Juvenile hormones biosynthesis

Brevioxime 25 is a natural product isolated from Penicillum brevicompactum and displays in vitro inhibition of juvenile hormone biosynthesis. Two different synthetic approaches have been described for this molecule. Different authors carried out the cyclization of the unsaturated ketoamide 409 in the presence of nitrosyl chloride that directly produced cyclization and led to the oxime <2001SL257, 2001T8699>. Starting from the same... 

Figure 3. Outline of juvenile hormone biosynthesis based on Ref. 23.

Gadot, M., Burns, E. and Schal, C. (1989). Juvenile hormone biosynthesis and oocyte development in adult female Blattella germanica effects of grouping and mating. Archives of Insect Biochemistry and Physiology 11 189-200. 

Schooley D. A. and Baker F. C. (1985) Juvenile hormone biosynthesis. In Comprehensive Insect Physiology, Biochemistry, and Pharmacology, eds G. A. Kerkut, and L. I. Gilbert, Vol. 7, pp. 363-389. Pergamon Press, Oxford. 

Taub-Montemayor T. E. Dahm K. H., Govindan B. and Rankin M. A. (1997a) Rates of juvenile hormone biosynthesis and degradation during reproductive development and diapause in the boll weevil, Anthonomus grandis. Physiol. Entomol. 22, 269-276. 

Chiang A.-S. and Schal C. (1994) Cyclic volumetric changes in corpus allatum cells in relation to juvenile hormone biosynthesis during ovarian cycles in cockroaches. Arch. Insect Biochem. Physiol. 27, 53-64. 

Gadot M., Chiang A.-S., Burns E. L. and Schal C. (1991) Cyclic juvenile hormone biosynthesis in the cockroach, Blattella germanica Effects of ovariectomy and corpus allatum denervation. Gen. Comp. Endocrinol. 82, 163-171. 

Smith A. F., Yagi K., Tobe S. S. and Schal C. (1989) In vitro juvenile hormone biosynthesis in adult virgin and mated female brown-banded cockroaches, Supella longipalpa. J. Insect Physiol. 35, 781-785. 

Propionate also serves as a precursor for juvenile hormone biosynthesis in Manduca sexta (1 ). The ethyl branch in JH II (and presumably those in JH I and JH 0) is derived from propionate which is incorporated into homomevalonate. The dji a presented by Schooley et a l. (1 ) on the incorporation of [2- C]-... 

Propionate is a key intermediate in JH and hydrocarbon biosynthesis In insects. It serves as a precursor for methyl branched hydrocarbons which in many insects are important compounds for communication and cuticular protection, and it is a precursor for juvenile hormone biosynthesis (JH 0, JH I and JH II). Sources of propionate have been shown to be succinate in a termite and certain amino acids such as valine in other species. 

In the Design of Inhibitors of Insect Juvenile Hormone Biosynthesis... 

The allatostatins are a family of brain peptides which rapidly and reversibly inhibit juvenile hormone biosynthesis in isolated insect corpora allata. Five allatostatic peptides from brains of the cockroach Diploptera punctata have now been structurally identified (i 2 our unpublished results), their size ranging from octapeptide to octadecapeptide. The currently identified allatostatins all possess the consensus C-terminal sequence (L/V)YXFGL-amide, which has no significant homology with other known peptides. It is likely that they are released locally from nerve terminals within the glands (3). 

Aedes aegypti, See Mosquito Allatal maturation, stimulation and inhibition in locusts, 152-161 Allatostatic ovary-derived factor, effect on juvenile hormone biosynthesis, 159-160,16U... 

Pratt, O F., and Finney, J.R. (1977 . Chemical inhibitors of juvenile hormone biosynthesis in vitro. In Crop Protection Ajiftvrr.v (Mcbarlane, N.R., ed), pp. II3-132 Academic Press. London. 

The action of precocenes on the molecular level is not understood. Pratt and Bowers (1977) demonstrated the inhibition of the final steps in juvenile hormone biosynthesis, including epoxidation of farnesenic acid, following administration of precocene II to the test insects. Based on their experimental findings, members of the Bristol research group hypothesised that precocene and its derivatives are epoxidised to 3,4-epoxides having alkylating properties. The formation of these epoxides competes with the epoxidation step in JH biosynthesis, thus destroying the ability of corpora allata to synthesise JH. 

In the search for chemicals inhibiting the enzymes O-methyl transferase and methyl farnesoate epoxidase, responsible for the methyl ester formation and for the terminal epoxidation in juvenile hormone biosynthesis. Brooks and co-workers (1984) prepared a number of acetylenic esters and 1,3-benzodioxole derivatives. These groupings are of particular interest in the context of JH biosynthesis inhibition. The acetylenic derivative 79 showed the strongest inhibitory action on both enzymes. 

Compounds 395a and 398a showed in vitro inhibitory activity of the juvenile hormone biosynthesis of Locusta migratoria, an agriculture pest in North Africa [57]. In order to study structure/activity relationships we prepared several derivatives of compounds 398a-c having different... 

A juvenile hormone biosynthesis inhibitor, isolated from fermentation broths of Penicillium brevicompac-tum C15H22N2O3, Mr 278.35, [a] -39° (CHCI3). 

Muthukrishnan J, Seifert K, Hoffmann KH, Lorenz MW (1999) Inhibition of juvenile hormone biosynthesis in Gryllus bimaculatus by Glycosmis pentaphylla leaf compounds. Phytochemistry 50 249-254... 

Fell (1996) noted that the primary use of TLC for terpinoids in entomological studies has been for work on juvenile hormone biosynthesis and metabolism. Because juvenile hormones are sesquiterpinoid compounds, his review was limited mainly to the TLC analysis of those compounds. He presented several exam-... 

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