Three new quinones from <i>Senna pluribracteata</i> (Fabaceae) and investigation of their bioactivity in BV-2 microglial cells

Three new quinones were isolated from <i>Senna pluribracteata</i>, identified as sennaquinone A (<b>1</b>), quinquangulin-6-<i>O</i>-[α-L-rhamnopyranoside-(1→6)-β-D-glucopyranoside] (<b>2</b>) and rubrofusarin-6-<i>O</i>-[β-(6'-(<i>E</i>)-crotonylglucopyranoside] (<b>3</b>), and nine other known compounds identified as quinquangulone (<b>4</b>) rubrofusarin-6-<i>O</i>-[<mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mi>α</mml:mi></mml:mrow></mml:math>-L-rhamnopyranoside-(1→6)-β-D-glucopyranoside] (<b>5</b>), norrubrofusarin-6-<i>O</i>-β-<i>D</i>-glucopyranoside (cassiaside) (<b>6</b>), rubrofusarin-6-<i>O</i>-β-D-glucopyranoside (<b>7</b>), vanillic acid (<b>8</b>), protocatechuic acid (<b>9</b>), quercetin-3-<i>O</i>-sambubioside (<b>10</b>), resveratrol (<b>11</b>), and vomifoliol (<b>12</b>). These compounds were determined by HR-ESI-MS, 1D and 2D NMR analyses and ECD calculation. The cytotoxicity of compounds <b>1</b>, <b>2</b>, and <b>3</b> was first assessed in BV-2 microglial cell line by MTT assay. Compounds <b>2</b> and <b>3</b> reduced cell viability by more than 20% only at 200 μM, while compound <b>1</b> was less cytotoxic. For anti-neuroinflammatory activity evaluation, LPS/IFN-γ co-stimulated microglial cells were treated with non-cytotoxic concentrations (25, 50, and 100 μM) of compounds <b>1</b>, <b>2</b>, and <b>3</b>, and NO production was determined by the Griess method. Our results showed that none of the three compounds reduced NO production, suggesting no anti-neuroinflammatory activity.

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Journal
Natural Product Research
Published
2025-08-19
DOI
https://doi.org/10.1080/14786419.2025.2547316
Primary Topic
Bioactive Compounds and Antitumor Agents
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article
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article

Three new quinones from Senna pluribracteata (Fabaceae) and investigation of their bioactivity in BV-2 microglial cells

Ranna Beatris de Lima Souza, Geraldo Moisés Wanderley Amorim, Maria de Fátima Agra, Ana Carolina Ferreira de Albuquerque et al.
Natural Product Research
Bioactive Compounds and Antitumor Agents
article

Three new quinones from Senna pluribracteata (Fabaceae) and investigation of their bioactivity in BV-2 microglial cells

Ranna Beatris de Lima Souza, Geraldo Moisés Wanderley Amorim, Maria de Fátima Agra, Ana Carolina Ferreira de Albuquerque, Raimundo Braz‐Filho, Marcelo Sobral da Silva, Marianna Vieira Sobral, Josean Fechine Tavares, Fernando Martins dos Santos, Paulo Bruno Araújo Loureiro, Ana Rita Rodrigues de Almeida Silva Brilhante
article en

Abstract

Three new quinones were isolated from <i>Senna pluribracteata</i>, identified as sennaquinone A (<b>1</b>), quinquangulin-6-<i>O</i>-[α-L-rhamnopyranoside-(1→6)-β-D-glucopyranoside] (<b>2</b>) and rubrofusarin-6-<i>O</i>-[β-(6'-(<i>E</i>)-crotonylglucopyranoside] (<b>3</b>), and nine other known compounds identified as quinquangulone (<b>4</b>) rubrofusarin-6-<i>O</i>-[<mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mi>α</mml:mi></mml:mrow></mml:math>-L-rhamnopyranoside-(1→6)-β-D-glucopyranoside] (<b>5</b>), norrubrofusarin-6-<i>O</i>-β-<i>D</i>-glucopyranoside (cassiaside) (<b>6</b>), rubrofusarin-6-<i>O</i>-β-D-glucopyranoside (<b>7</b>), vanillic acid (<b>8</b>), protocatechuic acid (<b>9</b>), quercetin-3-<i>O</i>-sambubioside (<b>10</b>), resveratrol (<b>11</b>), and vomifoliol (<b>12</b>). These compounds were determined by HR-ESI-MS, 1D and 2D NMR analyses and ECD calculation. The cytotoxicity of compounds <b>1</b>, <b>2</b>, and <b>3</b> was first assessed in BV-2 microglial cell line by MTT assay. Compounds <b>2</b> and <b>3</b> reduced cell viability by more than 20% only at 200 μM, while compound <b>1</b> was less cytotoxic. For anti-neuroinflammatory activity evaluation, LPS/IFN-γ co-stimulated microglial cells were treated with non-cytotoxic concentrations (25, 50, and 100 μM) of compounds <b>1</b>, <b>2</b>, and <b>3</b>, and NO production was determined by the Griess method. Our results showed that none of the three compounds reduced NO production, suggesting no anti-neuroinflammatory activity.

Natural Product Research
Universidade Federal Fluminense (BR), Universidade Federal da Paraíba (BR), Instituto Federal de Educação Ciência e Tecnologia da Paraíba (BR), Instituto Federal Fluminense (BR), Prefeitura Municipal de Campos dos Goytacazes (BR)
Openalex Percentile: Top 80%
Bioactive Compounds and Antitumor Agents
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