In vitro metabolism of 3beta-hydroxy-, and 3beta,14alpha-dihydroxy-[3alpha-3H]-5beta-cholest-7-en-6-one by the prothoracic glands of Manduca sexta.
alpha-Ecdysone (2beta,3beta,14alpha,22R,25-pentahydroxy-5beta-cholest-7-en-6-one) has been identified as the metabolism product of 3beta,14alpha-dihydroxy-5beta-cholest-7-en-6-one in isolated prothoracic glands of the tobacco hornworm, Manduca sexta. In contrast, 3beta-hydroxy-5beta-cholest-7-en-6-one is metabolized to 14-deoxy-alpha-ecdysone and a variety of intermediates all lacking the 14-hydroxy group. The results suggest that either the normal precursor for the synthesis of alpha-ecdysone by prothoracic glands is a sterol more highly oxygenated than cholesterol or that hydroxylation of a minimally oxygenated precursor at C-14 must precede introduction of the C-6 ketone and/or delta7 bond. The data further suggest that several alternative hydroxylation routes may exist for the latter steps of alpha-ecdysone biosynthesis.
D000818:Animals; D002782:Cholestenes / Q000378:metabolism*; D002783:Cholestenones / Q000378:metabolism*; D002845:Chromatography; D004440:Ecdysone / Q000378:metabolism; D006914:Hydroxysteroids / Q000378:metabolism; D007664:Ketosteroids / Q000378:metabolism; D007915:Lepidoptera / Q000378:metabolism*; D009036:Moths / Q000378:metabolism*; D012627:Sebaceous Glands / Q000378:metabolism; D012822:Silicon Dioxide; D013261:Sterols / Q000378:metabolism*; D013329:Structure-Activity Relationship
D002782:Cholestenes; D002783:Cholestenones; D006914:Hydroxysteroids; D007664:Ketosteroids; D013261:Sterols; D004440:Ecdysone; D012822:Silicon Dioxide