In Vitro Biological Screening Of The Anticholinesterase And Antiproliferative Activities Of Medicinal Plants Belonging To Annonaceae.

The aim of this research was to investigate the antiproliferative and anticholinesterase activities of 11 extracts from 5 Annonaceae species in vitro. Antiproliferative activity was assessed using 10 human cancer cell lines. Thin-layer chromatography and a microplate assay were used to screen the extracts for acetylcholinesterase (AchE) inhibitors using Ellman's reagent. The chemical compositions of the active extracts were investigated using high performance liquid chromatography. Eleven extracts obtained from five Annonaceae plant species were active and were particularly effective against the UA251, NCI-470 lung, HT-29, NCI/ADR, and K-562 cell lines with growth inhibition (GI50) values of 0.04-0.06, 0.02-0.50, 0.01-0.12, 0.10-0.27, and 0.02-0.04 µg/mL, respectively. In addition, the Annona crassiflora and A. coriacea seed extracts were the most active among the tested extracts and the most effective against the tumor cell lines, with GI50 values below 8.90 µg/mL. The A. cacans extract displayed the lowest activity. Based on the microplate assay, the percent AchE inhibition of the extracts ranged from 12 to 52%, and the A. coriacea seed extract resulted in the greatest inhibition (52%). Caffeic acid, sinapic acid, and rutin were present at higher concentrations in the A. crassiflora seed samples. The A. coriacea seeds contained ferulic and sinapic acid. Overall, the results indicated that A. crassiflora and A. coriacea extracts have antiproliferative and anticholinesterase properties, which opens up new possibilities for alternative pharmacotherapy drugs.

Ent-kaurane diterpenoids and other constituents from the stem of Xylopia laevigata (Annonaceae)

Phytochemical investigation of the hexane extract from the stem of Xylopia laevigata led to the isolation of the ent-kaurane diterpenoids, ent-kaur-16-en-19-oic acid, 4-epi-kaurenic acid, ent-16β-hydroxy-17-acetoxy-kauran-19-al, ent-3β-hydroxy-kaur-16-en-19-oic acid, and ent-16β,17-dihydroxy-kauran-19-oic acid, as well as spathulenol and a mixture of β-sitosterol, stigmasterol and campesterol. The identification of the compounds was performed on the basis of spectrometric methods including GC-MS, IR, and 1D and 2D NMR. Potent larvicidal activity against Aedes aegypti larvae with LC50 of 62.7 µg mL-1 was found for ent-3β-hydroxy-kaur-16-en-19-oic acid. This compound also showed significant antifungal activity against Candida glabrata and Candida dubliniensis with MIC values of 62.5 µg mL-1.

Florivory and sex ratio in Annona dioica St. Hil. (Annonaceae) in the Pantanal at Nhecolândia, southwestern Brazil

Annona dioica St. Hil. is a species that grows to approximately 2 m tall and is very widespread in the cerrados. Individual plants of this androdioecious species produce numerous hermaphroditic or male flowers, but few fruits. The aim of this study was to determine the sex ratio among the plants and to compare the frequency of herbivory between male and hermaphroditic flowers. The fieldwork was done by studying flowering plants in grasslands used as pasture for cattle at Fazenda Nhumirim. One hundred and forty-seven male plants and 71 hermaphroditic plants were examined and produced a total of 194 and 94 flowers, respectively, during the study period. The male:hermaphrodite sex ratio was 2.07:1, and was similar to the male:hermaphrodite flower ratio of 2.06:1. The frequency of florivory rate in hermaphrodites was significantly higher than in male flowers (33.0%, n = 31, and 25.7%, n = 50, respectively; G = 14.83; d.f. = 1; p < 0.001). The mean fresh weights of male and hermaphroditic flowers were significantly different (8.38 ± 2.40 g vs. 6.93 ± 2.68 g, respectively; 0 ± SEM; n = 50 each; t = 2.479; d.f. = 49; p = 0.017). These results indicate that the low fruit set in this species can be explained by the sex ratio, the greater herbivory of hermaphroditic flowers and the probable absence of pollinators.

Use of growth regulators to overcome seed dormancy in Xylopia aromatica (Annonaceae)

Xylopia aromatica is a species of the Annonaceae family, native to the Brazilian ""Cerrado"". Seeds of this species usually possess morphophysiological dormancy which makes propagation more difficult. The objective of the present study was to evaluate the efficiency of removing the aril and sarcotesta and applying plant growth regulators to overcome dormancy in X. aromatica seeds. Seeds were separated into two groups: one consisting of seeds with aril and sarcotesta and another without these two seed coat appendices. Seeds with and without these appendices were soaked for 48 hours in distilled water or Promalin (R) (gibberellin 4 [GA(4)] + gibberellin 7 [GA(7)] and cytokinin [6-Benziladenine]) solutions of 250, 500 and 1,000 mg.L(-1), and sown in ""Cerrado"" soil. Later, seeds without the aril and sarcotesta were soaked for 48 hours in distilled water. Promalin (R) or GA(4) + GA(7) solutions at same concentrations and sown in sand or ""Cerrado"" soil. The removal of the aril and sarcotesta had a positive effect on the seed germination. Application of plant growth regulators helped to overcome dormancy in X. aromatica, with the greatest percentage of seedling emergence being observed in seeds treated with Promalin at 250 and 500 mg.L(-1) then sown in sand.

In vitro antifungal activity of fatty acid methyl esters of the seeds of Annona cornifolia A.St.-Hil. (Annonaceae) against pathogenic fungus Paracoccidioides brasiliensis

INTRODUCTION: Fatty acids are abundant in vegetable oils. They are known to have antibacterial and antifungal properties. METHODS: Antifungal susceptibility was evaluated by broth microdilution assay following CLSI (formerly the NCCLS) guidelines against 16 fungal strains of clinical interest. RESULTS: In this work, fatty acid methyl esters (FAME) was able to inhibit 12 clinical strains of the pathogenic fungus Paracoccidioides brasiliensis and were also active in the bioautographic assay against Cladosporium sphaerospermum. CONCLUSIONS: FAME was a more potent antifungal than trimethoprim-sulfamethoxazole against P. brasiliensis under the experimental conditions tested.

A polinização e sua relação com a termogênese em espécies de Arecaceae e Annonaceae da Amazônia Central

O presente estudo compara a biologia floral e polinização de espécies de palmeiras e anonáceas que apresentam termogênese. Nos arredores de Manaus (AM) foram estudadas onze espécies de palmeiras pertencentes aos gêneros Astrocaryum, Attalea, Bactris e Oenocarpus e nove espécies de anonáceas dos gêneros Anaxagorea, Duguetia e Xylopia. As palmeiras que apresentam termogênese são monóicas e a antese das inflorescências ocorre em períodos que variam de dois dias até cinco semanas, sempre no período noturno. As flores das espécies de anonáceas são protogínicas com a antese ocorrendo entre dois dias, podendo ser diurna ou noturna. Nos representantes das duas famílias os insetos visitantes são atraídos pelo odor emitido pelas flores que é intensificado através da termogênese. Os odores podem ser agradáveis semelhante ao de frutos maduros ou desagradáveis e pungentes. Os insetos visitantes em sua maioria são coleópteros das famílias Scarabaeidae, Nitidulidae, Staphylinidae, Curculionidae e Chrysomelidae, trips e moscas Drosophilidae. Além desses, as flores das palmeiras são visitadas por abelhas, vespas, formigas e moscas. Na área estudada, a polinização por coleópteros foi o modo mais freqüente das espécies de palmeiras e anonáceas com termogênese. É notável que algumas espécies das duas famílias são visitadas pelas mesmas famílias, e inclusive espécies de coleópteros. Supõe-se que adaptações morfológicas e fisiológicas similares na biologia floral das duas famílias, inclusive dos componentes odoríferos sejam responsáveis por essa atração.

Insetos associados á gravioleira (Annona muricata L., Annonaceae) na região de Manaus, Amazonas, Brasil

Os insetos da graviola (Annonaceae: Annona muricata L.) foram estudados na região de Manaus, Amazonas, Brasil. Encontram-se 37 espécies, entre os quais, seis foram consideradas prejudiciais, quatro atacando o fruto (Bephratelloides pomorum F. (Eurytomidae), Cerconota anonella Sepp (Stenomatidae), Membracis suctifructus Boulard & Couturier (Membracidae) e Pinnaspis aspidistrae Signoret (Diaspididae); duas nas folhas jovens; (Aphis spiraecola Patch e A. gossypii Glover (Aphididae); e uma perfurando tronco e ramos, Cratosomus bombina (Curculionidae). Trinta e quatro espécies são registradas pela primeira vez.

Estudos florísticos no município de Presidente Figueiredo, Amazonas. Brasil: I. famílias Annonaceae e Gnetaceae

O Município de Presidente Figueiredo, no Estado do Amazonas, foi visitado durante três anos consecutivos, de 1996 a 1999, com o objetivo de se obter amostras botânicas da área, para estudos no Subprojeto "Elaboração de Revisões e Monografias Taxonômicas" com a finalidade de se elaborar uma Flórula para o Município. As coleções feitas neste período encontram-se depositadas no acervo do Herbário do INPA e as informações gerais sobre os taxa aqui estudados foram complementadas com as obtidas das coleções feitas anteriormente por outros pesquisadores. Para a família Annonaceae Juss. (Magnoliopsida) foram identificadas 39 espécies distribuídas em 15 gêneros. Destes, Duguetia A. St. Hill., Guatteria Ruiz & Pavon, Annona L., Unonopsis R.E.Fries e Xylopia L.destacaram-se pela diversidade em espécies, sendo os dois primeiros representados por oito e seis espécies, respectivamente, e os três últimos, com quatro espécies. A família Gnetaceae Lindl. (Gimnospermae) está representada no Município apenas pelo gênero Gnetum L., com a espécie G. leyboldii Tul.

Catálogo sistemático dos pólens das plantas arbóreas do Brasil meridional: I - Magnoliaceae, Annonaceae, Lauraceae e Myristicaceae

Wir beginnen mit dieser Arbeit einen Katalog der Baumpollen Suedbrasiliens, der als Unterlage zum spaeteren Studium der Humusablagerungen in Brasilien dienen soll. Die Reihenfolge der Familien stuetzt sich auf die Phylogenie der Pflanzenfamilien, weshalb wir mit den Polycarpicae, im besonderen der Magnoliaceae s. lat., Lauraceae, Annonaceae und Myristicaceae, beginnen. Obwohl die Abstammungsfolge der verschiedenen Familien noch sehr hypothetisch ist (vergleiche zum Beispiel WETTSTEIN, 1944, und HUTCHINSON, 1946 und 1959), konnten wir Aehnlichkeiten zwischen den Pollen der behandelten Familien feststellen. Vergleiche zwischen den verschiedenen Gattungen dieser Familien fuehren zu keinem sicheren phylogenetischen Schluss. Die Pollen der verschiedenen Lauraceengattugen, ausser Cryptocarya, aehneln sich untereinander so, dass dadurch die Gattungs-und Artbestimmungen unmoeglich gemacht werden. Im Gegensatz treffen wir bei den Annonaceengattungen, so wie auch bei den Magnoliaceen s. lat., typische Formen und Strukturen an. Hierzu machen wir auf die pollensystematische Zusammenfassung am Ende der Arbeit aufmerksam. Die Praeparate wurden nach der Acetolysemethode (beschrieben in ERDTMAN, 1952 und 1954) hergestellt. Da alle Pollen, ausser Drimys und Virola, eine sehr duenne Exine besitzen, war groesste Vorsicht geboten, um sie nicht zu zerstoeren. Gleichzeitig wurde zum Vergleich jeweils ein Objekt nach der Wodehouse'schen Methode (WODEHOUSE, 1935) behandelt.

Odontopus brevirostris (Hustache, 1936) (Coleoptera, Curculionidae) associated with new host plants belonging to Annona (Annonaceae)

Odontopus brevirostris (Hustache, 1936) feeding on Annona squamosa L., A. cherimola Mill., A. glabra L., and A. muricata L. was observed. The last three host plants are recorded for the first time. The endophitic oviposition occurs in the veins of the ventral surface of the young leaves. The larvae, leaf miners, eat the parenchyma and the adults make small holes in the leaves. The pupation occurs in spherical cocoons protected by a sort of nest (pupation chamber) between the two epidermal layers.

Mites associated to Xylopia aromatica (Lam.) Mart. (Annonaceae) in urban and rural fragments of semidecidual forest

Mites associated to Xylopia aromatica (Lam.) Mart. (Annonaceae) in urban and rural fragments of semidecidual forest. Native plants can shelter a great diversity of mites. Notwithstanding, the conservation of the forest fragments where the plants are located can influence the structure of the mites community. Generally, in homogenous environments the diversity is lower due to the dominance of one or a few species. In this work, we studied the mite community on Xylopia aromatica (Lam.) Mart. (Annonaceae) in two fragments of semidecidual forest: one on rural and other on urban area. Seven individuals of X. aromatica were monthly sampled from April 2007 to March 2008, in each of these fragments. Descriptive indexes of diversity, dominance and evenness were applied to verify the ecological patterns of the mite community, besides the Student's t-test to compare the abundance between the fragments. We collected 27,365 mites of 37 species belonging to 11 families. Calacarus sp. (Eriophyidae) was the most abundant species, representing 73% of the total sampled. The abundance was greater in the urban fragment (67.7%), with the diversity index reaching only 25% of the theoretical maximum expected. Probably, these values might have been influenced by the location of this fragment in the urban area, being more homogeneous and submitted directly to the presence of atmospheric pollution. In this manner, X. aromatica is able to shelter a higher diversity of mites when inserted in preserved ecosystems, since the highest diversity of available resources allows the establishment of richer and most diverse mite community.

First report and morphological redescription of Teleonemia morio (Stål) (Hemiptera, Tingidae) in Annona squamosa L. (Annonaceae) in Brazil

First report and morphological redescription of Teleonemia morio (Stål) (Hemiptera, Tingidae) in Annona squamosa L. (Annonaceae) in Brazil. This is the first report of a severe attack of Teleonemia morio (Stål, 1855) (Hemiptera, Heteroptera, Tingidae) on Annona squamosa L. (custard apple), causing up to 80% of losses of infested trees. In order to facilitate the identification of this insect pest, the adult female of T. morio is redescribed based on specimens collected in Palmeira dos Índios, Alagoas, Brazil.

Clonagem de quatro espécies de Annonaceae potenciais como porta-enxertos

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 (21º15'22"S e 48º18'58"W), 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.

Alkaloids and acetogenins in Annonaceae development: biological considerations

Chemical studies of the plant family Annonaceae have intensified in the last several decades due to the discovery of annonaceous molecules with medicinal potential (e.g., benzylisoquinoline alkaloids and acetogenins). Approximately 500 alkaloids have been identified in 138 Annonaceae species in 43 genera. In addition, until 2004, 593 annonaceous acetogenins (ACGs) had been identified, from 51 species in 13 genera.This suggests that plants from this family allocate important resources to the biosynthesis of these compounds. Despite the diversity of these molecules, their biological roles, including their physiological and/or ecological functions, are not well understood. In this study, it was provided new data describing the variety and distribution of certain alkaloids and ACGs in annonaceous plants in distinct stages of development. The potential relationships among some of these compounds and the seasonally climatic changes occurring in the plant habitat are also discussed. These data will improve our understanding of the secondary metabolism of these pharmacologically important molecules and their expression patterns during development, which will help to determine the optimal growth conditions and harvest times for their production.

Evolutionary steps in the reproductive biology of Annonaceae

Flowers of Annonaceae are characterized by fleshy petals, many stamens with hard connective shields and numerous carpels with sessile stigmas often covered by sticky secretions. The petals of many representatives during anthesis form a closed pollination chamber. Protogynous dichogamy with strong scent emissions especially during the pistillate stage is a character of nearly all species. Scent emissions can be enhanced by thermogenesis. The prevailing reproductive system in the family seems to be self-compatibility. The basal genus Anaxagorea besides exhibiting several ancestral morphological characters has also many characters which reappear in other genera. Strong fruit-like scents consisting of fruit-esters and alcohols mainly attract small fruit-beetles (genus Colopterus, Nitidulidae) as pollinators, as well as several other beetles (Curculionidae, Chrysomelidae) and fruit-flies (Drosophilidae), which themselves gnaw on the thick petals or their larvae are petal or ovule predators. The flowers and the thick petals are thus a floral brood substrate for the visitors and the thick petals of Anaxagorea have to be interpreted as an antipredator structure. Another function of the closed thick petals is the production of heat by accumulated starch, which enhances scent emission and provides a warm shelter for the attracted beetles. Insight into floral characters and floral ecology of Anaxagorea, the sister group of the rest of the Annonaceae, is particularly important for understanding functional evolution and diversification of the family as a whole. As beetle pollination (cantharophily) is plesiomorphic in Anaxagorea and in Annonaceae, characters associated with beetle pollination appear imprinted in members of the whole family. Pollination by beetles (cantharophily) is the predominant mode of the majority of species worldwide. Examples are given of diurnal representatives (e.g., Guatteria, Duguetia, Annona) which function on the basis of fruit-imitating flowers attracting mainly fruit-inhabiting nitidulid beetles, as well as nocturnal species (e.g., large-flowered Annona and Duguetia species), which additionally to most of the diurnal species exhibit strong flower warming and provide very thick petal tissues for the voracious dynastid scarab beetles (Dynastinae, Scarabaeidae). Further examples will show that a few Annonaceae have adapted in their pollination also to thrips, flies, cockroaches and even bees. Although this non-beetle pollinated species have adapted in flower structure and scent compounds to their respective insects, they still retain some of the specialized cantharophilous characters of their ancestors.