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Literature DB >> 16592086

Isolation, Structure, and Absolute Configuration of a New Natural Insect Juvenile Hormone from Manduca sexta.

K J Judy¹, D A Schooley, L L Dunham, M S Hall, B J Bergot, J B Siddall.

Abstract

Two juvenile hormones are isolated from organ cultures of corpora allata of the tobacco hornworm moth, Manduca sexta Johannson, and are purified by high-resolution liquid chromatography. These are identified as methyl (2E, 6E)-(10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate, a new natural hormone, and methyl (2E,6E) - (10R,11S) - 10,11 - epoxy - 3,7,11 - trimethyl-2,6-tridecadienoate. [(14)C]Methionine is incorporated only into their methoxycarbonyl group. Details of the in vitro techniques and the chemical proof of structures are presented. The significance of the occurrence of a new juvenile hormone and the new techniques used for production, isolation, and identification are discussed.

Entities: Chemical Species

Year: 1973 PMID： 16592086 PMCID： PMC433531 DOI： 10.1073/pnas.70.5.1509

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

11 in total

1. REGENERATING TISSUES FROM THE COCKROACH LEUCOPHAEA MADERAE; EFFECTS OF ENDOCRINE GLANDS IN VITRO.

Authors: E P MARKS; J P REINECKE
Journal: Gen Comp Endocrinol Date: 1965-04 Impact factor: 2.822

2. The two juvenile hormones from the cecropia silk moth.

Authors: A S Meyer; H A Schneiderman; E Hanzmann; J H Ko
Journal: Proc Natl Acad Sci U S A Date: 1968-07 Impact factor: 11.205

3. On the biosynthesis of juvenile hormone in the adult Cecropia moth.

Authors: M Metzler; K H Dahm; H Meyer D Röller
Journal: Z Naturforsch B Date: 1971-12 Impact factor: 1.047

Review 4. The action of hormones in insect cell and organ cultures.

Authors: E P Marks
Journal: Gen Comp Endocrinol Date: 1970-10 Impact factor: 2.822

5. Mass spectrometry in structural and stereochemical problems. 218. The electron impact induced behavior of terpenoid esters of the juvenile hormone class.

Authors: R J Liedtke; C Djerassi
Journal: J Org Chem Date: 1972-06-30 Impact factor: 4.354

6. The identity of juvenile hormone produced by Corpora allata in vitro.

Authors: H Röller; K H Dahm
Journal: Naturwissenschaften Date: 1970-09

7. The juvenile hormone of the giant silk moth Hyalophor gloveri (Strecker).

Authors: K H Dahm; H Röller
Journal: Life Sci II Date: 1970-12-22

8. The enzymatic synthesis of fatty acid methyl esters by carboxyl group alkylation.

Authors: Y Akamatsu; J H Law
Journal: J Biol Chem Date: 1970-02-25 Impact factor: 5.157

9. Juvenile and gonadotropic hormone activity of 10,11-epoxyfarnesenic acid methyl ester.

Authors: W S Bowers; M J Thompson; E C Uebel
Journal: Life Sci Date: 1965-12 Impact factor: 5.037

10. Absolute configuration of Cecropia juvenile hormone.

Authors: A S Meyer; E Hanzmann; R C Murphy
Journal: Proc Natl Acad Sci U S A Date: 1971-09 Impact factor: 11.205

20 in total

1. Common structural features facilitate the simultaneous identification and quantification of the five most common juvenile hormones by liquid chromatography-tandem mass spectrometry.

Authors: Cesar E Ramirez; Marcela Nouzova; Veronika Michalkova; Francisco Fernandez-Lima; Fernando G Noriega
Journal: Insect Biochem Mol Biol Date: 2019-11-21 Impact factor: 4.714

10. The influence of substrate concentrations on the rate of insect juvenile hormone biosynthesis by corpora allata of the desert locust in vitro.

Authors: S S Tobe; G E Pratt
Journal: Biochem J Date: 1974-10 Impact factor: 3.857

Isolation, Structure, and Absolute Configuration of a New Natural Insect Juvenile Hormone from Manduca sexta.

1. REGENERATING TISSUES FROM THE COCKROACH LEUCOPHAEA MADERAE; EFFECTS OF ENDOCRINE GLANDS IN VITRO.

2. The two juvenile hormones from the cecropia silk moth.

3. On the biosynthesis of juvenile hormone in the adult Cecropia moth.

Review 4. The action of hormones in insect cell and organ cultures.

5. Mass spectrometry in structural and stereochemical problems. 218. The electron impact induced behavior of terpenoid esters of the juvenile hormone class.

6. The identity of juvenile hormone produced by Corpora allata in vitro.

7. The juvenile hormone of the giant silk moth Hyalophor gloveri (Strecker).

8. The enzymatic synthesis of fatty acid methyl esters by carboxyl group alkylation.

9. Juvenile and gonadotropic hormone activity of 10,11-epoxyfarnesenic acid methyl ester.

10. Absolute configuration of Cecropia juvenile hormone.

1. Common structural features facilitate the simultaneous identification and quantification of the five most common juvenile hormones by liquid chromatography-tandem mass spectrometry.

Review 2. The utility of metabolomics in natural product and biomarker characterization.

3. Insect juvenile hormones and pheromones of isopentenoid biogenesis.

4. High specific activity enantiomerically enriched juvenile hormones: synthesis and binding assay.

5. In vitro growth of corpora allata from Diploptera punctata.

6. Fat Body Organ Culture System in Aedes Aegypti, a Vector of Zika Virus.

7. Biosynthesis of the Juvenile Hormones of Manduca sexta: Labeling Pattern from Mevalonate, Propionate, and Acetate.

8. The Secretion of alpha-Ecdysone by the Prothoracic Glands of Manduca sexta In Vitro.

9. Sources of propionate for the biogenesis of ethyl-branched insect juvenile hormones: Role of isoleucine and valine.

10. The influence of substrate concentrations on the rate of insect juvenile hormone biosynthesis by corpora allata of the desert locust in vitro.