Do Colletotrichum gloeosporioides and Rhizopus stolonifer induce alkaloidal and antifungal responses in Annona muricata seedlings?

The benzylisoquinoline alkaloids of Annona muricata have been isolated, but their physiological or ecological role is unknown. The objective was to explore whether these secondary metabolites are involved in defense against phytopathogenic fungi. To do this, the alkaloidal response of 6-leaf seedlings of A. muricata was analyzed, previously inoculated with Colletotrichum gloeosporioides and Rhizopus stolonifer. Before and after inoculation, alkaloidal extracts of roots, stems, and leaves were obtained, and the antifungal activity was evaluated in vitro. The alkaloids anonaine, reticuline, nornuciferine, assimilobine, and coreximine were identified. C. gloeosporioides caused variable increases in the production of anonaine, reticuline and nornuciferine (10-1200%), while R. stolonifer only stimulated the increase of nornuciferin and anonaine (10%) in the stems and leaves. The alkaloidal extracts of inoculated seedlings increased the antifungal activity, both against the pathogen elicitor and against the second target pathogen. These findings suggest that the alkaloids participate in the antifungal defense mechanism.

Spatio-Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity.

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.

Acetogenins and alkaloids during the initial development of Annona muricata L. (Annonaceae).

In plants, the presence and distribution of specialized metabolites during the early stages of development are not documented enough, even though their biosynthesis is one of the most important strategies for survival. In this study, five alkaloids and four acetogenins were detected in Annona muricata L. during early development seedling, including three phases of root emergence and three of seedling formation. Hexane and alkaloid extracts were obtained from each organ, which were analyzed in a gas-mass chromatograph and in a high-performance liquid chromatograph coupled with a photodiode array UV detector (HPLC-DAD). This research shows the presence of the acetogenins cis-uvarimicin IV, mosinone, muricina B, and cis-annonacin-10-one, as well as of the alkaloids reticuline, coreximine, anonaine, asimilobine, and nornuciferine, both groups with a variable organ-specific distribution, related with the formation of organs and tissues.