84184-56-5Relevant articles and documents
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.
Studies on the Chemical Constituents of Rutaceous Plants. Part 45. Novel Phenyl Propanoids: Cuspidiol, Boninenal, and Methyl Boninenalate
Ishii, Hisashi,Ishikawa, Tsutomu,Tohojoh, Toshiaki,Murakami, Keiko,Kawanable, Eri,et al.
, p. 2051 - 2058 (2007/10/02)
Cuspidiol, boninenal, and methyl boninenalate were established as having the structures 3-phenyl>propanol (1), (E)-3-phenyl>propenal (2), and (E)-3-phenyl>propenal (3) respectively.The three compounds were also independently synthesized.