Metabolism of [14C]cholesterol in Manduca sexta pupae: Isolation and identification of sterol sulfates, free ecdysteroids, and ecdysteroid acids

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Metabolism of [14C]cholesterol in Manduca sexta pupae: Isolation and identification of sterol sulfates, free ecdysteroids, and ecdysteroid acids

Year: 

1988

Source of publication :

Archives of Insect Biochemistry and Physiology

Authors :

סבובודה, ג'יימס

.

Volume :

Co-Authors: 

Lozano, R., Insect and Nematode Hormone Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, Maryland, United States
Thompson, M.J., Insect and Nematode Hormone Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, Maryland, United States
Lusby, W.R., Insect and Nematode Hormone Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, Maryland, United States
Svoboda, J.A., Insect and Nematode Hormone Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, Maryland, United States
Rees, H.H., Department of Biochemistry, University of Liverpool, Liverpool, United Kingdom

From page: 

249

To page: 

266

(

Total pages: 

18

)

Link :

Metabolism of [14C]cholesterol in Manduca sexta pupae: Isolation and identification of sterol sulfates, free ecdysteroids, and ecdysteroid acids

Abstract: 

[14C]Cholesterol was injected into fifth‐instar larvae of Manduca sexta, and the metabolites were isolated and identified from 8‐day‐old male and female pupae. A major portion of the metabolized cholesterol was esterified either with a sulfate group or with fatty acids. The predominant ecdysteroid metabolites were 20‐hydroxyecdysone, 20,26‐dihydroxyecdysone, 20‐hydroxyecdysonoic acid, and 3‐epi‐20‐hydroxyecdysonoic acid. Smaller amounts of ecdysteroids were identified as conjugates of 26‐hydroxyecdysone, 3‐epi‐20‐hydroxyecdysone, 20,26‐dihydroxyecdysone, and its 3α‐epimer. The metabolic profiles were similar for both male and female pupae. The two ecdysteroid acids were identified by nuclear magnetic resonance spectroscopy and chemical ionization mass spectrometry and by mass spectral analyses of their methyl esters. Detection of 3‐epi‐20‐hydroxyecdysonoic acid as a major metabolite is significant, as its occurrence has been scarcely reported. 3‐Epiecdysteroid acid formation is discussed as a possible ecdysteroid‐inactivating pathway that may be operating specifically in lepidopterous insects or in particular developmental stages such as eggs or pupae. Copyright © 1988 Wiley‐Liss, Inc.