Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity.
Norbergenin, which is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC(50) 13 microM in DPPH radical scavenging; 32 microM in superoxide anion scavenging). Modification of sugar part on norbergenin by coupling with a variety of fatty acids was employed for increasing its antioxidant activity. Selective esterification of hydroxyl groups on the sugar part enhanced greatly antioxidant activity. The most potent one is norbergenin 11-caproate, which not only exhibits stronger antioxidant activity than that of catechin but also prevents neuronal death at 10 microM on the primary culture of rat cortical neurons in DMEM supplemented with N2.
Takahashi
Hironobu
H
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Kosaka
Masamiti
M
Watanabe
Yasutoshi
Y
Nakade
Kousuke
K
Fukuyama
Yoshiyasu
Y
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002392:Catechin / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D002540:Cerebral Cortex / Q000166:cytology; D016166:Free Radical Scavengers / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D009474:Neurons / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship
D000975:Antioxidants; D001578:Benzopyrans; D016166:Free Radical Scavengers; D018696:Neuroprotective Agents; C063922:norbergenin; D002392:Catechin