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Identification of ecdysonoic acid and 20-hydroxyecdysonoic acid isolated from developing eggs of Schistocerca gregaria and pupae of Spodoptera littoralis.

ABSTRACT: Ecdysonoic acid and 20-hydroxyecdysonoic acid have been purified from developing eggs of the desert locust, Schistocerca gregaria, by high performance liquid chromatography (h.p.l.c.), and their structures were determined by p.m.r. spectroscopy and fast atom bombardment mass spectrometry of the free and methyl ester derivatives. 20-Hydroxyecdysonoic acid was also characterized from Spodoptera littoralis pupae. The occurrence of both 20-hydroxyecdysonoic acid and ecdysonoic acid in Sp. littoralis pupae was also established by h.p.l.c. comparison of the 3H-labelled acids formed from [3H]ecdysone and of their methyl esters with the corresponding substances from Sch. gregaria. The significance of ecdysteroid acids as products of ecdysteroid inactivation is discussed.

SUBMITTER: Isaac RE

PROVIDER: S-EPMC1152117 | biostudies-other | 1983 Jul

REPOSITORIES: biostudies-other

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Isolation and identification of ecdysteroid phosphates and acetylecdysteroid phosphates from developing eggs of the locust, Schistocerca gregaria.

Project description:Maturing eggs of the desert locust, Schistocerca gregaria, contain a variety of ecdysteroid (insect moulting hormone) conjugates and metabolites, four of which have been previously isolated from polar extracts and identified as ecdysonoic acid, 20-hydroxyecdysonoic acid, 3-acetylecdysone 2-phosphate and ecdysone 2-phosphate. In the present study we have isolated eight additional ecdysteroids from similar late-stage eggs by high-performance liquid chromatography. The 22-phosphate esters of ecdysone, 2-deoxyecdysone, 20-hydroxyecdysone and 2-deoxy-20-hydroxyecdysone, all of which were first identified as ecdysteroid components of newly-laid eggs of S. gregaria, were identified by co-chromatography with authentic compounds and by physicochemical techniques. The remaining compounds were identified as 3-acetyl-20-hydroxyecdysone 2-phosphate, 3-epi-2-deoxyecdysone 3-phosphate, 3-acetylecdysone 22-phosphate and 2-acetylecdysone 22-phosphate by fast atom bombardment mass spectrometry, p.m.r. spectroscopy and analysis of the steroid moieties after enzymic hydrolysis. The latter two compounds, after isolation, are susceptible to nonenzymic acetyl migration and deacetylation to give mixtures of ecdysone 22-phosphate and its 2- and 3-acetate derivatives. The possible role and significance of these ecdysteroid conjugates with respect to the control of hormone titres in insect eggs is discussed.

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