Anti-inflammatory withajardins from the leaves of Athenaea velutina. (November 2022)

• Record Type: Journal Article
• Authors: Dantas Rocha, Késya Amanda; de Freitas Paulo, Tércio; Ayala, Alejandro Pedro; da Silva Sampaio, Valéria; Gomes Nunes, Paulo Iury; Santos, Flávia Almeida; Canuto, Kirley Marques; Silveira, Edilberto Rocha; Loiola Pessoa, Otília Deusdenia
• Is Part Of: Phytochemistry. Volume 203(2022)
• Publication Date: 2022-11
• Subjects: Athenaea velutina -- Solanaceae -- Withanolides -- Withajardins -- Anti-inflammatory activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113338
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Withajardins, uncommon modified withanolide-type steroids, have been isolated exclusively from plants of the Solanaceae family so far. Two undescribed withajardins and the known tuboanosigenin were isolated from the hexane/EtOAc 1:1 extract from Athenaea velutina leaves. Their structures were established by an extensive analysis of 1D and 2D-NMR and HRMS data. The absolute configuration was determined by X-ray diffraction (withajardin L and tuboanosigenin) and circular dichroism (CD) analyses (withajardin M). The anti-inflammatory activity of compounds was evaluated through the inhibition of the lipopolysaccharide (LPS)-induced nitric oxide (NO), TNF- α, and IL-6 release in RAW264.7 cells. The cell viability effects to RAW 264.7 cells showed IC50 values of 74.4–354.4 μM. The compounds attenuated LPS-induced release of NO and decreased pro-inflammatory cytokines TNF- α and IL-6 in RAW264.7 cells. Graphical abstract: Image 1 Highlights: Three withajardins were isolated from the leaves of Athenaea velutina. Their absolute configuration was determined by X-ray diffraction and circular dichroism. Compounds reduced TNF-α and IL-6 production in LPS-stimulated RAW264.7 cells.