Antioxidant and anti-inflammatory activities of N-acetyldopamine dimers from Periostracum Cicadae.
A known N-acetyldopamine dimer, (2R,3S)-2-(3',4'-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2''-aminoethyl)-1,4-benzodioxane (1) and a new N-acetyldopamine dimer, (2R,3S)-2-(3',4'-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2''-aminoethylene)-1,4-benzodioxane (2) were isolated from the methanolic extracts of Periostracum Cicadae. Compounds 1 and 2 inhibited the Cu2+ -mediated, 2,2'-azobis(2-amidinopropane) hydrochloride (AAPH)-mediated, and 3-morpholinosydnonimine (SIN)-1-mediated LDL oxidation in the thiobarbituric acid-reactive substances (TBARS) assay. The antioxidant activities of 1 and 2 were tested with respect to other parameters, such as lag time of conjugated diene formation, relative electrophoretic mobility (REM), and apoB-100 fragmentation on copper-mediated LDL-oxidation. Compounds 1 and 2 also showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity. Compound 2 was more efficient than compound 1 at inhibiting the reactive oxygen species (ROS) generation, nitric oxide (NO) production, and nuclear factor-kappaB (NF-kappaB) activity as well as the expression of pro-inflammatory molecules such as inducible nitric oxide synthase (iNOS), interleukin (IL)-6, tumor necrosis factor (TNF)-alpha, and cyclooxygenase (COX)-2 in LPS-induced RAW264.7 cells.
Xu
Ming-Zhe
MZ
Insect Resources Research Center, KRIBB, Daejeon 305-806, Republic of Korea.
Lee
Woo Song
WS
Han
Jong-Min
JM
Oh
Hyun-Woo
HW
Park
Doo-Sang
DS
Tian
Guan-Rong
GR
Jeong
Tae-Sook
TS
Park
Ho-Yong
HY
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D019281:Dimerization; D004298:Dopamine / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000302:isolation & purification / Q000494:pharmacology*; D016166:Free Radical Scavengers; D015227:Lipid Peroxidation / Q000187:drug effects; D008077:Lipoproteins, LDL / Q000378:metabolism; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D010084:Oxidation-Reduction / Q000187:drug effects; D010936:Plant Extracts / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D017392:Thiobarbituric Acid Reactive Substances
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D004365:Drugs, Chinese Herbal; D016166:Free Radical Scavengers; D008077:Lipoproteins, LDL; D010936:Plant Extracts; D017392:Thiobarbituric Acid Reactive Substances; C006374:N-acetyldopamine; D004298:Dopamine