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A new synthesis of 9-oxodec-2-enoic acid, using thiophen as one of the starting materials, is described.

The sex pheromones of the moths Adoxophyes orana, Clepsis spectrana and Archips poda-na were found to be mixtures of positional or geometrical isomers. The predominant compound of the pheromone of A. orana is cis-9-tetradecenyl acetate (tda); the minor compound cis-11-tda, whereas for C. spectrana the predominant compound is cis-11-tda and the minor one cis-9-tda. In A. podana cis-11-tda and trans-11-tda were found in about equal amounts. The separate compounds are inactive, and mixtures of them are active only when the components are present in a definite, critical ratio. The geometrical isomers of the constituents of the pheromone of A. orana were found to be potent inhibitors. Zusammenfassung Kombinierte Sexualpheromone bei Tortriciden. Zur Rolle der positionellen and geometrischen Isomeren Die Sexualpheromone der Falter Adoxophyes orana, Clepsis spectrana und Archips podana sind immer ein Gemisch aus zwei Komponenten: entweder positionelle oder geo-metrische Isomere. Die Hauptkomponente des Pheromons von A. orana ist cis-9-tetra-dezenylazetat (tda); die Nebenkomponente ist cis-11-tda, wahrend fur C. spectrana cis-11-tda die Hauptkomponente ist und cis-9-tda die Nebenkomponente. Cis-11-tda und trans-11-tda wurden in A. podana in etwa gleichen Mengen gefunden. Die Separatkomponenaen sind nicht attraktiv, und Gemische haben nur die beste Lockwirkung, wenn die beiden Komponenten in einem sehr speziellen Verhaltnis anwesend sind. Die geometrischen Isomere der Komponenten des Pheromons von A. orana sind starke Lockstoffinhibitoren.

Direct detection of Streptococcus pneumoniae DNA in blood adds to culture results in the etiological diagnosis of patients with community-acquired pneumonia (CAP). Quantification of the amount of DNA, the bacterial DNA load (BDL), provides a measurement of DNAemia that may increase the understanding of the clinical relevance of S. pneumoniae DNA in blood. We evaluated the S. pneumoniae BDL as a diagnostic tool in adult patients with CAP. The BDL was determined in whole-blood samples collected simultaneously with blood for culture from 45 adult patients with CAP. After DNA extraction, S. pneumoniae DNA was detected with specific real-time PCR amplification, and the BDL was calculated with a standard curve. PCR and microbiological results were compared, and the BDL was related to clinical and laboratory parameters. S. pneumoniae DNA was detected in 10/13 patients with positive blood cultures and in 67% of patients with microbiologically confirmed pneumococcal pneumonia. The positive predictive values of the receiver operating characteristic curves for the BDLs for pneumococcal infection (100%) and pneumococcal bacteremia (69%) were higher than those for the level of C-reactive protein (CRP; 43% and 23%, respectively) and the white blood cell count (WBC; 42% and 35%, respectively); the negative predictive values of these three parameters were in the same range (±90 and ±97%, respectively). The BDL was higher in patients presenting with systemic inflammatory response syndrome and in patients with bacteremia. Positive correlations were observed for the BDL with WBC, CRP level, and length of stay. We conclude that the BDL supports the diagnosis of S. pneumoniae infection in patients with CAP and provides a putative marker of the severity of disease.

By means of electroantennographic detection and gas chromatography-mass spectrometry, the sex pheromone of Argyrotaenia sphaleropa was identified as a mixture of (Z)-11-tetradecenal, (Z)-11,13-tetradecadienal, (Z)-11-tetradecenyl acetate, and (Z)-11,13-tetradecadienyl acetate in the ratio of 1:4:10:40. Best trap catches were obtained with mixtures of (Z)-11-tetradecenal and (Z)-11,13-tetradecadienal in the ratio of 1:4 to 1:9.

Since much of the pathogenesis of cytomegalovirus (CMV) disease is still unknown and vascular involvement may be of importance, a rat model was used to study the nature and course of CMV-induced vascular pathology. In this model, local CMV infection was established by subcutaneous inoculation of rat-specific CMV (RCMV) in the sole of the foot. Signs of endothelial activation, including leucocyte adhesion, preceded detectable RCMV infection of these cells. Ultimately, vasculitis and thrombotic occlusion were accompanied by diffuse tissue inflammation and necrosis. Generalized RCMV infection was induced in rats by intraperitoneal administration of the virus, which resulted in multiple organ pathology, including haemorrhages, inflammation, and gastrointestinal ulceration. RCMV-encoded antigens were found especially in mononuclear inflammatory cells in the organs and peripheral blood. In addition, multiple haemorrhages and disturbed haematological parameters indicated diffuse intravascular coagulopathy. In conclusion, this study provides evidence for extensive vascular involvement and haematological consequences during disseminated CMV infection. The nature and chronology of RCMV-induced pathological vascular events were demonstrated, indicating the importance of endothelial damage. These data and further study may lead to a better understanding of the pathogenesis of CMV multiple-organ disease. © 1998 John Wiley & Sons, Ltd.

Objective : Recently, we have found that rat CMV (RCMV) infected smooth muscle cells (SMCs) in rat carotid arteries when administered 14 days after balloon injury. In the present study we investigated (1) the long term effects of CMV infection on neointimal cross-sectional area, and (2) whether the phenotype of the intimal SMCs influences their susceptibility to active CMV infection. Methods : In the first part of the study, rats received RCMV intravenously, two weeks after balloon catheterisation of the left carotid artery and were sacrificed twenty weeks after catheterisation. Continuous BrdU infusion was performed by subcutaneously implanted osmotic pumps during the last two weeks of life. In the second part RCMV was administered eight weeks after catheterisation and rats were sacrificed two weeks later. Immunohistochemistry was used to detect viral antigens, to determine BrdU incorporation as well as the contents of α-actin, desmin and vimentin in the carotid arteries. Intima and media cross-sectional areas were determined using computerized morphometry. Results and conclusions : RCMV infection did not induce any differences in intima or media cross-sectional areas of the injured carotid artery, nor in the extent of SMC proliferation as shown by BrdU incorporation, 20 weeks after balloon catheterisation. Eight weeks after balloon catheterisation, RCMV no longer infected neointimal SMCs. This non-responsiveness to RCMV was associated with ‘re-differentiation’ of the eight weeks old neointima, compared with two weeks after catheterization, as shown by the contents of α-actin, desmin and vimentin. Our data suggest that intimal SMC phenotype determines its susceptibility to active RCMV infection in vivo. Since de-differentiation of neointimal SMCs is associated with enhanced proliferation of these cells it is stated that de-differentiation or proliferation is prerequisite for infection.

Biological control of the silkworm pest (Exorista bombycis) was partly successful by using a new hymemopteran biocontrol agent Trichopria khandalus, recovered from the environs of a cocoon market in Hindupur district of Andhra Pradesh (India). T. khandalus is a tiny (1–1.5 mm) endoparasite, the females were found to parasitize the uzifly puparia. The progeny developed inside the uzi pupa, and the adults (140–160 individuals from a single pupa) emerged after about 18–25 days depending on the seasonal extrinsic factors. The lift cycle of T. khandalus averaged 32 days. Due to the favourable sex ratio (2:3 male/female) and high preference to parasitize uzi puparia it is qualified as a good biocontrol agent for the control of E. bombycis. Prospects for utilizing this hyperparasite to manage and eliminate the uzi populations are discussed in the light of its data on biology, and easily manageable mass multiplication in the insectary.

The American cockroach, Periplaneta americana, produces a multicomponent mixture as its sex pheromone. The publications of its identification by various groups have confused the nomenclature of the various compounds. Novel names are proposed for some of them: periplanone-A (IV-A), isoperiplanone-A (III-D), periplanone-C (V) and periplanone-D (VI).

By means of electroantennographic detection and gas chromatography-mass spectrometry, the sex pheromone of Argyrotaenia sphaleropa was identified as a mixture of (Z)-11-tetradecenal, (Z)-11,13-tetradecadienal, (Z)-11-tetradecenyl acetate, and (Z)-11,13-tetradecadienyl acetate in the ratio of 1:4:10:40. Best trap catches were obtained with mixtures of (Z)-11-tetradecenal and (Z)-11,13-tetradecadienal in the ratio of 1:4 to 1:9.

There is increasing evidence for cytomegalovirus (CMV) induced vascular pathology during acute infection in the immunocompromised host. Inflammation is involved in such processes, which is frequently associated with increased levels of oxidative mediators and reduced anti-oxidant protection. A relation between viral infection and oxidative stress has been recognized for human immunodeficiency virus and herpes simplex virus-1 infections, but little is known in this respect for CMV infections. We investigated if there is a relation between CMV infection of vascular cells and the intracellular redox status using an in vitro rat model. We measured intracellular glutathione levels and rat CMV (RCMV) permissiveness of rat heart endothelial cell lines (RHEC), rat smooth muscle cells (RSMC), and compared these with fully CMV-permissive rat fibroblasts (REF and Rat 2). In addition, the effects of the anti-oxidant N -acetylcysteine (NAC) and the glutathione synthesis inhibitor buthionine sulfoximide (BSO) on CMV permissiveness and replication were investigated in these cell lines. Finally, we investigated infection of vascular cells under inflammatory conditions in an in vivo rat model for acute CMV infection. The results show a very high endogenous glutathione level in RHEC compared to REF, Rat 2 cells and RSMC. This is associated with a low CMV permissiveness in RHEC as opposed to full permissiveness in REF, Rat 2 cells and RSMC in vitro. In addition, modulation of the intracellular thiol redox status affected CMV infection and replication only in RHEC, but not in RSMC and Rat 2 cells. During acute infection in vivo under immunosuppressed conditions rat endothelial cells first become activated and subsequently infected leading to vascular damage and pathology. This study suggests that a high endogenous thiol redox status may contribute to the apparent barrier function of endothelial cells with respect to CMV infection and that oxidative stress may facilitate CMV infection of the vascular wall.

1. Cytomegalovirus (CMV) is a major pathogen in immunocompromised individuals and may participate in the pathogenesis of atherosclerosis in the general population. We evaluated whether CMV-infection alters the function of arterial smooth muscle. 2. Blood pressure (BP) and arterial reactivity were recorded in immunosuppressed rats that had been infected with CMV (10(5) plaque forming units i.p.). Furthermore, the reactivity of isolated arteries was compared between CMV-infected rats and rats injected with bacterial endotoxin (LPS). 3. Initially resting BP and heart rate (HR) were not modified in CMV-infected rats, but baroreflex control of HR was impaired. By the eighth day post-CMV, BP dropped precipitously and could no longer be raised by phenylephrine (PHE). 4. In mesenteric resistance arteries, isolated at this stage from CMV-infected rats, contractile responses to nerve stimulation, noradrenaline, PHE and 5-hydroxytryptamine (5-HT) were virtually absent while those to high potassium and vasopressin (AVP) were not modified. In aortae of CMV-infected rats, responses to 5-HT and AVP were impaired while those to PHE or potassium were hardly affected. Reduced contractile responses could not be restored by NG-nitro-L-arginine methyl ester (L-NAME). 5. Continuous treatment of CMV-infected rats with prazosin (0.1 mg kg-1 day-1) prevented blood pressure lowering and resistance artery changes. 6. Observations in arteries of LPS-treated rats (5-10 mg kg-1, i.p.) differed markedly from those in vessels of CMV-infected animals. The contractile reactivity of their mesenteric resistance arteries was not altered while in their aortae, responses to PHE, 5-HT and AVP were reduced. With the exception of the AVP responses, this was more pronounced in the presence of 1-arginine and reversed by L-NAME. 7. These findings indicate that CMV-infection results in a reduction of resistance artery reactivity and hypotonia. This seems not to involve cytokine-mediated induction of NO synthase in the vascular wall but may be due to alterations of excitation-contraction coupling in arterial smooth muscle in response to increased sympathetic nervous input.

The susceptibility of medial and neointimal arterial smooth muscle cells (SMCs) to acute cytomegalovirus (CMV) infection was investigated in immunocompetent and immunocompromised rats. The left common carotid artery of all the rats was injured by balloon catheterization. On days 14 and 17 after injury, rats were either intravenously infected with a rat CMV (RCMV) or mock-infected. Active RCMV infection was shown in the neointima of the injured arteries of immunosuppressed rats, characterized by specific cytopathological changes in hematoxylin-eosin-stained sections and by the presence of early viral antigens and the presence of the virus at different stages of maturation at the electron-microscopic level. Viral genome was shown as well by use of in situ hybridization procedures. However, medial cells were hardly ever infected, and RCMV did not infect neointimal parts that were recovered by endothelial cells. No infection was seen in control right carotid arteries or in the injured arteries of immunocompetent rats. Acute intimal RCMV infection was accompanied by infiltration of inflammatory cells, predominantly mononuclear cells that stained positive with an ED-1 monoclonal antibody. The majority of infected neointimal cells were SMCs containing smooth muscle actin. No changes were found in medial or neointimal cross-sectional areas of the infected arteries. In the present study, an active RCMV infection of arterial SMCs was established in vivo, and it was concluded that neointimal SMCs are far more susceptible than are medial SMCs and that the absence of endothelium and immunosuppression are necessary conditions for arterial RCMV infection.

Two sex pheromones, periplanone A and periplanone B were isolated from the American cockroach Periplaneta americana. The technique is described for collecting periplanone B from the alimentary tracts of virgin females. Periplanone A was extracted from the excreta of the insects. Mass spectral analysis of the pheromones and related compounds were performed and the results are reported here. Evidence is presented suggesting that periplanone A is in fact a degradation product of periplanone B. A reaction scheme is considered for the pathway: periplanone B periplanone A (stable, but inactive) PA 22–VII.

Recent research, reviewed here, of the pheromone system of the potato tuberworm moth has led to the isolation, identification, and synthesis of its components.trans-4,cis-7-tridecadien-l-ol acetate (PTM 1) andtrans-4,cis-7,cis-10-tridecatrien-l-ol acetate (PTM 2), mixtures of which are much more attractive in the field than 2 virgin female moths or each compound on its own.

Antennal responses of male Adoxophyes orana and Clepsis spectrana to their two pheromone components, cis-9- and cis-11-tetradecenyl acetate (tda) were studied. Responses to a dilution series of the components alone and in five mixture ratios were recorded. The main pheromone component for A. orana (cis-9-tda) and for C. spectrana (cis-11-tda) gave the highest electroantennogram (EAG) responses, respectively, but mixtures corresponding to the optimum field attracting ratios for each species elicited higher responses than the separate components. The geometrical isomers, trans-9- and trans-11-tda, which inhibit male A. orana response in the field, do not appear to give an additive EAG response when mixed with the pheromone components.

The sex pheromone of the potato tuberworm moth, Phthorimaea operculella (Zell.) has been identified as a mixture of trans-4, cis-7-tridecadienyl acetate and trans-4, cis-1, cis-10 tridecatrienyl acetate. The identifications have been carried out by means of electroantennography, mass, infrared and n.m.r. spectroscopy. The identifications have been confirmed by synthesis. Both compounds occur in the insects in about equal amounts. The individual compounds are attractive to male moths in pheromone traps. The triolefinic ester was found to be much more attractive than the diolefinic ester. However, mixtures of both compounds in the ranges of 4:1 tot 1:4 are much more attractive than the individual compounds or traps baited with two virgin female moths. ZUSAMMENFASSUNG SEXUALPHEROMONE DER KARTOFFELMOTTE, PHTHORIMAEA OPERCULELLA. ISOLIE-RUNG, IDENTIFIKATION UND FREILANDBEWERTUNG Das Sexualpheromon von Phthorimaea operculella (Gelechiidae) wurde identifiziert als ein Gemisch von trans-4, cis-7-Tridecadienylacetat und trans-4, cis-1, cis-10-Tridecatrienylacetat. Die beiden Identifizierungen wurden durchgefuhrt mit Hilfe von Elektroantennografie, Massenspektroskopie, Ultrarotspektroskopie und Kernspinnresonanzspektroskopie. Die beiden Identifizierungen wurden durch Synthese bestatigt. Die Pheromonkomponenten wurden in etwa gleiche Mengen von den Faltern isoliert. Beide Substanzen erwiesen sich sowohl in naturlicher wie in synthetischer Form als aktiv in der Elektroantennografie sowie im biologischen Test und in Sexfallen. Ein Mischungsverhaltnis der beiden Komponenten von 4: 1 bis 1: 4 weist eine viel hohere Lockstoffwirkung auf als die beiden Einzelkomponenten oder als zwei lebende Weibchen. Ein Isomer des naturlichen Tridecatrienylacetat, namlich cis-4, trans-7, cis-10-Tridecatrienyl-acetate, war nur schwach aktiv in den verschiedenen Testen. In Sexfallen wurde die Aktivitat dieses Isomers durch Zusatz von trans-4, cis-7-Tridecadienylacetat nicht erhoht.

The currant clearwing moth,Synanthedon tipuliformis (Clerck) (Lepidoptera: Sesiidae), is a pest in many parts of the world. In field tests it was found that (E,Z)-2,13-octadecadien-1-ol acetate attracts males of this species. The synthesis of this compound and of its geometrical isomer (Z,Z)-2,13-octadecadien-1-ol acetate is described.

The sex pheromone of the American cockroach,Periplaneta americana, consists of two compounds, which we have named periplanone-A and periplanone-B. The two compounds can be isolated from fecal material in a ratio of 1∶10, and periplanone-B can also be isolated from intestinal tracts. A total amount of 200 μg of periplanone-B has been isolated from both fecal material and alimentary tracts. By means of gas chromatography-mass spectrometry, hydrogenation, infrared analysis, and NMR analysis, we were able to identify periplanone-B as (1Z,5E)-1,10(14)-diepoxy-4(15),5-germacradien-9-one. The overall structure was confirmed by comparison with a synthetic, biologically active epimer of periplanone-B.

Two independently biologically active compounds, periplanone A and periplanone B can be isolated from fecal material of the American cockroach,Periplaneta americana. In fecal material these occur in a ratio of 1 ∶ 10 while, in intestinal tracts only periplanone B has been found. The latter has been identified as (1Z,5E)-1,10(14)-diepoxy-4(15),5-germacradien-9-one; the identification was confirmed by synthesis. Only the CD (-) enantiomer (1R,2R,5E,7S,10R) exhibited activity. The lower threshold of activity of both natural and synthetic CD (-) pheromone, is 10(-6)-10(-7) μg. Periplanone A has been identified (apart from its stereochemical configuration) as 7-methylene-4-isopropyl-12-oxa-tricyclo[4.4.2.0(1,5)]-9-dodecen-2-one). The structure of this rather unstable compound could be deduced by comparing its NMR, UV, IR, and mass spectra with the NMR and mass spectra of its rearrangement product. Both structures still require confirmation by synthesis, but their spectral data are in complete agreement with the proposed structures. The presence of only periplanone B in the gut and the presence of both periplanone A and periplanone B in the feces suggests that periplanone B is a genuine sex pheromone, whereas peri-planone A might be a biologically active transformation product, which in turn can isomerize into a more stable, but inactive compound.

Two sex pheromones, periplanone A and periplanone B were isolated from the American cockroach Periplaneta americana. The technique is described for collecting periplanone B from the alimentary tracts of virgin females. Periplanone A was extracted from the excreta of the insects. Mass spectral analysis of the pheromones and related compounds were performed and the results are reported here. Evidence is presented suggesting that periplanone A is in fact a degradation product of periplanone B. A reaction scheme is considered for the pathway: periplanone B periplanone A (stable, but inactive) PA 22–VII.

By means of analytical and electroantennogram methods, cis-11-and trans-11-tetradecenyl acetate have been isolated and identified as the sex pheromones of the fruit tree tortrix moth, Archips podana. In contrast to the single compounds, mixtures in a ratio of about 1 : 1 are highly attractive to male moths in field experiments.

Both cis-9-and cis-11-tetradecenyl acetate were isolated from 2500 virgin females of the summer fruit tortrix moth Adoxophyes orana (F.v.R.) by gel permeation, column chromatography on silica gel, and gas chromatography. Their chemical, physical, and biological properties were identical to those of the synthetic compounds. In contrast to the single compounds, mixtures of these pheromones were highly active in laboratory and field tests. Catches, in traps, with the pheromone mixture were comparable to those obtained when live females were used as bait. This is the first example of a member of the lepidoptera in which the presence of two isomers is an absolute requirement for activity in laboratory and in field experiments.

Two tortricid mitoth species, Adoxophyes orana and Clepsis spectrana, utilize the samne two isomers, cis- 9- and cis- l1-tetradecenyl acetate, as their sex attractant. Commnlunication between the sexes of each species is separated effectively by a different blendinig of both compounds by the females and a different response to these blends by the males.