PINTO, T. R. M. Estudo do potencial farmacoquímico do óleo de batiputá (Ouratea fieldingiana (Gardner) Engl.) como insumo farmacêutico. 2017. 85 f. Dissertação (Mestrado em Ciências Farmacêuticas) - Faculdade de Farmácia, Odontologia e Enfermagem, Universidade Federal do Ceará, Fortaleza, 2017. / Submitted by ciências farmacêuticas pgcf (pgcf.ufc@gmail.com) on 2017-11-27T16:52:31Z No. of bitstreams: 1 2017_dis_trmpinto.pdf: 2030404 bytes, checksum: a3100a8628cf88a3a76970c18254e2a7 (MD5) / Approved for entry into archive by Erika Fernandes (erikaleitefernandes@gmail.com) on 2017-11-27T17:53:08Z (GMT) No. of bitstreams: 1 2017_dis_trmpinto.pdf: 2030404 bytes, checksum: a3100a8628cf88a3a76970c18254e2a7 (MD5) / Made available in DSpace on 2017-11-27T17:53:08Z (GMT). No. of bitstreams: 1 2017_dis_trmpinto.pdf: 2030404 bytes, checksum: a3100a8628cf88a3a76970c18254e2a7 (MD5) Previous issue date: 2017-10-25 / Ouratea fieldingiana (Gardner) Engl., popularly known in the northeast as batiputá, is a plant, essentially arboreal or shrub, belonging to the family ochnaceae, genus ouratea. From its fruit can be extracted an oil that is used in both cooking and folk medicine as anti-inflammatory, healing and in the treatment of cough and flu states. It was observed that extracts and fractions obtained from plants belonging to the genus ouratea have important biological activities such as antitumor, antiviral, vasodilator, antimicrobial and inhibition of DNA topoisomerase, making evident the therapeutic potential of these species, which justifies the necessity of conducting a pharmacochemical study and to explore the pharmaceutical potential of the input from the fruits of the native species of Ceará’s state. The present work had the objective of conducting the pharmacochemical study of batiputá oil from the fruits of Ouratea fieldingiana in order to determine its chemical composition and obtaining a pharmaceutical input. For this, preliminary tests were carried out to select the most suitable technique for fruit desiccation, with determination of the moisture content. In order to characterize its quality parameters, a phytochemical approach was performed, evidencing the presence of alkaloids, catechins, coumarins, steroids, free phenols, flavonoids, saponins, anthraquinones and triterpenoids and analysis of their mineral and metallic composition, which revealed richness of micro and macro nutrients with important functions in the body. Subsequently, tests were carried out, where the quality specifications of the oil extracted by hand and laboratory were obtained as organoleptic and physico-chemical characteristics, such as: density, refractive index, acidity, saponification, esthers and iodine, obtained. The analysis of the chemical composition of the artisanal (AO) and laboratory (LO) oils by CG-FID evidenced the presence of the acid methyl ethers, palmitic, oleic and linoleic. The results obtained in this work were unpublished and provide scientific evidence of the feasibility of applying the batiputá fruits in nutraceutical and batiputá oil in dermo-cosmetics, which encourages the maintenance and propagation of popular knowledge through scientific verification. / Ouratea fieldingiana (Gardner) Engl., conhecida popularmente no Nordeste como Batiputá, é uma planta, essencialmente arbórea ou arbustiva, pertencente à família Ochnaceae, gênero Ouratea. De seus frutos pode ser extraído um óleo que é usado tanto na culinária quanto na medicina alternativa como antinflamatório, cicatrizante e no tratamento de tosse e estados gripais. Estudiosos observaram que extratos e frações obtidas de plantas pertencentes ao gênero Ouratea possuem diversas atividades biológicas importantes como antitumoral, antiviral, vasodilatadora e antimicrobiana, tornando evidente o potencial terapêutico dessas espécies, o que justifica a necessidade de se realizar um estudo farmacoquímico e explorar o potencial farmacêutico do insumo proveniente dos frutos da espécie originária do Estado do Ceará. O presente trabalho teve como objetivo realizar o estudo farmacoquímico do óleo de batiputá a partir dos frutos de Ouratea fieldingiana com vista à determinação da sua composição química e obtenção de insumo farmacêutico. Para isso, realizou-se, preliminarmente ensaios para selecionar a técnica mais indicada para dessecação dos frutos e para a determinação do teor de umidade. Para caracterização dos seus parâmetros de qualidade realizou-se previamente, uma abordagem fitoquímica, evidenciando a presença de alcaloides, catequinas, cumarinas, esteroides, fenóis livres, flavonoides, saponinas, traços antraquinônicos e triterpenoides e análise da sua composição mineral, que revelou riqueza de micro e macro nutrientes com importantes funções no organismo. Posteriormente, foram realizados ensaios, onde foram obtidas as especificações de qualidade do óleo extraído artesanalmente e laboratorialmente como caracteres organolépticos e físico-químicos, tais como: densidade, índices: de refração, acidez, saponificação, éteres e iodo, das amostras de óleo obtidas. A análise da constituição química dos óleos artesanal (O.A) e laboratorial (O.L) por CG-FID evidenciou a presença majoritária dos ésteres metílicos dos ácidos palmítico, oleico e linoleico. Os resultados obtidos nesse trabalho foram inéditos e fornecem evidências científicas da viabilidade de aplicação do dos frutos na nutracêutica e do óleo de batiputá na dermo-cosmética, o que incentiva a manutenção e propagação dos saberes populares através de comprovação científica.

Orientador: Graziela Maciel Barroso / Dissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Biologia / Made available in DSpace on 2018-07-19T01:53:30Z (GMT). No. of bitstreams: 1 Yamamoto_Kikyo_M.pdf: 12344445 bytes, checksum: 1dec03cf69ca5057774750488394255d (MD5) Previous issue date: 1989 / Resumo: O genero, Duratea Aublet (Ochnaceae-Ochnoideae) é classificado, segundo os ultimos estudos taxonomicos, na subtribo Duratinae, e considerando restrito à região neotropical (Duratea s.s.). A última revisão taxonômica geral data de 1876. Como subsidio para uma futura revisão do gênero, fez-se um levantamento geral do valor diagnóstico dos caracteres morfológicos e uma avaliação dos dados anatômicos utilizados por P. van Tieghem na descrição de taxons criados a partir do genero Duratea s.l., entre os anos de 1902 a 1903¿Observação: O resumo, na íntegra poderá ser visualizado no texto completo da tese digital / Abstract: The genus Duratea Aublet (Ochnaceae-Ochnoideae), is classifyed, in the last taxonomic studies, in the subtribe Duratinae of the tribe Ochneae, and is considered restrict to the neotropical region (Duratea s.s.). The last revision of this genus was presented in 1876. In order to help a future taxonomic revision, it is presented here a general analysis of the taxonomic value of morphological characters, as well as of the anatomical characters applied by P. van Tieghem in the descriptions of taxa separated by this author from Duratea s.l. between 1902 and 1903...Note: The complete abstract is available with the full electronic digital thesis or dissertations / Mestrado / Biologia Vegetal / Mestre em Ciências Biológicas

The phytochemistry of Ochna serrulata (Hochst.) Walp. was investigated for the first time; two new dimeric chalcones (5-deoxyurundeuvine C and serrulone A) and two new biflavonoid derivatives (4,4’,7-tri-O-methylisocampylospermone A and 4”’-de-Omethylafzelone A) were isolated. These compounds were isolated along with the known compounds lophirone A, afzelone B, campylospermone A, isocampylospermone A, ochnaflavone, 2”,3”-dihydroochnaflavone, lophirone C, psilosin, 3’-O-methylpsilosin, a cyanoglucoside, epicatechin, (2’,4’- dihydroxyphenyl)acetic acid, methyl (2’,4’-dihydroxyphenyl)acetate, irisolone 4’- methyl ether, iriskumaonin 3’-methyl ether, 3',4'-dimethoxy-6,7-methylenedioxyisoflavone, lophirone L, syringaresinol and 16α,17-dihydroxy-entkauran-19-oic acid. The growth inhibitory effect of these compounds was evaluated against three cancer cell line panel of TK 10 (renal), UACC62 (melanoma) and MCF7 (breast) using a sulforhodamine B (SRB) assay. Ochnaflavone and 3’-methoxypsilosin demonstrated selectivity and only inhibited the growth of melanoma cancer cells. However, ochnaflavone showed higher activity by totally inhibiting the growth of melanoma cancer cells at 12.91 μM, whereas, 3’-O-methylpsilosin has this effect at a concentration of 14.11 μM. Lophirone C, a dimeric chalcone, demonstrated the highest cytotoxic activity amongst all isolated compounds against renal, melanoma and breast cancer cells with TGI at 35.63 μM, 11.67 μM and 30.35 μM, respectively. Lophirone A, a rearranged biflavonoid, showed TGI against these cancer cells at 58.96 μM, 26.23 μM and 40.01 μM, respectively. The rest of the compounds showed no significant cytotoxicity against the three cancer cells. The new biflavonoid, 4,4’,7-tri-O-methylisocampylospermone A demonstrated the highest antimalarial activity against chloroquine-resistant strains of Plasmodium falciparum (FCR-3) with IC50 of 11.46 μM, followed by ochnaflavone (17.25 μM). iv Serrulone A (26.52 μM), lophirone A (29.78 μM), 5-deoxyurundeuvine C (31.07 μM), lophirone C (35.31 μM), 4”’-de-O-methylafzelone A (38.43 μM), afzelone B (39.54 μM), irisolone 4’-methyl ether (40.72 μM) and syringaresinol (42.66 μM) were moderately active. The following compounds exhibited the lowest antimalarial activity, 2”,3”-dihydroochnaflavone (61.86 μM), iriskumaonin 3’-O-methyl ether (93.69 μM),3’- O-methylpsilosin (106.35 μM) and16α,17-dihydroxy-ent-kauran-19-oic acid (106.48 μM). Owing to the observed and reported biological/pharmacological activity, ochnaflavone (an ether-linked biflavone consisting of apigenin and luteolin moieties) was selected for synthetic studies. An older method, nucleophilic aromatic substitution (SNAr) was successfully applied in the construction of the diary ether. Oxidative ring cyclization of the ether-linked dimeric chalcone was achieved by using heated pyridine and iodine. The two methods can be extended further in the synthesis of other novel biflavones with ether linkage. / Thesis (Ph.D.)-University of KwaZulu-Natal, Pietermaritzburg, 2012.

In preliminary work done in a tree leaf screening project in the Phytomedicine Programme (www.up.ac.za/phyto) Ochna pretoriensis acetone leaf extracts had good antibacterial activity against several important bacterial pathogens. The main aim of this study was to isolate and characterize antibacterial compounds present in the acetone leaf extract of Ochna species growing in South Africa. In a preliminary screening, the minimum inhibitory concentration of acetone leaf extracts of Ochna natalitia, Ochna pretoriensis, Ochna pulchra, Ochna gamostigmata, and Ochna. Serullata, against Staphylococcus aureus, Escherichia coli, Enterococcus faecalisand Pseudomonas aeruginosa were determined by using a serial microplate dilution assay. The number of antibacterial compounds in the extracts was also determined by bioautography against the same bacteria. The MIC values of the five species ranged from 0.039 mg/ml to 1.25 mg/ml. The lowest average MIC values observed were for O. Pretoriensis especially against E. Faecalis and E. Coli. The most sensitive organism to all the plants was E. coli. O. Pretoriensis had the lowest average MIC value and the highest total activity value of 1538 ml/g. Based on bioautography some of the Ochna species had antibacterial compounds with similar Rf values. The thin layer chromatography chemical profiles of the five plant extracts may be useful in the taxonomy of the genus. O. Pretoriensis was chosen for fractionation and isolation of antibacterial compound because it has the lowest average MIC values and highest total activity especially against E. Faecalis and E. coli. The acetone extract of O. Pretoriensis was fractionated into seven fractions (hexane, carbon tetrachloride, chloroform, ethyl acetate, 35% water in methanol, 70% water in methanol and butanol) by solvent-solvent fractionation. Only three of the seven fractions (carbon tetrachloride, chloroform, ethyl acetate fractions) had clearly defined antibacterial spots/lines on bioautograms. The three fractions were further fractionated using column chromatography from which three compounds were successfully isolated. The chemical structures of the isolated compounds were determined using NMR spectroscopy as β-Sitosterol (SS), ochnaflavone (OF) and ochnaflavone 7-O- methyl ether (OFME). Compounds that are related to sitosterol have activity against neurodegenerative disorders as well as estrogenic, analgesic, anti-inflammatory, anthelminthic and antimutagenic activity. OF and OFME are biflavonoids which belong to the group ochnaflavones previously characterized from Ochna obtusata. These compounds have anti-atherosclerotic, anti-inflammatory, and anti-tumor activity. They also inhibit lymphocytes proliferation, archidonic acid release and phospholipase activity. Moreover, OFME was reported to inhibit HIV-1 activity as well as HIV-1 reverse transcriptase activity. The antibacterial activity, and potential cytotoxic, genotoxic and antigenotoxic effects of the isolated compounds were determined. The MIC values ranged from 31.3 to 250 μg/ml. SS was more active against P. Aeruginosa with an MIC of 62.5 μg/ml, OF against P. Aeruginosa and E. Faecalis with MICs of 0.03 mg/ml and OFME against P. Aeruginosa with an MIC of 31.3 μg/ml. The isolated compounds were much less active than the positive control gentamycin. The compounds had low cytotoxic activity, with LC50 values of 193.8 μg/ml for β-Sitosterol, 125.9 μg/ml for OF and 125.9 μg/ml for OFME against Vero cells. The therapeutic indexes of the crude extract and the isolated compounds varied between 0.77 and 3.27, which is an indication of non-specific antibacterial activity i.e. general toxicity, thus the crude plant extract and compounds isolated from O. Pretoriensis can only be recommended for external applications. e.g. topical treatments. None of the compounds tested had potential genotoxic and/or antigenotoxic effects. The number of revertants in the mutagenicity experiments was less than twice the number of revertants in the negative control. The percentage inhibition of 4NQO in the antimutagenicity experiments were less than 45%. The results obtained in this case may be principally associated with the general toxicity of the test samples to the bacteria used in this study. Comparison of the total activity of the crude extract and the fractions gave a clear indication of synergic interaction of compounds in the crude extract to successfully inhibit the growth of the test pathogens. Approximately 76% of activity was lost in the 34% of dry mass lost during fractionation. Twelve percent of activity was present in the chloroform fraction and 6% in the carbon tetrachloride fraction. Despite the evidence for synergistic activity, the crude extract was also relatively toxic to the Vero cells with a therapeutic index of 0.8. As far as could be established, the antibacterial activity of members of the Ochna genus and the cytotoxicity of ochnaflavones were determined for the first time in the current study. The two most active antibacterial compounds (ochnaflavone and ochnaflavone 7-O- methyl ether) are being reported from this species for the first time. The relative safety of the crude extract and the compounds isolated from this plant was relatively low. Preparations of O. Pretoriensis may be safe in a topical application but internal use cannot be recommended for treating antibacterial infections before animal toxicity studies have been carried out. Caution is also required in using the isolated compounds or crude extracts for other applications. Copyright / Dissertation (MSc)--University of Pretoria, 2009. / Paraclinical Sciences / unrestricted

Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2016-07-27T13:08:18Z No. of bitstreams: 1 2011 - Queli Cristina Fidelis.pdf: 8250271 bytes, checksum: f51d246c251bca4327f02da1e892ff77 (MD5) / Made available in DSpace on 2016-07-27T13:08:18Z (GMT). No. of bitstreams: 1 2011 - Queli Cristina Fidelis.pdf: 8250271 bytes, checksum: f51d246c251bca4327f02da1e892ff77 (MD5) Previous issue date: 2011-02-25 / Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico, CNPq, Brasil. / This work describes the phytochemical study of the stems and leaves of Ouratea ferruginea Engl., Ochnaceae. The material for study was collected in the campus of Embrapa in Bel?m, Par? state, and identified by Dra Silvane Taveres Rodrigues. The compounds described in this phytochemistry investigation were isolated by the solvents partition and chromatographyc techniques of the extracts obtained by maceration at room temperature with hexane, ethyl acetate and methanol. The structures were determined through analysis of data provided by IR, 1H and 13C NMR (1D an 2D techniques), mass spectrometry including GCMS and HPLC-MS of natural compounds and some derivatives. From the stem dichloromethane extract friedelin, friedelinol, sitosterol, stigmasterol, campesterol, 3-b-O-Dglucopyranosyl- stigmasterol, 2,6-dimethoxy?benzoquinine, 2,6-dimethoxy-hydroquinone, the isoflavones: 5,4'-dihydroxy-7,3',5'-trimethoxy-isoflavone, 5-hydroxy-7,3',4',5'-tetramethoxyisoflavone, 5,4'-dihydroxy-7,3'-dimethoxy-isoflavone, 7,5-dihydroxy-3',4',5'-trimethoxyisoflavone, 7,5,4?-trihydroxy-3?,5?-dimethoxy-isoflavone, and ferulic and syringic aldehyde were isolated. From the dichloromethane partition of the methanol extract of the stem vanillic acid, 4 ((1E)-3-hydroxy-1-propenyl)-2-methoxyphenol and 3,5-dimethoxy-4-hydroxydihydrocinamaldehyde were isolated. From hexane fraction of methanol extract from the leaves lupeone was isolated, and from the dichloromethane methanol partition were identified the biflavonoids amentoflavone and 7-methyl-amentoflavone, known as sequoiaflavone, along with syringic acid. From the ethyl acetate of the methanol extracts partition the epicatechin which absolute configuration was defined by circular dichroism spectral analysis was isolated. The sequioflanove is been identified in Ochnaceae for the first time. From the polar fraction the total phenol were determined by adapted Folin-Denis and precipitation with casein methods and by NMR spectral analysis. / Este trabalho descreve o estudo fitoqu?mico de caule e folhas da esp?cie vegetal Ouratea ferruginea Engl, Ochnaceae. O material para estudo foi coletado no campus da Embrapa em Bel?m do Par? e identificado pela Dra Silvane Tavares Rodrigues. As subst?ncias descritas nesta investiga??o fitoqu?mica foram isoladas atrav?s de parti??o com solventes e t?cnicas cromatogr?ficos de extratos obtidos atrav?s de macera??o a frio com hexano, acetato de etila e metanol. As estruturas foram determinadas atrav?s da an?lise de dados fornecidos por espectrometria na regi?o do infravermelho, RMN 1H e 13C (t?cnicas 1D e 2D), de massas incluindo CG-EM e CLAE-EM das subst?ncias naturais e de alguns derivados. Do extrato em diclorometano do caule foram isolados friedelina, friedelinol, sitosterol, estigmasterol, campesterol, 3-b-O-D-glicopiranosil-estigmasterol, 2,6-dimetoxi benzoquinona, 2,6-dimetoxi hidroquinona, as isoflavonas 5,4?-diidroxi-7,3?,5?-trimetoxiisoflavona, 5,4?-diidroxi-7,3?-dimetoxi-isoflavona, 5-hidroxi-7,3?,4?,5?-tetrametoxiisoflavona, 7,5-diidroxi-3?,4?,5?-trimetoxi-isoflavona, 7,5,4?-triidroxi-3?,5?-dimetoxiisoflavona, al?m dos alde?dos sir?ngico e fer?lico. Da parti??o em diclorometano do extrato metan?lico do caule foram isolados ?cido van?lico, 4((1E)-3-hidroxi-1-propenil)-2- metoxifenol e 3,5-dimetoxi-4-hidroxi-diidrocinamalde?do. Das folhas foi isolada a lupeona na parti??o em hexano do extrato metan?lico; e na parti??o em diclorometano foram identificados os biflavon?ides amentoflavona e 7-metil-amentoflavona, conhecida como sequoiaflavona, e o ?cido sir?ngico. Na parti??o em acetato de etila foi isolado a epicatequina cuja configura??o absoluta foi definida com an?lise do espectro de dicro?smo circular. A sequioflavona est? sendo registrada pela primeira vez em Ochnaceae. Das fra??es polares foram determinados o teor de fen?is totais e taninos por m?todos de Folin-Denis e precipita??o com case?na, adaptados, al?m de an?lise com espectros de RMN.

PhD (Botany) / Department of Botany / Brackenridgea zanguebarica Oliv. (Ochnaceae) commonly known as “Yellow Peeling Plane”, is an important medicinal plant species, and one of the most threatened tree species that is endemic to Thengwe village in Vhembe District, South Africa. It is widely harvested for traditional purposes and difficult to propagate sexually and asexually. Nowadays, it has become threatened and this unique plant population is believed to be declining in the Brackenridgea Nature Reserve (BNR). According to the Red List of South African plants, B. zanguebarica is considered a critically endangered medicinal plant. All these facts combined with a lack of knowledge on the conservation of this species prompted this study on its conservation. To ascertain the effective conservation and proper management of this multipurpose tree, this study was conducted with the aim to improve its conservation strategy by investigating current threats to the existence of B. zangueberica, the chemical constituents from the different plant parts, the propagation methods of the species, and the factors delaying the germination of its seeds. In this study, an assessment of the current population threats was important as a first step in conservation; this would update the status of the species in its natural habitat. The current status of Brackenridgea zanguebarica was conducted through an extensive field survey in the Brackenridgea Nature Reserve (BNR), where a belt transect method was deployed to record quantitative information, while the harvesting damage was estimated using a sliding scale from 0 to 5. The structure of the populations in terms of the stem diameter size classes showed a bell shape vi pattern. About 60% of individuals showed some signs of plant parts extraction as the stem bark was reported to be the main plant part harvested. The population structure, however, was dominated by juvenile plants due to the selective harvesting of mature individuals; this hinders fruit production leading to poor or slow seed production. The present study aimed to compare the chemical constituents and the antimicrobial activities of some parts of this plant species. The extracts were screened for phytochemicals using standard methods. Thin-layer chromatography (TLC) was carried out to compare the chemical constituents using various solvent systems of varying polarity. Agar well diffusion and broth microdilution methods were used to evaluate the antimicrobial activity and the minimum inhibitory concentrations (MIC) of plant extracts respectively, against three bacteria and four fungi. The phytochemical analysis revealed a close similarity of various phytoconstituents of the three plant parts (stem bark, twigs and leaves). TLC analysis showed a slight difference in the acetone extract of different plant parts with more bands on the leaves than the stem bark and twigs. Acetone extracts of the three plant parts exhibited varying degrees of antimicrobial activity against Staphylococcus aureus and Candida glabrata, while none of the extracts showed any activity against Escherichia coli, Klebsiella pneumonia, Candida albicans, C. krusei, and C. parapsilosis. However, analysis of the antibacterial activity of various extracts revealed that the best inhibitory activity was produced by the stem bark extract compared to the leaf and twig extract. vii The sustainable way to meet the growing demand of Brackenridgea zanguebarica is to increase its availability through propagation practices. Unfortunately, the conservation of B. zanguebarica is hampered by lack of information on how it can be propagated. Sexual and asexual propagations were conducted to determine an efficient method to increase the number of individuals of this plant species. Seed propagation was carried out to study the effect of various pre-treatments on germination, in order to understand the germination requirements; vegetative propagation was conducted to assess if B. zanguebarica could be successfully propagated via stem cuttings if the appropriate growth hormones and growing media were applied. Brackenridgea zanguebarica seed did not germinate at all under any of the conditions tested. However, the results, showed the potential of propagating this species from stem cutting despite the poor results obtained. Thus B. zanguebarica was found to be difficult to propagate sexually and asexually. Seeds serve as a means of reproduction and a vital element to ensure the survival of plant species. Seed germination is controlled by a number of factors. The propagation of B. zanguebarica via seed is very difficult and research has not been undertaken to understand possible factors that may delay its germination. This study was aimed to investigate and describe both the morphological and anatomical features of B. zanguebarica seed, in order to identify structural features implicated in its poor germination. To achieve this goal, a morphological and anatomical study was conducted based on the observation of seeds under a scanning electron microscope (SEM) and light microscopy (LM). Water uptake potential was assessed by the increase in seed mass. The morpho-anatomical analysis indicated that some structures of the seed, such as seed coat, and the presence of endosperm viii surrounding the embryo that consisted of two prominent cotyledons, seem to greatly hinder the germination of this species. The research findings provided information regarding the seed structure which is one important step in identifying useful techniques to improve seed germination for conservation purposes. / NRF