Abstract
Atemoya is an interspecific annonaceous hybrid between Annona cherimola Mill. and Annona squamosa L. Its phytochemical investigation led to seven alkaloids, including two aporphine (anonaine and asimilobine), three oxoaporphine (lanuginosine, liriodenine and lysicamine) and two proaporphine (pronuciferine and stepharine). These alkaloids were identified by a series of spectrometric methods, mainly MS and NMR (1D and 2D), as well as by comparison with literature data. Our findings showed that this species is an important source of aporphine alkaloids and have high relationship with other Annona species.
Article PDF
References
Campos, F.R., Batista, R.L., Batista, C.L., Costa, E.V., Barison, A., Santos, A.G., Pinheiro, M.L.B., 2008. Isoquinoline alkaloids from leaves of Annona sericea (Annonaceae). Biochem. Syst. Ecol. 36. 804–806.
Chatrou, L.W., Rainer, H., Maas, P.J.M., 2004. Annonaceae (Soursop family). In: Smith, N., et al. (Eds.), Flowering Plants of Neotropics. Botanical Garden, New York, pp. 18–20.
Chen, C.Y., Chang, F.R., Teng, C.M., Wu, Y.C., 1999. Cheritamine, a new n-fatty acyl tryptamine and other constituents from the stems of Annona cherimola. J. Chin. Chem. Soc. 46. 77–86.
Costa, E.V., Pinheiro, M.L., Xavier, C.M., Silva, J.R., Amaral, A.C., Souza, A.D., Barison, A., Campos, F.R., Ferreira, A.G., Machado, G.M., Leon, L.L., 2006. A pyrimidine-β- carboline and other alkaloids from Annona foetida with antileishmanial activity. J. Nat. Prod. 69. 292–294.
Costa, E.V., Pinheiro, M.L.B., Souza, A.D.L., Barison, A., Campos, F.R., Valdez, R.H., Nakamura, T.U., Dias-Filho, B.P., Nakamura, C.V., 2011. Trypanocidal activity of oxoaporphine and pyrimidine-β-carboline alkaloids from the branches of Annona foetida Mart. (Annonaceae). Molecules 16. 9714–9720.
Costa, E.V., Sampaio, M.F.C., Salvador, M.J., Nepel, A., Barison, A., 2015. Chemical constituents from the stem bark of Annona pickelii (Annonaceae). Quim. Nova, https://doi.org/10.5935/0100-4042.20150069 (in press).
Cruz, P.E.O., Costa, E.V., Moraes, V.R.S., Nogueira, P.C.L., Vendramin, M.E., Barison, A., Ferreira, A.G., Prata, A.P.N., 2011. Chemical constituents from the bark of Annona salzmannii (Annonaceae). Biochem. Syst. Ecol. 39. 872–875.
Dutra, L.M., Costa, E.V., Moraes, V.R.S., Nogueira, P.C.L., Vendramin, M.E., Barison, A., Prata, A.P.N., 2012. Chemical constituents from the leaves of Annona pickelii (Annonaceae). Biochem. Syst. Ecol. 41. 115–118.
Guo, Z.F., Wang, X.B., Luo, J.G., Luo, J., Wang, J.S., Kong, L.Y., 2011. A novel aporphine alkaloid from Magnolia officinalis. Fitoterapia 82. 637–641.
Harrigan, G.G., Gunatilaka, A.A., Kingston, D.G., Chan, G.W., Johnson, R.K., 1994. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. J. Nat. Prod. 57. 68–73.
Hocquemiller, R., Cavé, A., Jacquemin, H., Touche, A., Forgacs, P., 1982. Alkaloids of the Annonaceae. XXXVI. Alkaloids of Annona crassiflora Mart. Plant. Med. Phytother. 16. 4–6.
Lúcio, A.S.S.C., Almeida, J.R.G.S., Cunha, E.V.L., Tavares, J.F., Barbosa-Filho, J.M., 2015. Alkaloids of the Annonaceae: occurrence and a compilation of their biological activities. The Alkaloids: Chemistry and Biology, vol. 74., 1st ed. Elsevier, pp. 233–409.
Rabêlo, S.V., Costa, M.M., Libório, R.C., Almeida, J.R.G.S., 2014a. Atividade antioxidante e antimicrobiana de extratos de atemoia (Annona cherimola Mill. × A. squamosa L.). Rev. Bras. Frutic. 36. 265–271.
Rabêlo, S.V., Araújo, C.S., Costa, V.C.O., Tavares, J.F., Silva, M.S., Barbosa-Filho, J.M., Almeida, J.R.G.S., 2014. Occurrence of alkaloids in species of the genus Annona L. (Annonaceae): a review. In: Brar, S.K., Kaur, S., Dhillon, G.S. (Org.), Nutraceuticals and Functional Foods: Natural Remedy, 1st ed., vol. 1. Nova Science Publishers, Inc., New York, USA, pp. 41–60.
Silva, A.V.C., Muniz, E.N., 2011. Quality of atemoya fruits harvested at two maturity stages. Rev. Caatinga 24. 9–13.
Thuy, T.T., Sung, T.V., Franke, K., Wessjohann, L., 2005. Aporphine and proaporphine alkaloids from Stephania rotunda. J. Chem. 43. 619–623.
Wijeratne, E.M.K., Hatanaka, Y., Kikuch, T., Tezuka, Y., Gunatilaka, A.A.L., 1996. A dioxoaporphine and other alkaloids of two Annonaceous plants of Sri Lanka. Phytochemistry 42. 1703–1706.
Acknowledgments
The authors are grateful to CNPq (Processes: 470594/2013-6, 442209/2014-2, and 303587/2014-8), CAPES, FINEP and UFPR for financial support and fellowships as well as to Centro de Referência para Recuperação de Áreas Degradadas (CRAD/UNIVASF) for botanical identification of the plant material.
Author information
Authors and Affiliations
Contributions
SVR, XPN and MFCS were responsible for the collection, preparation of the extracts and phytochemical studies. EVC, AB and LMD conducted the experiments of nuclear magnetic resonance. JCT, GGO and NPL conducted the experiments of mass spectrometry. EVC and JRGSA analyzed and interpreted the data, and drafted the manuscript. All the authors have read the final manuscript and approved the submission.
Corresponding author
Ethics declarations
The authors declare no conflicts of interest.
Rights and permissions
This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
About this article
Cite this article
Rabêlo, S.V., Costa, E.V., Barison, A. et al. Alkaloids isolated from the leaves of atemoya (Annona cherimola × Annona squamosa). Rev. Bras. Farmacogn. 25, 419–421 (2015). https://doi.org/10.1016/j.bjp.2015.07.006
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1016/j.bjp.2015.07.006