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Conversion of ecdysone and 20‐Hydroxyecdysone into 26‐OIC derivatives is a major pathway in larvae and pupae of species from three insect orders
Author(s) -
Lafont René,
Blais Catherine,
Beydon Philippe,
Modde JeanFrançois,
Enderle Ulrike,
Koolman Jan
Publication year - 1983
Publication title -
archives of insect biochemistry and physiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.576
H-Index - 66
eISSN - 1520-6327
pISSN - 0739-4462
DOI - 10.1002/arch.940010106
Subject(s) - ecdysone , 20 hydroxyecdysone , pieris brassicae , biology , insect , metabolism , steroid , biochemistry , pupa , larva , stereochemistry , hormone , botany , chemistry
Abstract Insects convert ecdysone and 20‐hydroxyecdysone into their corresponding 26‐oic derivatives, named ecdysonoic acid and 20‐hydroxyecdysonoic acid respectively. The conversion takes piace in several tissues and can either be the only pathway for converting ecdysone into highly polar ecdysteroids, or coexist with various conjugating mechanisms. 20‐Hydroxyecdysonoic acid was isolated from Pieris brassicae pupae as its methyl ester derivative. Its chemical structure was identified by Cl/D mass spectrometry and compared with a synthetic compound (20‐hydroxy‐25‐deoxyecdysonoic acid) chemically prepared by oxidation of inokosterone (20,26‐dihydroxy‐25‐deoxyecdysone). Natural ecdysonoic acids appear to exist as a mixture of 25R and 25S isomers. The significance of this pathway is discussed in comparison with similar reactions occuring in the metabolism of steroid hormones in vertebrates.