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Arsenolipids in oil from blue whiting Micromesistius poutassou--evidence for arsenic-containing esters.

Taleshi MS, Raber G, Edmonds JS, Jensen KB, Francesconi KA - Sci Rep (2014)

Bottom Line: The polar lipid fraction constituting 24% of the total arsenolipid content (which totalled 2.16 μg As/g) contained four known dimethylarsinoyl fatty acids and three known dimethylarsinoyl hydrocarbons.The less polar fraction (ca 30% of the total arsenolipids) contained four new dimethylarsinoyl hydrocarbons with chain lengths 22-30 carbons, in addition to more complex arsenicals that hydrolysed to known dimethylarsinoyl fatty acids suggesting they were conjugated carboxylic acids, presumably esters.The rest of the lipid-soluble arsenic (ca 45% of the total) remained in the non-polar fraction together with the bulk of the fish oil lipids, a complex mixture of compounds that precluded identification of the small amounts of arsenolipids.

View Article: PubMed Central - PubMed

Affiliation: 1] Institute of Chemistry-Analytical Chemistry, University of Graz, Universitaetsplatz 1, 8010 Graz, Austria [2] Department of Marine Chemistry, Faculty of Marine Science, University of Mazandaran, Babolsar, Iran.

ABSTRACT
Arsenic-containing lipids in the oil from the blue whiting fish (Micromesistius poutassou) were separated into three broad polarity groups and investigated by HPLC and mass spectrometry. A total of 11 arsenolipids including 4 new compounds were identified. The polar lipid fraction constituting 24% of the total arsenolipid content (which totalled 2.16 μg As/g) contained four known dimethylarsinoyl fatty acids and three known dimethylarsinoyl hydrocarbons. The less polar fraction (ca 30% of the total arsenolipids) contained four new dimethylarsinoyl hydrocarbons with chain lengths 22-30 carbons, in addition to more complex arsenicals that hydrolysed to known dimethylarsinoyl fatty acids suggesting they were conjugated carboxylic acids, presumably esters. The rest of the lipid-soluble arsenic (ca 45% of the total) remained in the non-polar fraction together with the bulk of the fish oil lipids, a complex mixture of compounds that precluded identification of the small amounts of arsenolipids.

Show MeSH
Known arsenolipids found in blue whiting oil.For ease of reference, the arsenic fatty acids and arsenic hydrocarbons are referred to by the abbreviation As-FA and As-HC, respectively, followed by their nominal molecular mass.
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f1: Known arsenolipids found in blue whiting oil.For ease of reference, the arsenic fatty acids and arsenic hydrocarbons are referred to by the abbreviation As-FA and As-HC, respectively, followed by their nominal molecular mass.

Mentions: The aqueous methanol extract was fractionated by preparative anion-exchange chromatography into an acidic fraction and a non-acidic fraction, which were further investigated by using HPLC/electrospray ionisation-MS, in simultaneous elemental and molecular mode. This method records, at the same time, a signal for arsenic and for selected molecular masses for the HPLC peaks, thereby allowing the assignment of a molecular mass to arsenic-containing compounds12. The acidic fraction yielded four known arsenic fatty acids with molecular masses 362, 388, 436 and 390, identified by comparison with arsenolipids previously identified in cod-liver oil3 (Fig. 1, compounds 1–4). These four arsenic fatty acids were estimated to constitute less than 5% of the total arsenolipid content in blue-whiting oil. The non-acidic portion of the polar lipid fraction was similarly analysed by HPLC/ESI-MS and shown to contain three known arsenic-containing hydrocarbons (Fig. 1, compounds 5–7), first identified in capelin oil4.


Arsenolipids in oil from blue whiting Micromesistius poutassou--evidence for arsenic-containing esters.

Taleshi MS, Raber G, Edmonds JS, Jensen KB, Francesconi KA - Sci Rep (2014)

Known arsenolipids found in blue whiting oil.For ease of reference, the arsenic fatty acids and arsenic hydrocarbons are referred to by the abbreviation As-FA and As-HC, respectively, followed by their nominal molecular mass.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4265782&req=5

f1: Known arsenolipids found in blue whiting oil.For ease of reference, the arsenic fatty acids and arsenic hydrocarbons are referred to by the abbreviation As-FA and As-HC, respectively, followed by their nominal molecular mass.
Mentions: The aqueous methanol extract was fractionated by preparative anion-exchange chromatography into an acidic fraction and a non-acidic fraction, which were further investigated by using HPLC/electrospray ionisation-MS, in simultaneous elemental and molecular mode. This method records, at the same time, a signal for arsenic and for selected molecular masses for the HPLC peaks, thereby allowing the assignment of a molecular mass to arsenic-containing compounds12. The acidic fraction yielded four known arsenic fatty acids with molecular masses 362, 388, 436 and 390, identified by comparison with arsenolipids previously identified in cod-liver oil3 (Fig. 1, compounds 1–4). These four arsenic fatty acids were estimated to constitute less than 5% of the total arsenolipid content in blue-whiting oil. The non-acidic portion of the polar lipid fraction was similarly analysed by HPLC/ESI-MS and shown to contain three known arsenic-containing hydrocarbons (Fig. 1, compounds 5–7), first identified in capelin oil4.

Bottom Line: The polar lipid fraction constituting 24% of the total arsenolipid content (which totalled 2.16 μg As/g) contained four known dimethylarsinoyl fatty acids and three known dimethylarsinoyl hydrocarbons.The less polar fraction (ca 30% of the total arsenolipids) contained four new dimethylarsinoyl hydrocarbons with chain lengths 22-30 carbons, in addition to more complex arsenicals that hydrolysed to known dimethylarsinoyl fatty acids suggesting they were conjugated carboxylic acids, presumably esters.The rest of the lipid-soluble arsenic (ca 45% of the total) remained in the non-polar fraction together with the bulk of the fish oil lipids, a complex mixture of compounds that precluded identification of the small amounts of arsenolipids.

View Article: PubMed Central - PubMed

Affiliation: 1] Institute of Chemistry-Analytical Chemistry, University of Graz, Universitaetsplatz 1, 8010 Graz, Austria [2] Department of Marine Chemistry, Faculty of Marine Science, University of Mazandaran, Babolsar, Iran.

ABSTRACT
Arsenic-containing lipids in the oil from the blue whiting fish (Micromesistius poutassou) were separated into three broad polarity groups and investigated by HPLC and mass spectrometry. A total of 11 arsenolipids including 4 new compounds were identified. The polar lipid fraction constituting 24% of the total arsenolipid content (which totalled 2.16 μg As/g) contained four known dimethylarsinoyl fatty acids and three known dimethylarsinoyl hydrocarbons. The less polar fraction (ca 30% of the total arsenolipids) contained four new dimethylarsinoyl hydrocarbons with chain lengths 22-30 carbons, in addition to more complex arsenicals that hydrolysed to known dimethylarsinoyl fatty acids suggesting they were conjugated carboxylic acids, presumably esters. The rest of the lipid-soluble arsenic (ca 45% of the total) remained in the non-polar fraction together with the bulk of the fish oil lipids, a complex mixture of compounds that precluded identification of the small amounts of arsenolipids.

Show MeSH