Synthesis and conversion study of a radiolabeled putative ecdysone precursor, 5 beta-cholest-7-ene-3 beta,6 alpha,14 alpha-triol in Locusta migratoria prothoracic glands.
In previous studies, we have characterized the last three steps of the biosynthetic pathway of the insect molting hormone, ecdysone. They consist of a series of hydroxylations at the C-25, C-22, and C-2 positions. To explore an early step, we synthesized 5 beta-cholest-7-ene-3 beta,6 alpha,14 alpha-triol in tritiated form. Incubation of this triol with insect prothoracic glands, a well-known site of ecdysone biosynthesis, showed that this molecule can be hydroxylated at the C-25, C-22, and C-2 positions, but neither the triol nor the resulting compounds could be oxidized at the C-6 position to give ecdysone.
Schwab
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Laboratoire d'Endocrinologie et d'Immunologie des Insectes, UA CNRS 672, Strasbourg, France.
Hetru
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D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004440:Ecdysone / Q000096:biosynthesis* / Q000737:chemistry; D004702:Endocrine Glands / Q000378:metabolism*; D006110:Grasshoppers / Q000378:metabolism*; D006900:Hydroxylation; D007814:Larva / Q000378:metabolism; D015394:Molecular Structure; D011498:Protein Precursors / Q000096:biosynthesis*
D011498:Protein Precursors; D004440:Ecdysone