Fingerprinting of propolis by easy ambient sonic-spray ionization mass spectrometry

Chemical profiles of a representative set of 49 propolis ethanolic extracts collected worldwide (North and South America, Europe, Asia and Oceania) were obtained via easy ambient sonic-spray ionization mass spectrometry (EASI-MS). This simple and easily implemented fingerprinting technique analyses directly (without any pre-separation or sample manipulation) a tiny droplet of the ethanolic extract placed on a inert surface under ambient conditions. Data acquisition took about a minute per sample with no substantial sample carry-over. Extraction of propolis with ethanol by using an ultrasonic bath method gave EASI-MS data similar to the traditional maceration method, reducing total analysis time for the crude propolis resin from a week to just ca 1 h. Principal component analysis of the EASI-MS data is shown to group samples according to the plant sources of their resins, which characterizes their geographical origin. © 2009 Elsevier B.V. All rights reserved

A Review Of The Plant Origins,composition And Biological Activityof Red Propolis

Propolis is a mixture of various amounts of beeswax and resins collected by beesfrom plants, particularly from buds and resinous exudates. The composition of propolisvaries according to the kind of bee, geographic and plant origin of the samples. Propolisis important for the hive defense and has been used for its medicinal properties sinceancient times. Red propolis has been found in the northeastern coast of Brazil, as well asin Cuba, Venezuela, Mexico and China. Among the most frequently cited plant sourcesare species of the Leguminosae and Clusiaceace families. The composition of redpropolis varies both qualitatively and quantitatively, confirming different plant sources.The compounds that have been found in red propolis samples are listed herein. Redpropolis has shown diverse biological activities: antimicrobial activity against differentbacteria and yeast; against Leishmania amazonensis parasites; antioxidant, cytotoxic andpotential antitumor activity; antipsoriatic, anti-inflammatory and analgesic activities;anti-obesity and hepatoprotective effects. Many new studies of red propolis are beingdeveloped due to the promising therapeutic activity; however, future studies mustdifferentiate between red propolis from diverse geographic origins and chemical profiles. © 2012 by Nova Science Publishers, Inc. All rights reserved.7589Bankova, V.S., De Castro, S.L., Marcucci, M.C., Propolis: recent advances in chemistry and plant origin (2000) Apidologie, 31, pp. 3-15Gonnet, M., Propriétés phytoinhibitrices de la colone d'abeilles (Apis Mellifera L.) (1968) Annales des abeilles, 11 (2), pp. 105-116Simone-Finstrom, M., Spivak, M., Propolis and bee health: the natural history and significance of resin use by honey bees (2010) Apidologie, 41, pp. 295-311Chauvin, R., Progrès récents dans la biologie de l'abeille (1960) Annales de l'abeilleDerevici, A., Popesco, A., Popesco, N., Recherches sur certaines propriétés biologiques de la propolis (1964) Annales des abeilles, 7 (3), pp. 191-200Delaplane, K.S., Honey Bees and Beekeeping (2010) Learning for life, Bulletin, 1045Seeley, T.D., Morse, R.A., The nest of the honey bee (Apis Mellifera L) (1976) lnsectes Sociaux, Paris., 23 (4), pp. 495-512Atkinson, E., Ellis, J., Honey bee, Apis mellifera L., confinement behavior toward beetle invaders (2001) Insectes Sociaux, 58, pp. 495-503Drezner-Levy, T., Smith, B.H., Shafir, S., The effect of foraging specialization on various learning tasks in the honey bee (Apis mellifera) (2009) Behav Ecol Sociobiol, 64, pp. 135-148Ikeno, H., Ohtani, T., Reconstruction of honeybee behavior within the observation hive (2001) Neurocomputing, (38), pp. 1317-1323Manrique, A.J., Soares, A.E.E., Inicio de um programa de seleção de abelhas africanizadas para a melhora na produção de propolis e seu efeito na produção de mel (2002) Interciencia, 27 (6), pp. 312-316Inoue, H.T., De Sousa, E., De Oliveira Orsi, R., Funari, S.C., Carelli Barreto, L., Da Silva Dib, A., Produção de própolis por diferentes métodos de coleta (2007) Asociación Latinoamericana de Producción Animal, 15 (2), pp. 65-69Castaldo, S., Capasso, F., Propolis, an old remedy used in modern medicine (2002) Fitoterapia, 73 (SUPPL. 1), pp. S1-S6Louveaux, J., Recherches sur la récolte du pollen par les abeilles (Apis Mellifera L) (1958) Annales des abeilles.Salatino, A., Teixeira É, W., Negri, G., Message, D., Origin and Chemical Variation of Brazilian propolis eCam (2005), 2 (1), pp. 33-38Barth, O.M., Da Luz, C.F.P., Palynological analysis of Brazillian red propolis samples (2009) Journal of Apicultural Research and Bee world, 48 (3), pp. 181-188Silva, B.B., Rosalen, P.L., Cury, J.A., Ikegaki, M., Souza, V.C., Esteves, A., Alencar, S.M., Chemical Composition and Botanical Origin of Red Propolis a New Type of Brazilian Propolis eCAM (2008), 5 (3), pp. 313-316Sawaya, A.C.H.F., Tomazella, D.M., Cunha, I.B.S., Bankova, V.S., Marcucci, M.C., Custodio, A.R., Eberlin, M.N., Electrospray Ionization Mass Spectrometry Fingerprinting of Propolis (2004) Analyst (London), 129, pp. 739-744Daugsch, A., Moraes, C.S., Fort, P., Park, Y.K., Brazilian Red Propolis- Chemical Composition and Botanical Origin eCAM (2008), 5 (4), pp. 435-441Piccinelli, A.L., Lotti, C., Campone, L., Cuesta-Rubio, O., Fernandez, M.C., Rastrelli, L., Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography -Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry (2011) Journal of Agricultural and Food Chemistry, 59, pp. 6484-6491Trusheva, B., Popova, M., Naydenski, H., Tsvetkova, I., Rodriguez, J.G., Bankova, V., New polyisoprenylated benzophenones from Venezuelan propolis (2004) Fitoterapia, 75, pp. 683-689Lotti, C., Fernandez, M.C., Piccinelli, A.L., Cuesta-Rubio, O., Hernandez, I.M., Chemical Constituents of Red Mexican Propolis (2010) Journal of Agricultural and Food Chemistry, 58, pp. 2209-2213Izuta, H., Narahara, Y., Shimazawa, M., Mishima, S., Kondo, S.-I., Hara, H., 1, 1-Diphenyl-2-picrylhydrazyl Radical Scavenging Activity of Bee Products and Their Constituents Determined by ESR (2009) Biol. Pharm. Bull., 32 (12), pp. 1947-1951Nunes, L.C.C., Galindo, A.B., De Deus, A.D.O., Rufino, D.A., Randau, K.P., Satiro, H., Otros, Y., Variabilidade sazonal dos constituintes da própolis vermelha e bioatividade em Artermia salina (2009) Revista Brasileira de Farmacognosia, 19 (2 B), pp. 524-529Trusheva, B., Bioactive Constituents of Brazilian Red Propolis eCAM (2006), 3 (2), pp. 249-254Righi, A.A., Alves, T.R., Negri, G., Marques, L.M., Breyer, H., Salatino, A., Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities (2011) J Sci Food Agric, 91, pp. 2363-2370Cabral, I.R., Oldoni, T.L.C., Prado, A., Bezerra, R.M., De Alencar, S.M., Composição fenolica, atividade antibacteriana e antioxidante da própolis vermelha brasileira (2009) Quimica Nova, 32 (6), pp. 1523-1527Awale, S., Li, F., Onozuka, H., Esumi, H., Tezukaa, Y., Kadota, S., Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition (2008) Bioorganic & Medicinal Chemistry, 16, pp. 181-189Alencar, S., Oldoni, T., Castro, M., Cabral, I., Costa-Neto, C., Cury, J., Rosalen, P.L., Ikegaki, M., Chemical composition and biological activity of a new type of Brazilian propolis: Red propolis (2007) Journal of Ethnopharmacology, 113, pp. 278-283Oldoni, T.L., Cabrala, I.S., D'arcea, M.A.R., Rosalen, P.L., Ikegaki, M., Nascimento, A.M., Alencar, S.M., Isolation and analysis of bioactive isoflavonoids and chalcone from a new type of Brazilian propolis (2011) Separation and Purification Technology, 77, pp. 208-213Cuesta-Rubio, O., Piccinelli, A.L., Fernandez, M.C., Hernandez, I.M., Rosado, A., Rastrelli, L., Chemical Characterization of Cuban Propolis by HPLC-PDA, HPLC-MS, and NMR: the Brown, Red, and Yellow Cuban Varieties of Propolis (2007) J. 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Use Of Electrospray Ionization Mass Spectrometry To Fingerprint Beer

Mass spectrometry constitutes one of the most encompassing instrumental techniques in science, widely applied in the fi elds of chemistry, biology, medical science and technology. Direct insertion electrospray ionization mass spectrometry (ESI-MS) is a fast and sensitive method which differentiates diverse types of beer, in both positive and negative ion modes, characterizing their main constituents. Although the basic ingredients of beer (water, malt, hops and yeast) have not changed much since the dark ages, variations in these ingredients and in the manufacturing process result in diverse types of beer. The spectra or fi ngerprints of each type of beer permit not only the separation of samples according to their main characteristics, but also further information through the ESI-MS/MS fragmentation of the diagnostic ions of each type, adding another dimension to the analytical results. Fast and characteristic beer fi ngerprint mass spectra were obtained by ESI-MS in both the negative and positive modes. A total of 29 samples of ale produced in Brazil and other countries were divided into three groups by visual analysis of the positive [ESI(+)-MS] and negative [ESI(-)-MS] mode fi ngerprints as well as by chemometric analysis of the data. Many of the marker ions in both modes were found to be simple sugars and oligosaccharides, although their intensities varied depending on the type of ale (pale colored, dark colored and sweetened). This shows that direct infusion ESI-MS could distinguish between samples of ale with different compositions and is promising as a fast and effi cient method of beer characterization. © 2009 Elsevier Inc.923934Alcázar, A., Pablos, F., Martín, M.J., González, A.G., (2002) Talanta, 57, pp. 45-52Annesley, T.M., (2003) Clin. Chem., 49, pp. 1041-1044Araújo, A.S., Rocha, L.L.R., Tomazela, D.M., Sawaya, A.C.H.F., Almeida, R.R., Catharino, R.R., Eberlin, M.N., (2005) Analyst, 130, pp. 884-889Berlitz, H.D., Grosch, W., Schieberle, P., (2004) F ood Chemistry, , (3rd edn). Springer-Verlag, GermanyCatharino, R.R., Sawaya, A.C.H.F., Cunha, I.B.S., Fogaça, A.O., Facco, E.M.P., Godoy, H.T., Daudt, C.E., Eberlin, M.N., (2006) J. Mass Spectrom., 41, pp. 185-190Cole, R.B., (1997) Electrospray Ionization Mass Spectrometry, , John Wiley & Sons Inc., New YorkCole, R.B., (2000) J. Mass Spectrom., 35, pp. 763-772Cooks, R.G., Zhang, D.X., Koch, K.J., Gozzo, F.C., Eberlin, M.N., (2001) Anal. Chem., 73, pp. 3646-3655Degelmann, P., Becker, M., Herderich, M., Humpf, H.U., (1999) Chromatographia, 49, pp. 543-546Eberlin, M.N., Meurer, E., Santos, L.S., Pilli, R.A., (2003) Org. Lett., 5, pp. 1391-1394Gaumet, J.J., Strouse, G., (2000) J. Am. Soc. Mass Spectrom., 11, pp. 338-344Hans, X.L., Gross, R.W., (2001) A nalytic. Biochem., 265, pp. 88-100Hardwick, W.A., (1995) Handbook of Brewing, , Marcel Dekker, New YorkHofte, A.J.P., van der Hoeven, R.A.M., Fung, S.Y., Verpoorte, R., Tjaden, U.R., Van der Greef, J., (1998) J. Am. Soc. Brew. Chem., 56, pp. 118-122Klampfl, C.W., Himmelsbach, M., Buchberger, W., Klein, H., (2002) Anal. Chim. Acta, 454, pp. 185-191Koch, K.J., Gozzo, F.C., Nanita, S.C., Takats, Z., Eberlin, M.N., Cooks, R.G., (2002) Angew. Chem. Int. Ed. Engl., 41, p. 1721Kotiaho, T., Eberlin, M.N., Vainiotalo, P., Kostiainen, R., (2000) J. Am. Soc. Mass Spectrom., 11, pp. 526-535Mauri, P., Minoggio, M., Simonetti, P., Gardana, C., Pietta, P., (2002) Rapid Commun. Mass Spectrom., 16, pp. 743-748Möller, J.K., Catharino, R.R., Eberlin, M.N., (2005) Analyst, 130, pp. 890-897de la Mora, J.F., Berkel, G.J.V., Enke, C.G., Cole, R.B., Sanchez, M.M., Fenn, J.B., (2000) J. Mass Spectrom., 35, pp. 939-952Raftery, M.J., Geczy, C.L.J., (2002) J. Am. Soc Mass Spectrom., 13, pp. 709-718Rioli, V., Gozzo, F.C., Shida, C.S., Krieger, J.E., Heimann, A.S., Linardi, A., Almeida, P.C., Ferro, E.S., (2003) J. Biol. Chem., 278, pp. 8547-8555Russel, D.H., (1994) Experimental Mass Spectrometry, , Plenum Press, New YorkSawaya, A.C.H.F., Tomazela, D.M., Cunha, I.B.S., Bankova, V.S., Marcucci, M.C., Custódio, A.R., Eberlin, M.N., (2004) Analyst, 129, pp. 739-744Schoonjans, V., Taylor, N., Hudson, B.D., Massart, D.L., (2002) J. Pharm. Biomed. Anal., 28, pp. 537-548Siuzdak, G., (2005) An Introduction to Mass Spectrometry Ionization: An Excerpt from the Expanding Role of Mass Spectrometry in Biotechnology, , 2nd edn. MCC Press, San Diego, CAWhittle, N., Eldridge, H., Bartley, J., Organ, G., (1999) J. Inst. Brew., 105, pp. 89-99Williams, J.D., Flanagan, M., Lopez, L., Fischer, S., Miller, L.A.D., (2003) J. Chromatogr. A., 1020, pp. 11-26Zhang, X.R., Minear, R.A., Guo, Y.B., Hwang, C.J., Barret, S.E., Ikeda, K., Shimizu, Y., Matsui, S., (2004) W ater Res., 38, pp. 3920-393

Characterisation Of The Membrane Transport Of Pilocarpine In Cell Suspension Cultures Of Pilocarpus Microphyllus

Pilocarpine is an alkaloid obtained from the leaves of Pilocarpus genus, with important pharmaceutical applications. Previous reports have investigated the production of pilocarpine by Pilocarpus microphyllus cell cultures and tried to establish the alkaloid biosynthetic route. However, the site of pilocarpine accumulation inside of the cell and its exchange to the medium culture is still unknown. Therefore, the aim of this study was to determine the intracellular accumulation of pilocarpine and characterise its transport across membranes in cell suspension cultures of P. microphyllus. Histochemical analysis and toxicity assays indicated that pilocarpine is most likely stored in the vacuoles probably to avoid cell toxicity. Assays with exogenous pilocarpine supplementation to the culture medium showed that the alkaloid is promptly uptaken but it is rapidly metabolised. Treatment with specific ABC protein transporter inhibitors and substances that disturb the activity of secondary active transporters suppressed pilocarpine uptake and release suggesting that both proteins may participate in the traffic of pilocarpine to inside and outside of the cells. As bafilomicin A1, a specific V-type ATPase inhibitor, had little effect and NH4Cl (induces membrane proton gradient dissipation) had moderate effect, while cyclosporin A and nifedipine (ABC proteins inhibitors) strongly inhibited the transport of pilocarpine, it is believed that ABC proteins play a major role in the alkaloid transport across membranes but it is not the exclusive one. 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Phytochemical Markers Of Different Types Of Red Propolis

Propolis is a resin that bees collect from different plant sources and use in the defense of the bee community. The intricate composition of propolis varies depending on plant sources from different geographic regions and many types have been reported. Red coloured propolis found in several states in Brazil and in other countries has known antimicrobial and antioxidant activity. Different analytical methods have been applied to studies regarding the chemical composition and plant origins of red propolis. In this study samples of red propolis from different regions have been characterised using direct infusion electrospray ionisation mass spectrometry (ESI(-)-MS) fingerprinting. Data from the fingerprints was extracted and analysed by multivariate analysis to group the samples according to their composition and marker compounds. Despite similar colour, the red coloured propolis samples were divided into three groups due to contrasting chemical composition, confirming the need to properly characterise the chemical composition of propolis. © 2013 Elsevier Ltd. All rights reserved.146174180Alencar, S.M., Oldoni, T.L.C., Castro, M.L., Cabral, I.S.R., Costa-Neto, C.M., Cury, J.A., Rosalen, P.L., Ikegaki, M., Chemical composition and biological activity of a new type of Brazilian propolis: Red propolis (2007) Journal of Ethnopharmacology, 113 (2), pp. 278-283. , DOI 10.1016/j.jep.2007.06.005, PII S037887410700284XAwale, S., Li, F., Onozuka, H., Esumi, H., Tezuka, Y., Kadota, S., Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition (2008) Bioorganic & Medicinal Chemistry, 16 (1), pp. 181-189Bankova, V., Boudourova-Krasteva, G., Sforcin, J.M., Frete, X., Kujumgiev, A., Maimoni-Rodella, R., Popov, S., Phytochemical evidence for the plant origin of Brazilian propolis from Sao Paulo state (1999) Zeitschrift fur Naturforschung - Section C Journal of Biosciences, 54 (5-6), pp. 401-405Bankova, V.S., De Castro, S.L., Marcucci, M.C., Propolis: Recent advances in chemistry and plant origin (2000) Apidologie, 31 (1), pp. 3-15Banskota, A.H., Tezuka, Y., Prasain, J.K., Matsushige, K., Saiki, I., Kadota, S., Chemical constituents of Brazilian propolis and their cytotoxic activities (1998) Journal of Natural Products, 61 (7), pp. 896-900. , DOI 10.1021/np980028cBarth, M.O., Pinto Da Luz, C.F., Palynological analysis of Brazilian red propolis samples (2009) Journal of Apicultural Research and Bee World, 48 (3), pp. 181-188Cabral, I.S.R., Oldoni, T.L.C., Prado, A., Bezerra, R.M.N., Alencar, S.M., Ikegaki, M., Composição fenólica, atividade antibacteriana e antioxidante da própolis vermelha brasileira (2009) Química Nova, 32, pp. 1523-1527Cuesta-Rubio, O., Frontana-Uribe, B.A., Ramirez-Apan, T., Cardenas, J., Polyisoprenylated benzophenones in Cuban propolisbiological activity of nemorosone (2002) Zeitschrift fur Naturforschung - Section C Journal of Biosciences, 57 (3-4), pp. 372-378Cuesta-Rubio, O., Piccinelli, A.L., Fernandez, M.C., Hernandez, I.M., Rosado, A., Rastrelli, L., Chemical characterization of Cuban propolis by HPLC-PDA, HPLC-MS, and NMR: The brown, red, and yellow Cuban varieties of propolis (2007) Journal of Agricultural and Food Chemistry, 55 (18), pp. 7502-7509. , DOI 10.1021/jf071296wDaugsch, A., Moraes, C.S., Fort, P., Park, Y.K., Brazilian red propolis-chemical composition and botanical origin (2008) Evid Based Complement Alternat Med, 5 (4), pp. 435-441Fernandez, M.C., Cuesta-Rubio, O., Rosado Perez, A., De Oca, M., Porto, R., Marquez Hernandez, I., GC-MS determination of isoflavonoids in seven red Cuban propolis samples (2008) Journal of Agriculture and Food Chemistry, 56 (21), pp. 9927-9932Gonnet, M., Propriétés phytoinhibitrices de la colone d'abeilles (Apis Mellifera L.) (1968) Annales des Abeilles, 11 (2), pp. 105-116Ishida, V.F.D.C., Negri, G., Salatino, A., Bandeira, M.F.C.L., A new type of Brazilian propolis: Prenylated benzophenones in propolis from Amazon and effects against cariogenic bacteria (2011) Food Chemistry, 125 (3), pp. 966-972Izuta, H., Narahara, Y., Shimazawa, M., Mishima, S., Kondo, S., Hara, H., 1,1-Diphenyl-2-picrylhydrazyl radical scavenging activity of bee products and their constituents determined by ESR (2009) Biological & Pharmaceutical Bulletin, 32 (12), pp. 1947-1951Ledón, N., Casacó, A., González, R., Merino, N., González, A., Tolón, Z., Efectos antipsoriásico, antiinflamatorio y analgésico del propoleo rojo colectado en Cuba (1996) Revista Cubana de Farmacia, 30Li, F., Awale, S., Tezuka, Y., Kadota, S., Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship (2008) Bioorganic and Medicinal Chemistry, 16 (10), pp. 5434-5440. , DOI 10.1016/j.bmc.2008.04.016, PII S0968089608003295López, B.G.-C., Sawaya, A.C.H.F., A review of the plant origins, composition and biological activity of red propolis (1974) Natural Products: Structure, Bioactivity and Applications, pp. 83-96. , R.E. Goncalves, M. Cunha Pinto, Nova Science PublishersLotti, C., Campo Fernandez, M., Piccinelli, A.L., Cuesta-Rubio, O., Marquez Hernandez, I., Rastrelli, L., Chemical constituents of red Mexican propolis (2010) Journal of Agriculture and Food Chemistry, 58 (4), pp. 2209-2213Marcucci, M.C., Sawaya, A.C.H.F., Custódio, A.R., Paulino, N., Eberlin, M.N., HPLC and ESI-MS typification: New approaches for natural therapy with Brazilian propolis (2008) Scientific Evidence of the Use of Propolis in Ethnomedicine, pp. 33-54. , N. Oršolić, I. Bašić, Transworld Research Network Kerala, IndiaMorsy, A., Abdalla, A., Soltan, Y., Sallam, S.A., El-Azrak, K.-D., Louvandini, H., Effect of Brazilian red propolis administration on hematological, biochemical variables and parasitic response of Santa Inês ewes during and after flushing period (2013) Tropical Animal Health and Production, pp. 1-10Nunes, L.C.C., Galindo, A.B., Deus, A.D.S.O.D., Rufino, D.A., Randau, K.P., Xavier, H.S., Variabilidade sazonal dos constituintes da própolis vermelha e bioatividade em Artermia salina (2009) Revista Brasileira de Farmacognosia, 19, pp. 524-529Oldoni, T.L.C., Cabral, I.S.R., D'Arce, M.A.B.R., Rosalen, P.L., Ikegaki, M., Nascimento, A.M., Isolation and analysis of bioactive isoflavonoids and chalcone from a new type of Brazilian propolis (2011) Separation and Purification Technology, 77 (2), pp. 208-213Piccinelli, A.L., Lotti, C., Campone, L., Cuesta-Rubio, O., Campo Fernandez, M., Rastrelli, L., Cuban and Brazilian red propolis: Botanical origin and comparative analysis by high-performance liquid chromatography-photodiode array detection/electrospray ionization tandem mass spectrometry (2011) Journal of Agriculture and Food Chemistry, 59 (12), pp. 6484-6491Righi, A.A., Alves, T.R., Negri, G., Marques, L.M., Breyer, H., Salatino, A., Brazilian red propolis: Unreported substances, antioxidant and antimicrobial activities (2011) Journal of the Science of Food and Agriculture, 91 (13), pp. 2363-2370Rodriguez, S., Ancheta, O., Ramos, M.E., Remirez, D., Rojas, E., Gonzalez, R., Effects of cuban red propolis on galactosamine-induced hepatitis in rats (1997) Pharmacological Research, 35 (1), pp. 1-4. , DOI 10.1006/phrs.1996.9998Sawaya, A.C.H.F., Cunha, I.B.D.S., Marcucci, M.C., Aidar, D.S., Silva, E.C.A., Carvalho, C.A.L., Electrospray ionization mass spectrometry fingerprinting of propolis of native Brazilian stingless bees (2007) Apidologie, 38 (1), pp. 93-103Sawaya, A.C.H.F., Cunha, I.B.S., Marcucci, M.C., De Oliveira Rodrigues, R.F., Eberlin, M.N., Brazilian propolis of Tetragonisca angustula and Apis mellifera (2006) Apidologie, 37 (3), pp. 398-407. , http://www.edpsciences.org/articles/apido/pdf/2006/03/M6020.pdf?access=ok, DOI 10.1051/apido:2006011Sawaya, A.C.H.F., Tomazela, D.M., Cunha, I.B.S., Bankova, V.S., Marcucci, M.C., Custodio, A.R., Eberlin, M.N., Electrospray ionization mass spectrometry fingerprinting of propolis (2004) Analyst, 129 (8), pp. 739-744. , DOI 10.1039/b403873hSebrae, Origem garantida (2012) Empreender, Globo Rural, 323, pp. 1-3Silva, B.B., Rosalen, P.L., Cury, J.A., Ikegaki, M., Souza, V.C., Esteves, A., Chemical composition and botanical origin of red propolis, a new type of Brazilian propolis (2008) Evid Based Complement Alternat Med, 5 (3), pp. 313-316Simone-Finstrom, M., Spivak, M., Propolis and bee health: The natural history and significance of resin use by honey bees (2010) Apidologie, 41 (3), pp. 295-311Tomás-Barberán, F.A., García-Viguera, C., Vit-Olivier, P., Ferreres, F., Tomás-Lorente, F., Phytochemical evidence for the botanical origin of tropical propolis from Venezuela (1993) Phytochemistry, 34 (1), pp. 191-196Tosi, E.A., Re, E., Ortega, M.E., Cazzoli, A.F., Food preservative based on propolis: Bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli (2007) Food Chemistry, 104 (3), pp. 1025-1029. , DOI 10.1016/j.foodchem.2007.01.011, PII S0308814607000647Trusheva, B., Popova, M., Bankova, V., Simova, S., Marcucci, M.C., Miorin, P.L., Bioactive constituents of Brazilian red propolis (2006) Evid Based Complement Alternat Med, 3 (2), pp. 249-254Trusheva, B., Popova, M., Naydenski, H., Tsvetkova, I., Rodriguez, J.G., Bankova, V., New polyisoprenylated benzophenones from Venezuelan propolis (2004) Fitoterapia, 75 (7-8), pp. 683-689. , DOI 10.1016/j.fitote.2004.08.001, PII S0367326X04001832Zulueta, A., Esteve, M.J., Frígola, A., ORAC and TEAC assays comparison to measure the antioxidant capacity of food products (2009) Food Chemistry, 114 (1), pp. 310-31

Pilocarpine And Related Alkaloids In Pilocarpus Vahl (rutaceae)

Pilocarpine is mainly known as a drug for the treatment of glaucoma and it is also used as a stimulant of sweat and lachrymal glands. Species of the genus Pilocarpus are collectively named jaborandi in Brazil and their leaves are the only known source of this imidazole alkaloid. Pilocarpine is mainly obtained from two species, Pilocarpus microphyllus and Pilocarpus jaborandi and, despite the economical and pharmacological importance of this alkaloid, very little is known about pilocarpine, from basic information on the contents in different jaborandi species and plant tissues to the biosynthetic route and the metabolic control. This review will focus briefly on the genus jaborandi, then on what is known about pilocarpine biosynthesis followed by possible biotechnological applications aiming to produce the alkaloid in vitro. Finally, the alkaloids found in this genus, their plant sources and pharmacological applications will be reviewed. © 2010 Nova Science Publishers, Inc.6380Abreu, I.N., Andreazza, N.L., Sawaya, A.C.H.F., Eberlin, M.N., Mazzafera, P., Cell suspension as a tool to study the biosynthesis of pilocarpine in Jaborandi (2007) Plant Biology, 9, pp. 793-799Abreu, I.N., Mazzafera, P., Eberlin, M.N., Zullo, M.A.T., Sawaya, A.C.H.F., Characterization of the variation of the imidazole alkaloid profile of Pilocarpus microphyllus in different seasons and parts of the plant by electrospray ionization mass spectrometry fingerprinting and identification of novel alkaloids by tandem mass spectrometry (2007) Rapid Commun. Mass Spectr, 21, pp. 1205-1213Abreu, I.N., Sawaya, A.C.H.F., Eberlin, M.N., Mazzafera, P., Production of pilocarpine in callus of Jaborandi (Pilocarpus microphyllus Stapf) (2005) Vitro Cellular Developmental Biology - PLANT, 41, pp. 806-811Andrade, P., Willoughby, R., Pomponi, S.A., Kerr, R.G., Biosynthetic studies of the alkaloid, stevensine, in a cell culture of the marine sponge Teichaxinella morchella (1999) Tetrahedron Letters, 40, pp. 4775-4778Andrade-Neto, M., Mendes, P.H., Silveira, E.R., An imidazole alkaloid and other constituents from Pilocarpus trachyllophus (1996) Phytochemistry, 42, pp. 885-887Andreazza, N.L., (2009) Transporte de pilocarpina em suspensões celulares de Pilocarpus microphyllus, , Universidade estadual de CampinasAndreazza, N.L., Abreu, I.N., Sawaya, A.C.H.F., Eberlin, M.N., Mazzafera, P., Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH (2008) Biotechnology Letters, 31, pp. 607-614Avancini, G., Abreu, I.N., Saldaña, M.D.A., Mohamed, R.S., Mazzafera, P., Induction of pilocarpine formation in jaborandi leaves by salicylic acid and methyljasmonate (2003) Phytochemistry, 63, pp. 171-175Baricevic, D., Umek, A., Kreft, S., Maticic, B., Zupancic, A., Effect of water stress and nitrogen fertilization on the content of hyoscyamine and scopolamine in the roots of deadly nightshade (Atropa belladonna) (1999) Environmental and Experimental Botany, 42, pp. 17-24Braun, M., Buhne, C., Cougali, D., Schaper, K., Frank, W., Convergent diasteroselective synthesis of isopilocarpine by one-pot Michael-addition-alkylation reaction (2004) Synthesis, 17, pp. 2905-2909Cordell, G.A., (1981) Introduction to alkaloids: a biogenetic approach, , New York, John Wiley & SonsDavies, S.G., Roberts, P.M., Stephenson, P.T., Thomson, J.E., Syntheses of the racemic jaborandi alkaloids pilocarpine, isopilocarpine and pilosinine (2009) Tetrahedron Letters, 50 (3127), pp. 3509-3512Davies, S.G., Robets, P.M., Stephenson, P.T., Storr, H.R., Thomson, J.E., A practical and scalable total synthesis of the jaborandi alkaloid (+)-pilocarpine (2009) Tetrahedon, 65, pp. 8283-8296de Luca, L., Naturally occurring and synthetic imidazoles. Their chemistry and their biological activities (2006) Current Medical Chemistry, 13, pp. 1-23Dewick, P.M., (1997) Medicinal natural products: a biosynthetic approach, , New York, John Wiley & SonsGerard, A.W., Alkaloid and active principles of jaborandi (1875) Pharmaceutical Journal, 5, p. 865Godoy-Hernandez, G.C., Vazquez-Flota, F.A., Loyola-Vargas, V.M., The exposure to trans-cinnamic acid of osmotically stressed Catharanthus roseus cells cultured in a 14-L bioreactor increases alkaloid accumulation (2000) Biotechnology Letters, 22, pp. 921-925Goodman, L.S., Gilman, A., (2001) The pharmacological basis of therapeutics, , 10th edition, New York, McGraw Hill Companies IncHardy, M.E., Sur le jaborandi (Pilocarpus pinnatus) (1875) Bulletin Societe Chimi Paris, 24, pp. 497-500Hemscheidt, T., Spenser, I.D., Biosynthesis of anosmine, an imidazólico alkaloid of the orchid Dendrobium parishii (1991) Journal of Chemical Society - Chemical Communications, 7, pp. 494-497Hill, R.K., Barcza, S., Sterochemistry of the Jaborandi alkaloids (1966) Tetrahedon, 22, pp. 2889-2893Holmstead, B., Wassen, S.H., Schultes, R.E., Jaborandi: an interdisciplinary appraisal (1979) Journal of Ethnopharmacology, 1, pp. 3-21(1992) Instituto Brasileiro do Meio Ambiente e dos Recursos Naturais Renováveis., pp. 870-872. , IBAMA, Portaria n° 06N, Diário Oficial, Brasília, janeiro 15, 1992Joseph, C.J., Revisão sistemática do gênero Pilocarpus (ssp. brasileiras) (1967) Mecânica Popular, pp. 1-9. , OctoberKaastra, R.C., (1982) Pilocarpinae. 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Convergence Of A Specialized Root Trait In Plants From Nutrient-impoverished Soils: Phosphorus-acquisition Strategy In A Nonmycorrhizal Cactus

In old, phosphorus (P)-impoverished habitats, root specializations such as cluster roots efficiently mobilize and acquire P by releasing large amounts of carboxylates in the rhizosphere. These specialized roots are rarely mycorrhizal. We investigated whether Discocactus placentiformis (Cactaceae), a common species in nutrient-poor campos rupestres over white sands, operates in the same way as other root specializations. Discocactus placentiformis showed no mycorrhizal colonization, but exhibited a sand-binding root specialization with rhizosheath formation. We first provide circumstantial evidence for carboxylate exudation in field material, based on its very high shoot manganese (Mn) concentrations, and then firm evidence, based on exudate analysis. We identified predominantly oxalic acid, but also malic, citric, lactic, succinic, fumaric, and malonic acids. When grown in nutrient solution with P concentrations ranging from 0 to 100 μM, we observed an increase in total carboxylate exudation with decreasing P supply, showing that P deficiency stimulated carboxylate release. Additionally, we tested P solubilization by citric, malic and oxalic acids, and found that they solubilized P from the strongly P-sorbing soil in its native habitat, when the acids were added in combination and in relatively low concentrations. 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