Literature DB >> 708391

Mechanism of dealkylation of clionasterol in the insect Tenebrio molitor.

P J Pettler, W J Lockley, H H Rees, T W Goodwin.   

Abstract

1. 25-3H- and 26-14C-labelled (24S)-24-ethylcholest-5-en-3beta-ol (clionasterol) were synthesized from (24S)-24-ethylcholesta-5,25-dien-3beta-ol. 2. These labelled substrates were mixed and administered, together with the hypocholesterolemic agent, triparanol citrate, to Tenebrio molitor larvae. 3. The 3H label from the clionasterol substrate was retained in both the desmosterol and the cholesterol isolated from the larvae. 4. Location of this 3H label in the desmosterol showed that dealkylation of the clionasterol involved 3H migration from C-25 to C-24. A possible mechanism for dealkylation is presented.

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Year:  1978        PMID: 708391      PMCID: PMC1185927          DOI: 10.1042/bj1740397

Source DB:  PubMed          Journal:  Biochem J        ISSN: 0264-6021            Impact factor:   3.857


  8 in total

Review 1.  Recent developments in insect steroid metabolism.

Authors:  J A Svoboda; J N Kaplanis; W E Robbins; M J Thompson
Journal:  Annu Rev Entomol       Date:  1975       Impact factor: 19.686

2.  Letter: Stereospecificity in the conversion of fucosterol 24,28-epoxide to desmosterol in the silkworm, Bombyx mori.

Authors:  S M Chen; K Nakanishi; N Awata; M Morisaki; N Ikekawa
Journal:  J Am Chem Soc       Date:  1975-09-03       Impact factor: 15.419

3.  The relation of carnitine to the formation of phosphatidyl-beta-methylcholine by Tenebrio molitor L. larvae.

Authors:  L L Bieber; R E Monroe
Journal:  Lipids       Date:  1969-07       Impact factor: 1.880

4.  Metabolism of steroids in insects.

Authors:  M J Thompson; J N Kaplanis; W E Robbins; J A Svoboda
Journal:  Adv Lipid Res       Date:  1973

5.  Reaction of 24,28-epoxides of sterol side chain with boron trifluoride etherate.

Authors:  H Otaka; M Morisaki; N Ikekawa
Journal:  J Org Chem       Date:  1973-05-04       Impact factor: 4.354

6.  Identification of fucosterol as a metabllite and probable intermediate in conversion of beta-sitosterol to cholesterol in the tobacco hornworm.

Authors:  J A Svoboda; M J Thompson; W E Robbins
Journal:  Nat New Biol       Date:  1971-03-10

7.  Desmosterol, an intermediate in dealkylation of beta-sitosterol in the tobacco hornworm.

Authors:  J A Svoboda; M J Thompson; W E Robbins
Journal:  Life Sci       Date:  1967-02-15       Impact factor: 5.037

8.  Conversion of beta sitosterol to cholesterol blocked in an insect by hypocholesterolemic agents.

Authors:  J A Svoboda; W E Robbins
Journal:  Science       Date:  1967-06-23       Impact factor: 47.728

  8 in total

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