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Twigs of Nectandra barbellata were extracted using a solution of the ionic liquid 1-butyl-3-methylimidazolium bromide (BMImBr) in H2O, assisted by microwave (MAE). After successive chromatographic steps, one sesquiterpene, costic acid, and three new related lactones, (R)-3(7)-Z-3-hexadec-21-enylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (1), (R)-3(7)-Z-3-hexadecylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (2), and (R)-3(7)-Z-3-docosylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (3), were isolated. After structural elucidation using IR, UV, HRESIMS, NMR, ECD, and VCD, compounds 1-3 were tested against trypomastigote forms of Trypanosoma cruzi. The mechanism of action of bioactive isolated compounds was studied using different fluorescent-based approaches to investigate alterations of the plasma membrane, permeability/electric potential (ΔΨp), reactive oxygen species levels, mitochondria (electric membrane potential, ΔΨm/ATP levels), Ca2+ levels, and pH of the acidocalcisomes. In addition, in silico studies predicted no resemblance to pan assay interference compounds (PAINS).

Five new neocassane-like diterpenes (1-5) were isolated from the roots of Eragrostis plana. Their structures were elucidated by spectroscopic data, and the absolute configurations of the representative compounds neocassa-12(17),15-dien-3-one (2) and neocassa-12(13),15-diene-3,14-dione (5) were assigned by vibrational circular dichroism. The phytotoxic activity of compounds 3, 4, and 5 was evaluated against the germination and growth of Ipomoea grandifolia and Euphorbia heterophylla. Compound 4 exhibited the most potent activity for growth variables, resulting in the smallest radicle length of I. grandifolia and in the smallest aerial part length of E. heterophylla. Compound 5 reduced the germination speed index more effectively than the herbicide glyphosate (Roundup).

Three undescribed germacranolide sesquiterpene lactones, named macrocephalides A-C, along with known steroids, triterpenes and flavonoids were isolated from the aerial parts of Campuloclinium macrocephalum. The structures of the undescribed compounds were elucidated with basis on their 1D and 2D-NMR, and HR-ESI-MS data. Their absolute configurations were assigned by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Additionally, macrocephalides A-C were evaluated for their in vitro cytotoxic activities against nine human cancer cell lines. Macrocephalides A and B exhibited moderate to potent cytotoxic activity, inhibiting 50% of cell growth (GI50) at concentrations ranging from 0.576 to 6.37 μM.

The phytochemical study of Hippeastrum goianum led to the identification of 13 compounds by means of gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR). Compounds 7-demethoxy-9-O-methylhostasine (1) and 7-deoxi-trans-dihydronarciclasine (2) had their absolute configurations determined by vibrational circular dichroism (VCD). This is the first time that compound 1 is described in the Amaryllidaceae family. The cytotoxicity of all isolated compounds was tested against colorectal carcinoma (HCT 116), breast carcinoma (MCF-7), and non-tumor human retinal pigment epithelium (RPE) cell lines. The half-maximum inhibitory concentration (IC50) of compound 2 against each cell line was equivalent to the positive control (doxorubicin), indicating a considerable cytotoxic activity. Keywords: narciclasine; galasine; cytotoxic activity; absolute configuration; vibrational circular dichroism

Made available in DSpace on 2020-12-11T10:26:30Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-03-01 INCT Program [INCT-BioNat] Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Centre for Scientific Computing (NCC/GridUNESP) of Sao Paulo State University (UNESP) Ethnopharmacological relevance: Croton floribundus Spreng. (Euphorbiaceae), popularly known as Capixingui, stands out due to its widespread use in traditional medicine to treat wounds, syphilis, hemorrhoids, eye diseases and as a purgative. Aim of the study: To characterize clerodanes diterpenes from C. floribundus and to evaluate the effects of the fraction and diterpenes (1-5) on inhibition of nitrite production. Materials and methods: The hydroethanolic root extract of C. floribundus was fractionated on a solid phase extraction column to obtain the fraction named Fr80%. From this, five compounds were obtained and characterized. The absolute configuration of compound 1 was determined by a combination of electronic and vibrational circular dichroism spectroscopies. Additionally, compounds 1-5 were evaluated for their inhibitory effects on nitrite production induced by lipopolysaccharide (LPS) in RAW 264 macrophage cell. Results: Five clerodane diterpenoids were characterized, and the absolute stereochemistry of 1 was established as 3R,4R,5R,8R,9R,10S,12S. The IC50 values obtained through inhibition of nitrite production were 28.52 +/- 2.21 mu M (1), 40.26 +/- 2.79 mu M (2), 25.47 +/- 2.16 mu M (3), 35.78 +/- 2.93 mu M (4) and 40.58 +/- 4.78 mu M (5). In the tested concentrations, the samples presented low toxicity in macrophages. Conclusions: Four new diterpenes were characterized from C. floribundus, these being croflorins A-D (1-4) and a known halimane (5). These compounds exhibited inhibitory effect on nitrite production. Sao Paulo State Univ, Inst Chem, BR-14800060 Araraquara, SP, Brazil Fluminense Fed Univ, Inst Chem, BR-24020141 Niteroi, RJ, Brazil Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP, Brazil Sao Paulo State Univ, Sch Pharmaceut Sci, BR-01049010 Araraquara, SP, Brazil Sao Paulo State Univ, Inst Chem, BR-14800060 Araraquara, SP, Brazil Sao Paulo State Univ, Sch Pharmaceut Sci, BR-01049010 Araraquara, SP, Brazil INCT Program [INCT-BioNat]: 465637/2014-0 INCT Program [INCT-BioNat]: 2014/50926-0 FAPESP: 2013/07600-3 FAPESP: 2014/25222-9 FAPESP: 2017/19870-6 CAPES: 001 CAPES: 88887.313278/2019-00 CNPq: 142286/2016-8 CNPq: 142014/2018-4 FAPESP: 2017/17098-4 FAPESP: 2019/04381-5 FAPESP: 2017/18807-9

Made available in DSpace on 2021-06-25T11:23:26Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-10-23 National Institutes of Health Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) College of Agriculture & Life Sciences of the University of Arizona Center for Scientific Computing (NCC/GridUNESP) of Sa eo Paulo State University (UNESP) Incorporation of the epigenetic modifier suberoylanilide hydroxamic acid (SAHA) into a potato dextrose broth culture of the endophytic fungus Aspergillus sp. AST0006 affected its polyketide biosynthetic pathway providing two new 3-(4-oxopyrano)-chromen-2-ones, aspyranochromenones A (1) and B (2), and the isocoumarin, (-)-6,7-dihydroxymellein (3). Eight additional metabolites (4-11) and two biotransformation products of SAHA (12-13) were also encountered. The planar structures and relative configurations of the new metabolites 1-2 were elucidated with the help of high-resolution mass, 1D and 2D NMR spectroscopic data and the absolute configurations of 1-3 were determined by comparison of experimental and calculated ECD data. Possible biosynthetic pathways to 1 and 2 are presented. (C) 2020 Elsevier Ltd. All rights reserved. Univ Arizona, Coll Agr & Life Sci, Southwest Ctr Nat Prod Res, Sch Nat Resources & Environm, 250 E Valencia Rd, Tucson, AZ 85706 USA Sao Paulo State Univ, Inst Chem, BR-14800900 Araraquara, SP, Brazil Jiangsu Normal Univ, Key Lab Biotechnol Med Plants Jiangsu Prov, 101 Shanghai Rd, Xuzhou 221116, Jiangsu, Peoples R China Univ Arizona, Coll Agr & Life Sci, Sch Plant Sci, Tucson, AZ 85721 USA Fluminense Fed Univ, Chem Inst, Dept Organ Chem, BR-24020141 Niteroi, RJ, Brazil Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP, Brazil Sao Paulo State Univ, Inst Chem, BR-14800900 Araraquara, SP, Brazil National Institutes of Health: R01 CA90265 National Institutes of Health: P41 GM094060 FAPESP: 2018/05905-5 FAPESP: 2014/25222-9

Made available in DSpace on 2018-12-11T17:36:22Z (GMT). No. of bitstreams: 0 Previous issue date: 2018-05-01. Added 1 bitstream(s) on 2019-10-09T18:33:08Z : No. of bitstreams: 1 S0103-50532018000501105.pdf: 2907602 bytes, checksum: ef8123c16f0caba93af7dd13a547df64 (MD5) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Département Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Piper gaudichaudianum Kunth (Piperaceae) accumulates gaudichaudianic acid, a prenylated benzopyran, as its major component. Interestingly, this trypanocidal compound occurs as a racemic mixture. Herein, transcriptomic investigations of Piper gaudichaudianum using the RNA-seq approach are reported, and from the analysis of the transcripts expressed it was possible to propose a complete biosynthetic pathway for the production of gaudichaudianic acid, including the steps that originate its precursor, p-hydroxybenzoic acid. Peperomia obtusifolia (L.) A. Dietr. (Piperaceae) also accumulates racemic benzopyrans, however, its chromanes originate from the polyketide pathway, while the chromenes from Piper derives from the shikimate pathway. Recent transcriptomic and proteomic studies of the former species did not identify polyketide synthases involved in the production of the benzopyran moiety, but revealed the expression of tocopherol cyclase, which may be responsible for the cyclization of the 3,4-dihydro-2H-pyran ring. The analysis of the enzymes involved in the secondary metabolism of Piper gaudichaudianum and the comparison with the data previously obtained from Peperomia obtusifolia can provide valuable information on how these compounds are biosynthesized. Instituto de Química Universidade Estadual Paulista (UNESP) Departamento de Química Universidade Federal de São Carlos (UFSCar) Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP) Instituto de Química Universidade de São Paulo (USP) Instituto de Química Universidade Estadual Paulista (UNESP) Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP) FAPESP: 2013/07600-3 Département Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2014/25222-9 Département Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2014/50316-7 Département Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2015/07089-2 FAPESP: 2011/01003-8

Peperomia obtusifolia, an ornamental plant from the Piperaceae family, accumulates a series of secondary metabolites with interesting biological properties. From a biosynthesis standpoint, this species produces several benzopyrans derived from orsellinic acid, which is a polyketide typically found in fungi. Additionally, the chiral benzopyrans were reported as racemic and/or as diastereomeric mixtures, which raises questions about the level of enzymatic control in the cyclization step for the formation of the 3,4-dihydro-2H-pyran moiety. Therefore, this article describes the use of shotgun proteomic and transcriptome studies as well as phytochemical profiling for the characterization of the main biosynthesis pathways active in P. obtusifolia. This combined approach resulted in the identification of a series of proteins involved in its secondary metabolism, including tocopherol cyclase and prenyltransferases. The activity of these enzymes was supported by the phytochemical profiling performed in different organs of P. obtusifolia. However, the polyketide synthases possibly involved in the production of orsellinic acid could not be identified, suggesting that orsellinic acid may be produced by endophytes intimately associated with the plant. Fil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Dos Santos Pinto, José Roberto A.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Batista, Joao M.. Universidade Federal do São Carlos; Brasil Fil: Souza Moreira, Tatiana M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Santoni, Mariana M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Zanelli, Cleslei F.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Kato, Massuo J.. Universidade de Sao Paulo; Brasil Fil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina Fil: Palma, Mario S.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil

A reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia usingchiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMSas fenchyl-3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(3 00 -methyl-2 00 -butenyl)-2-(4 0 -methyl-1 0 ,3 0 -pentadie-nyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters describedpreviously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that itwas actually a mixture of two compounds, whose absolute configurations were determined by VCD mea-surements. Although, almost no vibrational transitions could be assigned to the chiral chromane, theexperimental VCD spectrum was largely opposite to that obtained for the average experimental VCD[(2S,1 000 R,2 000 R,4 000 S +2R,1 000 R,2 000 R,4 000 S)/2] for fenchol derivatives. These results allowed us to assign theputa-tive compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work. 2012 Elsevier Ltd. All rights reserved.

Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (+)-S and (-)-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P. gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (+)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers showed a synergistic effect, with the racemic mixture being the most active.

Previous analysis of the ECD spectra of two prenylated benzopyrans isolated from Peperomia obtusifolia, by means of the helicity rule for the chromane chromophore, resulted in the incorrect assignment of their absolute configuration, (S) instead of (R) for a deduced P-helicity of the chromane ring for the (+)-enantiomers. This was discovered by the application of DFT calculations and VCD spectroscopy. Experimental and calculated (B3LYP/6-31G(d)) VCD and IR spectra were compared, and a definitive absolute configuration of (+)-1 and (+)-2 is reassigned directly in solution as (R). The assumption of equatorial positioning of bulky groups, shown here to be invalid for the title molecules, is the underlying cause of the previous incorrect assignment of absolute configuration. Moreover, TDDFT (B3LYP/6-311++G(2d,2p)//B3LYP/6-31G(d)) calculations of ECD spectra have shown that both P- and M-helicity of the heterocyclic ring, for a given absolute configuration, lead to the same sign for the 1Lb ECD band, thus bringing into question the validity of the empirical ECD helicity rule for chromane molecules.

Phyllanthus niruri L., commonly known in Brazil as 'quebra-pedra', has long been used in the treatment of diverse diseases and especially urolithiasis. The therapeutic effects of P. niruri are attributed to various compounds present in the plant, including the hydrolysable tannin corilagin. In the present study, high-performance liquid chromatography (HPLC-/PAD) profiles of leaves and commercial extracts of P. niruri were examined and three compounds, found to be present in all of the samples studied, were isolated by open column chromatography over C18)silica gel followed by preparative HPLC. These compounds were identified by nuclear magnetic resonance as corilagin, rutin and ethyl 3,4,5-trihydroxybenzoate. Corilagin, which has been proposed as a phytochemical marker for P. niruri, was employed as an external standard in the development and validation of a rapid and efficient qualitative and quantitative HPLC assay for the analyte. The method may be applied in the standardization of herbs and phytomedicines commercialized in Brazil as quebra-pedra.

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:48:49Z No. of bitstreams: 1 S0100-40422010000200017.pdf: 242505 bytes, checksum: 178d6611bc19b0615dbbe4e4a7a24d81 (MD5) Made available in DSpace on 2013-08-22T18:48:49Z (GMT). No. of bitstreams: 1 S0100-40422010000200017.pdf: 242505 bytes, checksum: 178d6611bc19b0615dbbe4e4a7a24d81 (MD5) Previous issue date: 2010-01-01 Made available in DSpace on 2013-09-30T19:10:48Z (GMT). No. of bitstreams: 2 S0100-40422010000200017.pdf: 242505 bytes, checksum: 178d6611bc19b0615dbbe4e4a7a24d81 (MD5) S0100-40422010000200017.pdf.txt: 22081 bytes, checksum: 5051bd1ddcb22e79dd8517f88ca4eb98 (MD5) Previous issue date: 2010-01-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T14:21:21Z No. of bitstreams: 2 S0100-40422010000200017.pdf: 242505 bytes, checksum: 178d6611bc19b0615dbbe4e4a7a24d81 (MD5) S0100-40422010000200017.pdf.txt: 22081 bytes, checksum: 5051bd1ddcb22e79dd8517f88ca4eb98 (MD5) Made available in DSpace on 2014-05-20T14:21:21Z (GMT). No. of bitstreams: 2 S0100-40422010000200017.pdf: 242505 bytes, checksum: 178d6611bc19b0615dbbe4e4a7a24d81 (MD5) S0100-40422010000200017.pdf.txt: 22081 bytes, checksum: 5051bd1ddcb22e79dd8517f88ca4eb98 (MD5) Previous issue date: 2010-01-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Phytochemical investigations on three Brazilian Lauraceae species from the Cerrado region of São Paulo State, Ocotea corymbosa (Meins) Mez., O. elegans Mez. and Persea pyrifolia Nees & Mart. ex Nees resulted in the isolation of flavonoids, an ester of the 4-O-E-caffeoylquinic acid, an aromatic sesquiterpene besides furofuran lignans. This is the first chemical study on the leaves of Ocotea elegans and O. corymbosa as well as the first report of non-volatile compounds from Persea pyrifolia. Universidade Estadual Paulista Júlio de Mesquita Filho Instituto de Química Departamento de Química Orgânica Instituto Nacional de Pesquisas da Amazônia Divisão de Química de Produtos Naturais Departamento de Produtos Naturais Centro de Biotecnologia da Amazônia Universidade Estadual Paulista Júlio de Mesquita Filho Instituto de Química Departamento de Química Orgânica

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:57:49Z No. of bitstreams: 1 S0102-695X2011000300008.pdf: 910644 bytes, checksum: 192e0d04ab09adec67218e861f8a07a8 (MD5) Made available in DSpace on 2013-08-22T18:57:49Z (GMT). No. of bitstreams: 1 S0102-695X2011000300008.pdf: 910644 bytes, checksum: 192e0d04ab09adec67218e861f8a07a8 (MD5) Previous issue date: 2011-06-01 Made available in DSpace on 2013-09-30T19:52:54Z (GMT). No. of bitstreams: 2 S0102-695X2011000300008.pdf: 910644 bytes, checksum: 192e0d04ab09adec67218e861f8a07a8 (MD5) S0102-695X2011000300008.pdf.txt: 21094 bytes, checksum: 086dfc0f288f4d5d32d92111ef5d698d (MD5) Previous issue date: 2011-06-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T14:20:57Z No. of bitstreams: 2 S0102-695X2011000300008.pdf: 910644 bytes, checksum: 192e0d04ab09adec67218e861f8a07a8 (MD5) S0102-695X2011000300008.pdf.txt: 21094 bytes, checksum: 086dfc0f288f4d5d32d92111ef5d698d (MD5) Made available in DSpace on 2014-05-20T14:20:57Z (GMT). No. of bitstreams: 2 S0102-695X2011000300008.pdf: 910644 bytes, checksum: 192e0d04ab09adec67218e861f8a07a8 (MD5) S0102-695X2011000300008.pdf.txt: 21094 bytes, checksum: 086dfc0f288f4d5d32d92111ef5d698d (MD5) Previous issue date: 2011-06-01 Anidro do Brasil Extracoes Ltda (Botucatu, SP, Brazil) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Myrcia uniflora Barb. Rodr., Myrtaceae, popularly known as pedra-hume-caá in Brazil, is sold as dry extracts in capsules or as tinctures for the treatment of diabetes mellitus. Previous phytochemical studies on this species described the occurrence of the flavonoids mearnsitrin and myricitrin. In the present study, the chromatographic profiles of M. uniflora leaves and commercial extracts were determined using HPLC-PAD. Myricitrin was used as an external standard in the development and validation of the HPLC method. The proposed method is simple, rapid and reliable and can be successfully applied in industry for standardization of herbs and phytomedicines commercialised in Brazil as pedra-hume-caá. Universidade Estadual Paulista Instituto de Química Departamento de Química Orgânica Anidro do Brasil Extrações Ltda Universidade Estadual Paulista Instituto de Química Departamento de Química Orgânica CNPq: 500185/2006-9

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:57:49Z No. of bitstreams: 1 S0102-695X2010000500021.pdf: 2582101 bytes, checksum: 307e10b1cec799783e4a488586faafe6 (MD5) Made available in DSpace on 2013-08-22T18:57:49Z (GMT). No. of bitstreams: 1 S0102-695X2010000500021.pdf: 2582101 bytes, checksum: 307e10b1cec799783e4a488586faafe6 (MD5) Previous issue date: 2010-11-01 Made available in DSpace on 2013-09-30T19:52:53Z (GMT). No. of bitstreams: 2 S0102-695X2010000500021.pdf: 2582101 bytes, checksum: 307e10b1cec799783e4a488586faafe6 (MD5) S0102-695X2010000500021.pdf.txt: 30063 bytes, checksum: 2040e1187b63cfbff7a75f521119ec6c (MD5) Previous issue date: 2010-11-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T14:20:56Z No. of bitstreams: 2 S0102-695X2010000500021.pdf: 2582101 bytes, checksum: 307e10b1cec799783e4a488586faafe6 (MD5) S0102-695X2010000500021.pdf.txt: 30063 bytes, checksum: 2040e1187b63cfbff7a75f521119ec6c (MD5) Made available in DSpace on 2014-05-20T14:20:56Z (GMT). No. of bitstreams: 2 S0102-695X2010000500021.pdf: 2582101 bytes, checksum: 307e10b1cec799783e4a488586faafe6 (MD5) S0102-695X2010000500021.pdf.txt: 30063 bytes, checksum: 2040e1187b63cfbff7a75f521119ec6c (MD5) Previous issue date: 2010-11-01 Anidro do Brasil Extracoes Ltda (Botucatu-SP, Brazil) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Ptychopetalum olacoides Benth., Olacaceae, popularmente conhecida como marapuama, muirapuama ou miriantã, é uma espécie nativa da região da Amazônia do Brasil. Extratos das cascas da planta são tradicionalmente usados por suas propriedades estimulantes e afrodisíacas, e frequentemente comercializados como constituinte de uma grande variedade de formulações fitoterápicas. O fracionamento por coluna cromatográfica aberta seguida por CLAE-UV/PAD das cascas do caule de três extratos comerciais de P. olacoides permitiram o isolamento de três substâncias comuns em todos os extratos analisados. Os compostos foram identificados por RMN como ácido vanílico, ácido protocatecuíco e teobromina. O ácido vanílico foi utilizado como marcador fitoquímico para P. olacoides e empregado como padrão externo no desenvolvimento e validação de um método de análise qualitativo e quantitativo rápido por CLAE. O valor da recuperação do método desenvolvido foi de 99,02% e os valores de LOD e LOQ foram 0,033 e 0,11 mg.L-1; respectivamente. O método descrito poderá ser empregado para a padronização de plantas, extratos ou fitoterápicos comercializados como marapuama. Ptychopetalum olacoides Benth., Olacaceae, popularly known as marapuama or muirapuama or miriantã, is a species native to the Amazonian region of Brazil. Extracts of the bark of the plant have been used traditionally for its stimulating and aphrodisiac properties and currently commercialised by the herbal industry as constituents in a wide range of phytomedicines. Fractionation by open column chromatography followed by preparative HPLC-UV/PAD of the stem bark and of three commercial extracts of P. olacoides allowed the isolation of three components that were common to all extracts analysed, and these were identified by NMR to be vanillic acid, protocatechuic acid and theobromine. Vanillic acid, which has been proposed as a phytochemical marker for P. olacoides, was employed as an external standard in the development and validation of a rapid qualitative and quantitative HPLC assay for the analyte. The recoveries values of the developed method were 99.02% and the LOD and LOQ values were 0.033 and 0.11 mg.L-1, respectively. The described method may be applied to the standardisation of herbs, extracts or phytomedicines commercialised as marapuama. Universidade Estadual Paulista Instituto de Química Anidro do Brasil Extrações Ltda Universidade Estadual Paulista Instituto de Química CNPq: 500185/2006-9