Biomaterial Database

Mechanism of dealkylation of clionasterol in the insect Tenebrio molitor. 1978

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

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.

UI	MeSH Term	Description	Entries
D007814	Larva	Wormlike or grublike stage, following the egg in the life cycle of insects, worms, and other metamorphosing animals.	Maggots,Tadpoles,Larvae,Maggot,Tadpole
D002784	Cholesterol	The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.	Epicholesterol
D003640	Dealkylation	The removing of alkyl groups from a compound. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Dealkylations
D003897	Desmosterol	An intermediate in the synthesis of cholesterol.	24-Dehydrocholesterol,Demosterol,24 Dehydrocholesterol
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012855	Sitosterols	A family of sterols commonly found in plants and plant oils. Alpha-, beta-, and gamma-isomers have been characterized.
D013712	Tenebrio	A genus of beetles which infests grain products. Its larva is called mealworm.	Mealworm,Mealworms,Tenebrios