Effect of indole alkaloids from roots of Rauvolfia ligustrina in the noradrenergic neurotransmission

Magalhães, Herbert S.; Silva, Alison B. da; Nascimento, Nilberto Robson Falcão do; Sousa, Luis Gustavo Farias de; Fonseca, Maria Júlia Sousa; Loiola, Maria Iracema Bezerra; Monteiro, Norberto K.V.; Neto, Francisco Wagner Q. Almeida; Canuto, Kirley Marques; Pessoa, Otília Deusdênia Loiola

doi:10.1016/j.fitote.2020.104545

Cited by 4 publications

(4 citation statements)

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“…8). Concluding the chemical investigation from the roots of R. ligustrina, 18 monoterpene indole alkaloids, 7 of which are described here, were isolated [14]. These results corroborate the literature that shows the genus Rauvolfia as a producer of structurally diversified indole alkaloids.…”

Section: Docking Of the Anxiolytic Effect On The Gabaergic Systemsupporting

confidence: 88%

“…Based on the NMR and HRESIMS data, it was evident that compound 1 is a bisindole alkaloid bearing two different indole moieties (A and B). Detailed analysis showed a partial structure very similar to that of 21( R *)-( β -D-glucopyranosyl)-hydroxy-sarpagan-17-oic acid 14 , but containing an N,O -acetal-like carbon ( δ H 3.99, d, J = 9.9 Hz/ δ C 99.7, C-17) and a glucose moiety ( δ H 4.64, d, J = 7.6 Hz/ δ C 102.8, C-1″) that was positioned at C-21 by the HMBC correlation of the methine proton at δ H 4.99 (H-21) with the anomeric δ C 102.8 (C-1″), olefine δ C 125.7 (C-19), and methine 45.1 (C-3) carbons. Based on the aforementioned data, the structure corresponding part A of the molecule was determined.…”

Section: Resultsmentioning

confidence: 81%

Section: Docking Of the Anxiolytic Effect On The Gabaergic Systemmentioning

confidence: 85%

“…It is noteworthy that although R. ligustrina has already been investigated [14], the pharmacological properties exhibited by MIAs (anxiolytic, anticonvulsant, and antihypertensive activities) motivated the present work. Benzodiazepines (GABA receptor agonists) and serotonin reuptake inhibitors (SSRIs) are the drugs of choice for the treatment of anxiety [15].…”

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confidence: 99%

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

et al. 2023

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Rauvolfia species are well-known as producers of bioactive monoterpene indole alkaloids (MIAs) 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 from 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 zebrafish (Danio rerio) model. The possible GABAergic (diazepam: positive control) and serotoninergic (fluoxetine: 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 mechanism action by GABAA, while compound 1 by serotonin receptor (anxiolytic activity). Molecular docking studies showed that compounds 2 and 5 have a greater affinity by GABAA receptor when compared with diazepam, whereas 1 showed the best affinity for 5HT2AR channel when compared to risperidone.

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