The Degradative Metabolism of Juvenoids by Insects

Hammock, Bruce D.; Quistad, Gary B.

doi:10.1007/978-1-4684-7947-8_26

Cited by 22 publications

(13 citation statements)

References 49 publications

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“…A variety of authors demonstrated that in insects, the hydrolysis of the terpenoid insect juvenile hormone by a/b-fold esterases and epoxide hydrolases is as important in regulating its biology as it is the biosynthesis of the hormone (Hammock and Quistad, 1976). Similarly, with EpFA such as EETs and EpDPEs, the regulation of the titer of these chemical mediators by degradation seems as important as biosynthesis.…”

Section: Resultsmentioning

confidence: 99%

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The 2014 Bernard B. Brodie Award Lecture—Epoxide Hydrolases: Drug Metabolism to Therapeutics for Chronic Pain

Kodani¹,

Hammock²

2015

Drug Metab Dispos

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Dr. Bernard Brodie's legacy is built on fundamental discoveries in pharmacology and drug metabolism that were then translated to the clinic to improve patient care. Similarly, the development of a novel class of therapeutics termed the soluble epoxide hydrolase (sEH) inhibitors was originally spurred by fundamental research exploring the biochemistry and physiology of the sEH. Here, we present an overview of the history and current state of research on epoxide hydrolases, specifically focusing on sEHs. In doing so, we start with the translational project studying the metabolism of the insect juvenile hormone mimic R-20458 [(E)-6,7-epoxy-1-(4-ethylphenoxy)-3,7-dimethyl-2-octene], which led to the identification of the mammalian sEH. Further investigation of this enzyme and its substrates, including the epoxyeicosatrienoic acids, led to insight into mechanisms of inflammation, chronic and neuropathic pain, angiogenesis, and other physiologic processes. This basic knowledge in turn led to the development of potent inhibitors of the sEH that are promising therapeutics for pain, hypertension, chronic obstructive pulmonary disorder, arthritis, and other disorders.

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Section: Resultsmentioning

confidence: 99%

“…Another mimic from Stauffer Chemical Company retained the epoxide. It was during the study of this insect growth regulator that the sEH was discovered (Gill et al, 1972;Hammock and Quistad, 1976).…”

Section: A History Of Epoxide Hydrolasesmentioning

confidence: 99%

The 2014 Bernard B. Brodie Award Lecture—Epoxide Hydrolases: Drug Metabolism to Therapeutics for Chronic Pain

Kodani¹,

Hammock²

2015

Drug Metab Dispos

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“…It is also interesting that both of the major pathways of degradation of JH by insects involved proteins in the α/β‐hydrolase fold family, since both esterases and epoxide hydrolases have the same fold and fundamental catalytic mechanism. Several review papers have emphasized the degradation of juvenile hormone, but the diversity of insect species makes it difficult to draw generalized conclusions beyond the fact that in many species degradation of the hormone appears important in regulatory biology just as does biosynthesis, and that JHEH and JHE are often important routes of metabolism 31–34…”

Section: Insect Epoxide Hydrolasesmentioning

confidence: 99%

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Morisseau

Hammock

2008

Pest Management Science

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The pioneering work of Gerry Brooks on cyclodiene insecticides led to the discovery of a class of enzymes known as epoxide hydrolases. The results from four decades of work confirm Brooks' first observations that the microsomal epoxide hydrolase is important in foreign compound metabolism. Brooks and associates went on to be the first to carry out a systematic study of the inhibition of this enzyme. A second role for this enzyme family was in the degradation of insect juvenile hormone (JH). JH epoxide hydrolases have now been cloned and expressed from several species, and there is interest in developing inhibitors for them. Interestingly, the distantly related mammalian soluble epoxide hydrolase has emerged as a promising pharmacological target for treating hypertension, inflammatory disease and pain. Tight-binding transition-state inhibitors were developed with good ADME (absorption, distribution, metabolism and excretion). These compounds stabilize endogenous epoxides of fatty acids, including arachidonic acid, which have profound therapeutic effects. Now EHs from microorganisms and plants are used in green chemistry. From his seminal work, Dr Brooks opened the field of epoxide hydrolase research in many directions including xenobiotic metabolism, insect physiology and human health, as well as asymmetric organic synthesis. 

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“…Metabolism of JH was monitored by the methods previously described [7]. Hemolymph was diluted from 50to 400-fold in TTgM buffer and incubated with 13H]JH-I (10 nM) at 0 or 23°C for [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] min. The hormone and metabolites were extracted with n-hexane, ether, or ethyl acetate:hexane (3:7), and while the extraction efficiency has been 80-90% with n-hexane for cytosol, the efficiency for the samples reported was not monitored.…”

Section: Metabolism Of Jhmentioning

confidence: 99%

“…1). As with whole hernolymph, binding was maximal after [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] min, then decreased gradually during the 4-h incubation. Purified lipophorin also bound radiolabeled JH-I, and that binding was competitively inhibited by unlabeled hormone under the conditions of the assay.…”

Section: G E L Filtrationmentioning

confidence: 99%

Characterization of juvenile hormone‐binding proteins of hemolymph of Locusta migratoria

Roberts

1985

Arch Insect Biochem Physiol

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The binding of juvenile hormone (JH) by components from hemolymph of adult female Locusta rnigratoria was characterized to establish whether hemolymph JH-binding proteins could be distinguished from a protein of fat body (BP-I) that may be a JH receptor. Hemolymph was analyzed by the hydroxyapatite assay, gel separation chromatography, polyacrylamide gel electrophoresis, and density gradient centrifugation. Three fractions that bound JH were separated from whole hemolymph by DEAE cellulose column chromatography, and these differed from all three cytosol-binding com- of methoprene and hydroprene. The data indicated that unlabeled JH-Ill was bound more effectively than its radioactive counterpart. The sedimentation values determined by sucrose density gradient ultracentrifugation were 13-14 S for hemolymph, and the sedimentation value was not altered by the inclusion of 0.4 M KCI throughout the gradient. The data indicated that H-A resembled the specific J H carriers and differed from the putative receptor of fat body cytosol by several criteria.

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The Degradative Metabolism of Juvenoids by Insects

Cited by 22 publications

References 49 publications

The 2014 Bernard B. Brodie Award Lecture—Epoxide Hydrolases: Drug Metabolism to Therapeutics for Chronic Pain

The 2014 Bernard B. Brodie Award Lecture—Epoxide Hydrolases: Drug Metabolism to Therapeutics for Chronic Pain

Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical

Characterization of juvenile hormone‐binding proteins of hemolymph of Locusta migratoria

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