3-O-hydrosulphato-4-hydroxyphenethylamine (dopamine 3-O-sulphate), a metabolite involved in the sclerotization of insect cuticle.
Dopamine 3-O-sulphate (3-O-hydrosulphato-4-hydroxyphenethylamine) was isolated from newly ecdysed cockroaches, Periplaneta americana (L.), and its structure established by chemical and physical techniques and by synthesis. Relatively high concentrations (about 1mumol/g wet. wt.) of dopamine 3-O-sulphate exist in the newly ecdysed insect, and these concentrations decrease sharply as sclerotization of the cuticle proceeds. At least 40% of the radioactivity of (14)C-labelled dopamine 3-O-sulphate injected into newly ecdysed nymphs was recovered in the sclerotized cuticle 7-12 days after the injection. However, less than 1% of the radioactivity of injected dopamine 3-O-[(35)S]sulphate was recovered, and this value was not appreciably different from that for the incorporation of Na(2) (35)SO(4). Apparently, little or none of the sulphate moiety of dopamine 3-O-sulphate is incorporated directly into the cuticle as the intact sulphate ester. These observations are discussed in relation to current concepts of cuticular sclerotization in insects.
D000818:Animals; D002250:Carbon Radioisotopes; D002498:Centrifugation; D002850:Chromatography, Gel; D002852:Chromatography, Ion Exchange; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D003058:Cockroaches / Q000254:growth & development / Q000378:metabolism*; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification*; D008675:Metamorphosis, Biological; D009758:Nymph / Q000378:metabolism; D012964:Sodium / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013431:Sulfates / Q000302:isolation & purification / Q000378:metabolism; D013462:Sulfur Radioisotopes
D002250:Carbon Radioisotopes; D013431:Sulfates; D013462:Sulfur Radioisotopes; D012964:Sodium; D004298:Dopamine