LC/MS/MS identification of 20-hydroxyecdysone in a scorpion (Liocheles australasiae) and its binding affinity to in vitro-translated molting hormone receptors

Insect Biochemistry and Molecular Biology

Volumn 41, Issue 12, 2011, Pages 932-937

  Miyashita, Masahiro ^a   Matsushita, Kaori ^a   Nakamura, Shunsuke ^a   Akahane, Sho ^a   Nakagawa, Yoshiaki ^a   Miyagawa, Hisashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

20 Hydroxyecdysone; Ecdysteroids; EcR; Liocheles australasiae; Scorpion; Tebufenozide

Indexed keywords

ECDYSTERONE;

ANIMAL; ARTICLE; CHEMISTRY; FEMALE; HEMOLYMPH; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; METABOLISM; NYMPH; SCORPION; TANDEM MASS SPECTROMETRY;

ANIMALS; CHROMATOGRAPHY, LIQUID; ECDYSTERONE; FEMALE; HEMOLYMPH; NYMPH; SCORPIONS; TANDEM MASS SPECTROMETRY;

ARTHROPODA; HEXAPODA; LIOCHELES; POA; SCORPIONES;

EID: 80355132012     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibmb.2011.09.002     Document Type: Article

References (44)

1. Asazuma H., Nagata S., Kono M., Nagasawa H. Molecular cloning and expression analysis of ecdysone receptor and retinoid X receptor from the kuruma prawn, Marsupenaeus japonicus. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 2007, 148:139-150.
2. Baker G.C., Rees H.H. Ecdysteroids in nematodes. Parasitol. Today 1990, 6:384-387.
3. Barrington J.W. Hormones and Evolution 1979, vii-xxi. Academic Press. E.J.W. Barrington (Ed.).
4. Beckstead R.B., Lam G., Thummel C.S. Specific transcriptional responses to juvenile hormone and ecdysone in Drosophila. Insect Biochem. Mol. Biol. 2007, 37:570-578.
5. Blais C., Blasco T., Maria A., Dauphin-Villemant C., Lafont R. Characterization of ecdysteroids in Drosophila melanogaster by enzyme immunoassay and nano-liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt Technol. Biomed. Life Sci. 2010, 878:925-932.
6. Bollenbacher W.E., Smith S.L., Goodman W., Gilbert L.I. Ecdysteroid titer during larval-pupal-adult development of the tobacco hornworm, Manduca sexta. Gen. Comp. Endocrinol. 1981, 44:302-306.
7. Carlson G.R., Dhadialla T.S., Hunter R., Jansson R.K., Jany C.S., Lidert Z., Slawecki R.A. The chemical and biological properties of methoxyfenozide, a new insecticidal ecdysteroid agonist. Pest Manag. Sci. 2001, 57:115-119.
8. Destrez B., Pinel G., Bichon E., Monteau F., Lafont R., Le Bizec B. Detection of 20-hydroxyecdysone in calf urine by comparative liquid chromatography/high-resolution mass spectrometry and liquid chromatography/tandem mass spectrometry measurements: application to the control of the potential misuse of ecdysteroids in cattle. Rapid Commun. Mass Spectrom. 2008, 22:4073-4080.
9. Feldlaufer M.F., Svoboda J.A., Herbert E.W. Makisterone A and 24-methylenecholesterol from the ovaries of the honey bee, Apis mellifera L. Experientia 1986, 42:200-201.
10. Gefen E., Ar A. Comparative water relations of four species of scorpions in Israel: evidence for phylogenetic differences. J. Exp. Biol. 2004, 207:1017-1025.
11. Gelman D.B., Blackburn M.B., Hu J.S. Identification of the molting hormone of the sweet potato (Bemisia tabaci) and greenhouse (Trialeurodes vaporariorum) whitefly. J. Insect Physiol. 2005, 51:47-53.
12. Gilbert L.I., Warren J.T. A molecular genetic approach to the biosynthesis of the insect steroid molting hormone. Vitam Horm. 2005, 73:31-57.
13. Graham L.D., Johnson W.M., Pawlak-Skrzecz A., Eaton R.E., Bliese M., Howell L., Hannan G.N., Hill R.J. Ligand binding by recombinant domains from insect ecdysone receptors. Insect Biochem. Molec. 2007, 37:611-626.
14. Graham L.D., Johnson W.M., Tohidi-Esfahani D., Pawlak-Skrzecz A., Bliese M., Lovrecz G.O., Lu L., Howell L., Hannan G.N., Hill R.J. Ecdysone receptors of pest insects - molucular cloning, characterization, and a ligand binding domain-based fluoresceince polarization screen. Ecdysone: Structures and Functions 2009, 447-474. Springer Science + Buisiness Media B.V. G. Smagghe (Ed.).
15. Hatle J.D., Juliano S.A., Borst D.W. Hemolymph ecdysteroids do not affect vitellogenesis in the lubber grasshopper. Arch. Insect Biochem. Physiol. 2003, 52:45-57.
16. Henrich V.C. The ecdysteroid receptor. Comprehensive Molecular Insect Science 2005, 243-285. Elsevier, Oxford. L.I. Gilbert, K. Iatrou, S.S. Gill (Eds.).
17. Hodgetts R.B., Sage B., O'Connor J.D. Ecdysone titers during postembryonic development of Drosophila melanogaster. Dev. Biol. 1977, 60:310-317.
18. Hsiao T.H., Hsiao C., Wilde J.D. Molting hormone production in isolated larval abdomen of Colorado beetle. Nature 1975, 255:727-728.
19. Kelly T.J., Aldrich J.R., Woods C.W., Borkovec A.B. Makisterone A: its distribution and physiological role as the molting hormone of true bugs. Experientia 1984, 40:996-997.
20. Koelle M.R., Talbot W.S., Segraves W.A., Bender M.T., Cherbas P., Hogness D.S. The Drosophila EcR gene encodes an ecdysone receptor, a new member of the steroid receptor superfamily. Cell 1991, 67:59-77.
21. Kraminsky G.P., Clark W.C., Estelle M.A., Gietz R.D., Sage B.A., O'connor J.D., Hodgetts R.B. Induction of translatable mRNA for dopa decarboxylase in Drosophila: an early response to ecdysterone. Proc. Natl. Acad. Sci. U S A 1980, 77:4175-4179.
22. Lachaise F., Meister M.F., Hetru C., Lafont R. Studies on the biosynthesis of ecdysone by the Y-organs of Carcinus maenas. Mol. Cell Endocrinol. 1986, 45:253-261.
23. Lanzrein B., Gentinetta V., Abegglen H., Baker F.C., Miller C.A., Schooley D.A. Titers of ecdysone, 20-hydroxyecdysone and juvenile hormone III througout the life cycle of a hemimetabolous insect, the ovoviviparous cockroach Nauphoeta cinerea. Experientia 1985, 41:913-917.
24. Makioka T. Reproductive biology of the viviparous scorpion, Liocheles australasiae (Fabricius) (Arachnida, Scorpiones, Ischnuridae) IV. Pregnancy in females isolated from infancy, with notes on juvenile stage duration. Invertebr Reprod. Dev. 1993, 24:207-212.
25. Mazzarino M., Botre F. A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids. Rapid Commun. Mass Spectrom. 2006, 20:3465-3476.
26. Mendis A.H.W., Rose M., Rees H.H., Goodwin T.W. Ecdysteroids in adults of the nematode, Dirofilaria immitis. Molec Biochem. Parasit. 1983, 9:209-226.
27. Minakuchi C., Nakagawa Y., Kamimura M., Miyagawa H. Binding affinity of nonsteroidal ecdysone agonists against the ecdysone receptor complex determines the strength of their molting hormonal activity. Eur. J. Biochem. 2003, 270:4095-4104.
28. Minakuchi C., Nakagawa Y., Kamimura M., Miyagawa H. Measurement of receptor-binding activity of non-steroidal ecdysone agonists using in vitro expressed receptor proteins (EcR/USP complex) of Chilo suppressalis and Drosophila melanogaster. New Discoveries in Agrochemicals 2005, 191-200. American Chemical Society, Washington, DC. J.M. Clark, H. Ohkawa (Eds.).
29. Minakuchi C., Ogura T., Miyagawa H., Nakagawa Y. Effects of the structures of ecdysone receptor (EcR) and ultraspiracle (USP) on the ligand-binding activity of the EcR/USP heterodimer. J. Pest Sci. 2007, 32:379-384.
30. 3H]ponasterone A binding by ecdysone agonists in the intact Sf-9 cell line. Steroids 2000, 65:537-542.
31. Nakagawa Y., Sakai A., Magata F., Ogura T., Miyashita M., Miyagawa H. Molecular cloning of the ecdysone receptor and the retinoid X receptor from the scorpion Liocheles australasiae. FEBS J. 2007, 274:6191-6203.
32. Nakagawa Y., Henrich V.C. Arthropod nuclear receptors and their role in molting. FEBS J. 2009, 276:6128-6157.
33. Nakatsuji T., Sonobe H. Regulation of ecdysteroid secretion from the Y-organ by molt-inhibiting hormone in the American crayfish, Procambarus clarkii. Gen. Comp. Endocrinol. 2004, 135:358-364.
34. Nishioka T., Fujita T., Nakajima M. Effect of chitin synthesis inhibitiors on cuticle formation of the cultured integument of the Chilo suppressalis. J. Pestic. Sci. 1979, 4:367-374.
35. Ogura T., Minakuchi C., Nakagawa Y., Smagghe G., Miyagawa H. Molecular cloning, expression analysis and functional confirmation of ecdysone receptor and ultraspiracle from the Colorado potato beetle Leptinotarsa decemlineata. FEBS J. 2005, 272:4114-4128.
36. Oikawa N., Nakagawa Y., Nishimura K., Ueno T., Fujita T. Quantitative structure-activity studies of insect growth regulators X. Substituent effects on larvicidal activity of 1-tert-butyl-1-(2-chlorobenzoyl)-2-(substituted benzoyl)hydrazines against Chilo suppressalis and design synthesis of potent derivatives. Pestic. Biochem. Physiol. 1994, 48:135-144.
37. Oro A.E., Mckeown M., Evans R.M. Relationship between the product of the Drosophila ultraspiracle locus and the vertebrate retinoid X receptor. Nature 1990, 347:298-301.
38. Romer F. Ecdysteroids in snails. Naturwissenschaften 1979, 66:471-472.
39. Stevens J.F., Reed R.L., Morre J.T. Characterization of phytoecdysteroid glycosides in Meadowfoam (Limnanthes alba) seed meal by positive and negative ion LC-MS/MS. J. Agric. Food Chem. 2008, 56:3945-3952.
40. Tohidi-Esfahani D., Graham L.D., Hannan G.N., Simpson A.M., Hill R.J. An ecdysone receptor from the pentatomomorphan, Nezara viridula, shows similar affinities for moulting hormones makisterone A and 20-hydroxyecdysone. Insect Biochem. Molec. Biol. 2011, 41:77-89.
41. Tohidi-Esfahani D., Lawrence M.C., Graham L.D., Hannan G.N., Simpson A.M., Hill R.J. Isoforms of the heteropteran Nezara viridula ecdysone receptor: protein characterisation, RH5992 insecticide binding and homology modelling. Pest Manag. Sci. 2011, doi:10.1002/ps.2200.
42. Truman J.W., Riddiford L.M. The origins of insect metamorphosis. Nature 1999, 401:447-452.
43. Wang S.F., Ayer S., Segraves W.A., Williams D.R., Raikhel A.S. Molecular determinants of differential ligand sensitivities of insect ecdysteroid receptors. Mol. Cell Biol. 2000, 20:3870-3879.
44. Wang Y.H., Avula B., Jadhav A.N., Smillie T.J., Khan I.A. Structural characterization and identification of ecdysteroids from Sida rhombifolia L. in positive electrospray ionization by tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22:2413-2422.