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Introduction Mass spectrometry in natural products research has been used as a first step to identify possible chemical structures and to guide subsequent efforts to isolate novel compounds. Preparations of Ampelozizyphus amazonicus Ducke (AA) are known for their high content of saponins, especially dammarane-type triterpenoid aglycones. In the Amazon, where it is known as "saracura-mira", roots and bark are widely used for the treatment and prevention of malaria, while the wood is discarded. The extract prepared from the wood is also saponin-rich, but its exact chemical composition has not been described. Objective This study provides information on the chemical profiling and tentative structural identification of the major compounds (saponins) present in aqueous and ethanol extracts of bark and wood of AA by mass spectrometry. Methods The strategy used to identify compounds present in all samples was ultra-high-performance liquid chromatography with an ultraviolet detector coupled to tandem mass spectrometry (UHPLC-UV-MS/MS) for the analysis of fragmentation patterns through product ion scan using MZmine 2 software. Also, direct sample injection and electrospray ionisation combined with high-resolution mass spectrometry (DI-ESI-HRMS) measurements were performed. Results The extracts showed chemical similarity, and 95 saponins were tentatively identified in AA wood and bark, including 73 which are described for the first time as tentative structures for this plant species. Conclusion This research describes a useful method for the fast and simultaneous tentative identification of major saponins in AA, contributing to the study of the chemical properties of this genus and family. Furthermore, it demonstrates the importance of the qualitative dereplication process, allowing a straightforward way to propose the tentative identification of compounds.

Ampelozizyphus kuripacorum from the upper rio Cuyari, Guiania department, Colombia, is described, illustrated, and its relationship with related species discussed. This new species differs from A. guaquirensis (the only other tree species in the genus) by its larger petioles, elliptic leaves, the domatia located only in the base the midrib on the lower surface, the glands (nectaries) on the leaf blades different in form, place and size, and the shorter, few- to single-flowered inflorescence. Updated keys to identify the genera of Rhamnaceae of Colombia and the species of Ampelozizyphus are provided.

Made available in DSpace on 2018-11-26T16:22:23Z (GMT). No. of bitstreams: 0 Previous issue date: 2016-02-03 Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Ethnopharmacological relevance: This is the first intercultural report of antimalarial plants in this region. The aim of this study was to document the medicinal plants used against malaria by indigenous people in the Upper Rio Negro region and to review the literature on antimalarial activity and traditional use of the cited species. Materials and methods: Participant observation, semi-structured interviews, and ethnobotanical walks were conducted with 89 informants in five indigenous communities between April 2010 and November 2013 to obtain information on the use of medicinal plants against malaria. We reviewed academic databases for papers published in scientific journals up to January 2014 in order to find works on ethnopharmacology, ethnobotany, and antimalarial activity of the species cited. Results: Forty-six plant species belonging to 24 families are mentioned. Fabaceae (17.4%), Arecaceae (13.0%) and Euphorbiaceae (6.5%) account together for 36.9% of these species. Only seven plant species showed a relatively high consensus. Among the plant parts, barks (34.0%) and roots (28.0%) were the most widely used. Of the 46 species cited, 18 (39.1%) have already been studied for their antimalarial properties according to the literature, and 26 species (56.5%) have no laboratory essays on antimalarial activity. Conclusions: Local traditional knowledge of the use of antimalarials is still widespread in indigenous communities of the Upper Rio Negro, where 46 plants species used against malaria were recorded. Our studies highlight promising new plants for future studies: Glycidendron amazonicum, Heteropsis tenuispadix, Monopteryx uaucu, Phenakospermum guianensis, Pouteria ucuqui, Sagotia brachysepala and notably Aspidosperma schultesii, Ampelozizyphus amazonicus, Euterpe catinga, E. precatoria, Physalis angulata, Cocos nucifera and Swartzia argentea with high-use consensus. Experimental validation of these remedies may help in developing new drugs for malaria. (C) 2015 Elsevier Ireland Ltd. All rights reserved. Univ Estadual Paulista, Fac Ciencias Agron Botucatu, Dept Hort, Rua Jose Barbosa de Barros 1780, BR-18610307 Botucatu, SP, Brazil Cunuri Indigenous Community, Sao Gabriel Da Cachoeira, Amazonas, Brazil CNRS Guyane USR 3456, 2 Ave Gustave Charlery, Cayenne 97300, French Guiana Herbario EAFM, Inst Educ Ciencia & Tecnol Amazonas IFAM, Manaus, Amazonas, Brazil Univ Estadual Paulista, Fac Ciencias Agron Botucatu, Dept Hort, Rua Jose Barbosa de Barros 1780, BR-18610307 Botucatu, SP, Brazil CNPq: 555.669/2009-2 CAPES: 201062/2012-7 FAPESP: 2009/53638-7

The rare earth element contents of plant specimens of the families Rhamnaceae, Ampelozizyphus amazonicus Ducke (local name: Saracura-Mira) and of Pteridofitas from genus Gleichenia sp. e Adiantum sp. (ferns) were determined and compared to those of the soils, in the Pitinga Mine area, Amazon, Brazil. The Pitinga mine district has large tin reserves genetically related to two granite bodies, Agua Boa e Madeira, both intrusive in volcanic rocks included in the Iricoume Group. This deposit contains, also, bodies of cryolite and rare metals, such as Zr, Nb, Ta, Y and REE. The REE biogeochemical signatures, shown by the collected plants, reflect the patterns of the respective soils. The Eu and Ce anomalies shown by some plant samples are inherited from soils, as well. The higher contents of REE observed in fern samples confirm they are accumulators and reflect the abundance of REE in the soils of Pitinga Mine region. Additionally, that supports their potential use in geochemical exploration and bioremediation. The results of this study stress the importance of biogeochemical research integrated with geochemistry of soils, rocks and minerals.

This works describes the use of experimental design and surface response methodology for optimization of saponin extraction from Ampelozizyphus amazonicus. For this purpose, a method employing extraction based on maceration assisted by ultrasound technique was utilized. The following factors were studied: extraction length of time and solvent composition. The total saponin was determined by using a gravimetric method and the results expressed by their relative proportion to total crude extract. For the specific condition, 60% hydro-alcoholic solution and 18 minutes extraction length of time has shown the best results. This method can be useful for extraction of substances with biological importance

Um levantamento etnobotânico realizado em comunidades quilombolas de Oriximiná, Pará, destacou a saracuramirá (SAR), Ampelozizyphus amazonicus Ducke, com vasto uso popular no tratamento da malária, como tônica e depurativa. Por este motivo, o presente trabalho objetivou realizar um estudo etnofarmacognóstico da SAR nas respectivas comunidades. Por meio de uma análise etnobotânica quantitativa, foi verificado que SAR apresentou-se dentre as 10 espécies mais versáteis pela elevada importância relativa (1,3), dentre as cinco espécies com maior importância cultural pelo elevado índice de saliência (0,311) e a espécie com maior concordância de uso principal para malária (85,7%). Uma análise do índice de espuma e do índice de hemólise para SAR demonstra a presença de saponinas com elevado índice de espuma (833) e uma baixa atividade hemolítica (CH50 2,6 mg mL-1). Para realizar uma análise das agliconas das saponinas de SAR, a bebida preparada pelo método tradicional quilombola (BMT) foi hidrolisada e, após reação com diazometano, foi analisada por cromatografia gasosa. Dois sinais majoritários foram caracterizados por espectrometria de massas, um referente a um triterpeno de esqueleto damarânico, característico das saponinas da SAR, e outro referente ao éster metílico do ácido betulínico. Partindo das informações de uso popular da SAR, foi avaliada in vitro a atividade inibidora da acetilcolinesterase. Apesar de BMT não ter mostrado atividade neste ensaio, é possível supor que as indicações de uso desta planta pelos quilombolas como fortificante e contra malária podem estar relacionadas a uma possível atividade adaptógena e imunoestimulante, dada à presença das saponinas e do ácido betulínico em BMT.

Ampelozizyphus guaquirensis, native to the central portion of the Coastal Cordillera of Venezuela, is newly described and illustrated. It differs from the only other species in the genus, A. amazonicus, in its arborescent (vs. lianoid) habit, subsessile (vs. pedunculate) inflorescence, deciduous (vs. persistent) calyx lobes in fruit, and presence (vs. absence) of nectaries at the base of the leaf blades. Ampelozizyphus is now a prime example of the disjunct distribution of closely related species between Amazonia and the Coastal Cordillera of Venezuela.

The vegetal species Ampelozizyphus amazonicus Ducke (Rhamnaceae Family) was chosen as a sampling medium for the lateritic surfaces of the Pitinga Mine in the Amazon region, in order to study the biogeochemical behavior of this species and compare it with the chemical composition of a reference plant. The Pitinga mining district is one of the largest producers of tin in the world. This district contains unique deposits of cryolite and rare metals such as Zr, Nb, Ta, Y and REEs related to granitic bodies that intrude into the volcanic and acid pyroclastic rocks. The results showed that the species A. amazonicus predominantly concentrates significant levels of Zr, Nb, Ta, Th, Be, Sc over U, Hf, Ga and In. These elements are characteristic of the mineral paragenesis for the region, suggesting that this plant can provide a representative sampling medium future geochemical exploration programs in the region.

Ampelozizyphus amazonicus Ducke is a medicinal plant used in the Amazon region to prepare a drink with tonic, immunomodulatory and adaptogenic properties. Due to the growing interest in dietary supplements with these properties and, to provide a new functional ingredient, barks from A. amazonicus were extracted. The extract was spray dried without drying adjuvants, resulting in a powder (SARF), which was characterized by its physico-chemical properties and proximate, mineral and saponin contents. The SARF saponins were characterized by ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry (HPLC-HRMSn) analysis. The SARF particles tended to have a spherical shape and a unimodal size distribution. The particles also had good rehydration characteristics and high saponin content (33%). The effect of SARF on antibody production was investigated, and we found that SARF increased the basal levels of anti-ovalbumin, anti-LPS and anti-dextran IgM antibodies, and the anti-dextran IgG antibodies in unimmunized mice. No increase in antibody titers was observed after SARF treatment in immunized mice. These results suggest that SARF could be an interesting new functional ingredient for food applications or pharmaceutical products.

PMID: 26664012 WOS: 000362879000003 BACKGROUND: Ampelozizyphus amazonicus Ducke, a plant that is widely used by the population of the Amazonian region to prevent and treat malaria, was investigated in this work, which describes, for the first time, the antiplasmodial activity of its extracts and associates this activity with its isolated constituents. METHODS: Different extracts with solvents of increasing polarity (hexane, chloroform, ethanol, and water) were obtained of the root bark. This procedure resulted in extracts that were characterized for their constituents. The cytotoxicity and activity of the extracts against Plasmodium berghei (schizontocidal activity, liver stage) and Plasmodium falciparum (3D7 and Dd2 strains, erythrocyte stage) were assessed in vitro. RESULTS: Of the four extracts assayed against P. berghei, the chloroform extract showed the greatest activity, with an inhibitory concentration 50% (IC50) value of 30.1 µg/mL, followed by the aqueous extract (IC50 = 39.9 µg/mL). The chloroform extract exhibited the highest antiplasmodial activity in the erythrocyte stage of P. falciparum, with an IC50 value lower than 15 µg/mL. Fractionation of this more active extract led to the isolation and elucidation of pentacyclic triterpenes, lupeol, betulin and betulinic acid, which showed antiplasmodial activities with IC50 values ranging from 5.6 to 80.30 µM. The most active of these, betulinic acid, was further quantified in the extracts by high-performance liquid chromatography-photodiode array detector analyzes. The higher amount was found in the chloroform extract, which was the most active one against P. falciparum. CONCLUSION: The results obtained in this work may partly explain the popular intake of A. amazonicusas an antimalarial remedy in the Amazon region. publishersversion published

Background In this article we present the plants used for the treatment of malaria and associated symptoms in Santa Isabel do Rio Negro in the Brazilian Amazon. The region has important biological and cultural diversities including more than twenty indigenous ethnic groups and a strong history in traditional medicine. Objective The aims of this study are to survey information in the Baniwa, Bare, Desana, Piratapuia, Tariana, Tukano, Tuyuca, Yanomami ethnic communities and among caboclos (mixed-ethnicity) on: a) plant species used for the treatment of malaria and associated symptoms; b) dosage forms and c) distribution of these anti-malarial plants in the Amazon. Methods Information was obtained through classical ethnobotanical and ethnopharmacological methods from interviews with 146 informants in Santa Isabel municipality on the upper Negro River, Brazil. Results Fifty-five mainly native neotropical plant species from 34 families were in use. The detailed uses of these plants were documented. The result was 187 records (64.4%) of plants for the specific treatment of malaria, 51 records (17.5%) of plants used in the treatment of liver problems and 28 records (9.6%) of plants used in the control of fevers associated with malaria. Other uses described were blood fortification (‘dar sangue’), headache and prophylaxis. Most of the therapeutic preparations were decoctions and infusions based on stem bark, root bark and leaves. These were administered by mouth. In some cases, remedies were prepared with up to three different plant species. Also, plants were used together with other ingredients such as insects, mammals, gunpowder and milk. Conclusion This is the first study on the anti-malarial plants from this region of the Amazon. Aspidosperma spp. and Ampelozizyphus amazonicus Ducke were the most cited species in the communities surveyed. These species have experimental proof supporting their anti-malarial efficacy. The dosage of the therapeutic preparations depends on the kind of plant, quantity of plant material available, the patient's age (children and adults) and the local expert. The treatment time varies from a single dose to up to several weeks. Most anti-malarial plants are domesticated or grow spontaneously. They are grown in home gardens, open areas near the communities, clearings and secondary forests, and wild species grow in areas of seasonally flooded wetlands and terra firme (“solid ground”) forest, in some cases in locations that are hard to access. Traditional knowledge of plants was found to be falling into disuse presumably as a consequence of the local official health services that treat malaria in the communities using commercial drugs. Despite this, some species are used in the prevention of this disease and also in the recovery after using conventional anti-malarial drugs.

In this review we discuss the ongoing situation of human malaria in the Brazilian Amazon, where it is endemic causing over 610,000 new acute cases yearly, a number which is on the increase. This is partly a result of drug resistant parasites and new antimalarial drugs are urgently needed. The approaches we have used in the search of new drugs during decades are now reviewed and include ethnopharmocology, plants randomly selected, extracts or isolated substances from plants shown to be active against the blood stage parasites in our previous studies. Emphasis is given on the medicinal plant Bidens pilosa, proven to be active against the parasite blood stages in tests using freshly prepared plant extracts. The anti-sporozoite activity of one plant used in the Brazilian endemic area to prevent malaria is also described, the so called "Indian beer" (Ampelozizyphus amazonicus, Rhamnaceae). Freshly prepared extracts from the roots of this plant were totally inactive against blood stage parasites, but active against sporozoites of Plasmodium gallinaceum or the primary exoerythrocytic stages reducing tissue parasitism in inoculated chickens. This result will be of practical importance if confirmed in mammalian malaria. Problems and perspectives in the search for antimalarial drugs are discussed as well as the toxicological and clinical trials to validate some of the active plants for public health use in Brazil.

Specimens of Ampelozizyphus amazonicus and Adiantum sp., together with adjacent soils, were sampled in the Pitinga Mine District, Amazonian region, in order to investigate the distribution of some trace elements in plants and soils, and their relation to the presence of mineral deposits. The Pitinga Mine contains large deposits of tin, with high concentrations of niobium and zirconium, hosted by the Madeira Granite, which is intrusive into a volcanic sequence named the Iricoume group, all of them with Paleoproterozoic age. Our results point to the potential use, for both plants, of the Biological Absorption Coefficient (BAC) as an indicator of mineral deposits when the elements involved in this process have moderate to high mobility in the supergene environment. The high BAC for gold indicates that this element can be used as an indicator of gold deposits. The presence of sulfide deposits is indicated by high BAC for Cu, Zn and Pb, whereas tin deposits are indicated by increasing BAC for Y and Sn. This suggests that the BAC of some trace elements in both plants is a good indicator of geochemical enrichment associated with mineral deposits. The importance of biogeochemistry for mineral exploration is confirmed for areas with thick vegetal cover.

Ampelozizyphus amazonicus Ducke (Rhamnaceae) is an Amazonian medicinal plant popularly known as “saracura-mira”, from which barks and roots an aqueous drink can be prepared. In an ethnopharmacological study conducted in the “quilombola” communities of Oriximina (PA), Brazil, we learnt the plant is used in the treatment of liver disorders, and as a tonic, among other uses. A trypanocidal activity for an extract of this plant has been demonstrated in literature. In this work, we investigated the effect of A. amazonicus on Trypanosoma cruzi in murine macrophages. Barks of the plant were collected and extracted twice with boiling water, filtered and dried to obtain a powder (SART). Peritoneal macrophages from BALB/c mice were infected with metacyclic forms of the Trypanosoma cruzi clone Dm 28c (3 parasites per macrophage) and some cultures were treated with A. amazonicus. Three days after infection the number of amastigotes forms was evaluated. The numbers of trypomastigote forms were determined by counting of the supernatant in a hemocytometer after 7 and 9 days of culture. In addition, we tested whether nitric oxide was involved in the mechanism of resistance to infection in our in vitro model. To address that hypothesis, peritoneal macrophages were stimulated with LPS, INF-γ and treated with A. amazonicus, and nitric oxide concentration was measured. Statistical analysis was performed using the Student t-test for independent samples, with the level of significance set at p < 0,05. Our results have shown that A. amazonicus reduces significantly the replication of amastigotes forms (35% reduction), the release of trypomastigotes forms (75% reduction) in murine macrophages infected byTrypanosoma cruzi in vitro, and that this effect does not depend on nitric oxide production. Taken together, our results suggest that A. amazonicus is a promissing natural product with important trypanocidal action in intracellular infection. Support: FAPERJ and CNPq.

Araracuara Fern. Alonso, a new genus of Rhamnaceae only known from the sandstone plateaus of the Colombian Amazon, is described and illustrated. Its possible affinities are discussed and it is proposed that this is a relictual genus related to the pantropical Colubrina and to a lesser degree with the Amazonian Ampelozizyphus . Also included are both a key to the Colombian genera of Rhamnaceae and a list of representative specimens of the genera studied (some of which have been poorly documented in Colombia).

Ethnopharmacological relevance Ampelozizyphus amazonicus Ducke is a plant used in Brazilian folk medicine to both prevent malaria and act as a depurative. Aim of the study We have investigated the effects of an ethanol crude extract of roots of Ampelozizyphus amazonicus (CE Aa D), a chemically characterized saponin mixture (SAP Aa D), as well as a saponin-free fraction (SAP Aa D-free) obtained from CE Aa D on diuresis in rats. Materials and methods Wistar rats under ad libitum water conditions or water deprivation for 12 h prior to the start of the experiment were volume-expanded with 0.9% NaCl (4% body weight, by gavage) containing either CE Aa D, SAP Aa D, or SAP Aa D-free at the doses indicated in the text. Rats were individually housed in metabolic cages, and urine volume was measured every 30 min throughout the experiment (3 h). Results CE Aa D increased urine volume in rats under conditions of both free access to water and under water deprivation. In the latter condition, CE Aa D (150 mg/kg) increased the urine volume from zero to 0.9 ± 0.1 ml/120 min, n = 6). Similarly, the SAP Aa D-free (50–200 mg/kg) mixture also increased the urine volume. In contrast, SAP Aa D (12.5–1000 mg/kg) produced a significant reduction ( p Conclusion Our data indicate that CE Aa D contains compounds that cause both diuresis and antidiuresis and that the antidiuretic effect is due mainly to the presence of saponins.

Ampelozizyphus amazonicus Ducke is a tree commonly found in the Amazon region and an extract of its stem bark is popularly used as an antimalarial and anti-inflammatory agent and as an antidote to snake venom. Ursolic acid; five lupane type triterpenes: betulin, betulinic acid, lupenone, 3beta-hydroxylup-20(29)-ene-27,28-dioic acid, and 2alpha,3beta-dihydroxylup-20(29)-ene-27,28-dioic acid, and three phytosteroids: stigmasterol, sitosterol and campesterol, have been isolated from stem extracts of A. amazonicus Ducke. Their structures were characterized by spectral data including COSY and HMQC. In an in vitro biological screening of the isolated compounds, 3beta-hydroxylup-20(29)-ene-27,28-dioic acid was cytotoxic against the SKBR-3 human adenocarcinoma cell line (1 to 10 mg/mL), while 2alpha,3beta-dihydroxylup-20(29)-ene-27,28-dioic acid exhibited cytotoxicity against both SKBR-3 human adenocarcinoma and C-8161 human melanoma tumor cell lines (>0.1 mg/mL). In the present study, different extracts and some fractions of this plant were also investigated for trypanocidal activity due to the presence of pentacyclic triterpenes. The triterpene classes are potent against Trypanosoma cruzi. The bioassays were carried out using blood collected from Swiss albino mice by cardiac puncture during the parasitemic peak (7th day) after infection with the Y strain of T. cruzi. The results obtained showed that A. amazonicus is a potential source of bioactive compounds since its extracts and fractions isolated from it exhibited in vitro parasite lysis against trypomastigote forms of T. cruzi at concentrations >100 microg/mL. Fractions containing mainly betulin, lupenone, 3beta-hydroxylup-20(29)-ene-27,28-dioic acid, and 2alpha,3beta-dihydroxylup-20(29)-ene-27,28-dioic acid showed more activity than crude extracts.

A new triterpene saponin was isolated from the roots of Ampelozizyphus amazonicus together with the known 3-O-beta-D-glucopyranosyl-20-O-alpha-L-rhamnopyranosyljujubogenin and the known triterpenes melaleucic acid, 3 beta,27 alpha-dihydroxylup-20(29)-en-28 beta-oic acid, betulinic acid, betulin, lupeol. The structure of this saponin was elucidated as 3-O-[beta-D-glucopyranosyl(1----2)alpha-L-arabinopyranosyl]- 20-O-alpha-L-rhamnopyranosyljujubogenin by spectral analysis and chemical transformations.

A new C31 dammarane-type triterpenoid saponin has been isolated from the roots of Ampelozizyphus amazonicus. Its structure was elucidated to be ampelozigenin-15 alpha-O-acetyl- 3-O-alpha-L-rhamnopyranosyl-(1--2)-beta-D-glucopyranoside by 1D and 2D NMR spectroscopic methods, and by chemical transformations. Ampelozigenin is a novel triterpene, (20R,22R)-16 beta,22:16 alpha, 30-diepoxydammar-24(24')- methylene-3 beta, 15 alpha, 20-triol.

Laboratorio de Malaria, Centro de Pesquisas Rene Rachou/FIOCRUZ, Av. Augusto de Lima 1715, CEP 30190-002, Belo Horizonte, MG, Brazil Departamento de Parasitologia-ICB, Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG, Brazil Laboratorio de Farmacognosia, Faculdade de Farmacia, UFMG, CEP 31270-000, Belo Horizonte, MG, Brazil Centro de Malaria e outras Doenc as Tropicais, Instituto de Higiene e Medicina Tropical, Universidade Nova de Lisboa, Rua da Junqueira, 96 – 1349-008 Lisboa, Portugal