6-Alkyl-3,4-dihydro-2H-pyrans: Chemical Secretion Compounds in Neotropical Harvestmen

The defensive, secretions, of five neotropical) species of harvestmen, (Opiliones: Gonyleptidae) from the Brazilian Atlantic Forest were analyzed and chemically characterized by GC-MS and NMR Methods. Three of the species, Cobania picea, Roweria virescens, and Serracutisoma proximum, secrete a mixture of 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3methyl-1,4,4-benzoquinone. The secretions produced,by the Other two species Iporangaia pustulosa and Neosadocus maximus, contain 1-hepten-3-one, 5-methyl-1-hexen-3-one, and 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone. (1)as major components, as well as,2,3-dimethyl-1.,4-benzoquinone and 2-ethyl-3 methyl-1,4-benzoquinone as minor,constituents. The. dihydropyran 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) is a new natural product, composed of two 1-hepten-3-one, subunits formally linked in a hetero-Diels-Alder reaction. The natural product was proven to be racemic, and its biogenetic origin is discussed.

A comparative analysis of the chemical nature of defensive secretions of Gonyleptidae (Arachnida : Opiliones : Laniatores)

The arachnids of the order Opiliones (harvestmen) produce substances used in defense. In the present paper, we analyzed 22 species of Gonyleptidae to explore the use of defensive substances in taxonomy and evolutionary biology. Thirty-seven different compounds were detected, 18 of which were preliminarily identified. These compounds were mapped onto a phylogenetic tree showing the relationships within the Gonyleptidae. Data from Cosmetidae were used as an outgroup. Five ketones and six alkyl phenols were reported for the first time in harvestmen. (c) 2005 Elsevier Ltd. All rights reserved.

Semiochemicals and social signaling in the wild European rabbit in Australia: II. Variations in chemical composition of chin gland secretion across sampling sites

The volatile components of the chin gland secretion of the wild European rabbit, Oryctolagus cuniculus (L.), were investigated with the use of gas chromatography. Studies of the chemical nature of this secretion by previous workers demonstrated that it was important in the maintenance of social structure in this species. This study identified 34 different volatile components that consist primarily of aromatic and aliphatic hydrocarbons. Especially common are a series of alkyl-substituted benzene derivatives that provide most of the compound diversity in the secretion. Samples of chin gland secretion collected from animals at three different geographical locations, separated by more than 100 km, showed significant differences in composition. This work suggests that variation among populations needs to be considered when undertaking semiochemical research. Alternate nonparametric methods are also used for the analysis of chromatographic data.

Chemical composition of the dufour gland secretion in queens of Melipona bicolor (Hymenoptera, Meliponini)

We describe differences in the chemical composition of the Dufour gland secretion of virgin and physogastric queens of Melipona bicolor through gas chromatography and mass spectrometry. The Dufour gland secretion of virgin queens consists only of hydrocarbons, while that of physogastric queens contains, besides these, a variety of other compounds, such as isobutyrate and acetate esters. Such differences may indicate the queen fecundity condition and the oxygenated compounds of the physogastrics secretion may help to increase their attractiveness.

The chemical composition of the mandibular gland secretion of Melipona bicolor lepeletier, 1836 (Hymenoptera, Apidae, Meliponini): A comparative study among castes and sexes

The mandibular gland secretions of newly emerged, nurse and forager workers, virgin and physogastric queens and males of Melipona bicolor were analyzed by gas chromatography-mass spectrometry. The secretion is composed of a blend of hydrocarbons, alcohols, esters, and acids. The secretion is caste-sex specific and also differs with the tasks performed by the workers and the physiological reproductive condition of the queens.

Chemical Chaperones Curcumin and 4-Phenylbutyric Acid Improve Secretion of Mutant Factor H R127H by Fibroblasts from a Factor H-Deficient Patient

Factor H (FH) is one of the most important regulatory proteins of the alternative pathway of the complement system. Patients with FH deficiency have a higher risk for development of infections and kidney diseases because of the uncontrolled activation and subsequent depletion of the central regulatory component C3 of the complement system. In this study, we investigated the consequences of the Arg(127)His mutation in FH (FHR127H) previously described in an FH-deficient patient, on the secretion of this protein by skin fibroblasts in vitro. We observed that, although the patient cells stimulated with IFN-gamma were able to synthesize FHR127H, the mutant protein was largely retained within the endoplasmic reticulum (ER), whereas normal human fibroblasts stimulated with IFN-gamma secrete FH without retention in the ER. Moreover, the retention of FHR127H provoked enlargement of ER cisterns after treatment with IFN-gamma. A similar ER retention was observed in Cos-7 cells expressing the mutant FHR127H protein. Despite this deficiency in secretion, we show that the FHR127H mutant is capable of functioning as a cofactor in the Factor I-mediated cleavage of C3. We then evaluated whether a treatment could increase the secretion of FH, and observed that the patient's fibroblasts treated with the chemical chaperones 4-phenylbutiric acid or curcumin increased the secretion rate of FH. We propose that these chemical chaperones could be used as alternative therapeutic agents to increase FH plasma levels in FH-deficient patients caused by secretion delay of this regulatory protein. The Journal of Immunology, 2012, 189: 3242-3248.

Chemical chaperones mediate increased secretion of mutant α1-antitrypsin (α1-AT) Z: A potential pharmacological strategy for prevention of liver injury and emphysema in α1-AT deficiency

In α1-AT deficiency, a misfolded but functionally active mutant α1-ATZ (α1-ATZ) molecule is retained in the endoplasmic reticulum of liver cells rather than secreted into the blood and body fluids. Emphysema is thought to be caused by the lack of circulating α1-AT to inhibit neutrophil elastase in the lung. Liver injury is thought to be caused by the hepatotoxic effects of the retained α1-ATZ. In this study, we show that several “chemical chaperones,” which have been shown to reverse the cellular mislocalization or misfolding of other mutant plasma membrane, nuclear, and cytoplasmic proteins, mediate increased secretion of α1-ATZ. In particular, 4-phenylbutyric acid (PBA) mediated a marked increase in secretion of functionally active α1-ATZ in a model cell culture system. Moreover, oral administration of PBA was well tolerated by PiZ mice (transgenic for the human α1-ATZ gene) and consistently mediated an increase in blood levels of human α1-AT reaching 20–50% of the levels present in PiM mice and normal humans. Because clinical studies have suggested that only partial correction is needed for prevention of both liver and lung injury in α1-AT deficiency and PBA has been used safely in humans, it constitutes an excellent candidate for chemoprophylaxis of target organ injury in α1-AT deficiency.

An inquiry into the nature and treatment of diabetes, calculus, and other affections of the urinary organs : with remarks on the importance of attending to the state of the urine in organic diseases of the kidney and bladder : and some practical rules for determining the nature of the disease from the sensible and chemical properties of that secretion /

Includes bibliographical references and index.

Semiochemicals and social signaling in the wild European rabbit in Australia: I. Scent profiles of chin gland secretion from the field

The European rabbit (Oryctolagus cuniculus) uses the secretion of the chin gland in the maintenance of social status. Previous work has concentrated on secretion collected directly from the animal. In this study, the analysis was conducted by collecting scent marks made by free-ranging animals. Scent marks were found to be concentrated at the center of the area controlled by a social group, and at the boundaries between two adjacent social groups. Only the mark from dominant animals could be identified. Marks were also collected from the skin of rabbits, where they had been placed by the dominant individual. The mark found on the head of a subordinate animal may, in the future, be used to identify the dominant animal of the social group, who placed the mark.

To fix or not to fix: The role of 2-phenoxyethanol in rabbit, Oryctolagus cuniculus, chin gland secretion

The European rabbit (Oryctolagus cuniculus) uses the secretion of the chin gland to maintain dominance hierarchies in the wild. Recent work has investigated changes in the secretion when social status is manipulated in the rabbit. When a rabbit becomes dominant, a new compound appears in his secretion, 2-phenoxyethanol. This compound is used as a fixative in the perfume industry. This study investigates whether the compound performs a similar function in the secretion of the rabbit. 2-Phenoxyethanol is not detected olfactorially by rabbits, and slows the release rate of some of the compounds that occur naturally in rabbit chin gland secretion. We suggest that when a rabbit becomes dominant, he adds a fixative to his secretion so that his scent will persist in the environment and not dissipate. He will thus come to dominate the olfactory environment, in much the same way as he does the physical environment.

Protective effect of Calendula officinalis extract against UVB-induced oxidative stress in skin: Evaluation of reduced glutathione levels and matrix metalloproteinase secretion

Background and purpose: Calendula officinalis flowers have long been employed time in folk therapy, and more than 35 properties have been attributed to decoctions and tinctures from the flowers. The main uses are as remedies for burns (including sunburns), bruises and cutaneous and internal inflammatory diseases of several origins. The recommended doses are a function both of the type and severity of the condition to be treated and the individual condition of each patient. Therefore, the present study investigated the potential use of Calendula officinalis extract to prevent UV irradiation-induced oxidative stress in skin. Methods: Firstly, the physico-chemical composition of marigold extract(ME) (hydroalcoholic extract)was assessed and the in vitro antioxidant efficacy was determined using different methodologies. Secondly, the cytotoxicity was evaluated in L929 and HepG2 cells with the MTT assay. Finally, the in vivo protective effect of ME against UVB-induced oxidative stress in the skin of hairless mice was evaluated by determining reduced glutathione (GSH) levels and monitoring the secretion/activity of metalloproteinases. Results and conclusions: The polyphenol, flavonoid, rutin and narcissin contents found in ME were 28.6 mg/g, 18.8 mg/g, 1.6 mg/g and 12.2 mg/g, respectively and evaluation of the in vitro antioxidant activity demonstrated a dose-dependent effect of ME against different radicals. Cytoxicity experiments demonstrated that ME was not cytotoxic for L929 and HepG2 cells at concentrations less than or equal to of 15 mg/mL However, concentrations greater than or equal to 30 mg/mL, toxic effects were observed. Finally, oral treatment of hairless mice with 150 and 300 mg/kg of ME maintained GSH levels close to non-irradiated control mice. In addition, this extract affects the activity/secretion of matrix metalloproteinases 2 and 9 (MMP-2 and -9) stimulated by exposure to UVB irradiation. However, additional studies are required to have a complete understanding of the protective effects of ME for skin. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

Defining secretion processes in astrocytes

During the last decade, evidence that release of chemical transmitters from astrocytes might modulate neuronal activity (the so-called "gliotransmission") occurs in situ has been extensively provided. Nevertheless, gliotransmission remains a highly debated topic because of the lack of direct morphological and functional evidence. Here we provided new information supporting gliotransmission, by i) deepen knowledge about specific properties of regulated secretion of glutamatergic SLMVs, and ii) investigating the involvement of astrocytes in the transmission of dopamine, a molecule whose interaction with astrocytes is likely to occur, but it's still not proven.¦VGLUT-expressing glutamatergic SLMVs have been previously identified both in situ and in vitro, but description of kinetics of release were still lacking. To elucidate this issue, we took advantage of fluorescent tools (styryl dyes and pHluorin) and adapted experimental paradigms and analysis methods previously developed to study exo-endocytosis and recycling of glutamatergic vesicles at synapses. Parallel use of EPIfluorescence and total internal reflection (TIRF) imaging allowed us to find that exo-endocytosis processes in astrocytes are extremely fast, with kinetics in the order of milliseconds, able to sustain and follow neuronal signalling at synapses. Also, exocytosis of SLMVs is under the control of fast, localized Ca2+ elevations in close proximity of SLMVs and endoplasmatic reticulum (ER) tubules, the intracellular calcium stores. Such complex organization supports the fast stimulus-secretion coupling we described; localized calcium elevations have been recently observed in astrocytes in situ, suggesting that these functional microdomains might be present in the intact tissue. In the second part of the work, we investigated whether astrocytes possess some of the benchmarks of brain dopaminergic cells. It's been known for years that astrocytes are able to metabolize monoamines by the enzymes MAO and COMT, but to date no clear information that glial cells are able to uptake and store monoamines have been provided. Here, we identified a whole apparatus for the storage, degradation and release of monoamines, at the ultrastructural level. Electron microscopy immunohistochemistry allowed us to visualize VMAT2- and dopamine-positive intracellular compartments within astrocytic processes, i.e. dense -core granules and cisterns. These organelles might be responsible for dopamine release and storage, respectively; interestingly, this intracellular distribution is reminiscent of VMAT2 expression in dendrites if neurons, where dopamine release is tonic and plays a role in the regulation of its a basal levels, suggesting that astrocytic VMAT2 is involved in the homeostasis of dopamine in healthy brains of adult mammals.¦Durant cette dernière décennie, de nombreux résultats sur le relâchement des transmetteurs par les astrocytes pouvant modulé l'activité synaptique (gliotransmission) ont été fournis. Néanmoins, la gliotransmission reste un processus encore très débattu, notamment à cause de l'absence de preuves directes, morphologique et fonctionnelle démontrant ce phénomène. Nous présentons dans nos travaux de nombreux résultats confortant l'hypothèse de la gliotransmission, dont i) une étude approfondie sur les propriétés spatiales et temporelles de la sécrétion régulée du glutamate dans les astrocytes, et ii) une étude sur la participation des astrocytes dans la transmission de la dopamine, une neuromodulateur dont l'interaction avec les astrocytes est fortement probable, mais qui n'a encore jamais été prouvée. L'expression des petites vésicules (SLMVs - Synaptic Like Micro Vesicles) glutamatergiques exprimant les transporteurs vésiculaires du glutamate (VGLUTs) dans les astrocytes a déjà été prouvé tant in situ qu'in vitro. Afin de mettre en évidence les propriétés précises de la sécrétion de ces organelles, nous avons adapté à nos études des méthodes expérimentales conçues pour observer les processus de exocytose et endocytose dans les neurones. Les résolutions spatiale et temporelle obtenues, grâce a l'utilisation en parallèle de l'épi fluorescence et de la fluorescence a onde évanescente (TIRF), nous ont permis de montrer que la sécrétion régulée dans les astrocytes est un processus extrêmement rapide (de l'ordre de la milliseconde) et qu'elle est capable de soutenir et de suivre la transmission de signaux entre neurones. Nous avons également découvert que cette sécrétion a lieu dans des compartiments subcellulaires particuliers où nous observons la présence du reticulum endoplasmique (ER) ainsi que des augmentations rapides de calcium. Cette organisation spatiale complexe pourrait être la base morphologique du couplage rapide entre le stimulus et la sécrétion. Par ailleurs, plusieurs études récentes in vivo semblent confirmer l'existence de ces compartiments. Depuis des années nous savons que les astrocytes sont capables de métaboliser les monoamines par les enzymes MAO et COMT. Nous avons donc fourni de nouvelles preuves concernant la présence d'un appareil de stockage dans les astrocytes participant à la dégradation et la libération de monoamines au niveau ultrastructurelle. Grâce à la microscopie électronique, nous avons découvert la présence de compartiments intracellulaires exprimant VMAT2 dans les processus astrocytaires, sous forme de granules et des citernes. Ces organelles pourraient donc être responsables à la fois du relâchement et du stockage de la dopamine. De manière surprenante, cette distribution intracellulaire est similaire aux dendrites des neurones exprimant VMAT2, où la dopamine est libérée de façon tonique permettant d'agir sur la régulation de ses niveaux de base. Ces résultats, suggèrent une certaine participation des VMAT2 présents dans les astrocytes dans le processus d'homéostase de la dopamine dans le cerveau.¦A de nombreuses reprises, dans des émissions scientifiques ou dans des films, il est avancé que les hommes n'utilisent que 10% du potentiel de leur cerveau. Cette légende provient probablement du fait que les premiers chercheurs ayant décrit les cellules du cerveau entre le XIXème et le XXeme siècle, ont montré que les neurones, les cellules les plus connues et étudiées de cet organe, ne représentent seulement que 10% de la totalité des cellules composant du cerveau. Parmi les 90% restantes, les astrocytes sont sans doute les plus nombreuses. Jusqu'au début des années 90, les astrocytes ont été plutôt considérés peu plus que du tissu conjonctif, ayant comme rôles principaux de maintenir certaines propriétés physiques du cerveau et de fournir un support métabolique (énergie, environnement propre) aux neurones. Grace à la découverte que les astrocytes ont la capacité de relâcher des substances neuro-actives, notamment le glutamate, le rôle des astrocytes dans le fonctionnement cérébral a été récemment reconsidérée.¦Le rôle du glutamate provenant des astrocytes et son impact sur la fonctionnalité des neurones n'a pas encore été totalement élucidé, malgré les nombreuses publications démontrant l'importance de ce phénomène en relation avec différentes fonctions cérébrales. Afin de mieux comprendre comment les astrocytes sont impliqués dans la transmission cérébrale, nous avons étudié les propriétés spatio-temporelles de cette libération grâce à l'utilisation des plusieurs marqueurs fluorescents combinée avec différentes techniques d'imagerie cellulaires. Nous avons découvert que la libération du glutamate par les astrocytes (un processus maintenant appelé "gliotransmission") était très rapide et contrôlée par des augmentations locales de calcium. Nous avons relié ces phénomènes à des domaines fonctionnels subcellulaires morphologiquement adaptés pour ce type de transmission. Plus récemment, nous avons concentré nos études sur un autre transmetteur très important dans le fonctionnement du cerveau : la dopamine. Nos résultats morphologiques semblent indiquer que les astrocytes ont la capacité d'interagir avec ce transmetteur, mais d'une manière différente comparée au glutamate, notamment en terme de rapidité de transmission. Ces résultats suggèrent que le astrocytes ont la capacité de modifier leurs caractéristiques et de s'adapter à leur environnement par rapport aux types de transmetteur avec lequel ils doivent interagir.

Morphological, chemical and developmental aspects of the Dufour gland in some eusocial bees (Hymenoptera, Apidae): a review

Morphological, chemical and developmental aspects of the Dufour gland in some eusocial bees (Hymenoptera, Apidae): a review. The present revision focused on the more recent data about the Dufour gland in some eusocial bees, taking in account general aspects of its morphology, secretion chemical nature, bio-synthetic pathway and development. Many functions have been attributed to this gland in eusocial bees, but none are convincing. With the new data about this gland, not only the secretion chemical pathway of the Dufour gland may be reasonable understood, as its function in some eusocial bees, especially Apis mellifera Linné, 1758, which has been extensively studied in the last years.

Botulinum neurotoxin type A blocks the morphological changes induced by chemical stimulation on the presynaptic membrane of Torpedo synaptosomes.

The action of botulinum neurotoxin on acetylcholine release, and on the structural changes at the presynaptic membrane associated with the transmitter release,was studied by using a subcellular fraction of cholinergic nerve terminals (synaptosomes) isolated from the Torpedo electric organ. Acetylcholine and ATP release were continuously monitored by chemiluminescent methods.To catch the membrane morphological changes, the quick-freezing method was applied. Our results show that botulinum neurotoxin inhibits the release of acetylcholine from these isolated nerve terminals in a dose-dependent manner, whereas ATP release is not affected. The maximal inhibition (70%) is achieved at neurotoxin concentrations as low as 125 pM with an incubation time of 6 min. This effect is not linked to an alteration of the integrity of the synaptosomes since, after poisoning by botulinum neurotoxin type A, they show a nonmodified occluded lactate dehydrogenase activity. Moreover, membrane potential is not altered by the toxin with respect to the control, either in resting condition or after potassium depolarization. In addition to acetylcholine release inhibition, botulinum neurotoxin blocks the rearrangement of the presynaptic intramembrane particles induced by potassium stimulation. The action of botulinum neurotoxin suggests that the intramembrane particle rearrangement is related to the acetylcholine secretion induced by potassium stimulation in synaptosomes isolated from the electric organ of Torpedo marmorata.