated long-chain hydrocarbons (three compounds), fatty acids (two monounsaturated long chain compounds). arsenic group was introduced through sodium dimethylarsenide or bis(dimethylarsenic) oxide. latter route provided higher more reproducible yields, consequently, this pathway followed synthesize compounds. Mass spectral properties described assist identification samples. pure synthesized arsenolipids will be used for vitro experiments with cells test uptake, biotransformation, possible toxic effects.

参考文章(32)
Masatoshi Morita, Yasuyuki Shibata, Isolation and identification of arseno-lipid from a brown alga, () Chemosphere. ,vol. 17, pp. 1147- 1152 ,(1988) , 10.1016/0045-6535(88)90180-4
William E. Hill, Mohammad Q. Islam, Thomas R. Webb, Charles A. McAuliffe, Unsymmetrical bisphosphorus compounds. Routes to the successful preparation of Ph2P(CH2)nPR2 (n = 6, 8; R = Me, Et) Inorganica Chimica Acta. ,vol. 146, pp. 111- 114 ,(1988) , 10.1016/S0020-1693(00)80035-3
Kenneth O Amayo, Andrea Raab, Eva M Krupp, Jörg Feldmann, Identification of arsenolipids and their degradation products in cod-liver oil. Talanta. ,vol. 118, pp. 217- 223 ,(2014) , 10.1016/J.TALANTA.2013.09.056
J. S. Edmonds, K. A. Francesconi, R. V. Stick, Arsenic compounds from marine organisms Natural Product Reports. ,vol. 10, pp. 421- 428 ,(1993) , 10.1039/NP9931000421
Uriel Arroyo-Abad, Jürgen Mattusch, Sibylle Mothes, Monika Möder, Rainer Wennrich, Maria P. Elizalde-González, Frank-Michael Matysik, Detection of arsenic-containing hydrocarbons in canned cod liver tissue Talanta. ,vol. 82, pp. 38- 43 ,(2010) , 10.1016/J.TALANTA.2010.03.054
Veronika Sele, Jens J. Sloth, Anne-Katrine Lundebye, Erik H. Larsen, Marc H.G. Berntssen, Heidi Amlund, Arsenolipids in marine oils and fats: A review of occurrence, chemistry and future research needs Food Chemistry. ,vol. 133, pp. 618- 630 ,(2012) , 10.1016/J.FOODCHEM.2012.02.004
R. V. Cooney, R. O. Mumma, A. A. Benson, Arsoniumphospholipid in algae Proceedings of the National Academy of Sciences of the United States of America. ,vol. 75, pp. 4262- 4264 ,(1978) , 10.1073/PNAS.75.9.4262
Uriel Arroyo-Abad, Susanne Lischka, Christian Piechotta, Jürgen Mattusch, Thorsten Reemtsma, Determination and identification of hydrophilic and hydrophobic arsenic species in methanol extract of fresh cod liver by RP-HPLC with simultaneous ICP-MS and ESI-Q-TOF-MS detection. Food Chemistry. ,vol. 141, pp. 3093- 3102 ,(2013) , 10.1016/J.FOODCHEM.2013.05.152
Ines Mancini, Graziano Guella, Maryvonne Frostin, Edouard Hnawia, Dominique Laurent, Cecile Debitus, Francesco Pietra, On the First Polyarsenic Organic Compound from Nature: Arsenicin A from the New Caledonian Marine Sponge Echinochalina bargibanti Chemistry: A European Journal. ,vol. 12, pp. 8989- 8994 ,(2006) , 10.1002/CHEM.200600783