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Cathepsin K is a papain-like cysteine protease and is responsible for collagen degradation in bone tissue and thus represents an important target for the development of new therapies for treating diseases such as osteoporosis. Quinolines are an important class of heterocyclic molecular leads with a great pharmacological potential and represent a relevant scaffold to explore the chemical space of cathepsin K (CatK) inhibitors. This study presents the synthesis of nine 2,4-diphenylquinolines, including five phthalonitrile quinolines dyads, and the evaluation of their CatK inhibitory activity. Among the evaluated compounds, 4b was the most potent inhibitor with an IC50 (half-maximal inhibitory concentration) value of 1.55 µM (against Z-Phe-Arg-MCA substrate) acting in an uncompetitive inhibition mode. Molecular docking studies provided important information on the interaction of the inhibitor with the enzyme showing that these quinoline derivatives can play an important role as CatK inhibitors.

The rises of toxic effects caused by pesticides are of concern. However, Brazilian legislation still needs scientific subsides to improve the water quality requirements. This can be attributed in part to the few existing studies showing the occurrence and levels of multi-residue pesticides. Therefore, the objective of this study was to investigate the presence and the residue-levels of pesticides in surface, ground and drinking water of Tibagi River micro-basin in Paraná State, Brazil. Data obtained over a year for the physical-chemical parameters, screening and quantification, made by liquid chromatography-tandem mass spectrometry (LC-MS/MS), confirmed the contamination by several pesticides. Alarming concentrations of diuron and imazethapyr in a permanent preservation area and in groundwater were observed. The absence of legislation for most pesticides under study makes difficult the prohibition of their use and the control of their residue-levels on the environment. The results draw attention to further discussion and engagement around the pesticide regulations.

Onze alcaloides acridonicos isolados de Swinglea glutinosa (Bl.) Merr. foram avaliados para suas atividades in vitro contra linhagens de Plasmodium falciparum sensiveis a cloroquina 3D7, Trypanosoma brucei rhodesiense STIB9000 e Leishmania donovani L82. Ensaios com celulas KB foram tambem executados com o objetivo de se determinar o grau de toxicidade das substâncias ativas contra os parasitas. Nove dos compostos apresentaram IC 50 entre 0,3 e 11,6 µM contra P. falciparum. Em contraste, um pequeno numero de compostos mostrou atividade significativa contra T. brucei rhodesiense e nenhum apresentou atividade contra L. donovani. Entre os alcaloides tres tiveram IC 50 < 1,0 µM contra P. falciparum, enquanto que contra T. b. rhodesiense cinco mostraram IC 50 < 10 µM. A caracterizacao dos alcaloides, 1,3,5-triidroxi-4-metoxi-10-metil-2,8bis(3-metilbut-2-enil)acridin-9(10H)-ona (1), 2,3-diidro-4,9-diidroxi-2-(2-hidroxipropan-2-il)11-metoxi-10-metilfuro[3,2-b]acridin-5(10H)-ona (2) e 3,4-diidro-3,5,8-triidroxi-6-metoxi-2,2,7trimetil-2H-pirano[2,3-a]acridin-12(7H)-ona (3), e aqui discutida. Discute-se tambem a relacao estrutura-atividade para todos os compostos ensaiados. O isolamento e dados espectrais para os alcaloides 1-3 estao sendo aqui descritos pela primeira vez, embora em trabalho anterior tenham sido relatadas as suas atividades citotoxicas. Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC 50 values ranging from 0.3 to 11.6 µM against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC 50 < 1.0 µM against P. falciparum, whereas against T. b. rhodesiense five had IC 50 < 10 µM. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9(10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro[3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their citotoxicities to cancer cells have been described before.

A methanol-soluble fraction of the dichloromethane extract from the culture broth of A. alternata AT4303 strain afforded the following five known mycotoxins: alternariol, alternariol monomethyl ether, altenusin, altenuene and altertoxin I. A hexane-soluble fraction of the dichloromethane extract yielded the steroids ergosterol and ergosterol peroxide, and alternariol monomethyl ether. The concentrated ethyl acetate extract afforded the nucleoside uridine, uracil and inosine. The micro-extracts obtained from this strain in solid media were analyzed using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS), and the following five known toxins were identified: ACTG-C, D, E and F and AK-toxin II. The major toxins produced by the tangerine pathotype ACT-toxins appear to be absent in strain AT4303. However, the low concentration of ACT-toxins appears to be responsible for their lack of detection in this study. Some compounds isolated from citrus plants were tested for in vitro activity against this strain. The results indicated that 17.3 µM apigenin-7-O-rutinoside inhibited by 80% conidial germination and appressorium development.

Eucalyptus is frequently attacked by the Brazilian eucalyptus brown looper, Thyrinteina arnobia. This caterpillar is regarded as the main lepidopterous pest of Eucalyptus and yet no practical and environmentally acceptable method of control currently exists. Electroantennographic techniques (EAG) have never before been used to detect semiochemicals that affect the behavior of T. arnobia. Thus, in this work, the ability of T. arnobia males and females to detect volatile essential oils of seven Eucalyptus species was investigated by EAG. We demonstrated that T. arnobia antennal olfactory system clearly showed differential sensitivity to several compounds, by coupled gas chromatography-electroantennographic detection (GC-EAD). Twenty-eight compounds were identified that elicited responses in T. arnobia, indicating that GC-EAD analysis may well be a useful means of screening active plant extracts for compounds that contribute to the observed behavior of this defoliator. The results also suggest that this species uses several volatile cues to find its host. A lagarta-parda, Thyrinteina arnobia, causa grandes prejuízos à cultura do eucalipto, destacando-se como o principal lepidóptero desfolhador; portanto, medidas alternativas de controle são necessárias. Neste trabalho foi avaliada, pela técnica de eletroantenografia (EAG), a interação dos voláteis dos óleos essenciais de sete espécies de Eucalyptus, frente às antenas de fêmeas e de machos de T. arnobia. Foram também identificados 28 compostos voláteis bioativos contidos no óleo essencial de E. grandis, utilizando a detecção eletroantenográfica acoplada à cromatografia a gás (CG-EAD). Estes resultados indicam que CG-EAD é uma ferramenta muito útil na triagem de compostos bioativos presentes em extratos de plantas e sugerem que T. arnobia utiliza vários destes terpenos como sinais para encontrar seu hospedeiro.

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:21:40Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:44:04Z : No. of bitstreams: 1 2-s2.0-30844469087.pdf: 433625 bytes, checksum: 7e43a44a1c89ec162ef81c1cf7be6c26 (MD5) Made available in DSpace on 2014-05-27T11:21:40Z (GMT). No. of bitstreams: 0 Previous issue date: 2005-11-01 Phytochemical survey of roots extracts of the South Brazilian endemic plant Raulinoa echinata Cowan, Rutaceae led to the isolation of known degraded limonoids: fraxinellone, fraxinellonone and epoxy-fraxinellone. The latter was previously isolated also from the stems, but the relative configuration could not be solved by NMR experiments. This paper deals with the X-ray diffraction analysis of epoxy-fraxinellone and its toxicity to leaf-cutting ants, describes the isolation of fraxinellonone and fraxinellone for the first time in Raulinoa. Epoxy-fraxinellone showed no toxicity to the leaf-cutting ants (Atta sexdens rubropilosa). The limonoid limonexic acid, isolated from stems, presented high toxicity to the leaf-cutting ants, diminishing considerably their longevity. ©2005 Sociedade Brasileira de Química. Universidade do Vale do Itajaí Programa de Pós-Graduação em Ciências Farmacêuticas, CP 360, 88303-202 Itajaí - SC Departamento de Química Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos - SP Centro de Estudos de Insetos Sociais Universidade Estadual de São Paulo, Rio Claro - SP Instituto de Física de São Carlos Universidade de São Paulo, São Carlos - SP Centro de Estudos de Insetos Sociais Universidade Estadual de São Paulo, Rio Claro - SP

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:21:39Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:34:40Z : No. of bitstreams: 1 2-s2.0-30844463027.pdf: 71397 bytes, checksum: 550b166106cdd8a5ba7d64ac0e5c3f25 (MD5) Made available in DSpace on 2014-05-27T11:21:39Z (GMT). No. of bitstreams: 0 Previous issue date: 2005-11-01 The chemical investigation of the fruits of Cipadessa fruticosa (Meliaceae) afforded the new limonoid cipadesin B and the known swietemahonolide. From the roots of Cedrela fissilis (Meliaceae) were isolated the limonoid 3β-acetoxycarapin, new as natural product, along with the triterpenes oleanolic and oleanonic acid. These compounds and other six mexicanolide limonoids previously isolated from C. fruticosa showed insecticidal activity against the leaf-cutting ants Atta sexdens rubropilosa. ©2005 Sociedade Brasileira de Química. Departamento de Química Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos - SP Centro de Estudos de Insetos Sociais Universidade Estadual Paulista, CP 199, 13506-900 Rio Claro - SP Centro de Estudos de Insetos Sociais Universidade Estadual Paulista, CP 199, 13506-900 Rio Claro - SP

O estudo da fracao acetato de etila do extrato metanolico das folhas de Almeidea rubra A. St.- Hil. (Rutaceae) permitiu o isolamento de duas substâncias ineditas: 4-metoxi-6-(2-(metilamino)fenil)- 2H-piran-2-ona e acetato de rel-(7R,8R)-8-((E)-3-hidroxi-3-metil-1-butenil)-4,8-dimetoxi-5,6,7,8- tetraidrofuro(2,3-b)quinolin-7-ila; e dos alcaloides arborinina, N-metil-1-hidroxi-3-metoxiacridona, esquimianina, cocusagina, isodutaduprina, isoesquimianina e isococusagina. Atraves da analise dos dados espectroscopicos foram estabelecidas as estruturas quimicas das substâncias isoladas sendo que para os alcaloides ineditos tais dados sao descritos pela primeira vez. Alem disso, os ensaios bilogicos sobre as formas tripomastigotas do Trypanosoma cruzi das substâncias isoladas mostraram que elas possuem atividade tripanocida moderada. The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-(2-(methylamino)phenyl)-2H- pyran-2-one and rel-(7R,8R)-8-((E)-3-hydroxy-3-methyl-1-butenyl)-4,8-dimethoxy-5,6,7,8- tetrahydrofuro(2,3-b)quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl- 1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity.

Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by 1H NMR and ESI-MS/MS and only those which showed features of anthranilate alkaloids and flavonoids absent in the previous investigations were examined. Stems afforded the alkaloids flindersine, skimmianine, 8-methoxyflindersine and dictamnine; leaves yielded 3',4',7,8-tetramethoxy-5,6-(2",2"-dimethylpyrano)-flavone, 3',4',5,7,8-pentamethoxyflavone, 5-hydroxy-3',4',6,7-tetramethoxyflavone, 3',4'-methylenedioxy-5,6,7-trimethoxyflavone and 5-hydroxy-3',4'-methylenedioxy-6,7-dimethoxyflavone. The alkaloids have remained undiscovered for 10 years. A number of flavonoids isolated from N. paraensis, N. magnifica, Murraya paniculata, Citrus sinensis graft (Rutaceae), Lonchocarpus montanus (Leguminosae) were evaluated for their ability to inhibit the enzymatic activity of the protein glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. Highly oxygenated flavones and isoflavone were the most actives.

Light and rare earths (RE) have a long lived relationship that dates from the discoveries of these elements in the nineteenth century. Since then, the increasing comprehension of their spectroscopic properties conducted to a wide and alluring literature about light absorption and emission by this particular and fascinating group. For more than 50 years, RE-containing solid-state optical materials have undoubtfully been an important subject for the development of more efficient lighting, visualization, communication and health everyday applications. Therefore, this review introduces the spectroscopic properties of rare earth materials and their applications, with a brief discussion of the main mechanisms of light absorption and emission from a 4f elements inorganic physical chemistry perspective. Special attention is devoted to the use of these elements in systems concerning photoprotection and to the fundamentals of visible light generation for lighting and visualization.

Catalytic combustion of soot was performed over ZnO:CeO2 catalysts obtained via a non‑alkoxide sol-gel route. Different kinetics parameters were calculated through thermal analyses, thus, enabling the correlation between the experimental data and the decomposition mechanisms probably associated with the soot decomposition in each case.

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:58:50Z No. of bitstreams: 1 S0103-50532002000100010.pdf: 111633 bytes, checksum: 948a33853b0c70773b801608c065cd0c (MD5) Made available in DSpace on 2013-08-22T18:58:50Z (GMT). No. of bitstreams: 1 S0103-50532002000100010.pdf: 111633 bytes, checksum: 948a33853b0c70773b801608c065cd0c (MD5) Previous issue date: 2002-02-01 Made available in DSpace on 2013-09-30T19:54:55Z (GMT). No. of bitstreams: 2 S0103-50532002000100010.pdf: 111633 bytes, checksum: 948a33853b0c70773b801608c065cd0c (MD5) S0103-50532002000100010.pdf.txt: 18997 bytes, checksum: 15f311958bc1daf0297cf74c527b3936 (MD5) Previous issue date: 2002-02-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T15:14:16Z No. of bitstreams: 2 S0103-50532002000100010.pdf: 111633 bytes, checksum: 948a33853b0c70773b801608c065cd0c (MD5) S0103-50532002000100010.pdf.txt: 18997 bytes, checksum: 15f311958bc1daf0297cf74c527b3936 (MD5) Made available in DSpace on 2014-05-20T15:14:16Z (GMT). No. of bitstreams: 2 S0103-50532002000100010.pdf: 111633 bytes, checksum: 948a33853b0c70773b801608c065cd0c (MD5) S0103-50532002000100010.pdf.txt: 18997 bytes, checksum: 15f311958bc1daf0297cf74c527b3936 (MD5) Previous issue date: 2002-02-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) A investigação fitoquímica dos extratos de caules e folhas da espécie endêmica Raulinoa echinata Cowan, Rutaceae, levou ao isolamento de alcalóides furoquinolínicos (esquimianina, kokusaginina, maculina e flindersiamina) e quinolônicos (1-metil-2-n-nonil-4-quinolona, 2-n-nonil-4-quinolona e 2-fenil-1-metil-4-quinolona). Os alcalóides isolados mostraram atividade antifúngica contra Leucoagaricus gongylophorus, o fungo simbionte de formigas cortadeiras (Atta spp). Quando testados in vitro contra formas tripomastigotas de Trypanosoma cruzi, os alcalóides foram inativos ou parcialmente ativos. Neste trabalho descrevem-se o isolamento dos alcalóides, a elucidação estrutural dos alcalóides quinolônicos e a estrutura obtida por difração de raio-X da flindersiamina, juntamente com os resultados dos bioensaios realizados. Phytochemical survey of stems and leaves extracts of the South Brazilian endemic plant Raulinoa echinata Cowan, Rutaceae, led to the isolation of known furoquinoline alkaloids: the widespread skimmianine; kokusaginine, maculine, flindersiamine, and also quinolone derivatives: 1-methyl-2-n-nonyl-4-quinolone, 2-n-nonyl-4-quinolone and 1-methyl-2-phenyl-4-quinolone. These alkaloids showed antifungal activity against Leucoagaricus gongylophorus; the symbiotic fungus of leaf-cutting ants (Atta sexdens). They were inactive or displayed weak inhibitory activity when assayed in vitro against trypomastigote forms of Trypanosoma cruzi. In this paper, the isolation, structure elucidation and bioactivity results of these compounds are reported together with the X-ray structure of flindersiamine. Universidade Federal de São Carlos (UFSCar) Departamento de Química Universidade Estadual Paulista Centro de Estudos de Insetos Sociais Universidade de São Paulo Faculdade de Ciências Farmacêuticas Universidade de São Paulo Instituto de Química Universidade Estadual Paulista Centro de Estudos de Insetos Sociais

Differential equations describing the evolution of defect concentrations inside ultra-thin films are developed and numerically resolved for the growth of passivating films under transient galvanostatic conditions. For this, the injection and recombination of defects together with the increase of the film thickness are taken into account. In the simulation, the defect concentrations pass through a maximum during the growth and increase with the current, becoming independent of it for higher values. To obtain reasonable values of defect concentrations the work shows the need to consider that only a part of the current is used in defect generation. For the film, the specific ionic resistivity passes through a minimum and the overpotential increases almost linearly with thickness. Analysis of the transients leads to the idea that the recombination rate constant can depend on the current density. All these aspects are analyzed and discussed from a physical point of view. Para o caso de crescimentos transientes de filmes de passivação em condições galvanostáticas foram formuladas e resolvidas, por método numérico, equações diferenciais descrevendo a variação das concentrações de defeitos em filmes ultra-finos. Nas equações levou-se em conta a injeção de defeitos, a recombinação de alguns destes e o aumento na espessura do filme. Nos resultados das simulações as concentrações passam por um máximo durante o crescimento, com este máximo aumentando com a corrente e tornando-se independente da mesma para altos valores desta. Para que se obtenham valores razoáveis da concentração de defeitos nos filmes, o trabalho mostra que nem toda a corrente deve ser utilizada para a geração de defeitos. Nessas condições, os cálculos mostram que a resistividade iônica específica nos filmes passa por um mínimo com o aumento de sua espessura e o sobrepotencial neles varia quase linearmente com a mesma. A análise dos transientes leva à idéia de que a constante de velocidade de recombinação de defeitos poderia depender da densidade de corrente utilizada. Todos estes dados são analisados e discutidos do ponto de vista físico.

The methanol extract of stems of Trichilia claussenii yielded three new sesquiterpenoids: 14-hydroxyelemol, germacra-10(14)-en-9,11,15-triol and germacra-3,10(14)-dien-9,11-diol-4-carbaldehyde. Two known sesquiterpenoids beta-eudesmol, cryptomeridiol and the triterpenoid 22,25-dihydroxy-9beta,19-cyclolanost-23-en-3-one were also isolated. The dichloromethane extract from the leaves of T. lepidota afforded a mixture of hydrocarbons (C29H60, C31H64 and C33H68), a mixture of the sesquiterpenes caryophyllene and humulene epoxides, spathulenol, and a series of sterols: 24-methylene-12b-hydroxycholesterol, 24-methyl-12beta-hydroxycholest-4-en-3-one, 24-methylene-12beta-hydroxycholest-5-ene-3-palmitate; a mixture of 24-methylenecholesterol, campesterol, stigmasterol and beta-sitosterol; besides alpha-tocoferol and phytol. From the methanol extract it was isolated N-methyl-4-hydroxyproline. The structures of the isolated compounds were determined on the basis of spectroscopic analysis. O trabalho descreve o isolamento de três novos sesquiterpenóides do extrato metanólico dos galhos de Trichilia claussenii: 14-hidroxielemol, germacra-10(14)-en-9,11,15-triol e germacra-3,10(14)-dien-9,11-diol-4-carbaldeído. Também foram isolados os sesquiterpenos beta-eudesmol, criptomeridiol e o triterpeno 22,25-diidroxi-9beta,19-ciclolanost-23-en-3-ona. Do extrato diclorometânico das folhas de T. lepidota foram isolados mistura de hidrocarbonetos (C29H60, C31H64 e C33H68), mistura dos sesquiterpenos epóxido de cariofileno e epóxido de humuleno, espatulenol e os esteróides 24-metileno-12beta-hidroxicolesterol, 24-metil-12beta-hidroxicolest-4-en-3-ona, 3-palmitato de 24-metil-12beta-hidroxicolest-5-eno, mistura de 24-metilenocolesterol, campesterol, estigmasterol e beta-sitosterol, além de alfa-tocoferol e fitol. O extrato metanólico forneceu a N-metil-4-hidroxiprolina. As estruturas das substâncias isoladas foram estabelecidas com base em dados espectroscópicos.

The C25-quassinoids 20(R)- and 20(S)-simarolide were isolated from Simaba cuneata, Simaroubaceae. The structures of these two compounds were characterized by spectral data, including 1D and 2D NMR spectra which were also used for the complete assignment of the carbon and hydrogen atom chemical shifts. Os quassinóides C25 20(R)- e 20(S)-simarolídeo foram isolados de Simaba cuneata, Simaroubaceae. As estruturas destas substâncias foram caracterizadas por dados espectrais, incluindo espectros de RMN 1D e 2D que foram também usados para a completa atribuição dos deslocamentos químicos dos átomos de carbono e hidrogênio.

Leishmanicidal galloylquinic acids were isolated from the ethyl acetate extract of Byrsonima coccolobifolia. These phenols and gallic acid showed to be a new class of potent noncompetitive inhibitors of arginase ARG (Ki ranging from 0.10 to 0.68 µmol L -1 ) from Leishmania amazonensis. Quinic acid did not exhibit significant inhibition of ARG, indicating that galloyl moiety has important features that allows the enzyme-inhibitor interactions. The significant inhibitory activity of gallic acid on ARG can be a clue to understand the immune response previously observed on L. donovani, since ARG activity is associated with the decrease of the levels of NO in Leishmania infection.

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:21:53Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:33:12Z : No. of bitstreams: 1 2-s2.0-33744720361.pdf: 1070947 bytes, checksum: 4161de1058fb99e0bb593686bcfe1cd8 (MD5) Made available in DSpace on 2014-05-27T11:21:53Z (GMT). No. of bitstreams: 0 Previous issue date: 2006-06-08 Nine limonoids were isolated from Carapa guianensis and Cedrela fissilis. Among them, 1,2-dihydro-3β-hydroxy-7-deacetoxy-7-oxogedunin is a new compound. Moreover, the assignments of some chemical shifts of xyloccensin k have been corrected and 1H NMR data of 7-deacetylgedunin have been assigned for the first time. These isolated limonoids were assayed on Atta sexdens rubropilosa workers showing moderate insecticidal activities. ©2006 Sociedade Brasileira de Química. Departamento de Química Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos - SP Centro de Estudos de Insetos Sociais Universidade Estadual Paulista, CP 199, 13506-900 Rio Claro - SP Centro de Estudos de Insetos Sociais Universidade Estadual Paulista, CP 199, 13506-900 Rio Claro - SP