Phosphatidylarsenocholine, one of the major arsenolipids in marine organisms: Synthesis and metabolism in mice

Food and Chemical Toxicology

Volumn 49, Issue 7, 2011, Pages 1598-1603

  Fukuda, Syoko ^a   Terasawa, Misaki ^a   Shiomi, Kazuo ^a  

^a TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Arsenic; Arsenobetaine; Arsenocholine; Arsenolipid; Metabolism; Phosphatidylarsenocholine

Indexed keywords

ARSENIC; ARSENOBETAINE; ARSENOCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; PHOSPHATIDYLARSENOCHOLINE; PHOSPHOLIPASE D; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; ELECTROSPRAY MASS SPECTROMETRY; ENZYME MECHANISM; GASTROINTESTINAL ABSORPTION; ION MONITORING; LIPID METABOLISM; LIPID SOLUBILITY; LIPOGENESIS; LIQUID CHROMATOGRAPHY; MALE; MARINE SPECIES; MOUSE; NONHUMAN; TRANSPHOSPHATIDYLATION; URINARY EXCRETION;

ADMINISTRATION, ORAL; ANIMALS; AQUATIC ORGANISMS; ARSENIC; ARSENICALS; CHROMATOGRAPHY, LIQUID; GASTROINTESTINAL TRACT; MALE; MASS SPECTROMETRY; MICE; PHOSPHATIDYLCHOLINES; WATER;

MUS;

EID: 79957644388     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2011.03.053     Document Type: Article

References (22)

1. Devalla S., Feldmann J. Determination of lipid-soluble arsenic species in seaweed-eating sheep from Orkney. Appl. Organomet. Chem. 2003, 17:906-912.
2. Ebisuda K., Kunito T., Fujihara J., Kubota R., Shibata Y., Tanabe S. Lipid-soluble and water-soluble arsenic compounds in blubber of ringed seal (Pusa hispida). Talanta 2003, 61:779-787.
3. Edmonds J.S., Shibata Y., Francesconi K.A., Yoshinaga J., Morita M. Arsenic lipids in the digestive gland of the western rock lobster Panulirus cygnus: an investigation by HPLC ICP-MS. Sci. Total Environ. 1992, 122:321-335.
4. Francesconi K.A., Edmonds J.S. Arsenic and marine organisms. Adv. Organomet. Chem. 1997, 44:147-189.
5. Hanaoka K., Goessler W., Yoshida K., Fujitaka Y., Kaise T., Irgolic K.J. Arsenocholine- and dimethylated arsenic-containing lipids in starspotted shark Mustelus manazo. Appl. Organomet. Chem. 1999, 13:765-770.
6. Hanaoka K., Tanaka Y., Nagata Y., Yoshida K., Kaise T. Water-soluble arsenic residues from several arsenolipids occurring in the tissues of the starspotted shark Mustelus manazo. Appl. Organomet. Chem. 2001, 15:299-305.
7. Hayakawa J., Okabayashi Y. Simultaneous analysis of phospholipids in rabbit bronchoalveolar lavage fluid by liquid chromatography/mass spectrometry. J. Pharm. Biomed. Anal. 2004, 35:583-592.
8. Hosokawa M., Shimatani T., Kanada T., Inoue Y., Takahashi K. Conversion to docosahexaenoic acid-containing phosphatidylserine from squid skin lecithin by phospholipase D-mediated transphosphatidylation. J. Agric. Food Chem. 2000, 48:4550-4554.
9. Imamura S., Horiuti Y. Purification of Streptomyces chromofuscus phospholipase D by hydrophobic affinity chromatography on palmitoyl cellulose. J. Biochem. 1979, 85:79-95.
10. Kaise T., Horiguchi Y., Fukui S., Shiomi K., Chino M., Kikuchi T. Acute toxicity and metabolism of arsenocholine in mice. Appl. Organomet. Chem. 1992, 6:369-373.
11. Morita M., Shibata Y. Isolation and identification of arseno-lipid from a brown alga, Undaria pinnatifida (Wakeme). Chemosphere 1988, 17:1147-1152.
12. Nagao A., Ishida N., Terao J. Synthesis of 6-phosphatidyl-l-ascorbic acid by phospholipase D. Lipids 1991, 26:390-394.
13. Ninh T.D., Nagashima Y., Shiomi K. Quantification of seven arsenic compounds in seafood products by liquid chromatography/electrospray ionization-single quadrupole mass spectrometry (LC/ESI-MS). Food Addit. Contam. 2006, 23:1299-1307.
14. Ninh T.D., Nagashima Y., Shiomi K. Water-soluble and lipid-soluble arsenic compounds in Japanese flying squid Todarodes pacificus. J. Agric. Food Chem. 2007, 55:3196-3202.
15. Rumpler A., Edmonds J.S., Katsu M., Jensen K.B., Goessler W., Raber G., Gunnlaugsdottir H., Francesconi K.V. Arsenic-containing long-chain fatty acids in cod-liver oil: a result of biosynthetic infidelity?. Angew. Chem. Int. Ed. 2008, 47:2665-2667.
16. Schmeisser E., Goessler W., Francesconi K.A. Human metabolism of arsenolipids present in cod liver. Anal. Bioanal. Chem. 2006, 385:367-376.
17. Shiomi K. Arsenic in marine organisms. Arsenic in the Environments. Part II: Human Health and Ecosystem Effects 1994, 261-282. John Wiley and Sons, New York. J.O. Nriagu (Ed.).
18. Shiomi K., Horiguchi Y., Kaise T. Acute toxicity and rapid excretion in urine of tetramethylarsonium salts found in some marine animals. Appl. Organomet. Chem. 1988, 2:385-389.
19. Shuto S., Ito H., Ueda S., Imamura S., Fukukawa K., Tsujino M., Matsuda A., Ueda T. Chem. Pharm. Bull. 1988, 36:209-217.
20. Taleshi M.S., Jensen K.B., Raber G., Edmonds J.S., Gunnlaugsdottir H., Francesconi K.A. Arsenic-containing hydrocarbons: natural compounds in oil from the fish capelin, Mallotus villosus. Chem. Commun. 2008, 39:4706-4707.
21. Vahter M., Marafante E., Dencker L. Metabolism of arsenobetaine in mice, rats, and rabbits. Sci. Total Environ. 1983, 30:197-211.
22. Yamauchi H., Takahashi K., Yamamura Y., Kaise T. Metabolism and excretion of orally and intraperitoneally administered trimethylarsine oxide in the hamster. Toxicol. Environ. Chem. 1989, 22:69-76.