Succinylated octopamine ascarosides and a new pathway of biogenic amine metabolism in caenorhabditis elegans

Journal of Biological Chemistry

Volumn 288, Issue 26, 2013, Pages 18778-18783

  Artyukhin, Alexander B ^a,b   Yim, Joshua J ^a   Srinivasan, Jagan ^c,e   Izrayelit, Yevgeniy ^a   Bose, Neelanjan ^a   Von Reuss, Stephan H ^a,f   Jo, Yeara ^c   Jordan, James M ^d   Baugh, L Ryan ^d   Cheong, Micheong ^b   Sternberg, Paul W ^a   Avery, Leon ^b   Schroeder, Frank C ^a  

^a Boyce Thompson Institute for Plant Research   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^c CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^d DUKE UNIVERSITY   (United States)

^e Life Science and Bioengineering Center   (United States)

^f MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL PATHWAY; BIOGENIC AMINES; BUILDING BLOCKES; CAENORHABDITIS ELEGANS; COMBINATORIAL ASSEMBLY; PHYSIOLOGICAL CONCENTRATIONS; POST-TRANSLATIONAL MODIFICATIONS; SMALL MOLECULES;

ACETYLATION; AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; METABOLISM; MOLECULES; NEUROPHYSIOLOGY;

AMINES;

ACETIC ACID DERIVATIVE; ASCAROSIDE; BIOGENIC AMINE; DOPAMINE; GLYCOSIDE; LYSINE; OCTOPAMINE; SEROTONIN; SUCCINIC ACID; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BIOGENESIS; BIOSYNTHESIS; CAENORHABDITIS ELEGANS; CARBOHYDRATE ANALYSIS; CHEMICAL MODIFICATION; DEVELOPMENTAL STAGE; LARVA; METABOLISM; METABOLOME; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROCESSING; REGULATORY MECHANISM; SIGNAL TRANSDUCTION; STARVATION;

BIOSYNTHESIS; DAUER; DOPAMINE; NEUROTRANSMITTERS; PHEROMONE; SEROTONIN; SMALL-MOLECULE SIGNALING;

ADRENERGIC ALPHA-AGONISTS; ANIMALS; BEHAVIOR, ANIMAL; BIOGENIC AMINES; CAENORHABDITIS ELEGANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOPAMINE; GLYCOSIDES; MASS SPECTROMETRY; NEUROTRANSMITTER AGENTS; OCTOPAMINE; PHEROMONES; SEROTONIN; SIGNAL TRANSDUCTION; SUCCINATES;

CAENORHABDITIS ELEGANS; NEMATODA;

EID: 84879588338     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.C113.477000     Document Type: Article

References (35)

1. Jeong, P. Y., Jung, M., Yim, Y. H., Kim, H., Park, M., Hong, E., Lee, W., Kim, Y. H., Kim, K., and Paik, Y. K. (2005) Chemical structure and biological activity of the Caenorhabditis elegans dauer-inducing pheromone. Nature 433, 541-545 (Pubitemid 40204313)
2. Butcher, R. A., Fujita, M., Schroeder, F. C., and Clardy, J. (2007) Small-molecule pheromones that control dauer development in Caenorhabditis elegans. Nat. Chem. Biol. 3, 420-422 (Pubitemid 46956322)
3. Ludewig, A. H., Izrayelit, Y., Park, D., Malik, R. U., Zimmermann, A., Mahanti, P., Fox, B. W., Bethke, A., Doering, F., Riddle, D. L., and Schroeder, F. C. (2013) Pheromone sensing regulates Caenorhabditis elegans lifespan and stress resistance via the deacetylase SIR-2.1. Proc. Natl. Acad. Sci. U.S.A. 110, 5522-5527
4. Ludewig, A. H., and Schroeder, F. C. (2013) WormBook, Ascaroside signaling in C. elegans. pp. 1-22, The C. elegans Research Community, Pasadena, CA
5. Kaplan, F., Alborn, H. T., von Reuss, S. H., Ajredini, R., Ali, J. G., Akyazi, F., Stelinski, L. L., Edison, A. S., Schroeder, F. C., and Teal, P. E. (2012) Interspecific nematode signals regulate dispersal behavior. PLoS ONE 7, e38735
6. Srinivasan, J., von Reuss, S. H., Bose, N., Zaslaver, A., Mahanti, P., Ho, M. C., O'Doherty, O. G., Edison, A. S., Sternberg, P. W., and Schroeder, F. C. (2012) A modular library of small molecule signals regulates social behaviors in Caenorhabditis elegans. PLoS Biol. 10, e1001237
7. Srinivasan, J., Kaplan, F., Ajredini, R., Zachariah, C., Alborn, H. T., Teal, P. E., Malik, R. U., Edison, A. S., Sternberg, P. W., and Schroeder, F. C. (2008)Ablend of small molecules regulates both mating and development in Caenorhabditis elegans. Nature 454, 1115-1118
8. Izrayelit, Y., Srinivasan, J., Campbell, S. L., Jo, Y., von Reuss, S. H., Genoff, M. C., Sternberg, P. W., and Schroeder, F. C. (2012) Targeted metabolomics reveals a male pheromone and sex-specific ascaroside biosynthesis in Caenorhabditis elegans. ACS Chem. Biol. 7, 1321-1325
9. Macosko, E. Z., Pokala, N., Feinberg, E. H., Chalasani, S. H., Butcher, R. A., Clardy, J., and Bargmann, C. I. (2009) A hub-and-spoke circuit drives pheromone attraction and social behaviour in C. elegans. Nature 458, 1171-1175
10. Pungaliya, C., Srinivasan, J., Fox, B. W., Malik, R. U., Ludewig, A. H., Sternberg, P. W., and Schroeder, F. C. (2009) A shortcut to identifying small molecule signals that regulate behavior and development in Caenorhabditis elegans. Proc. Natl. Acad. Sci. U.S.A. 106, 7708-7713
11. von Reuss, S. H., Bose, N., Srinivasan, J., Yim, J. J., Judkins, J. C., Sternberg, P. W., and Schroeder, F. C. (2012) Comparative metabolomics reveals biogenesis of ascarosides, a modular library of small-molecule signals in C. elegans. J. Am. Chem. Soc. 134, 1817-1824
12. Choe, A., von Reuss, S. H., Kogan, D., Gasser, R. B., Platzer, E. G., Schroeder, F. C., and Sternberg, P. W. (2012) Ascaroside signaling is widely conserved among nematodes. Curr. Biol. 22, 772-780
13. Choe, A., Chuman, T., von Reuss, S. H., Dossey, A. T., Yim, J. J., Ajredini, R., Kolawa, A. A., Kaplan, F., Alborn, H. T., Teal, P. E., Schroeder, F. C., Sternberg, P. W., and Edison, A. S. (2012) Sex-specific mating pheromones in the nematode Panagrellus redivivus. Proc. Natl. Acad. Sci. U.S.A. 109, 20949-20954
14. Bose, N., Ogawa, A., von Reuss, S. H., Yim, J. J., Ragsdale, E. J., Sommer, R. J., and Schroeder, F. C. (2012) Complex small-molecule architectures regulate phenotypic plasticity in a nematode. Angew Chem. Int. Ed Engl. 51, 12438-12443
15. Izrayelit, Y., Robinette, S. L., Bose, N., von Reuss, S. H., and Schroeder, F. C. (2013) 2D NMR-based metabolomics uncovers interactions between conserved biochemical pathways in the model organism Caenorhabditis elegans. ACS Chem. Biol. 8, 314-319
16. Butcher, R. A., Ragains, J. R., Li, W., Ruvkun, G., Clardy, J., and Mak, H. Y. (2009) Biosynthesis of the Caenorhabditis elegans dauer pheromone. Proc. Natl. Acad. Sci. U.S.A. 106, 1875-1879
17. Joo, H. J., Yim, Y. H., Jeong, P. Y., Jin, Y. X., Lee, J. E., Kim, H., Jeong, S. K., Chitwood, D. J., and Paik, Y. K. (2009) Caenorhabditis elegans utilizes dauer pheromone biosynthesis to dispose of toxic peroxisomal fatty acids for cellular homoeostasis. Biochem. J. 422, 61-71
18. Hilliard, M. A., Bargmann, C. I., and Bazzicalupo, P. (2002) C. elegans responds to chemical repellents by integrating sensory inputs from the head and the tail. Curr. Biol. 12, 730-734 (Pubitemid 34455426)
19. Johnson, T. E., Mitchell, D. H., Kline, S., Kemal, R., and Foy, J. (1984) Arresting development arrests aging in the nematode Caenorhabditis elegans. Mech Ageing Dev. 28, 23-40 (Pubitemid 15222463)
20. Lee, B. H., and Ashrafi, K. (2008) A TRPV channel modulates C. elegans neurosecretion, larval starvation survival, and adult lifespan. PLoS Genet. 4, e1000213
21. Lee, I., Hendrix, A., Kim, J., Yoshimoto, J., and You, Y. J. (2012) Metabolic rate regulates L1 longevity in C. elegans. PLoS ONE 7, e44720
22. Fukuyama, M., Rougvie, A. E., and Rothman, J. H. (2006) C. elegans DAF-18/PTEN mediates nutrient-dependent arrest of cell cycle and growth in the germline. Curr. Biol. 16, 773-779
23. Baugh, L. R., and Sternberg, P. W. (2006) DAF-16/FOXO regulates transcription of cki-1/Cip/Kip and repression of lin-4 during C. elegans L1 arrest. Curr. Biol. 16, 780-785
24. Deyrup, S. T., Eckman, L. E., McCarthy, P. H., Smedley, S. R., Meinwald, J., and Schroeder, F. C. (2011) 2D NMR-spectroscopic screening reveals polyketides in ladybugs. Proc. Natl. Acad. Sci. U.S.A. 108, 9753-9758
25. Chase, D. L., and Koelle, M. R. (2007) WormBook, Biogenic amine neurotransmitters in C. elegans. pp. 1-15, The C. elegans Research Community, Pasadena, CA
26. Cho, B. T., Kang, S. K., and Shin, S. H. (2002), Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-aminoalcohols with very high enantiomeric purity. Synthesis of enantiopure(R)-octopamine, (R)-tembamide and (R)-aegeline. Tetrahedron-Asymmetry 13, 1209-1217
27. Erspamer, V. (1952) Identification of octopamine as L-p- hydroxyphenylethanolamine. Nature 169, 375-376
28. Harris, G., Mills, H., Wragg, R., Hapiak, V., Castelletto, M., Korchnak, A., and Komuniecki, R. W. (2010) The monoaminergic modulation of sensory-mediated aversive responses in Caenorhabditis elegans requires glutamatergic/peptidergic cotransmission. J. Neurosci. 30, 7889-7899
29. Alkema, M. J., Hunter-Ensor, M., Ringstad, N., and Horvitz, H. R. (2005) Tyramine functions independently of octopamine in the Caenorhabditis elegans nervous system. Neuron 46, 247-260 (Pubitemid 40545780)
30. Horvitz, H. R., Chalfie, M., Trent, C., Sulston, J. E., and Evans, P. D. (1982) Serotonin and octopamine in the nematode Caenorhabditis elegans. Science 216, 1012-1014 (Pubitemid 12025047)
31. Roeder, T. (1999) Octopamine in invertebrates. Prog. Neurobiol. 59, 533-561
32. Isaac, R. E., MacGregor, D., and Coates, D. (1996) Metabolism and inactivation of neurotransmitters in nematodes. Parasitology 113, S157-S173 (Pubitemid 27095163)
33. Isaac, R. E., Eaves, L., Muimo, R., and Lamango, N. (1991)N-Acetylation of biogenic amines in Ascaridia galli. Parasitology 102, 445-450
34. Isaac, R. E., Muimo, R., and MacGregor, A. N. (1990) N-acetylation of serotonin, octopamine and dopamine by adult Brugia pahangi. Mol. Biochem. Parasitol. 43, 193-198 (Pubitemid 20349683)
35. Lin, H., Su, X., and He, B. (2012) Protein lysine acylation and cysteine succination by intermediates of energy metabolism. ACS Chem. Biol. 7, 947-960