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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.

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.

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.

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.

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.

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.

Reversed-phase high-performance liquid chromatography (RP-HPLC) fractionation, monitored by liquid chromatography/electrospray mass spectrometry (LC/ESI-MS), led to the isolation of two new bioactive annonaceous acetogenins, rollidecin C (1) and rollidecin D (2), from the bioactive aqueous methanol fraction of the leaves of Rollinia mucosa (Annonaceae). The structures were confirmed by analyses of the 1H and 13C NMR data. In addition, a known adjacent bis-tetrahydrofuran (THF) acetogenin, desacetyluvaricin (3), was isolated from this plant for the first time utilizing the LC/ESI-MS monitoring approach. Compound 1 exhibited selective cytotoxicity toward the colon tumor cell line (HT-29), while 2 showed only borderline cytotoxicity in a panel of six human tumor cell lines.

A novel application of Mosher's method to epimeric carbinols is described and demonstrated in eight known Annonaceous acetogenins. The procedure requires the preparation and analysis of either the R or S Mosher esters. As an example, the absolute stereochemistries of 12-hydroxy-bullatacins A and B, two new epimeric acetogenins from Rollinia mucosa, were determined by this new procedure.

The activities of 44 Annonaceous acetogenins, which were originally isolated by monitoring plant fractionations with the brine shrimp lethality test (BST), were evaluated in the yellow fever mosquito larvae microtiter plate (YFM) assay. The results clearly demonstrate that most acetogenins have pesticidal properties. The structure–activity relationships indicate that the compounds bearing adjacent bis-THF (tetrahydrofuran) rings with three hydroxyl groups are the most potent. Bullatacin (1) and trilobin (7) gave the best activities against YFM with LC50 values of 0·10 and 0·67 mg litre-1, respectively. Compounds showing LC50 values below 1·0 mg litre-1 in this assay are usually considered significant as new lead candidates for pesticidal development. In the BST, the corresponding LC50 values were 1·6×10-3 (1) and 9·7×10-3 (7) mg litre-1. This is the first report of pesticidal structure–activity relationships for a series of Annonaceous acetogenins which are known to act, at least in part, as potent inhibitors of mitochondrial NADH: ubiquinone oxidoreductase.

From the methanol seed extract of Rollinia occidentalis five acetogenins were isolated, sylvaticin (1), rolliniastatin-1 (2), rolliniastatin-2 (3), motrilin (4) and desacetyluvaricin (5), and evaluated for their toxicity and nutritional alterations on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). All but one of the compounds produced more than 90% mortality on early larval instars at 50 and 100 microg per g of diet. Sylvaticin caused 15 and 60% mortality at 50 and 100 microg/g, respectively, while the methanol seed extract reached 35 and 50% at 100 and 250 microg/g, respectively. The addition of R. occidentalis methanolic seed extract (100 and 250 microg/g) and sylvaticin (100 microg/g) to the larval diet brought about significant changes to the nutritional indices in connection with larvae fed the control diet. This is the first report on the isolation of acetogenins from R. occidentalis and their insecticidal effects on S. frugiperda.

Using a high throughput colorimetric bioassay three aporphine alkaloids, annonaine, nornuciferine and roemerine, were isolated and identified as the CD45 protein tyrosine phosphatase inhibitor metabolites of Rollinia ulei . The nor-aporphine alkaloids, anonaine ( 1 ) and nornuciferine ( 3 ), exhibited more potent inhibitory activity than that of the N-methylated alkaloid roemerin ( 2 ).

This chapter on soursop (Annona muricata) and Rollinia (R. mucosa) provides information on taxonomy, areas of origin and distribution, environmental requirements for cultivation (soil physical and chemical properties, rainfall, air temperature, light and photoperiod, and wind), morphology (flowers, stems and fruits), development (flowering, pollination, fruit set, and fruit growth and ripening), cytology (chromosome number) and genetic improvement, cultivar development, propagation (through seeds and clonal propagation), cultural practices (field preparation, transplanting and spacing, irrigation, pruning, and fertilizer application), bacterial and fungal disease management (mainly through cultural control), insect pest management (through chemical and biological control), weed management (through chemical, physical and cultural control), harvesting and postharvest handling, and utilization and processing.

The acetogenins are strongly bioactive natural compounds present in the bark, roots, leaves, and seeds of manyAnnonaceae plants. They are modified fatty acids and their cytotoxicities have been determined for different biological models including the in vitro growth inhibition of several human cancer cell lines.

Organic anion-transporting polypeptides 1B1 and 1B3 (OATP1B1 and OATP1B3) are liver-specific transporters that mediate the uptake of a broad range of drugs into hepatocytes, including statins, antibiotics, and many anticancer drugs. Compounds that alter transport by one or both of these OATPs could potentially be used to target drugs to hepatocytes or improve the bioavailability of drugs that are cleared by the liver. In this study, we applied a bioassay-guided isolation approach to identify such compounds from the organic extract of Rollinia emarginata Schlecht (Annonaceae). Fractions of the plant extract were screened for effects on OATP1B1- and OATP1B3-mediated transport of the model substrates estradiol-17β-glucuronide and estrone-3-sulfate. We isolated three compounds, ursolic acid, oleanolic acid, and 8-trans-p-coumaroyloxy-α-terpineol, which inhibited estradiol-17β-glucuronide uptake by OATP1B1 but not OATP1B3. In addition, a rare compound, quercetin 3-O-α-l-arabinopyranosyl(1→2) α-L-rhamnopyranoside, was identified that had distinct effects on each OATP. OATP1B1 was strongly inhibited, as was OATP1B3-mediated transport of estradiol-17β-glucuronide. However, OATP1B3-mediated uptake of estrone-3-sulfate was stimulated 4- to 5-fold. Kinetic analysis of this stimulation revealed that the apparent affinity for estrone-3-sulfate was increased (decreased K(m)), whereas the maximal rate of transport (V(max)) was significantly reduced. These results demonstrate a mechanism through which the hepatic uptake of drug OATP substrates could be stimulated.

Tetrahydrojatrorrhizine, discretamine, anonaine and roemerine were isolated from the roots of Rollinia leptopetala R. E. Fries. They were identified and characterized by nuclear magnetic resonance spectroscopy ( 1 H and 13 C) with the aid of two–dimensional techniques ( 1 H- 1 H COSY, HETCOR, HMQC and HMBC). With the exception of tetrahydrojatrorrhizine, the presence of these alkaloids in R. leptopetala has not been reported previously.

The fractionation of the cytotoxic MeOH extract of the seeds of Rollinia membranarea (Annonaceae) led to the isolation of two new adjacent bis-tetrahydrofuran acetogenins, rioclarin [1] and membranacin [2], and two other known acetogenins, squamocin [3] and rolliniastarin 1 [4]. In addition to these bioactive acetogenins, a new furofuranic lignan (membrin [5]) and a known one (magnolin [6]), have been obtained. Rioclarin [1] is an original terrahydroxylared bis-tetrahydrofuran acetogenin. Its structure was established on the basis of ms and 1D and 2D nmr experiments

Rollipyrrole 1 , a novel pyrromethenone derivative was isolated from the leaves of Rollinia mucosa in the continuing research into Formosan annonaceous plants. This type of compound was isolated from plants for the first time and the structure of 1 was elucidated mainly on the basis of 1D and 2D NMR spectroscopic data.

This study evaluated possible CNS effects of a hexane extract of leaves from Rollinia mucosa (Jacq.) Baill. (Annonaceae). This plant extract induced anxiolytic-like actions similar to those induced by diazepam in the avoidance exploratory behavior paradigm. Its significant activity was shown at doses from 1.62 to 6.25 mg/kg. It also enhanced pentobarbital-induced hypnosis time, and at high doses produced motor coordination impairment. The benzodiazepine (BDZ) receptor binding, evaluated by in vitro autoradiography following a single administration of R. mucosa, revealed that this plant extract reduced BDZ binding in the hippocampus (29%), amygdala (26%), and temporal cortex of mice (36%). In conclusion, the present findings support the proposal that R. mucosa may induce central nervous system (CNS) depressant effects, presumably through an interaction with the GABA/benzodiazepine receptor complex.

Rollipyrrole 1 , a novel pyrromethenone derivative was isolated from the leaves of Rollinia mucosa in the continuing research into Formosan annonaceous plants. This type of compound was isolated from plants for the first time and the structure of 1 was elucidated mainly on the basis of 1D and 2D NMR spectroscopic data.

Laurifolin ( 1 ), a novel mono-tetrahydrofuran acetogenin, has been isolated from Rollinia laurifolia leaves. The structure of 1 was elucidated by spectroscopic methods.

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.

Sylvaticin (I), a new tetrahydroxy annonaceous acetogenin with nonadjacent tetrahydrofuran rings, has been isolated from the dried fruits of Rollinia sylvatica St. Hil. (Annonaceae). This compound is extremely cytotoxic to human tumor cells and shows promising insect control properties.

The Annonaceous acetogenins are a series of apparently polyketide-derived fatty acid derivatives that possess tetrahydrofuran rings and a methylated gamma-lactone (sometimes rearranged to a methyl ketolactone) with various hydroxyl, acetoxyl, and/or ketoxyl groups along the hydrocarbon chain. They exhibit a broad range of potent biological activities (cytotoxicity, antitumor, antimalarial, antimicrobial, immunosuppressant, antifeedant, and pesticidal). The sources, isolation, chemistry, biogenesis, and biological actions of these compounds, published to date, are tabulated and discussed. Strategies for structural elucidation are reviewed, and structural revisions and refinements are suggested for some of the previously published compounds.

A new cytotoxic acetogenin, jimenezin (1), containing a hydroxylated tetrahydropyran ring along with an adjacent tetrahydrofuran ring and representing a novel carbon skeleton, was isolated from the seeds of Rollinia mucosa. The structure was elucidated by means of chemical and spectral methods including MS and NMR measurements. Compound 1 exhibited potent cytotoxic activity against six human solid tumor cell lines.

[structure: see text] The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.

Chromatography of an ethyl acetate extract of the fruits of Rollinia mucosa led to the isolation of two new γ-lactone acetogenins, epomusenins A and B, which are the first examples of the rare C37-type annonaceous acetogenins having an epoxide and a double bond along the aliphatic chain in place of the usual tetrahydrofuran moeity. The three known acetogenins, rolliniastatin-1, rolliniastatin-2 and squamocin were also isolated. The structures were established by means of one and two dimensional NMR experiments.