2-Aminoethylphosphonic Acid Metabolism in the Rat

Overview

Journal Lipids

Specialty Biochemistry

Date 1977 Jan 1

PMID 834125

Citations 3

Authors

J C Joseph

T O Henderson

Affiliations

Soon will be listed here.

Abstract

Time course studies of the incorporation of radioactive 2-aminoethylphosphonic acid (AEP) into the tissues of rats demonstrated that maximum incorporation into the liver lipids occurred within 12 to 30 hr after injection, compared to 2 to 3 hr for the incorporation of phosphorylethanolamine. Little incorporation of AEP was observed in the other tissues investigated (heart, lung, spleen, adipose, kidney). The AEP was incorporated to the greatest extent into 1,2-diacylglyceryl-aminoethylphosphonate (diacylglyceryl-AEP), the phosphonate analogue of phosphatidylethanolamine, with some incorporation into the lyso derivative. Diacylglycerol-AEP apparently was not further metabolized by the rat; no methylation of diacylglyceryl-AEP to phosphonolecithin was observed. Subcellular fractionation was performed on the livers of rats who received (3)H-AEP 12,30,36, and 48 hr prior to sacrifice. The greatest amount of radioactivity was recovered in the soluble fractions. Lipid extraction was performed on the subcellular fractions, and most of the radioactivity present in the lipids was found in the microsomal fraction, with the next highest recovery in the mitochondrial and nuclear fractions

Citing Articles

Maternal Nutrient Restriction Disrupts Gene Expression and Metabolites Associated with Urea Cycle, Steroid Synthesis, Glucose Homeostasis, and Glucuronidation in Fetal Calf Liver.

Muroya S, Zhang Y, Otomaru K, Oshima K, Oshima I, Sano M Metabolites. 2022; 12(3).

PMID: 35323646 PMC: 8949217. DOI: 10.3390/metabo12030203.

Pcyt2 deficiency causes age-dependant development of nonalcoholic steatohepatitis and insulin resistance that could be attenuated with phosphoethanolamine.

Grapentine S, Singh R, Basu P, Sivanesan S, Mattos G, Oresajo O Sci Rep. 2022; 12(1):1048.

PMID: 35058529 PMC: 8776951. DOI: 10.1038/s41598-022-05140-y.

Maternal Undernutrition during Pregnancy Alters Amino Acid Metabolism and Gene Expression Associated with Energy Metabolism and Angiogenesis in Fetal Calf Muscle.

Muroya S, Zhang Y, Kinoshita A, Otomaru K, Oshima K, Gotoh Y Metabolites. 2021; 11(9).

PMID: 34564398 PMC: 8465837. DOI: 10.3390/metabo11090582.

References

Sellinger O, BEAUFAY H, Jacques P, Doyen A, DE DUVE C . Tissue fractionation studies. 15. Intracellular distribution and properties of beta-N-acetylglucosaminidase and beta-galactosidase in rat liver. Biochem J. 1960; 74:450-6. PMC: 1204241. DOI: 10.1042/bj0740450. View

Alhadeff J, VAN BRUGGEN J, Daves Jr G . Biosynthetic studies on 2-aminoethylphosphonic acid in a mammalian (rat) system. Biochim Biophys Acta. 1972; 286(1):103-6. DOI: 10.1016/0304-4165(72)90095-5. View

COOPERSTEIN S, LAZAROW A . A microspectrophotometric method for the determination of cytochrome oxidase. J Biol Chem. 1951; 189(2):665-70. View

SCHNEIDER W . INTRACELLULAR DISTRIBUTION OF ENZYMES. XIII. ENZYMATIC SYNTHESIS OF DEOXYCYTIDINE DIPHOSPHATE CHOLINE AND LECITHIN IN RAT LIVER. J Biol Chem. 1963; 238:3572-8. View

McMurray W, Dawson R . Phospholipid exchange reactions within the liver cell. Biochem J. 1969; 112(1):91-108. PMC: 1187645. DOI: 10.1042/bj1120091. View

Yang S, Freer S, Benson A . Transphosphatidylation by phospholipase D. J Biol Chem. 1967; 242(3):477-84. View

Smith J, Law J . Phosphatidylcholine biosynthesis in Tetrahymena pyriformis. Biochim Biophys Acta. 1970; 202(1):141-52. DOI: 10.1016/0005-2760(70)90225-0. View

Liang C, Rosenberg H . The biosynthesis of the phosphonic analogue of cephalin in tetrahymena. Biochim Biophys Acta. 1966; 125(3):548-62. DOI: 10.1016/0005-2760(66)90043-9. View

Curley J, Henderson T . The incorporation of 2-aminoethylphosphonic acid into rat liver diacylglyceroaminoethylphosphonate. Lipids. 1972; 7(10):676-9. DOI: 10.1007/BF02533076. View

10.

DE DUVE C, PRESSMAN B, GIANETTO R, WATTIAUX R, APPELMANS F . Tissue fractionation studies. 6. Intracellular distribution patterns of enzymes in rat-liver tissue. Biochem J. 1955; 60(4):604-17. PMC: 1216159. DOI: 10.1042/bj0600604. View

11.

PONTICORVO L, Rittenberg D, Bloch K . The utilization of acetate for the synthesis of fatty acids, cholesterol, and protoporphyrin. J Biol Chem. 1949; 179(2):839-42. View

12.

KRAUSE R, BEAMER K, LOTSPEICH F . Phosphonolipid metabolism in control and vitamin A deficient rats. Proc Soc Exp Biol Med. 1972; 140(2):544-7. DOI: 10.3181/00379727-140-36499. View

13.

Alhadeff J, Daves Jr G . 2-Aminoethylphosphonic acid: distribution in human tissues. Biochim Biophys Acta. 1971; 244(1):211-3. DOI: 10.1016/0304-4165(71)90139-5. View

14.

Smith J, Law J . Phosphonic acid metabolism in Tetrahymena. Biochemistry. 1970; 9(10):2152-7. DOI: 10.1021/bi00812a018. View

15.

Hildebrand J, Law J . FATTY ACID DISTRIBUTION IN BACTERIAL PHOSPHOLIPIDS. THE SPECIFICITY OF THE CYCLOPROPANE SYNTHETASE REACTION. Biochemistry. 1964; 3:1304-8. DOI: 10.1021/bi00897a020. View

16.

Stein O, STEIN Y . Lecithin synthesis, intracellular transport, and secretion in rat liver. IV. A radioautographic and biochemical study of choline-deficient rats injected with choline-3H. J Cell Biol. 1969; 40(2):461-83. PMC: 2107631. DOI: 10.1083/jcb.40.2.461. View

17.

Thompson Jr G . The metabolism of 2-aminoethylphosphonate lipids in Tetrahymena pyriformis. Biochim Biophys Acta. 1969; 176(2):330-8. DOI: 10.1016/0005-2760(69)90191-x. View

18.

Kennedy E, Weiss S . The function of cytidine coenzymes in the biosynthesis of phospholipides. J Biol Chem. 1956; 222(1):193-214. View

19.

Alhadeff J, Daves Jr G . Occurrence of 2-aminoethylphosphonic acid in human brain. Biochemistry. 1970; 9(25):4866-9. DOI: 10.1021/bi00827a006. View

20.

Bjerve K . Lecithin biosynthesis in the rat studied with phosphonate analogues of phosphorylcholine. Biochim Biophys Acta. 1972; 270(3):348-63. DOI: 10.1016/0005-2760(72)90199-3. View