52328-99-1Relevant academic research and scientific papers
Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells
Jirsek, Petr,Amslinger, Sabine,Heilmann, J?rg
, p. 2206 - 2217 (2014/12/11)
A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 ～M without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 ～M. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.
ANTI-OXIDATIVE AND ANTI-INFLAMMATORY CURCUMIN-RELATED PHENOLICS FROM RHIZOMES OF CURCUMA DOMESTICA
Masuda, Toshiya,Jitoe, Akiko,Isobe, Junko,Nakatani, Nobuji,Yonemori, Sigetomo
, p. 1557 - 1560 (2007/10/02)
Two new natural phenolics were isolated from the rhizomes of Curcuma domestica along with four known curcuminoids.The structures of the former were determined to be 1,5-bis(4-hydroxy-3-methoxyphenyl)penta-(1E,4E)-1,4-dien-3-one and 1-(4-hydroxy-3-methoxyphenyl)-5-(4-hydroxyphenyl)-penta-(1E,4E)-1,4-dien-3-one, respectively, by spectral data and syntheses.Anti-oxidant activity of the phenolics was determined by the inhibition of autoxidation of linoleic acid in a water-alcohol system.Anti-inflammatory activity of the isolated compounds was determined on mouse ears by using a tumour promoter, TPA (12-O-tetradecanoylphorbol-13-acetate) as an inducer. Key Word Index: Curcuma domestica; Zingiberaceae; rhizome; curcuminoid; phenolic; anti-inflammatory activity; antioxidant activity.
