Insect Juvenile Hormone Activity Research Articles

Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

(+)-Juvabione, a natural sesquiterpene exhibiting insect juvenile hormone activity, has been synthesized from sigma-symmetric 4-(2-formyl-ethyl)cyclohexanone by employing organocatalytic asymmetric aldolization and Norrish I-type fragmentation as the key steps.

Quantitative structure-activity relationship modeling of insect juvenile hormone activity of 2,4-dienoates using computed molecular descriptors

Juvenile hormone (JH) activity of one hundred and eighty 2,4-dienoates reported for the larvae/pupae of six insect species was modeled using 915 atom pairs and 258 global molecular descriptors (topological and geometrical). Ridge regression, principal component regression and partial least square regression methods were used to model each of the JH activities. The use of all of the available parameters did not yield any good models, and extensive predictor trimming was necessary to improve the models. Ridge regression was found to give the best results among the three statistical tools used. The top ten molecular descriptors selected based on the t-statistic for each of the six models were found to be mostly atom pairs containing heteroatoms and topochemical descriptors. This suggests the importance of the chemical nature of the ligand rather than mere space-filling as the basis of the JH bioactivity. The residual plots indicate the existence of some non-linear relations, and recursive partitioning was used to capture any nonlinear relation between the bioassays and the molecular descriptors.

THE ALKALOIDS OF TRIBULUS TERRESTRIS: A REVISED STRUCTURE FOR THE ALKALOID TRIBULUSTERINE

ISHS III WOCMAP Congress on Medicinal and Aromatic Plants - Volume 3: Perspectives in Natural Product Chemistry THE ALKALOIDS OF TRIBULUS TERRESTRIS: A REVISED STRUCTURE FOR THE ALKALOID TRIBULUSTERINE

ORGANOELEMENT JUVENILE HORMONE MIMETICS

The synthesis of new organophosphorus and organosilicon compounds possessing insect juvenile hormone activity is described. The structure of the prepared compounds is confirmed by NMR spectra.

A lipase-mediated route to (+)-juvabione and (+)-epijuvabione from racemic norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized from (±)-norcamphor via the both enantiomeric intermediates having bicyclo[3.2.1]octane framework by employing a lipase-mediated kinetic ester-hydrolysis reaction and cyclopropane ring-expansion reaction as the key steps.

Stereo- and enantio-controlled synthesis of (+)-juvabione and (+)-epijuvabione from (+)-norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized with complete stereo- and enantio-control using (+)-norcamphor as the chiral precursor via both the enantiomeric bicyclo[3.2.1]octenone intermediates.

SYNTHESIS OF THE TERTIARY PHOSPHINE OXIDES POSSESSING JUVENILE HORMONE ACTIVITY

Abstract The synthesis of the first organophosphorus compounds (1a–d) possessing insect juvenile hormone activity is described. The structure of the compounds (1a–d) is confirmed by IR and NMR spectra.

Insect anti-juvenile hormone and juvenile hormone activity from plants in the genusNama

The insect anti-juvenile hormones precocene I and II (7-methoxy-2,2-dimethyl-2H-1-benzopyran and 6,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran) were identified in three of nineNama (Hydrophyllaceae) species. Precocene I occurred inN. lobbii while precocene II occurred inN. hispidum, N. lobbii andN. sandwicense. N. hispidum contained the highest concentration (ca 0.5% dry weight) of precocene II, which was found in the leaves, stems, seed capsules, corolla, glandular trichomes, and seeds. In addition to the anti-juvenile hormone, insect juvenile hormone activity was detected in the organosoluble extracts ofN. rothrockii andN. sandwicense. N. sandwicense is the first plant discovered to contain compounds with both anti- and juvenile hormone activity.

Metabolism and insect juvenile hormone activity of methoprene and three major metabolites in Tribolium castaneum (Herbst) pupae

A new juvenile hormone (JH) assay using newly-formed pupae of Tribolium castaneum is described. The technique is simple and has a number of advantages over existing JH-assays. Using the insecticide-susceptible strain (FSS II) of Tribolium castaneum the assay was used to compare the activities of methoprene (isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate) and three of the major metabolic products of methoprene produced by T. castaneum pupae in vivo. The parent 11-methoxy ester (methoprene) was the most active of the materials tested. However, the 11-hydroxy ester metabolite retained considerable biological activity whereas neither the 11-methoxy acid nor the 11-hydroxy acid metabolites had any measurable activity. The significance of these results in relation to the sensitivity of T. castaneum and other insects to methoprene is discussed.

ChemInform Abstract: Development of JH Active Compounds as Insecticides

Extensive research has been done to get the ideal “third generation insecticides” in the area of compounds showing insect juvenile hormone (JH) activity since the discovery of JH activity in insect extracts. Although some JH mimics have been commercialized and practically used as proper insecticides in some specific fields, it has become apparent that researchers have now recognized the inherent disadvantage of JH mimics as insecticides and they do not seem to have such enthusiasm that they showed once.Here, I would like to present a brief review of JH and JH mimics as well as a prospective view of insecticidal JH mimics, while showing the recent JH active compounds discovered in our laboratory.

Biotransformation of 2-(4-methoxybenzyl)-l-cyclohexanone by cell cultures ofSolatium aviculare

During the search for compounds with insect juvenile hormone activity, the biotransformation of 2-(4-methoxybenzyl)-l-cyclohexanone, of 2-(4-methoxybenzyl)-l-cyclohexanone ethylene acetal and of both isomers of 2-(4-methoxybenzyl)-l-cyclohexanol by plant cells was examined. The compounds were metabolized by cell suspension culture of Solatium aviculare Forst. The reaction conditions were optimized and the metabolic products isolated and identified. A scheme of biotransformation pathway has been proposed.

昆虫幼若ホルモン活性化合物の殺虫剤としての発展

Extensive research has been done to get the ideal “third generation insecticides” in the area of compounds showing insect juvenile hormone (JH) activity since the discovery of JH activity in insect extracts. Although some JH mimics have been commercialized and practically used as proper insecticides in some specific fields, it has become apparent that researchers have now recognized the inherent disadvantage of JH mimics as insecticides and they do not seem to have such enthusiasm that they showed once.Here, I would like to present a brief review of JH and JH mimics as well as a prospective view of insecticidal JH mimics, while showing the recent JH active compounds discovered in our laboratory.

Evaluation of three compounds with insect juvenile hormone activity as grain protectants against insecticide-susceptible and resistant strains of Sitophilus species (Coleoptera: Curculionidae)

Three compunds with insect juvenile hormone activity have been tested as protectants for wheat grain against one insecticide-susceptible and two insecticide-resistant strains of Sitophilus granarius. Neither JH I nor methoprene gave complete control of S. granarius at 100 ppm whereas ethyl[2-( p-phenoxy)ethyl]carbamate was effective at only 5 ppm. There was no loss of biological activity of this last compound even after treated grain was stored at 25°C and 70% r.h. for 12 months, and it was also found to be highly active against susceptible strains of Sitophilus oryzae and Sitophilus zeamais. There was no evidence that two insecticide-resistant strains of S. granarius were cross-resistant to any of the compounds tested.

Juvadecene: Discovery of a juvenile hormone mimic in the plant, Macropiper excelsum

AbstractA compound with significant insect juvenile hormone activity was isolated from the plant, Macropiper excelsum. The chemical structure was determined by spectral methods to be 1‐(3,4‐methylenedioxyphenyl)‐trans‐3‐decene(l), and confirmed by synthesis. The hormonally active substance applied topically to last (fifth)‐instar nymphs of the milkweed bug (Oncopeltus fasciatus) induced a supernumerary metamorphosis at 30 μg. Higher doses were toxic.

Products active on arthropod. II. Insect juvenile hormone mimics. 2. Insect juvenile hormone mimics based on bakuchiol.

Several derivatives of bakuchiol, a meroterpenoid from Psoralea corylifolia Linn., have been prepared and evaluated for insect juvenile hormone activity against Dysdercus koenigii nymphs. Almost all of these were found to be more active than the standard farnesyl methyl ether, while some of these proved to be many times more potent.

Insect juvenile hormone activity of optically active alkyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoates and of arylterpenoid analogs

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTInsect juvenile hormone activity of optically active alkyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoates and of arylterpenoid analogsClive A. Henrick, Richard J. Anderson, Gerardus B. Staal, and George F. LudvikCite this: J. Agric. Food Chem. 1978, 26, 3, 542–550Publication Date (Print):May 1, 1978Publication History Published online1 May 2002Published inissue 1 May 1978https://doi.org/10.1021/jf60217a019RIGHTS & PERMISSIONSArticle Views174Altmetric-Citations33LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts

ChemInform Abstract: AMINO ACID DERIVATIVES WITH ACYL AND CHLOROACYL PROTECTING GROUPS ‐ SYNTHESIS AND INSECT JUVENILE HORMONE ACTIVITY

AbstractSynthesis and Insect Juvenile Hormone Activity.

ChemInform Abstract: NATURAL AND SYNTHETIC MATERIALS WITH INSECT HORMONE ACTIVITY. XXXII. AROMATIC C ETHERS WITH INSECT JUVENILE HORMONE ACTIVITY

Chemischer InformationsdienstVolume 7, Issue 26 Natural Products ChemInform Abstract: NATURAL AND SYNTHETIC MATERIALS WITH INSECT HORMONE ACTIVITY. XXXII. AROMATIC C ETHERS WITH INSECT JUVENILE HORMONE ACTIVITY K. HEJNO, K. HEJNOSearch for more papers by this authorF. SORM, F. SORMSearch for more papers by this author K. HEJNO, K. HEJNOSearch for more papers by this authorF. SORM, F. SORMSearch for more papers by this author First published: June 29, 1976 https://doi.org/10.1002/chin.197626348Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume7, Issue26June 29, 1976 RelatedInformation

Insect juvenile hormone activity of alkyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoates. Variations in the ester function and in the carbon chain.

Insect juvenile hormone activity of alkyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoates. Variations in the ester function and in the carbon chain.

Amino acid derivatives with acyl and chloroacyl protecting groups-synthesis and insect juvenile hormone activity

Amino acid derivatives with acyl and chloroacyl protecting groups-synthesis and insect juvenile hormone activity