Planta Med
DOI: 10.1055/a-2058-3710
Original Papers

Indole Alkaloids of Rauvolfia ligustrina and Their Anxiolytic Effects in Adult Zebrafish

1   Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE, Brazil
Alison Batista da Silva
1   Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE, Brazil
Maria Kueirislene Amâncio Ferreira
2   Programa de Graduação em Ciências Naturais, Universidade Estadual de Ceará, Fortaleza-CE, Brazil
Antonio Wlisses da Silva
3   Programa de Graduação em Biotecnologia, Universidade Estadual de Ceará, Fortaleza-CE, Brazil
Jane Eire Silva Alencar de Menezes
2   Programa de Graduação em Ciências Naturais, Universidade Estadual de Ceará, Fortaleza-CE, Brazil
Emmanuel Silva Marinho
2   Programa de Graduação em Ciências Naturais, Universidade Estadual de Ceará, Fortaleza-CE, Brazil
Márcia Machado Marinho
4   Curso de Química, Universidade Estadual do Vale do Acaraú, Sobral-CE, Brazil
Helcio Silva dos Santos
4   Curso de Química, Universidade Estadual do Vale do Acaraú, Sobral-CE, Brazil
1   Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE, Brazil
› Author Affiliations
This work was supported by grants from Conselho Nacional de Desenvolvimento Científico e Tecnológico – CNPq (No. 420454/2016-0 and 310183/2020-0).


Rauvolfia species are well known as producers of bioactive monoterpene indole alkaloids, which exhibit a broad spectrum of biological activities. A new vobasine-sarpagan-type bisindole alkaloid (1) along with six known monomeric indoles (2, 3/4, 5, and 6/7) were isolated from the ethanol extract of the roots of Rauvolfia ligustrina. The structure of the new compound was elucidated by interpretation of their spectroscopic data (1D and 2D NMR and HRESIMS) and comparison with published data for analog compounds. The cytotoxicity of the isolated compounds was screened in a zebrafish (Danio rerio) model. The possible GABAergic (diazepam as the positive control) and serotoninergic (fluoxetine as the positive control) mechanisms of action in adult zebrafish were also evaluated. No compounds were cytotoxic. Compound 2 and the epimers 3/4 and 6/7 showed a mechanism action by GABAA, while compound 1 showed a mechanism action by a serotonin receptor (anxiolytic activity). Molecular docking studies showed that compounds 2 and 5 have a greater affinity by the GABAA receptor when compared with diazepam, whereas 1 showed the best affinity for the 5HT2AR channel when compared to risperidone.

Supporting Information

Publication History

Received: 02 August 2022

Accepted after revision: 20 March 2023

Accepted Manuscript online:
20 March 2023

Article published online:
15 May 2023

© 2023. Thieme. All rights reserved.

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Rüdigerstraße 14, 70469 Stuttgart, Germany

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