Controlling Factors Determining The Selective Hscn Addition To Double Bonds And Their Application To The Synthesis Of 7-isothiocyano-7,8-α-dihydro-bisabolene

The reactivity of terminal and trisubstituted double bonds of monoterpenes with HSCN has been examined by GC giving evidence that kinetics is responsible for the chemoselective addition to terminal double bonds in terpenes. The results show that the addition to the terminal double bond is about 17 times faster than for trisubstituted double bonds and that the presence of the first SCN group in the molecule prevents a second addition. The presence of a hydroxyl or methoxy group in the molecule, decreases the reaction kinetics. Based on these kinetic experiments a two steps synthesis of the natural product 7-isothiocyano-7,8-dihydro-α-bisabolene using bisabolol as starting material, was planned and successfully accomplished.125661666Drobnica, L., Kristían, P., Augustín, J., The Chemistry of the Cyanates and Their Thio Derivatives, , Saul Patai Ed., John Wiley & Sons, New YorkEdenborough, M.S., Herbert, R.B., (1988) Nat. Prod., p. 229Faulkner, D.J., (1994) Nat. Prod., p. 355(1993) Nat. Prod., p. 497(1992) Nat. Prod., p. 323(1991) Nat. Prod., p. 97(1990) Nat. Prod., p. 269(1988) Nat. Prod., p. 613Fraga, B.M., (1994) Nat. Prod. Rep., p. 533Piers, E., Young, B.W.A., Rettig, S.J., (1987) Tetrahedron, 43 (23), p. 5521Piers, E., Yeung, B.W., (1986) Can. J. Chem., 64, p. 2475Chenera, B., Chuang, C.P., Hart, D.J., Lai, C.S., (1992) J. Org. Chem., 57, p. 2018Da Silva, C.C., Almagro, V., Zukerman-Schpector, J., Castellano, E.E., Marsaioli, A.J., (1994) J. Org. Chem., 59, p. 2880Da Silva, C.C., Almagro, V., Marsaioli, A.J., (1993) Tetrahedron Lett., 34, p. 6717Martin, V.S., Woodward, S.S., Katsuki, T., Yamada, Y., Ikeda, M., Sharpless, K.B., (1981) J. Am. Chem. Soc., 103, p. 6237Rakels, J.L., Straathof, A.J.J., Heijnin, J.J., (1993) Enzyme Microb. Technol, 15, p. 1051Diveley, W.R., Buntin, G.A., (1969) J. Org. Chem., 34, p. 616Queiroga, C.L., Ferracini, V.L., Marsaioli, A.J., (1996) Phytochemistry, 42, p. 1097(-)Bisabolol (8) [(αS, 1S)-1-methanol-α,4-dimethyl-α-4-methyl-3-pentenyl-3-cyclohexene] was obtained from commercial candeia oil (CITRÓLEO - S.Paulo, SP, Brazil)Sullivan, B.W., Faulkner, D.J., Okamoto, K.T., Chen, M.H.M., Clardy, J., (1986) J. Org. Chem., 51, p. 5134Dubois, J.E., Lomas, J.S., (1971) Tetrahedron Lett., 7, p. 599Delay, F., Ohloff, F., (1979) Helv. Chem. Acta, 62, p. 326A sample of dihydrolimonene was kindly provided by Prof. Marcio C. S. de Mattos from IQ/UFRJ, RJ, Brazi

Classification of brain tumor extracts by high resolution ¹H MRS using partial least squares discriminant analysis

High resolution proton nuclear magnetic resonance spectroscopy (¹H MRS) can be used to detect biochemical changes in vitro caused by distinct pathologies. It can reveal distinct metabolic profiles of brain tumors although the accurate analysis and classification of different spectra remains a challenge. In this study, the pattern recognition method partial least squares discriminant analysis (PLS-DA) was used to classify 11.7 T ¹H MRS spectra of brain tissue extracts from patients with brain tumors into four classes (high-grade neuroglial, low-grade neuroglial, non-neuroglial, and metastasis) and a group of control brain tissue. PLS-DA revealed 9 metabolites as the most important in group differentiation: γ-aminobutyric acid, acetoacetate, alanine, creatine, glutamate/glutamine, glycine, myo-inositol, N-acetylaspartate, and choline compounds. Leave-one-out cross-validation showed that PLS-DA was efficient in group characterization. The metabolic patterns detected can be explained on the basis of previous multimodal studies of tumor metabolism and are consistent with neoplastic cell abnormalities possibly related to high turnover, resistance to apoptosis, osmotic stress and tumor tendency to use alternative energetic pathways such as glycolysis and ketogenesis.14916

Triterpenes Of Schinus Terebenthefolius

[No abstract available]133659660Kaistha, Keir, Structural studies on terebinthone fromSchinus terebinthefolius (1962) Journal of Pharmaceutical Sciences, 51, p. 245Kaistha, Kier, (1962) J. Pharm. Sci., 51, p. 1136Kier, Lehn, Ourisson, (1963) Bull. Soc. Chim. Fr., p. 911Yamaguchi, (1970) Spectral Data of Natural Products, 1. , Elsevier, New YorkDevon, Scott, (1972) Handbook of Naturally Occurring Compounds, 3. , Academic Press, New YorkFisher, Hertel, Dünnschichtchromatographie isomerer triterpene an Anasil B und kieselgel/AgNo3 (1968) Journal of Chromatography A, 38, p. 274Basu, Rastogi, (1967) Phytochemistry, 6, p. 1249Kulshreshtha, Kulshresshtha, Rastogi, (1972) Phytochemistry, 11, p. 2369Aplin, Arthur, Hui, (1966) J. Chem. Soc., p. 125

Biocatalysis: Facts And Trends [fatos E Tendências Da Biocatálise]

Brazil is renowned for its biodiversity; however, its economy is based on exotic plants, extraction and unsustainable use of natural resources. This issue was addressed in a recent QN review entitled "Chemistry without Borders." In order to explore the potential of Brazilian biodiversity fully, sustainable development is required in key technological areas, such as biotechnology. This research field is consistent with the green chemistry and white technology principles. Therefore, biotechnology is a sustainable alternative to conventional technologies and is expected to account for 20% of global chemicals by 2020. Brazil is the second largest grower of biotech crops and biodiesel, but its main activities rely on the fermentative process. In order to stimulate the national biotechnology development, the Brazilian Federal Government launched a national policy for biotechnology in 2007 and the National Committee of Biotechnology was created. Among the outstanding biotechnological processes, biocatalysis is one of the most important alternatives to conventional processing, and this field has changed dramatically with the advent of recombinant DNA technology in the 1970s, when large quantities of enzymes were accessible. The direct evolution methodology in the 1990s was a breakthrough and allowed tailoring of enzymes possessing high stability and stereoselectivity. However, about 60 years after the first industrial enzymatic biotransformation of steroids, the full potential of biocatalysis is far from being achieved. Future challenges in this field concern the multienzyme cascade reactions associated with optimized chemoenzymatic processes, and some recent industrial application of biocatalysts are also highlighted in this perspective. Copyright © 2013 Sociedade Brasileira de Quimica.361015871590Pinto, A.C., Zucco, C., Galembeck, F., De Andrade, J.B., Vieira, P.C., (2012) Quim. Nova, 35, p. 2092Meyer, H.-P., (2011) Org. Process Res. Dev., 15, p. 180Jegannathan, K.R., Nielsen, P.H., (2013) J. Cleaner Prod., 42, p. 228http://thomsonreuters.com/press-releases/032013/759960, acessada em Agosto 2013http://www.mct.gov.br/, acessada em Agosto 2013http://www.isaaa.org/resources/publications/ biotech_country_facts_and_trends/download/Facts%20and%20Trends%20-%20Brazil.pdf, acessada em Agosto 2013http://www.biodieselbr.com/noticias/bio/brasil-segundo-maior-produtor- biodiesel-030811.htmhttp://www.cebrap.org.br/v1/upload/pdf/Brazil_Biotec_Map_2011.pdf, acessada em Agosto 2013Reetz, M.T., (2013) J. Am. Chem. Soc., 135, p. 12480Turner, N.J., O'Reilly, E., (2013) Nat. Chem. Biol., 9, p. 285Woodley, J.M., (2013) Curr. Opin. Chem. Biol., 17, p. 310Reetz, M.T., (2012) Tetrahedron, 68, p. 7530Bornscheuer, U.T., Huisman, G.W., Kazlauskas, R.J., Lutz, S., Moore, J.C., Robins, K., (2012) Nature, 485, p. 185Hult, K., Berglund, P., (2003) Curr. Opin. Biotechnol., 14, p. 395Jaeger, K.-E., Reetz, M.T., (2000) Curr. Opin. Chem. Biol., 4, p. 68Liang, J., Lalonde, J., Borup, B., Mitchell, V., Mundorff, E., Trinh, N., Kochrekar, D.A., Pai, G.G., (2010) Org. Process. Res. Dev., 14, p. 193Harles, H.C., Dalby, P.A., Woodley, J.M., (2007) J. Chem. Technol. Biotechnol., 82, p. 1063De Lange, B., Hyett, D.J., Maas, P.J.D., Mink, D., Van Assema, F.B.J., Sereinig, N., De Vries, A.H.M., De Vries, J.G., (2011) ChemCatChem, 3, p. 289De Graaff, C., Ruijter, E., Orru, R.V.A., (2012) Chem. Soc. Rev., 41, p. 3969Ruijter, E., Scheffelaar, R., Orru, R.V.A., (2011) Angew. Chem. Int. Ed., 50, p. 6234Oroz-Guinea, I., Gárcia-Junceda, E., (2013) Curr. Opin. Chem. Biol., 17, p. 236Sánchez-Moreno, I., Hélaine, V., Poupard, N., Charmantray, F., Légeret, B., Hecquet, L., García-Junceda, E., Lemaire, M., (2012) Adv. Synth. Catal., 354, p. 1725Schrittwieser, J.H., (2011) Curr. Opin. Chem. Biol., 15, p. 249Ricca, E., Brucher, B., Schittwieser, J.H., (2011) Adv. Synth. Catal., 353, p. 2239Siirola, E., Mutti, F.G., Grischek, B., Hoefler, S.F., Fabian, W.M.F., Grogan, G., Kroutil, W., (2013) Adv. Synth. Catal., 355, p. 1703Sehl, T., Hailes, H.C., Ward, J.M., Wardenga, R., Von Lieres, E., Offermann, H., Westphal, R., Rother, D., (2013) Angew. Chem. Int Ed., 52, p. 6772Goddard, J.-P., Reymond, J.-L., (2004) Curr. Opin. Biotechnol., 15, p. 314Haugland, R.P., (1996) Handbook of Fluorescence Probes and Research Chemicals, , 6th ed, Molecular Probes: Eugene, OregonDe Vasconcellos, S.P., Angolini, C.F.F., García, I.N.S., Dellagnezze, B.M., Da Silva, C.C., Marsaioli, A.J., Santos Neto, E.V., De Oliveira, V.M., (2010) Org. Geochem., 41, p. 675Da Cruz, G., Angoline, C.F.F., De Oliveira, L.G., Lopes, P.F., De Vasconcellos, S.P., Crespim, E., De Oliveira, V.M., Marsaioli, A.J., (2010) Appl. Microbiol. Biotechnol., 87, p. 319Mantovani, S.M., De Oliveira, L.G., Marsaioli, A.J., (2010) J. Braz. Chem. Soc., 21, p. 1484Mantovani, S.M., De Oliveira, L.G., Marsaioli, A.J., (2008) J. Mol. Catal. B: Enzym., 52-53, p. 173Pinheiro, L., Marsaioli, A.J., (2007) J. Mol. Catal. B: Enzym., 44, p. 78Sicard, R., Chen, L.S., Marsaioli, A.J., Reymond, J.-L., (2005) Adv. Synth. Catal., 347, p. 1041Bicalho, B., Chen, L.S., Grognux, J., Reymond, J.-L., Marsaioli, A.J., (2004) J. Braz. Chem. Soc., 15, p. 911Gonçalves, R.A.C., Porto, A.L.M., Pinheiro, L., Cagnon, J.R., Manfio, G.P., Marsaioli, A.J., (2004) Food Technol. Biotechnol., 4, p. 35

Proton And Carbon-13 Nuclear Magnetic Resonance Spectroscopy And Conformational Aspects Of The Curine Class Of Bis(benzylisoquinoline) Alkaloids

[No abstract available]46112385238

Indole Alkaloids From Peschiera Campestris

The investigation of leaf, bark and root extracts of Peschiera campestris, a new species discovered in Brasilia, Brazil, afforded ten indole alkaloids. The main component from the root extract was 12-methoxy-Nb-methylvoachalotine (ca 0.25 % of the dried roots). The structures were elucidated by spectroscopic methods and comparison with authentic samples. © 1986.251229082910Allorge, (1985) Ph.D. Thesis, , Université de Potiers, U.E.R. Sciences Fondamentales et Appliquées, FranceVan Beek, Verpoorte, Svendsen, Leeuwenberg, Bisset, (1984) J. Ethnopharmacol., 10, p. 1Gabetta, Mustich, (1974) Spectral Data of Indole Alkaloids, , Lib. Sci. A. Cortina, MilanBiáka, Koblicova, Trojánek, Chiroptical investigations on the iboga and voacanga alkaloids (1974) Collection of Czechoslovak Chemical Communications, 39, p. 2258Herrera, Reis, (1986) Phytochemistry, , in pres

Terebenthifolic Acid And Bauerenone: New Triterpenoid Ketones From Schinus Terebenthifolius

[No abstract available]141023002302Kaistha, Kier, (1962) J. Pharm. Sci., 51, p. 145Kaistha, Kier, (1962) J. Pharm. Sci., 51, p. 1136Kier, Lehn, Ourisson, (1963) Bull. Soc. Chim. Fr., p. 911Campello, Marsaioli, (1974) Phytochemistry, 13, p. 659Budzikiewicz, Wilson, Djerassi, (1963) J. Am. Chem. Soc., 85, p. 3688Barton, Seone, (1956) J. Pharm. Sci., p. 4150Seone, (1959) J. Chem. Soc., p. 4158Monaco, Caputo, Palumbo, Mangoni, (1973) Phytochemistry, 12, p. 93

Natural Processes Of Petroleum Biodegradation In Reservoirs [processos Naturais De Biodegradação Do Petróleo Em Reservatórios]

Petroleum biodegradation in reservoirs is a process caused by different microorganisms affecting many oil deposits which modifies the oil composition in a quasi-stepwise process starting from n-alkanes and isoprenoids through to diasteranes. This causes oil souring and increased viscosity, sulfur and metal content, having a direct impact on oil production and refining costs.35816281634Van Hamme, J.D., Singh, A., Ward, O.P., (2003) Microbiol. Mol. Biol. Rev., 67, p. 503Aquino Neto, F.R., (1984) Quim. Nova, 7, p. 79Peters, K.E., Moldowan, J.M., (1993) The Biomarker Guide: Interpreting Molecular Fossil in Petroleum and Ancient Sediments., , Prentice Hall Englewood Clifts: New JerseyHolba, A.G., Dzou, L., (2004) Org. Geochem., 34, p. 441Restlé, A., (1994) O Petróleo, Tradução e Adaptação: Mello, , M. R.Hessel, M. A.Soldan, A. L.Petrobrás/CENPES: Rio de JaneiroBrocks, J.J., Buick, R., Summons, R.E., Logan, G.A., (2003) Geochim. Cos-mochim. 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Predicting The Claisen Rearrangement Regioselectivity Of Allylindanyl And Allyltetrahydronaphthalenyl Ether Derivatives By 1h Nmr Experiments

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