taraxasteryl-acetate and taraxasterol

Neuroinflammation plays a significant role in various chronic and acute pathological conditions of the central nervous system. In the Indian system of medicine, Pluchea lanceolata is used to treat the neurological disorders. We investigated the effect of major pentacyclic triterpene and its naturally occurring acetate derivative isolated from P. lanceolata on lipopolysaccharide (LPS)-stimulated neuroinflammatory condition associated to inflammatory cytokine production in rat astrocytoma cell line (C6). The log concentration dependence of Pluchea bioactive taraxasterol (Tx) significantly (p < 0.05) attenuates the release of pro-inflammatory cytokines, such as TNF-α, IFN-γ, and IL-6, while its in situ produced acetyl derivative, i.e., taraxasterol acetate (TxAc), did not inhibit the LPS-induced IL-6 production at lower concentration (p > 0.05). Surflex-Dock molecular modeling study was performed to simulate the binding capacity of compounds into the active site of the TNF-α (2AZ5), tumor protein P53 (2VUK), and NF-kappa-B (1RAM). The differential inhibition of cytokines by Tx and TxAc was further confirmed by high docking scores showing the high affinity to target proteins. Findings of the study demonstrated the comparatively greater role of Pluchea triterpene than its in situ produced acetate derivate in neuroinflammation-associated disorders.

Topics: Animals; Anti-Inflammatory Agents; Asteraceae; Cell Line, Tumor; Cell Survival; Encephalitis; Interferon-gamma; Interleukin-6; Lipopolysaccharides; Molecular Docking Simulation; Neuroglia; Neuroprotective Agents; NF-kappa B; Plant Components, Aerial; Plant Extracts; Rats; Sterols; Triterpenes; Tumor Necrosis Factor-alpha; Tumor Suppressor Protein p53

To investigate the chemical constituents of Ligularia xanthotricha.. Silica gel column chromatography and preparative TLC were employed for the isolation and purification. The structures were identified on the basis of spectral data (IR, EI-MS, 1H-NMR, 13C-NMR, DEPT) and chemical evidence.. Seven compounds were isolated and identified as follows: lupeol (1), lupeol palmitate (2), 3, 28-dihydroxyl-lupeol (3), betulinic acid (4), taraxasterol (5), taraxasteryl palmitat (6) and taraxasteryl acetate(7).. All the compounds were isolated from this plant for the first time.

Topics: Asteraceae; Betulinic Acid; Chromatography, Gel; Chromatography, Thin Layer; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Spectrometry, Mass, Electrospray Ionization; Sterols; Triterpenes