Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1988 Aug 1;253(3):703–710. doi: 10.1042/bj2530703

Formation of methylphosphoryl inositol phosphates by extractions that employ methanol.

J E Brown 1, M Rudnick 1, A J Letcher 1, R F Irvine 1
PMCID: PMC1149362  PMID: 2845928

Abstract

Fixatives that contain methanol extract an unknown compound from several tissues including the retinas of squid (Loligo). We have determined that the compound probably contains (1) a myo-inositol ring that is phosphorylated in more than one position (including at the 5-hydroxyl), (2) a charged moiety that is not susceptible to alkaline phosphatase, and (3) a methyl group. We have found that the compound can be made by treating either phosphatidylinositol bisphosphate or human red cell ghosts with acidic methanol. We have confirmed the observation of Lips, Bross & Majerus [Proc. Natl. Acad. Sci. U.S.A. 85, 88-92] that the compound also can be made by methanolysis of inositol (cyclic 1:2,4,5)trisphosphate; however, we have not found inositol (cyclic 1:2,4,5)trisphosphate in either stimulated or unstimulated squid retinas. We tentatively identify the compound as (1-methylphosphoryl)inositol 4,5-bisphosphate formed by methanolysis of phosphatidylinositol 4,5-bisphosphate. By using this methanolysis to incorporate label from [14C]methanol, we have estimated the mass of inositol 1,4,5-trisphosphate in squid retinas to be approx. 30 mumol/l of retinal volume.

Full text

PDF
703

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Anctil M., Shimomura O. Mechanism of photoinactivation and re-activation in the bioluminescence system of the ctenophore Mnemiopsis. Biochem J. 1984 Jul 1;221(1):269–272. doi: 10.1042/bj2210269. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Batty I. R., Nahorski S. R., Irvine R. F. Rapid formation of inositol 1,3,4,5-tetrakisphosphate following muscarinic receptor stimulation of rat cerebral cortical slices. Biochem J. 1985 Nov 15;232(1):211–215. doi: 10.1042/bj2320211. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Berridge M. J., Irvine R. F. Inositol trisphosphate, a novel second messenger in cellular signal transduction. Nature. 1984 Nov 22;312(5992):315–321. doi: 10.1038/312315a0. [DOI] [PubMed] [Google Scholar]
  4. Brown D. M., Stewart J. C. The structure of triphosphoinositide from beef brain. Biochim Biophys Acta. 1966 Dec 7;125(3):413–421. doi: 10.1016/0005-2760(66)90029-4. [DOI] [PubMed] [Google Scholar]
  5. Brown J. E., Watkins D. C., Malbon C. C. Light-induced changes in the content of inositol phosphates in squid (Loligo pealei) retina. Biochem J. 1987 Oct 15;247(2):293–297. doi: 10.1042/bj2470293. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Burgess G. M., Godfrey P. P., McKinney J. S., Berridge M. J., Irvine R. F., Putney J. W., Jr The second messenger linking receptor activation to internal Ca release in liver. Nature. 1984 May 3;309(5963):63–66. doi: 10.1038/309063a0. [DOI] [PubMed] [Google Scholar]
  7. Clarke N. G., Dawson R. M. Alkaline O leads to N-transacylation. A new method for the quantitative deacylation of phospholipids. Biochem J. 1981 Apr 1;195(1):301–306. doi: 10.1042/bj1950301. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Cohen A. I. An ultrastructural analysis of the photoreceptors of the squid and their synaptic connections. I. Photoreceptive and non-synaptic regions of the retina. J Comp Neurol. 1973 Feb 1;147(3):351–378. doi: 10.1002/cne.901470304. [DOI] [PubMed] [Google Scholar]
  9. Dawson R. M., Clarke N. D-myoinositol 1:2-cyclic phosphate 2-phosphohydrolase. Biochem J. 1972 Mar;127(1):113–118. doi: 10.1042/bj1270113. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Downes C. P., Michell R. H. The polyphosphoinositide phosphodiesterase of erythrocyte membranes. Biochem J. 1981 Jul 15;198(1):133–140. doi: 10.1042/bj1980133. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Downes C. P., Mussat M. C., Michell R. H. The inositol trisphosphate phosphomonoesterase of the human erythrocyte membrane. Biochem J. 1982 Apr 1;203(1):169–177. doi: 10.1042/bj2030169. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. EICHBERG J., DAWSON R. M. THE NON-ENZYMATIC TRANSPHOSPHORYLATION OF LOWER ALIPHATIC ALCOHOLS BY ADENOSINE TRIPHOSPHATE. Biochim Biophys Acta. 1964 Nov 8;93:425–426. doi: 10.1016/0304-4165(64)90397-6. [DOI] [PubMed] [Google Scholar]
  13. GRADO C., BALLOU C. E. Myo-inositol phosphates obtained by alkaline hydrolysis of beef brain phosphoinositide. J Biol Chem. 1961 Jan;236:54–60. [PubMed] [Google Scholar]
  14. Hawkins P. T., Berrie C. P., Morris A. J., Downes C. P. Inositol 1,2-cyclic 4,5-trisphosphate is not a product of muscarinic receptor-stimulated phosphatidylinositol 4,5-bisphosphate hydrolysis in rat parotid glands. Biochem J. 1987 Apr 1;243(1):211–218. doi: 10.1042/bj2430211. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Irvine R. F., Anggård E. E., Letcher A. J., Downes C. P. Metabolism of inositol 1,4,5-trisphosphate and inositol 1,3,4-trisphosphate in rat parotid glands. Biochem J. 1985 Jul 15;229(2):505–511. doi: 10.1042/bj2290505. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Irvine R. F., Letcher A. J., Lander D. J., Berridge M. J. Specificity of inositol phosphate-stimulated Ca2+ mobilization from Swiss-mouse 3T3 cells. Biochem J. 1986 Nov 15;240(1):301–304. doi: 10.1042/bj2400301. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Irvine R. F., Letcher A. J., Lander D. J., Downes C. P. Inositol trisphosphates in carbachol-stimulated rat parotid glands. Biochem J. 1984 Oct 1;223(1):237–243. doi: 10.1042/bj2230237. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Irvine R. F., Moor R. M. Inositol(1,3,4,5)tetrakisphosphate-induced activation of sea urchin eggs requires the presence of inositol trisphosphate. Biochem Biophys Res Commun. 1987 Jul 15;146(1):284–290. doi: 10.1016/0006-291x(87)90723-6. [DOI] [PubMed] [Google Scholar]
  19. Ishii H., Connolly T. M., Bross T. E., Majerus P. W. Inositol cyclic triphosphate [inositol 1,2-(cyclic)-4,5-triphosphate] is formed upon thrombin stimulation of human platelets. Proc Natl Acad Sci U S A. 1986 Sep;83(17):6397–6401. doi: 10.1073/pnas.83.17.6397. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Lips D. L., Bross T. E., Majerus P. W. Isolation of 1-monomethylphosphoinositol 4,5-bisphosphate [a product of methanolysis of inositol 1,2-(cyclic)-4,5-trisphosphate] from Swiss mouse 3T3 cells. Proc Natl Acad Sci U S A. 1988 Jan;85(1):88–92. doi: 10.1073/pnas.85.1.88. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Saltiel A. R., Fox J. A., Sherline P., Cuatrecasas P. Insulin-stimulated hydrolysis of a novel glycolipid generates modulators of cAMP phosphodiesterase. Science. 1986 Aug 29;233(4767):967–972. doi: 10.1126/science.3016898. [DOI] [PubMed] [Google Scholar]
  22. Seiffert U. B., Agranoff B. W. Isolation and separation of inositol phosphates from hydrolysates of rat tissues. Biochim Biophys Acta. 1965 Jun 1;98(3):574–581. doi: 10.1016/0005-2760(65)90154-2. [DOI] [PubMed] [Google Scholar]
  23. Sekar M. C., Dixon J. F., Hokin L. E. The formation of inositol 1,2-cyclic 4,5-trisphosphate and inositol 1,2-cyclic 4-bisphosphate on stimulation of mouse pancreatic minilobules with carbamylcholine. J Biol Chem. 1987 Jan 5;262(1):340–344. [PubMed] [Google Scholar]
  24. Shears S. B., Storey D. J., Morris A. J., Cubitt A. B., Parry J. B., Michell R. H., Kirk C. J. Dephosphorylation of myo-inositol 1,4,5-trisphosphate and myo-inositol 1,3,4-triphosphate. Biochem J. 1987 Mar 1;242(2):393–402. doi: 10.1042/bj2420393. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. Slater E. C., Rosing J., Mol A. The phosphorylation potential generated by respiring mitochondria. Biochim Biophys Acta. 1973 Apr 5;292(3):534–553. doi: 10.1016/0005-2728(73)90003-0. [DOI] [PubMed] [Google Scholar]
  26. Szuts E. Z., Wood S. F., Reid M. S., Fein A. Light stimulates the rapid formation of inositol trisphosphate in squid retinas. Biochem J. 1986 Dec 15;240(3):929–932. doi: 10.1042/bj2400929. [DOI] [PMC free article] [PubMed] [Google Scholar]
  27. Walker J. W., Somlyo A. V., Goldman Y. E., Somlyo A. P., Trentham D. R. Kinetics of smooth and skeletal muscle activation by laser pulse photolysis of caged inositol 1,4,5-trisphosphate. Nature. 1987 May 21;327(6119):249–252. doi: 10.1038/327249a0. [DOI] [PubMed] [Google Scholar]
  28. Wilson D. B., Connolly T. M., Bross T. E., Majerus P. W., Sherman W. R., Tyler A. N., Rubin L. J., Brown J. E. Isolation and characterization of the inositol cyclic phosphate products of polyphosphoinositide cleavage by phospholipase C. Physiological effects in permeabilized platelets and Limulus photoreceptor cells. J Biol Chem. 1985 Nov 5;260(25):13496–13501. [PubMed] [Google Scholar]
  29. Wreggett K. A., Irvine R. F. A rapid separation method for inositol phosphates and their isomers. Biochem J. 1987 Aug 1;245(3):655–660. doi: 10.1042/bj2450655. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES