-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. Index terms: early development, secondary metabolism, ecological functions, phenology. ALCALOIDES E ACETOGENINAS NO DESENVOLVIMENTO DE ANNONACEAE: CONSIDERAÇÕES BIOLÓGICASRESUMO -Estudos químicos em plantas da família Annonaceae se intensificaram nas últimas décadas, devido à descoberta de moléculas de anonáceas com potencial medicinal (por exemplo, alcalóides benzilisoquinolina e acetogeninas). Aproximadamente 500 alcaloides têm sido identificados em 138 espécies de Annonaceae em 43 gêneros. Além disso, até 2004, 593 acetogeninas de annonaceas (ACGs) foram identificados, a partir de 51 espécies em 13 gêneros. Isto sugere que as plantas desta família atribuem recursos importantes para a biossíntese destes compostos. Apesar da diversidade destas moléculas, suas funções biológicas, incluindo as suas funções fisiológicas e/ou ecológicas, não são bem compreendidas. Neste estudo, foram fornecidos novos dados que descrevem a variedade e a distribuição de certos alcaloides e ACGs em annonaceas em fases distintas de desenvolvimento. As possíveis relações entre alguns destes compostos e as alterações climáticas sazonais ocorrendo no habitat são também discutidas. Estes dados vão melhorar a nossa compreensão do metabolismo secundário dessas moléculas farmacologicamente importantes e seus padrões de expressão durante o desenvolvimento, o que ajudará a determinar as condições ideais de crescimento e épocas de colheita para a sua produção. Termos para indexação: desenvolvimento inicial, metabolismo secundário, funções ecológicas, fenologia.
Annona lutescens Saff. (Annonaceae) grows as a native tree in Chiapas, Mexico in Tropical Dry Forest habitat. Like most Annonaceae, it biosynthesizes benzylisoquinoline alkaloids, mostly liriodenine. To determine the influence of seasonal changes in the accumulation of liriodenine, the monthly variation of liriodenine content in roots, stems and leaves of mature and young trees was observed. These parts of young and mature A. lutescens trees were collected monthly over a 1 year period and the alkaloids were extracted; the liriodenine was quantified by high-resolution liquid chromatography. The phenological stages of the species were also assessed (leaf development, flowering and fruiting) using the Biologische Bundesanstalt, Bundessortenamt und Chemische Industrie (BBCH) scale. The analysis of both young and mature trees showed a significant increase in the liriodenine concentration occurs within roots during the dry season, which coincides with leaf fall. A significant decrease also occurred at the beginning of the rainy season (the period of leaf growth); the liriodenine content for the next rainy season did not reach the levels of the previous dry season. The climatic variation induced phenological and physiological changes in this species.
Annona purpurea grows in the areas of low elevation in deciduous forests of Mexico, those areas have marked rainy and dry seasons. This species produces more than 30 bioactive alkaloids that could have potential in the control of phytopathogens. This research provides data on the variation of the content and number of alkaloids during an annual cycle and the associated inhibitory potential of the compounds against three phytopathogenic fungi. For one year, alkaloidal extracts of stems and leaves were obtained every two months. The extract profiles were determined by gas chromatography with tandem mass spectrometry and their antifungal activity was examined in vitro. The alkaloids, annomontine and oxopurpureine, obtained from the roots and leaves, respectively, were also evaluated individually. The yields, profiles and activities of the extracts, as well as the abundance of annomontine and oxopurpureine in the extracts, were contrasted with the seasonality and phenological phases of the plant. The data indicate that the alkaloid content was higher at the height of the dry season. High yields also occurred during flowering. The strongest inhibitory effect was obtained from the root extracts during the last month of dry season. This finding seems to be explained by the higher chemodiversity of alkaloids in extracts from this season. Annomontine and oxopurpureine inhibited all three phytopathogens; however, they were not solely responsible for the activity of A. purpurea.
Background. Phenological descriptions of plant species are used to understand cycles of foliation, flowering and fruiting. These studies provide useful means for understanding the relationships between plants and their environment. Conclusions. The species studied could be grouped according to their leaf pattern as brevideciduous or deciduous and according to their reproductive pattern as having long-term or short-term strategies.
Background and Aims: The phytochemistry study of Annonaceae has intensified in the last decades due to the discovery of secondary metabolites with antimicrobial activities. The inhibitory activities of extracts and compounds from these species for phytopathogens are less known. The antifungal activity of Sapranthus microcarpus was determined in vitro against six fungal pathogens of important crops.Methods: Hexane, methanol, and alkaloid extracts of the leaves and root and stem bark of S. microcarpus were evaluated to determine whether they could inhibit the mycelial growth of the phytopathogens. The combined activity of the most active extracts for each phytopathogen was also determined. The alkaloid liriodenine was isolated and identified as an antifungal principle.Key results: All extracts inhibited the growth of the six phytopathogens to some extent. The root bark alkaloid extract showed the highest activity. Fusarium oxysporum f. sp. lycopersici and Curvularia lunata were the most sensitive phytopathogens. Liriodenine was active against all the plant pathogens (minimum inhibitory concentrations of 125-500 nmol ml-1).Conclusions: Sapranthus microcarpus is a native natural resource with great phytochemical potential.
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