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Synthesis of (+)-muconin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran (THF-THP) ring moiety was performed using diastereoselective oxypalladation in the presence of CuCl2. The cross-coupling reaction of the THF-THP moiety with the γ-lactone portion followed by reduction of the enyne and removal of the protecting groups afforded (+)-muconin.

CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Outra Agência Para a descontaminação de solos com metais pesados são propostos diversos métodos e procedimentos. Dentre eles, tem-se a fitorremediação. O presente estudo investiga a fitorremediação por fitólitos. Neste texto foram investigadas três plantas nativas do bioma Cerrado com capacidade de produzir sílico-fitólitos. As plantas estudadas foram: Rollinia leptopetala, Piptadenia gonoacantha e Sida sp. Os resultados revelaram que as espécies estudadas concentraram metais pesados nos sílico-fitólitos em concentraçõesdiferentes para os órgãos (raízes, caules, folhas) das plantas. A concentração nas plantas aumenta com a maior concentração disponível no solo. Si-fitólitos extraídos do solo (com pequenas quantidades de outros compostos, como óxidos; argilas < 1-3 %) mostram concentrações médias comparáveis às concentrações médias das plantas estudadas. Assim, os metais disponíveis são transformados em metais não-disponíveis, o que permite o uso destas plantas para a descontaminação. For the decontamination of soils, rich in heavy metals are proposed various methods and procedures. Among them, one is the phytoremediation. The present study investigates the phytoremediation by phytoliths. In this text three native plants from the Cerrado biome with ability to produce Si-phytoliths, were investigated. The studied plants are Rollinia leptopetala, Piptadenia gonoacantha and Sida sp. The results showed that the studied species concentrated heavy metals in Si-phytoliths in different concentrations in their organs (leaves, stems, roots). The concentration in plants increases with the highest available concentration in the soil. Si-phytoliths extracted from the soil (with small amounts of other compounds such as oxides, clays

The present work consists of the evaluation of antimicrobial activity and inhibition of the enzyme acetylcholinesterase (AChE) of fixed oils and hexane extracts of nine fruits with the following native names: abiu (Pouteria caimito), acerola (Malpighia emarginata), araca (Psidium cattleianum), bacupari (Rheedia gardneriana), biriba (Rollinia mucosa), camu-camu (Myrciaria dubia), fruta-do-conde (Annona squamosa), graviola (Annona muricata) and tapereba (Spondias mombin L.). Different evaluations were carried out with different parts of the fruits, pulp, seed and barks. The antimicrobial assay was carried out with the following microorganisms: Candida albicans ATCC 18804, Staphylococcus aureus ATCC 29212, Bacillus cereus ATCC 11778, Escherichia coli ATCC 25922 and Salmonella typhimurium ATCC 14028. Of these microorganisms, the best inhibition results were obtained for yeast C. albicans with percent inhibition of 94.46% by tapereba barks extracts, acerola barks (87.12%), araca seed (85.23%) and tapereba pulp (85.22%). Against the bacteria tested, percent inhibition was low, showing that the extracts have good antifungal selectivity. Some extracts were able to inhibit the enzyme AChE and high percentage of inhibition was observed for the oils, especially from biriba barks, with 86.39% inhibition, tapereba seeds with 62.17% and acerola pulp with 52.18%. Methods of Multivariate Analysis were applied through Principal Component Analysis (PCA) and Hierarchical component analysis (HCA), to establish correlations and groupings between the data obtained, justifying 82.3% of cases for pulps, 73.2% for the barks and 65.7% for the seeds according to the PCA. Key words: Bacteria, yeasts, Alzheimer, principal component analysis (PCA), hierarchical component analysis (HCA).

The concentrations of 3,4-dihydroxybenzoic acid, caffeic acid, catechin, chlorogenic acid, epicatechin, gallic acid, p-coumaric acid, quercetin, rutin, ferulic acid, and the major metals in graviola (Annona muricata), atemoya (A. squamosa x A. cherimola), fruta do conde (A. squamosa), biriba (Rollinia mucosa), and the North American pawpaw (Asimina triloba) were determined by UPLC-ESI (−)-MS/MS. It enabled the identification and quantification of phenolic compounds. Catechin was only found in atemoya, at a concentration of 38.6 μg/g-dw. Only 3,4-dihydroxybenzoic acid was found in the fruit pulps of all five fruits analyzed. Atemoya stands out for not only having catechin but also for having much more epicatechin (239 μg/g-dw) than the other fruits. At the same time, graviola had more p-coumaric acid (62.6 μg/g-dw), and the North American pawpaw had more chlorogenic acid (48.1 μg/g-dw) than the other fruits. Metals were determined by ICP equipped with axially viewed plasma. All five fruit pulps had relatively high levels of potassium, with concentrations ranging from 7640 to 15,000 μg/g-dw, with pawpaw being the lowest and atemoya being the highest. The concentrations of other metals ranged from Ca 547 to 1110, Na 14.3 to 123, P 1210 to 1690, Mg 472 to 980, Mn 1.86 to 5.27, and Zn 5.55 to 7.32 μg/g-dw. All five fruits in the Annonaceae family that were analyzed in this study have several phenolic compounds in them and were good sources of potassium, calcium, phosphorus, and magnesium.

As a result of concerted efforts of the community of Annonaceae taxonomists, increasingly detailed knowledge of the diversity of the Neotropical genera has been documented. With the exception of just two large genera, Annona and Xylopia, all Neotropical Annonaceae have been revised within the last 25 years. Subsequent to these publications, many new specimens have been collected and sent to us in Leiden for identification. These included a number that, despite the advanced state of taxonomic knowledge, proved to represent rarely collected, undescribed species. Here we describe 12 new species of Annona, Guatteria, Klarobelia, Tetrameranthus, and Xylopia. These species serve to illustrate the still underestimated diversity of the Neotropical flora, even in well studied plant groups like Annonaceae.

The lace bug, Corythucha gossypii (Fabricius) is a serious pest affecting over 24 wild and commercially important plant species of the families Annonaceae, Passiflorcae, Caricaceae, Euphorbiaceae, and Solanaceae. Thus far, commercial insecticides, such as 0.1% Dimethoate and 0.1% Imidacloprid have shown effectiveness against this insect, but no botanical pesticides are available to control this bug. In the present study, a Rollinia mucosa (Jacq.) Baillon ethanol extractwas evaluated as a biological control agent against the lace bug. Through a toxicity assay involving Artemia salina, the median lethal concentration (LC50) of a raw ethanol extract of R. mucosa seeds was determined, as well as that of its Acetogenin (F1) and Alkaloid (F2) fractions; these LC50 were 0.184, 0.082, and 0.0493 g/mL, respectively. In addition, with an insecticide assay on lace bug nymphs, a mortality percentage of 86.67% at 5 g/mL after 72h was observed. These data demonstrate that the R. mucosa seed extract is highly active. Further chemical characterization studies revealed that the main active metabolites contributing to extract activity were acetogenins and alkaloids.

This review reports the nutritional, phytochemical compounds and biological properties of 4 fruits commonly consumed by people living in Amazon region, namely Biribá (Rollinia mucosa Jacq.), Rambutan (Nephelium lappaceum L.), Pupunha (Bactris gasipaes Kunth) and Tucumã (Astrocaryum aculeatum Meyer). These fruits have been high held nutritional, functional and economic potential and contribute to the daily intake of nutrients, energy and bioactive compounds by people living in Amazon rainforest region. Phytochemical compounds with biological properties were detected in these fruits, for instance (but not limited to), annonaceous acetogenins in Biribá, geraniin and corilagin in Rambutan, rutin and catechin in Pupunha, and β-carotene and flavonoids in Tucumã. The biological properties of Biribá, Rambutan, Pupunha and Tucumã have been evaluated by in vitro and in vivo assays, especially antioxidant and antimicrobial activities. Therefore, these Amazonian fruits can be exploited by the food industry as a food and therapeutic plant-material to develop valuable products, such as medicine products and can be used as sources for obtaining compounds for the food, cosmetics and pharmaceutical applications.

Se evaluó la germinación y supervivencia in situ y ex situ de plántulas de Aspidosperma megalocarpon, Eugenia sp., Lonchocarpus castilloi, Manilkara zapota, Ormosia macrocalyx y Rollinia mucosa. En campo se sembraron 2 160 semillas en nueve bloques de 5 m x 20 m distribuidos en bosque tropical, acahual maduro y acahual joven. El experimento se replicó en condiciones de vivero bajo sombra de 40, 60 y 80%. Los tipos de cobertura vegetal no mostraron diferencias significativas en las tasas de germinación y de crecimiento; sin embargo, estos sí influyeron en la capacidad de germinación de A. megalocarpon y O. macrocalyx, y en las tasas de depredación de M. zapota y L. castilloi. En el acahual joven se presentó la mayor depredación de semillas, sin embargo, las plántulas remanentes presentaron mayor supervivencia que en las otras coberturas vegetales. En el vivero no se encontró diferencia en la proporción de semillas germinadas, ni en las tasas de germinación y de crecimiento. R. mucosa, fue la única especie que presentó menor supervivencia (42%). Las condiciones ambientales de las diferentes clases de cobertura vegetal en el área de estudio mantienen condiciones adecuadas para el proceso de germinación, crecimiento y establecimiento de plántulas de las especies estudiadas, lo cual permite sugerir su utilización en la rehabilitación de áreas degradadas del bosque original sembrando de manera directa, siempre y cuando se realice de manera inmediata después de la recolecta. Es necesario continuar con estos estudios para promover el uso de especies nativas en la rehabilitación y restauración de bosques tropicales.

An in situ collection composed of 167 accessions of the species Annona cherimola, A. glabra, A. reticulata, and A. squamosa, Rollinia sp ., and the interspecific hybrid A. squamosa × A. cherimola was established through bioprospecting of genetics resources of the Annonaceae family in the Colombian Andean and Caribbean regions. These accessions were distributed in 13 departments and 48 municipalities. The most representative species of this collection are A. squamosa and A. reticulata , which are derived from traditional cultivars of populated centers with a variable altitude range of up to 1,021 m a.s.l. The morpho-agronomic evaluation was carried out on 98 accessions using 25 qualitative and quantitative descriptors, which identified the phenotypic traits in A. squamosa and A. reticulata that are related to fruit quality , such as size, weight, symmetry, degrees Brix, pH, acidity, seed weight and seed number, which are the more discriminating descriptors, differentiating six clusters in A. squamosa and four clusters in A. reticulata .

Rollinia mucosa fruit has generated great interest due to the presence of bioactive compounds, which exhibit promising biological activities. Fingerprinting analytical techniques, chromatographic-diode array detection (DAD), infrared, mass spectrometric, 1H and 13C nuclear magnetic resonance (NMR) spectra, associated with chemometric analysis and mixture design, were used to determine chemical discriminations of sun-exposed and self-shaded leaves of Rollinia mucosa in each of the four seasons. Sunlit leaves in winter presented higher metabolite signals related to the acetogenins, whereas shaded leaves have higher abundances of carbohydrates and terpenes. Sunlit leaves harvested in the summer had the smallest metabolite abundances. Fingerprints confirmed the presence of two acetogenins, annonacin A and annonastatin. Ternary and quaternary mixtures of the statistical mixture design were most effective for revealing important discriminations.

O biribazeiro (Rollinia mucosa [Jacq.]) é uma frutífera nativa da América Central e América do Sul que se destaca das demais espécies do gênero por apresentar frutos grandes e comestíveis. Tendo em vista que pouco se conhece a respeito da anatomia da planta, tipo de reserva da semente, como também sobre o conteúdo de DNA de espécies da família anonáceas, este trabalho teve por objetivos caracterizar histoquimicamente as sementes e anatomicamente as plântulas, e determinar o conteúdo de DNA de biribazeiro. As plântulas foram obtidas de sementes coletadas na região Amazônica pela Embrapa Roraima e enviadas à Universidade Federal de Lavras. Os frutos foram despolpados, e suas sementes foram previamente lavadas e semeadas em bandejas de 48 células, contendo como substrato pó de serragem, permanecendo em câmara de germinação a 30ºC por 90 dias. Nas plantas obtidas, procedeu-se à análise histoquímica, à caracterização anatômica e à determinação do conteúdo de DNA. As principais conclusões deste trabalho foram que: (1) as sementes da Rollinia mucosa apresentam reserva principal lipídica; (2) as secções transversais da lâmina foliar indicam organização dorsiventral, do tipo hipoestomática com estômatos paracíticos e tricomas em ambas as faces da folha; (3) as folhas de biribazeiro apresentam, em média, 4,77 pg de DNA. The biribazeiro (Rollinia mucosa [Jacq.]) is a native fruit of Central America and South America that stands out from the other species of the genus because it has large and edible fruits. Considering that little is known about the anatomy of the plant, the type of reserve of the seed, as well as little is known about the DNA content of species of Annonaceae family, this study aimed to characterize seeds histochemically and seedlings anatomically, and determine DNA content of biribazeiro (Rollinia mucosa [Jacq.]). The seedlings were obtained from seeds collected in the Amazon region by Embrapa Roraima and then, sent to UFLA, Federal University of Lavras, Minas Gerais State. The pulp of the fruits were extracted and the seeds were previously washed and sown in trays of 48 cells containing sawdust as substrate, remaining in a germination chamber at 30ºC for 90 days. A histochemical analysis, anatomical characterization and determination of DNA content of the plants obtained were made. The main conclusions of this research were: (1) the seeds of Biribazeiro (Rollinia mucosa) present mainly lipid reserve, (2) The cross-sections of the leaf blade indicate dorsiventral organization, hypostomatic with paracitic stomata and trichomes on both sides of the sheet (3) the leaves of biribazeiro have on average 4.77 pg of DNA.

With the objective of stimulating the cultivation and consumption of native Brazilian fruits, the physicochemical composition and antioxidant potential of three native species, namely the araticu-do-mato (Rollinia sylvatica A. St.-Hil.), pindo palm (Butia capitata (Mart.) Becc.) and mandacaru-de-tres-quinas (Cereus hildmannianus K. Schum.) were determined in this study. The pindo palm fruit stood out because of its elevated carotenoid content (39.6 μg/g) and greater antioxidant capacity (26 μM trolox/g of fresh sample) by the ABTS (2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic) method, although by the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, the pindo palm fruit (3847.5 g of fresh sample/g DPPH) and mandacaru-de-tres-quinas fruit (3249.8 g of fresh sample/g DPPH) were considered to have the same antioxidant potential with no difference between them. The mandacaru-de-tres-quinas fruit also showed the highest total phenolic compound content (1337.3 mg/100 g). Although the araticu-do-mato presented the highest vitamin C content (0.32 mg/g), it did not differ statistically from the mandacaru-de-tres-quinas fruit (0.25 mg/g); on the other hand, it was considered to be equal to the pindo palm fruit (0.23 mg/g). The araticu-do-mato also showed the best result for the TSS/TTA (total soluble solids/total titratable acidity) ratio (41.92), thus it was adequate for in natura consumption and for processing as well.

A família Annonaceae possui representantes de distribuição tropical e subtropical, que sintetizam metabólitos bioativos como alcaloides, flavonoides, óleos essenciais, mucilagem e acetogeninas. Estas últimas têm sido investigadas por apresentarem diversas atividades farmacológicas de interesse. Rollinia rugulosa é uma planta arbórea nativa empregada na medicina popular como diurético e anti-infeccioso, enquanto que R. mucosa é uma árvore cultivada no Brasil e utilizada para tratar problemas de garganta. Face à escassez de informações, este trabalho investigou a anatomia foliar e caulinar dessas plantas medicinais, antevendo uma aplicabilidade no controle de qualidade farmacognóstico. Lâminas semipermanentes e permanentes foram preparadas para serem observadas em microscopia de luz. Adicionalmente, foram realizados testes microquímicos e análise ultraestrutural por microscopia eletrônica de varredura. Os caracteres anatômicos de folha e caule das duas espécies são semelhantes. Ambas apresentam folha hipoestomática com estômatos paracíticos, tricomas tectores pluricelulares e mesofilo dorsiventral. A nervura central é côncavo-convexa e atravessada por feixes vasculares colaterais. No caule, ocorrem células pétreas e são observados os mesmos idioblastos presentes na folha, ou seja, cristais de oxalato de cálcio e células contendo mucilagem. Esses caracteres revelam-se de importância diagnóstica para o nível de família e devem ser associados a outros dados morfológicos para permitirem a diferenciação de espécies correlatas.

Three different Myrtaceae species and one species of Annonaceae were analyzed for the fatty acid composition of their seed oil. All species were characterized by high concentrations of unsaturated fatty acids that ranged from 54.61 to 91.65 g/100 g of the total fatty acid content. The main fatty acid presented by Feijoa sellowiana was linoleic acid (84.44 g/100 g). Oleic acid was the main fatty acid found in the seed oil from Myrcianthes pungens and Rollinia sylvatica, whose contents were 57.03 and 54.41 g/100 g, respectively. For Eugenia uniflora oil seed, the main fatty acid detected was palmitic acid (40.07 g/100 g).

In this paper six new Neotropical species in four genera are described, viz. Annona oxapampae, Duguetia vaupesana, Guatteria castilloi, G. pachyphylla, G. sanctae-crucis and Pseudoxandra xylopiifolia. Furthermore additional data on four poorly known species of Guatteria (G. denudata, G. glauca, G. modesta and G. terminalis) are added.

In this paper six new Neotropical species in four genera are described, viz. Annona oxapampae, Duguetia vaupesana, Guatteria castilloi, G. pachyphylla, G. sanctae-crucis and Pseudoxandra xylopiifolia. Furthermore additional data on four poorly known species of Guatteria (G. denudata, G. glauca, G. modesta and G. terminalis) are added.

Se analizó el efecto de hongos micorrizógenos arbusculares (HMA) sobre el crecimiento y la supervivencia de plántulas de una especie dependiente de luz (Piper auritum) y una tolerante a la sombra (Rollinia jimenezii), las cuales fueron trasplantadas a áreas deteri o radas derivadas de una selva tropical húmeda en la región de Los Tuxtlas, Veracruz, México. En invernadero se realizó un experimento considerando tres factores: especie, micorrización (con o sin HMA) y suelo (de selva o de pastizal). Se hizo un análisis clásico de crecimiento para siete vari ables y los análisis de varianza correspondientes mostraron que el factor micorrización produjo diferencias significativas para el peso seco de hojas, la Proporción de Área Foliar (PAF) y la Tasa de Asimilación Neta (TAN); en especial la interacción especie × HMA fue una fuente muy importante de va riación. Después de 120 días, las plántulas fueron transplantadas a dos sitios en un pastizal donde se sembraron al azar de acuerdo con el tratamiento; siete meses después fueron cosechadas. En este segundo experimento, Piper obtuvo las mayores medias y fue diferente significativamente de Rollinia en casi todas las variables de crecimiento , mientras que el factor suelo no generó ninguna diferencia significativa y el factor micorrización sólo produjo dife rencias en tres variables; el nivel sin HMA (M-) produjo los valores mayores en la Tasa Relativa de Crecimiento (TRC) y Área Foliar Específica (AFE), y el nivel con HMA (M+) tuvo el mismo efecto en la TAN. La combinación especie × micorrización fue significativa y la combinación Piper sin micorrizas obtuvo la media con los valores mayores. La triple interacción fue solamente significativa para la TRC, siendo la media menor y diferente para Rollinia con micorrizas en suelo de selva. Sin embargo , la presencia de HMA promovió la supervivencia en campo en las dos especies. El uso de especies pertenecientes a diferentes gremios permite tener mayores posibilidades de éxito en la restauración, ya que tienen respuestas ecofisiológicas diferentes de acuerdo con las condiciones ambientales prevalecientes; el uso de HMA antes del transplante aseguró un mayor crecimiento en Piper pero no en Rollinia, pero la supervivencia en campo fue mayor para ambas con M+; asimismo, en la mayoría de los casos el suelo de selva determinó la mayor respuesta en Rollinia, y el de pastizal en Piper.

Extracts of 32 plants from the Brazilian northeastern semi-arid region called Caatinga were evaluated through DPPH radical scavenging assay, β-carotene bleaching, and brine shrimp lethality tests (BST). Among the extracts studied Byrsonima cf. gardneriana , Mascagnia coriacea , Cordia globosa , Diodia apiculata and Hypenia salzmannii showed the highest activities in DPPH radical scavenging test. In the β-carotene bleaching test the highest activities were observed for Passiflora cincinnata , Chamaecrista repens , B. cf. gardneriana , Rollinia leptopetala , Serjania glabrata , Diospyros gaultheriifolia , C. globosa , Mimosa ophtalmocentra , M. coriacea and Lippia cf. microphylla . In contrast, R. leptopetala , Zornia cf. brasiliensis and Leonotis nepetifolia were the most active species in the BST.

The phytochemical investigation of the stem bark of Annona pickelii yielded four steroids (β-sitostenone, β-sitosterol, stigmasterol and campesterol), three lignans (eudesmin, magnolin and yangambin), twelve alkaloids (liriodenine, lysicamine, atherospermidine, anonaine, analobine, asimilobine, discretamine, stepholidine, coclaurine, orientaline, juziphine and stepharine), and a benzenoid (2-methoxybenzoic acid). These compounds support their recent reclassification from Rollinia to Annona, and that it is a typical species of the family Annonaceae. Significant antifungal and antioxidant activities were found for the methanol crude extract as well as for the lignans eudesmin, magnolin, yangambin and the alkaloid discretamine. In addition, several items of NMR data for the alkaloids were reviewed and unequivocally described in this work.

Species of the Annonaceae family are used in traditional medicine, and several antitumor acetogenins have been isolated from the leaves of Annona muricata and Rollinia mucosa. Leaves samples (self-shaded and sun-exposed) of these species were collected during winter and summer seasons. Extraction media were prepared from mixtures of five solvents according to a simplex centroid design. Plant extracts were analysed by injection into a high-performance liquid chromatography with diode array detection (HPLC-DAD) and evaluated after applying by multivariate curve resolution-alternating least-squares (MCR-ALS) and discriminant-unfolded partial least-squares (D-UPLS). The objective was to check whether the chemometric resolution of chromatographic profiles could help in the discrimination of samples according to taxonomic classification, sun exposition and/or harvest season. The results indicate that extraction media containing ethanol as main solvent achieved discrimination of self-shaded versus sun-exposed plants and harvest season of Annona muricata. Also, D-UPLS analysis allowed taxonomic discrimination between Annona muricata and Rollinia mucosa extract samples.

An enantioselective total synthesis of the proposed structure of mucoxin (1) is described. Mucoxin, an annonaceous acetogenin isolated from bioactive leaf extracts of Rollinia mucosa, is the first acetogenin containing a hydroxylated trisubstituted tetrahydrofuran (THF) ring. This natural product is a highly potent and specific antitumor agent against MCF-7 (breast carcinoma) cell lines (ED50 = 3.7 x 10(-3) microg/mL compared to adriamycin, ED50 = 1.0 x 10(-2) microg/mL). The total synthesis described herein features two regio- and stereoselective THF ring-forming reactions. The 2,3,5-trisubstituted THF portion (C13-C17) was accessed using a highly regioselective cyclization of a methylene-interrupted epoxydiol, and the 2,5-disubstituted THF ring (C8-C12) was conveniently assembled via a 1,2-n-triol cyclization strategy. The spectral data of the synthetic material and two of its diastereomers did not match the reported data for the natural product. On the basis of detailed spectroscopic analysis of the synthesized molecule, we reason that the spectral discrepancies are due to stereochemical misassignment of the natural product.

RESUMO São apresentadas as espécies de Annonaceae da Reserva Biológica da Represa do Grama. A Reserva está localizada em Descoberto, Minas Gerais, e abrange uma área de 263,8 hectares de floresta estacional semidecidual. São encontrados cinco gêneros e sete espécies: Annona cacans, Guatteria nigrescens, G. sellowiana, Rollinia dolabripetala, Unonopsis bauxitae, Xylopia brasiliensis, X. sericea e a nova espécie Unonopsis bauxitae, aqui descrita. São apresentadas chave de identificação das espécies, descrições, ilustrações, e informações sobre floração, frutificação, distribuição geográfica e hábitats.

From the EtOH extract of the leaves of Rollinia laurifolia Schl. (Annonaceae), a novel acetogenin, rolifolin (= 3-(9-{(2R*,5S*)-5-[(1S*,4S*)-1,4-dihydroxy-4-{(2S*,5R*)-5-[(1S*)-1-hydroxyundecyl]tetrahydrofuran-2-yl}butyl]tetrahydrofuran-2-yl}-2,3-dihydroxynonyl)-5-methylfuran-2(5H)-one; 1) was isolated, together with the known acetogenin annonin-I (2). Also, from the corresponding hexane extract, a mixture of rolilaurin (3, a novel compound), uvariamicin-I (4), and uvariamicin-II (5) was obtained. The structures of compounds 1–5 were elucidated by NMR and MS analysis, and relative configurations were established. Compounds 2 and 5 have never been obtained before from Rollinia.

The male and female of Pseudotectococcus rolliniae Hodgson & Goncalves 2004 induce leaf galls on Rollinia laurifolia Schltdl. The galls occur in similar proportions but are morphologically distinct. This study recorded the occurrence and characterized both morphologically and morphometrically the galls on R. laurifolia. In addition, we evaluated the impact of galls induced by P. rolliniae males and females on the differentiation of the host plant leaf tissues. Galls induced by females were spherical, with an average volume of 36.5 mm1(± 16.9), whereas galls induced by males were conical with an average volume of 3.5 mm3 (± 2.6). Most of the sampled leaves were galled (93.8%). The presence of more than 5 galls per leaf caused the leaf area to be reduced on average by 57.3% compared with ungalled leaves. Leaves with the majority of galls induced by females had a greater area reduction than leaves with the majority of galls induced by males. The reduction of leaf area was directly related to the translocatio...

Este trabalho é parte integrante do Projeto Flora Paraibana e teve como objetivo realizar o tratamento taxonômico da família Annonaceae para o Estado. Para sua elaboração foram realizadas coletas em diversos municípios do Estado, além do levantamento das exsicatas depositadas nos herbários JPB, EAN e IPA. A identificação do material foi feita com o auxílio de chaves analíticas, bibliografia especializada e fototipos. As descrições e as ilustrações foram elaboradas com base nas observações de material herborizado e/ou plantas vivas. Foram registrados para a Paraíba seis gêneros, compreendendo 15 espécies: Anaxagorea (1), Annona (6), Duguetia (2), Guatteria (2), Rollinia (2) e Xylopia (2), sendo 11 delas novas referências para o Estado.

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:47:30Z No. of bitstreams: 1 S0100-29452003000200026.pdf: 1020870 bytes, checksum: 56b07d58c26f5c40fc320022590eb733 (MD5) Made available in DSpace on 2013-08-22T18:47:30Z (GMT). No. of bitstreams: 1 S0100-29452003000200026.pdf: 1020870 bytes, checksum: 56b07d58c26f5c40fc320022590eb733 (MD5) Previous issue date: 2003-08-01 Made available in DSpace on 2013-09-30T17:58:19Z (GMT). No. of bitstreams: 2 S0100-29452003000200026.pdf: 1020870 bytes, checksum: 56b07d58c26f5c40fc320022590eb733 (MD5) S0100-29452003000200026.pdf.txt: 20721 bytes, checksum: 6bc32862bd480dbf5930e9eac835f1fc (MD5) Previous issue date: 2003-08-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T13:16:54Z No. of bitstreams: 2 S0100-29452003000200026.pdf: 1020870 bytes, checksum: 56b07d58c26f5c40fc320022590eb733 (MD5) S0100-29452003000200026.pdf.txt: 20721 bytes, checksum: 6bc32862bd480dbf5930e9eac835f1fc (MD5) Made available in DSpace on 2014-05-20T13:16:54Z (GMT). No. of bitstreams: 2 S0100-29452003000200026.pdf: 1020870 bytes, checksum: 56b07d58c26f5c40fc320022590eb733 (MD5) S0100-29452003000200026.pdf.txt: 20721 bytes, checksum: 6bc32862bd480dbf5930e9eac835f1fc (MD5) Previous issue date: 2003-08-01 O trabalho objetivou o estudo da capacidade de enraizamento de quatro espécies de Annonaceae potenciais como porta-enxertos (Annona glabra L., Annona montana Macfad, Rollinia emarginata e Rollinia mucosa Baill.) em três épocas do ano (verão, outono e inverno). Experimento conduzido em câmara de nebulização intermitente pertencente à UNESP/FCAV (21º15'22S e 48º18'58W), utilizando-se de estacas apicais enfolhadas em tratamento rápido (5 segundos) com ácido indolbutírico (IBA) (0; 1000; 3000; 5000 e 7000 mg.L-1), em esquema fatorial. Após 90 dias, avaliaram-se a porcentagem de estacas enraizadas, sobrevivência, comprimento e número de raízes. Como resultados, o IBA não incrementou a capacidade de enraizamento das espécies. A época do ano foi grande influente no sucesso de enraizamento, sendo o verão mais adequado. A. glabra e A. montana mostraram-se promissoras na propagação vegetativa via estaquia (clonagem). R. emarginata apresentou baixos valores para as características avaliadas, devendo ser intensificados experimentos na promoção do enraizamento em relação aos atuais valores obtidos. R. mucosa não apresentou resultados satisfatórios, ocorrendo necrose de tecido na base das estacas, devendo as causas serem melhor investigadas. O sucesso no enraizamento de Annonaceae é dependente da espécie, tendo aquelas do gênero Annona apresentado resultados superiores em relação às do gênero Rollinia. This work aimed to study the rooting capacity of four rootstocks (Annona glabra L., Annona montana Macfad, Rollinia emarginata and Rollinia mucosa Baill.) for Annonaceae species. The experiment was carried out at UNESP/FCAV (21º15'22S and 48º18'58W). Apical leafy cuttings were treated (5 seconds) with different concentrations of indolbutiric acid (IBA) (0, 1000, 3000, 5000 and 7000 mg.L-1). After the treatment, the cuttings were placed in drilled box supplied with vermiculite under intermitent mist inside a lathhouse. It was used experimental design completely randomized in factorial scheme. After 90 days the evaluations were made for: percentage of rooted and survived cuttings, number and length of roots. The IBA did not increase the rooting in the species. A. glabra and A. montana showed to be promising to cutting in summer. R. emarginata presented low values for all the evaluated characteristics and experiments must be intensified to promote the rooting. R. mucosa did not present satisfactory results, and the causes must be investigated better. For all the evaluated characteristics, the Annona species presented better values in relation to Rollinia. UNESP FCAV Dep. Produção Vegetal UNESP FCAV Dep. Produção Vegetal

Phytochemical investigation of hexanic extract of leaves of Rollinia laurifolia afforded three known acetogenins, uvariamicin-I (1), solamin(2) and gonionenin(3), for the first time isolated from Rollinia genus. The structures of 1, 2 and 3 were elucidated by spectroscopic methods.

Crude seed extract of three tropical fruits belonging to the family Annonaceae, viz., sweetsop ( Annona squamosa L.), soursop ( A. muricata L.) and biriba ( Rollinia mucosa Baill.) were investigated for their repellent effects on the Asian subterranean termite Coptotermes gestroi Wasmann (Isoptera: Rhinotermitidae ). Results of laboratory feeding bioassay (choice and no-choice) indicated that crude extract of A. squamosa, A. muricata and R. mucosa had feeding deterrent effects on C. gestroi . Termites showed significant avoidance behavior to filter paper treated with extracts of the three Annona species investigated. Soil barrier test revealed that Annona extracts were able to limit penetration of C. gestroi in laboratory tunneling test. The results suggest that Annona seed extracts may offer an alternative source of natural insecticide against subterranean termites.

Annonaceae is an ancient family of plants including approximately 50 genera growing worldwide in a quite restricted area with specific agroclimatic requirements. Only few species of this family has been cultivated and exploited commercially and most of them belonging to the genus Annona such as A. muricata, A. squamosa, the hybrid A. cherimola x A. squamosa and specially Annona cherimola: the cherimoya, commercially cultivated in Spain, Chile, California, Florida, México, Australia, Ecuador, Peru, Brazil, New Zealand and several countries in South and Central America. The cherimoya shows a high degree of heterozygosis, and to obtain homogeneous and productive orchards it is necessary to avoid the propagation by seeds of this species. Additionally, the traditional methods of vegetative propagation were inefficient and inadequate, due to the low morphogenetic potential of this species, and the low rooting rate. The in vitro tissue culture methods of micropropagation can be applied successfully to cherimoya and other Annona sp to overcome these problems. Most of the protocols of micropropagation and regeneration were developed using the cultivar Fino de Jete, which is the major cultivar in Spain. First it is developed the method to micropropagate the juvenile material of cherimoya (ENCINA et al., 1994), and later it was optimized a protocol to micropropagate adult cherimoya genotypes selected by outstanding agronomical traits (PADILLA and ENCINA, 2004) and further it was improved the process through micrografting (PADILLA and ENCINA, 2011).At the present time we are involved in inducing and obtaining new elite genotypes, as part of a breeding program for the cherimoya and other Annonas, using and optimizing different methodologies in vitro: a) Adventitious organogenesis and regeneration from cellular cultures (ENCINA, 2004), b) Ploidy manipulation of the cherimoya, to obtain haploid, tetraploid and triploid plants (seedless), c) Genetic transformation, for the genes introduction to control the postharvest processes and the genes introduction to provide resistance to pathogen and insects and d) Micropropagation and regeneration of other wild Annona or related Annonaceae species such as: Annona senegalensis, A. scleroderma, A. montana, A. reticulata, A. glabra, A. diversifolia and Rollinia sp. Annonaceae é uma antiga família de plantas, incluindo cerca de 50 gêneros com crescimento em todo o mundo em uma área bastante restrita, com requisitos agroclimáticos específicos. Poucas espécies desta família tem sido cultivadas e exploradas comercialmente e a maioria delas pertencem ao gênero Annona, tais como A. muricata, A. squamosa, o híbrido A. cherimola x A. squamosa e especialmente a A. cherimola: a cherimóia, cultivada comercialmente na Espanha, Chile, Califórnia, Flórida, México, Austrália, Equador, Peru, Brasil, Nova Zelândia e vários países da América do Sul e Central.O cherimoia mostra um elevado grau de heterozigoze e a obtenção de pomares produtivos e homogêneos é necessário para evitar a propagação de sementes desta espécie. Além disso, os métodos tradicionais de propagação vegetativa foram ineficientes e inadequados, devido ao baixo potencial morfogenético e à sua baixa taxa de enraizamento. Os métodos de cultura de tecidos in vitro (micropropagação) podem ser aplicados com êxito para cherimoia o outras Annona sp. a fim de superar estes problemas. A maioria dos protocolos de micropropagação e regeneração foram desenvolvidos utilizando o cultivar 'Fino de Jete', que é o principal cultivar na Espanha.Primeiramente nós desenvolvemos o método de micropropagação do material juvenil de graviola (ENCINA et al., 1994), e mais tarde otimizamos este protocolo para micropropagação de genótipos de cherimoia em fase adulta, selecionando-os por características agronômicas (PADILLA; ENCINA, 2004) e ainda melhorou-se o processo através da microenxertia (PADILLA; ENCINA, 2011).Atualmente, estamos envolvidos na indução e obtenção de novos genótipos de elevada qualidade, como parte de um programa de melhoramento genético para a cherimóia e outras anonáceas, utilizando e otimizando diferentes metodologias in vitro: a) organogênese adventícia e regeneração de culturas celulares (ENCINA, 2004), b) Manipulação 'ploidia' da cherimoia, para obter plantas haplóides, tetraplóides, triplóides (sem sementes), c) transformação genética com introdução de genes objetivando controlar os processos de pós-colheita e para fornecer resistência à patógenos e insetos, d) micropropagação e regeneração de outras espécies selvagens do gênero Annona ou da família Annonaceae, tais como: A. senegalensis, A. esclerodermia, A. montana, A. reticulata, A. glabra, A. diversifolia e Rollinia sp..

Bioassay-directed fractionation of the stems of Rollinia mucosa led to the isolation of new N-methoxycarbonyl aporphine alkaloids, romucosine A (1), romucosine B (2), romucosine C (3), and romucosine D (4), along with the known alkaloid, N-methoxylcarbonyl-nornuciferine (5). Alkaloids 1 and 4 exhibited significant inhibition of collagen, arachidonic acid, and platelet activating factor-induced platelet aggregation, and alkaloid 3 also showed an inhibitory effect on arachidonic acid induced platelet aggregation.

The chemical composition of the essential oil of Rollinia sericea (R.E.Fr.) R.E.Fr. leaves was determined by GC and GC/MS analysis. The analysis revealed the presence mainly of sesquiterpenes: β-elemene (10%), β-caryophyllene (10.0%), bicyclogermacrene (9.1%), germacrene-D (8.2%), bicycloelemene (6.2%) and (Z)-nerolidol (5.3%). Rollinia sericea oil was able to inhibit the growth of both fungi Aspergillus niger (16404) and Candida albicans (ATCC 10231) as well as the Gram-positive bacterium Staphyloccocus aureus (ATCC 6538) but it was inactive against the Gramnegative bacteria Escherichia coli (ATCC 8739) and Pseudomonas aeruginosa (ATCC 9027).

Four new compounds, a mixture of 20,23-cis-2,4-trans-bullatalicinone (1) and 20,23-cis-2,4-cis-bullatalicinone (2), rollimusin (3), and rolliacocin (4), along with eight known acetogenins, were isolated from an ethyl acetate extract of the unripe fruits of Rollinia mucosa. The structures and stereochemistry of 1-4 were determined on the basis of spectral data and chemical evidence.

Bioactivity-directed fractionation of a CHCl(3)-MeOH (1:1) extract prepared from the seeds of Rollinia mucosa led to the isolation of a mixture of eight novel tryptamine amides. Extensive HPLC allowed the isolation of the major component of the mixture, which was characterized as N-lignoceroyltryptamine (6) using a combination of spectroscopic and chemical methods. The minor amides were identified by GC-MS analysis as N-palmitoyltryptamine (1), N-stearoyltryptamine (2), N-arachidoyltryptamine (3), N-behenoyltryptamine (4), N-tricosanoyltryptamine (5), N-pentacosanoyltryptamine (7), and N-cerotoyltryptamine (8). Two lignans (pinoresinol dimethyl ether and magnolin) and six acetogenins [membranacin (9), desacetyluvaricin (10), rolliniastatin 1, bullatacin, squamocin, and motrilin] were also isolated. The cytotoxicity of membranacin (9) and desacetyluvaricin (10) against six human solid tumor cell lines was determined. The absolute configuration of the former is reported.

Rollinia mucosa produces furofuranic lignans (magnolin, epiyangambin, yangambin) that are antagonists of platelet-activating factor (PAF). The biosynthetic capacity and the potential for the accumulation of furofuranic lignans, including epieudesmin, of the plants cultured both in vivo and in vitro conditions were evaluated. The production and the pattern of lignans accumulated were dependent on the origin of the plant material and the plant organ. The major accumulation of lignans was observed in leaves. In the mature leaves of in vivo grown seedlings magnolin and yangambin predominated, in contrast to leaves from in vitro propagated plants that presented epiyangambin as the major lignan.

[structure: see text] An efficient total synthesis of the annonaceous acetogenin jimenezin was achieved. The key steps used were a highly stereoselective intramolecular allylboration to establish the tetrahydropyran ring and an intramolecular Williamson reaction to close the tetrahydrofuran ring.