Behavioral and electroantennogram responses of periplanone analogs

The biological activities of synthetic periplanone analogs, including four candidates of periplanone-A (P-A), were evaluated by behavioral and electroantennogram (EAG) assays. Among 16 periplanone analogs, six compounds evoked pheromonal activity from the male American cockroaches. The threshold dosages of these biological active analogs were 10–10⁵ times lower than that of the known periplanone mimic, germacrene-D. The conformation required for eliciting the pheromonal activity is discussed in terms of the structure-activity relationship of these analogs. Hauptmann's P-A elicited the strongest pheromonal activity among four candidates of P-A in our bioassay, suggesting that Hauptmann's P-A is a natural P-A produced from female cockroaches.     

Behavioral responses of malePeriplaneta americana L. to female sex pheromone components,periplanone-A and periplanone-B

Bioassays were performed on malePeriplaneta americana L. using synthetic (–)-periplanone-B (P-B) and Hauptmann's (–)-periplanone-A (P-A), and their mixtures at various ratios to estimate the roles of both periplanones for the sexual communication of the species. Both P-A and P-B elicited qualitatively the same responses, such as antennal movement, rapid locomotion, wing raising, and homosexual behavior of male cockroaches, but the threshold of the pheromone activities for P-B was two orders of magnitude lower than that of P-A. Neither synergistic nor inhibitory but only a simple integrated effect on the responses was observed when mixtures of P-A and P-B were applied.     

Isolation,identification, and synthesis of male-produced sex pheromone of papaya fruit fly,Toxotrypana curvicauda Gerstaecker (Diptera: Tephritidae)

A male-produced sex pheromone of the papaya fruit fly,Toxotrypana curvicauda Gerstaecker, was isolated from volatiles collected from air passed over calling males and was identified as 2-methyl-6-vinylpyrazine by comparative gas-liquid chromatographic and spectroscopic evidence. Synthetic 2-methyl-6-vinylpyrazine elicited typical pheromonal responses from unmated mature female flies such as walking, running, and flying in an arena bioassay; flying upwind with a zigzag flight pattern; and hovering in the pheromone plume in a wind-tunnel bioassay. These responses were similar quantitatively and qualitatively to responses to naturally occurring pheromone from calling male papaya fruit flies.This article reports the results of research only. Mention of a proprietary product does not constitute an endorsement or the recommendation for its use by USDA.     

Enhancement of recombinant soluble dengue virus 2 envelope domain III protein production in Escherichia coli trxB and gor double mutant

The dengue virus is currently the most important flavivirus causing human diseases in the tropical and subtropical regions of the world. The envelope protein domain III of dengue virus type 2 (D2EIII), which induces protective and neutralizing antibodies, was expressed as an N-terminal fusion to a hexa-histidine tag in Escherichia coli. The expression of recombinant D2EIII of 103 amino acids in the soluble form can be achieved using suitable host strains, such as Origami, at a low induction temperature of 18 degrees C. The enhanced production of the soluble protein could be attributed to the thioredoxin reductase (trxB) and glutathione reductase (gor) double mutations in the Origami genome. The soluble and refolded D2EIII proteins were recognized by different antibodies including human patient antiserum. The immunization of rats with soluble D2EIII protein elicited the production of antibodies that could recognize the D2EIII protein in the D2EIII precursor protein and in C-terminal truncated dengue envelope protein type 1-4. Thus, this protein production system is suitable for the production of authentic recombinant dengue proteins that may be used in the diagnosis of the dengue virus infection or in vaccine development.     

Profiling of arachidonic acid metabolites in rabbit platelets by radio gas chromatography

A method for profiling arachidonic acid metabolites by radio gas chromatography (GC) is described. The incubation mixture of rabbit platelets with [¹⁴C]arachidonic acid was purified on a Sep-Pak C₁₈ cartridge and derivatized with diazomethane,O-methylhydroxylamine and dimethylisopropylsilylimidazole. The recovery of total¹⁴C-radioactivity was 93.1±7.2%. Loss of radioactivity during derivatization was negligible. Baseline separations for [¹⁴C]arachidonic acid and its metabolites were obtained in a single run within 45 min by GC using a synchronized accumulating radioisotope detector (GC/SARD). The recovery of radioactivity from the GC column was virtually 100%. The chemical structures of the metabolites were confirmed by GC/mass spectrometry; peaks of arachidonic acid metabolites were assigned by comparison of the methylene unit values with those of radioactive peaks in GC/SARD analyses. The intra-assay coefficients of variation in GC/SARD analyses were less than 10%. The method was used to map the profile of arachidonic acid metabolites formed by rabbit platelets in the presence of indomethacin, baicalein or glutathione.     

Formation, Transformation, and Decomposition of Y2TeO6

A metastable modification of Y₂TeO₆ crystallizes at 770°C to 870°C at a heating rate of 10°C·min⁻¹ in air from an amorphous material prepared by the simultaneous hydrolysis of yttrium and tellurium alkoxides. It has a tetragonal unit cell with a=1.0428 nm and c=1.7524 nm. The tetragonal-to-hexagonal phase transformation occurs at 920° to 960°C. Hexagonal Y₂TeO₆ decomposes into Y₆TeO₁₂ and TeO₃↑ at 1220° to 1320°C; only Y₆TeO₁₂ is obtained as the decomposition product. Both modifications of Y₂TeO₆ are built up by octahedral TeO₆ groups.     

Lasioderma chemistry sex pheromone of cigarette beetle (Lasioderma serricorne F.)

A chemical study of the sex pheromone of the cigarette beetle was carried out. Seven components were isolated from active fractions of column chromatography of the female extract, and their structures were elucidated by spectroscopic evidence and confirmed by synthesis to be (4S,6S,7S)-4,6-di-methyl-7-hydroxynonan-3-one (serricornin) (I), 2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran (anhydroserricornin) (II), 4,6-dimethylnonan-3,7-dione (III), 4,6-dimethylnonan-3,7-diol (IV), 4,6-dimethyl-7-hydroxy-4-nonen-3-one (V), (2S,3R)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(l-methyl-2-oxobutyl)-4H-pyran-4-one (serricorone) (VI) and (2S,3R)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(1-methyl-2-hydroxybutyl)-4H-pyran-4-one (serricorole) (VII).These structural features suggested that the occurrence of these components might be related to the polyketide biosynthesis. The behavioral bioassay and BAG experiments revealed the biological role of each component in the copulatory behavior of this insect.     

Female-produced oviposition deterrents of the cigarette beetle,Lasioderma serricorne (F.) (Coleoptera: Anobiidae)

Oviposition deterrents of the cigarette beetle,Lasioderma serricorne, were isolated from its adult body extract and found to be identical to (2S,3R,1'S)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(l-methyl-2-oxobutyl)-4H-pyran-4-one (-serricorone) and its lR-epimer (-serricorone) by spectroscopic evidence. Serricorone was previously found as one of the minor sex pheromone components of the same insect, and hence indicating bi-functional nature. The presence of two isomers in the body was proved by careful treatment. Each of them exhibited the same level of oviposition deterring activity, which was less potent than the crude body extract at an increased concentration.