Juvenile Hormone: Identification of an Active Compound from Balsam Fir

Bowers, William S.; Fales, Henry M.; Thompson, Malcolm J.; Uebel, E. C.

doi:10.1126/science.154.3752.1020

Cited by 191 publications

(65 citation statements)

References 8 publications

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“…I The activity of (R)-ABA is almost equal to that of (S)-ABA (12). 3 The (RS)-methyl ester was tested and has about one-half the activity of (RS)-ABA (12). 4 This substance was tested as the racemate and appears to be as active as ABA in several assays (2).…”

Section: Resultsmentioning

confidence: 99%

Structure-Activity Correlations with Compounds Related to Abscisic Acid

Sondheimer¹,

Walton²

1970

Plant Physiol.

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Section: Resultsmentioning

confidence: 99%

Structure-Activity Correlations with Compounds Related to Abscisic Acid

Sondheimer¹,

Walton²

1970

Plant Physiol.

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“…3), a compound found in American paper products derived from the balsam fir. [67][68][69] Among the Hemiptera, only the Pyrrhocoridae are highly sensitive to juvabione, but it has a weak juvenilizing effect in the Tenebrio pupal bioassay 69) although no activity in the lepidopteran pupal bioassay. 67) Moreover, Bowers and Nishida isolated juvocimenes (Fig.…”

Section: Natural and Synthetic Jh Mimics As Insect Growth Regulatorsmentioning

confidence: 99%

Insect juvenile hormone action as a potential target of pest management

Minakuchi

Riddiford

2006

J. Pestic. Sci.

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Juvenile hormone (JH) is a sesquiterpenoid hormone that regulates growth and development in insects. Since JH is a hormone specific to insects and other arthropods, compounds disrupting JH action in insects are expected to be ideal insecticides with low toxicity to non-target organisms. Many natural or synthetic analogs with JH-like or anti-JH activity have been identified, and some potent JH mimics have been used as insecticides. Recent studies on the enzymes in JH biosynthetic and metabolic pathways should be helpful for the discovery of more potent analogs and for the establishment of new means of pest management using recombinant DNA technology. © Pesticide Science Society of Japan Keywords: juvenile hormone (JH), insect metamorphosis, insect growth regulators, biosynthesis and metabolism of JH. Review* To whom correspondence should be addressed. E-mail: chieka_minakuchi@yahoo.com © Pesticide Science Society of Japan doptera. 17,18) Higher Diptera such as D. melanogaster and the blowfly Calliphora vomitoria produce JH III bisepoxide. 19,20) A small amount of methyl farnesoate, a precursor of JH III, was found in cockroach embryos and larvae. [20][21][22] Methyl farnesoate has also been identified in crustaceans 23) and is thought to have a JH-like action in female reproduction. 24)12Ј-OH JH III identified from the corpora allata of the African locust Locusta migratoria migratorioides was reported to exhibit JH activity when a high dose of this compound was topically applied to Tenebrio pupae. 25,26) Biosynthesis, Transport and Metabolism of Juvenile HormoneIn insects, JH is synthesized in the corpora allata via the mevalonate pathway (Fig. 2).27) The mevalonate pathway also exists in mammals and plants, and the early steps from acetylCoA to farnesyl diphosphate are conserved among these organisms. Importantly, insects and other arthropods do not synthesize cholesterol de novo but have to acquire it from dietary sources because they lack the genes encoding squalene synthase and other subsequent enzymes of the sterol branch. 28,29) Another peculiarity of the mevalonate pathway in insects is the capacity to synthesize JH via the isoprenoid branch.The genes encoding the enzymes in the mevalonate pathway from acetyl-CoA to farnesyl diphosphate have been identified in the genome of D. melanogaster and the malaria mosquito Anopheles gambiae, and in an EST library of the pine engraver Ips pini.27) However, it has been difficult to identify the genes encoding enzymes from farnesyl diphosphate to JH

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“…Previously, Balsam fir juvabione has been found to inhibit the metamorphosis of the linden bug, Pyrrhocoris apterus, suggesting that plants could use JHAs as resistance factors against insect herbivores (10,11). However, screening of plants for JH activity revealed only a few JHAs (12).…”

mentioning

confidence: 99%

Identification of plant compounds that disrupt the insect juvenile hormone receptor complex

Lee

Fāng

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Insects impact human health through vector-borne diseases and cause major economic losses by damaging crops and stored agricultural products. Insect-specific growth regulators represent attractive control agents because of their safety to the environment and humans. We identified plant compounds that serve as juvenile hormone antagonists (PJHANs). Using the yeast twohybrid system transformed with the mosquito JH receptor as a reporter system, we demonstrate that PJHANs affect the JH receptor, methoprene-tolerant (Met), by disrupting its complex with CYCLE or FISC, formation of which is required for mediating JH action. We isolated five diterpene secondary metabolites with JH antagonist activity from two plants: Lindera erythrocarpa and Solidago serotina. They are effective in causing mortality of mosquito larvae at relatively low LD 50 values. Topical application of two diterpenes caused reduction in the expression of Met target genes and retardation of follicle development in mosquito ovaries. Hence, the newly discovered PJHANs may lead to development of a new class of safe and effective pesticides. Diseases transmitted by insects result in a million deaths per year (1), and insect infestation leads to annual losses of agricultural products worth billions of US dollars (2). The high toxicity of currently available insecticides presents environmental and health risks, and growing resistance and cross-resistance of insects to these existing insecticides gravely complicates the situation. Hence, there is an urgent need to develop novel effective insecticides.Insect growth regulators (IGRs) have been devised based on insect-specific functions. Three major classes of IGRs are commercially available (3). These IGRs include juvenile hormone (JH) agonists (methoprene and pyriproxyfen), ecdysone agonists (halofenozide and tebufenozide), and chitin synthase inhibitors (buprofezine). They possess low off-target toxicity and environmental danger and have been used to control pests. JHbased IGRs are of particular interest because JH is an insectspecific hormone. JH agonists (JHAs) disrupt insect endocrine regulation, causing abnormal development and larval fatality (4). However, JHAs have limitations in the scope of their applications because they mimic and enhance the JH mode of action. Theoretically, JH antagonists (JHANs) could be used as a powerful alternative, but no effective JHANs have yet been developed.Recent studies identified methoprene-tolerant (Met) as the JH receptor (5, 6). Met is a member of the family of basic helixloop-helix (bHLH)-Per-Arnt-Sim (PAS) transcription factors that requires homo-or heterodimerization for DNA binding and transcriptional regulation (7). In the Aedes aegypti mosquito, Met forms a heterodimer with other bHLH-PAS factors, the steroid receptor coactivator (SRC/FISC), or Cycle (CYC) in a JHdependent manner (8, 9). JH-mediated Met-CYC binding has been quantitatively simulated using the two-hybrid yeast β-galactosidase assay in a yeast cell, Y187 (9). Thus, it is possible to test both J...

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Juvenile Hormone: Identification of an Active Compound from Balsam Fir

Abstract: A sesquiterpenoid ester with high juvenile hormone activity for Pyrrhocoris apterus (L.) was isolated from balsam fir, Abies balsamea (L.) Miller, and identified as the methyl ester of todomatuic acid.

Cited by 191 publications

References 8 publications

Structure-Activity Correlations with Compounds Related to Abscisic Acid

Structure-Activity Correlations with Compounds Related to Abscisic Acid

Insect juvenile hormone action as a potential target of pest management

Identification of plant compounds that disrupt the insect juvenile hormone receptor complex

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