40285-97-0Relevant academic research and scientific papers
Structural requirements of sesquiterpene lactones to inhibit LPS-induced nitric oxide synthesis in RAW 264.7 macrophages
Dirsch, Verena M,Stuppner, Hermann,Ellmerer-Mueller, Ernst P,Vollmar, Angelika M
, p. 2747 - 2753 (2000)
Some sesquiterpene lactones were recently demonstrated to inhibit inducible nitric oxide synthase (iNOS)-dependent nitric oxide (NO) synthesis. The primary objective of the present study was, therefore, to find evidence for structural requirements of sesquiterpene lactones regarding their capability to inhibit iNOS-dependent NO synthesis. Sesquiterpene lactones 1-11 were examined for their influence on nitrite accumulation in cell culture supernatants of LPS-induced RAW 264.7 macrophages. Except the taraxinic acid β-D-glucopyranosylester 8 all compounds showed a dose-dependent inhibition of nitrite accumulation in cell culture supernatants with IC50 values ranging from 0.5 to 36.8 μM. High activity seemed to be dependent on an α-methylene-γ-lactone functionality. Cytotoxicity and the ability to inhibit activation of transcription factor NF-κB are further biological activities of sesquiterpene lactones. The second point of interest was, therefore, whether the structural requirements of sesquiterpene lactones for these activities may differ or be the same for those needed to inhibit iNOS-dependent NO synthesis. Using concentrations of 1-11 required to inhibit NO synthesis cell viability was determined and NF-κB binding activity was measured by gel-shift experiments. Interestingly, compounds almost equally effective in inhibiting nitrite accumulation did not show the same cytotoxic potential, and most sesquiterpene lactones inhibited nitrite accumulation at concentrations where inhibition of NF-κB activation was not significant. These results suggest that different biological activities of sesquiterpene lactones have different structural requirements. Copyright (C) 2000 Elsevier Science Ltd.
Isolation, Chemical Transformation, and Antifungal Potential of Sesquiterpene Lactones from Inula Racemosa
Kaur, Ramandeep,Chahal,Urvashi
, p. 207 - 212 (2020/04/17)
The present study reports the isolation of two eudesmanolide type sesquiterpenoid lactones, viz. alantolactone and isoalantolactone, from the roots of Inula racemosa Hook L. and their chemical transformations using various reagents. All the compounds isol
Sesquiterpenolides from Inula racemosa and their chemical transformations
Kaur, Ramandeep,Chahal,Bhardwaj, Urvashi
, p. 568 - 570 (2017/02/19)
Inula racemosa roots are rich source of sesquiterpene lactones. Soxhlet extraction of roots using chloroform followed by column chromatography on silver nitrate impregnated silica gel led to the isolation of two sesquiterpene lactones namely alantolactone
Synthesis of Deuterium-Labeled Sesquiterpene Lactones Isolated from Inula helenium L.
Schaeffer, Marcel,Stampf, Jean-Luc,Benezra, Claude
, p. 6106 - 6113 (2007/10/02)
Reduction of the vinyl sulfoxides 9 and 10 derived from isoalantolactone (1) and alantolactone (2) with NaBD4 yielded deuterium-labeled lactones 11 and 12.Amalgam reduction of sulfides 7 and 8 or sulfoxides 9 and 10 gave labeled products but not the expected deuterated lactones 11 and 12.Satisfactory deuteration of alantolactone 2 could be achieved by CF3COOD hydrolysis of (tributylstannyl)alantolactone (23) obtained in four steps from alantolactone 2.
