Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Dec 13;15(12):9205-13.
doi: 10.3390/molecules15129205.

Alkaloids from stems of Esenbeckia leiocarpa Engl. (Rutaceae) as potential treatment for Alzheimer disease

Elaine Monteiro Cardoso-Lopes  1 , James Andreas Maier, Marcelo Rogério da Silva, Luis Octávio Regasini, Simone Yasue Simote, Norberto Peporine Lopes, José Rubens Pirani, Vanderlan da Silva Bolzani, Maria Cláudia Marx Young
Affiliations

Alkaloids from stems of Esenbeckia leiocarpa Engl. (Rutaceae) as potential treatment for Alzheimer disease

Elaine Monteiro Cardoso-Lopes et al. Molecules. .

Abstract

Esenbeckia leiocarpa Engl. (Rutaceae), popularly known as guarantã, goiabeira, is a native tree from Brazil. Bioactivity-guided fractionation of the ethanol stems extract afforded the isolation of six alkaloids: leiokinine A, leptomerine, kokusaginine, skimmianine, maculine and flindersiamine. All isolated compounds were tested for acetyl cholinesterase inhibition, in vitro and displayed anticholinesterasic activity. The alkaloid leptomerine showed the highest activity (IC₅₀ = 2.5 mM), similar to that of the reference compound galanthamine (IC₅₀ = 1.7 mM). The results showed for the first time the presence of alkaloids leptomerine and skimmianine in E. leiocarpa (Engl.) with potent anticholinesterasic activity.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Acetylcholinesterase inhibition by ethanol extract, alkaloid and hexane fractions (0.2 to 100.0 μg/mL).
Figure 2
Figure 2
Analytical chromatographic profile of alkaloid fraction from E. leiocarpa by HPLC and their respectives molecular ion peaks [M+H]+ data in the ESI-MS.
Figure 3
Figure 3
Chemical structures of alkaloids with anticholinesterasic activities, ALK 1 to 6. The alkaloids isolated are: 1 – leiokinine A, 2 – leptomerine, 3 – kokusaginine, 4 – skimmianine, 5 – maculine, 6 – flindersiamine.
Figure 4
Figure 4
Acetylcholinesterase inhibition of physostigmine, galanthamine, leptomerine, kokusaginine, leiokinine A and skimmianine (10-10 to 10-3 M).
See this image and copyright information in PMC

References

    1. Barros-Filho B.A., Nunes F.M., Oliveira M.C.F., Andrade-Neto M., Mattos M.C., Barbosa F.G., Mafezoli J., Pirani J.R. Secondary Metabolites of Esenbeckia almawillia Kaastra (Rutaceae) Quím. Nova. 2007;30:1589–1591. doi: 10.1590/S0100-40422007000700017. - DOI
    1. Guilhon G.M.S.P., Baetas A.C.S., Maia J.G.S., Conserva L.M. 2-alkyl-4-quinolone alkaloids and cinnamic acid derivatives from Esenbeckia almawillia. Phytochemistry. 1994;37:1193.
    1. Nakatsu T., Johns T., Kubo I., Sakai M., Chatani, Saito K., Tamagiwa, Kamikawa T. Isolation, structure, and synthesis of novel 4-quinolinone alkaloids from Esenbeckia leiocarpa. J. Nat. Prod. 1990;53:1508–1513. doi: 10.1021/np50072a017. - DOI - PubMed
    1. Johnstone R.A.W., Rose M.E. A rapid, simple and mild procedure for alkylation of phenols, alcohols, amides and acids. Tetrahedron. 1979;35:2169–2173. doi: 10.1016/0040-4020(79)87035-0. - DOI
    1. Lorenzi H. Brazilian Trees: A Guide to the Identification and Cultivation of Brazilian Native Trees. Plantarum; Nova Odessa, SP, Brazil: 1992. p. 307.

Publication types

MeSH terms