Antioxidant effects of quinoline alkaloids and 2,4-di-tert-butylphenol isolated from Scolopendra subspinipes.
The oxidized low-density lipoprotein (ox-LDL) plays a critical role at the early stages of atherosclerosis. Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinoline (3), and 2,4-di-tert-butylphenol (2) were isolated from the dried body of Scolopendra subspinipes. Compounds 1-3 exhibited antioxidant activities on copper-mediated (1: IC50=2.6 microM, 2: IC50=8.2 microM, 3: IC50=63.0 microM), AAPH-mediated oxidation (1: IC50=3.9 microM, 2: IC50=9.9 microM, 3: IC50=71.8 microM), and SIN-1-mediated oxidation (1: 70%, 2: 52%, 3: 29% at 5.0 microM) in the TBARS assay. The antioxidant activities of compounds 1-3 were tested with respect to other parameters, such as the lag time of conjugated diene fromation, relative electrophoretic mobility (REM) of ox-LDL, and apoB-100 fragmentation on copper-mediated LDL-oxidation. In addition, compounds 1-3 showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity and compound 1 also exhibited metal chelating activity.
Yoon
Mi-Ae
MA
Insect Resources Laboratory, Korea Research Institute of Bioscience and Biotechnology, Daejeon, Korea.
Jeong
Tae-Sook
TS
Park
Doo-Sang
DS
Xu
Ming-Zhe
MZ
Oh
Hyun-Woo
HW
Song
Kyoung-Bin
KB
Lee
Woo Song
WS
Park
Ho-Yong
HY
D000470:Alkaloids / Q000494:pharmacology*; D000578:Amidines / Q000737:chemistry; D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D053299:Apolipoprotein B-100; D001055:Apolipoproteins B / Q000378:metabolism; D001181:Arthropods / Q000737:chemistry*; D001713:Biphenyl Compounds; D002614:Chelating Agents / Q000494:pharmacology; D003300:Copper / Q000737:chemistry; D024202:Electrophoretic Mobility Shift Assay; D016166:Free Radical Scavengers / Q000494:pharmacology; D008077:Lipoproteins, LDL / Q000097:blood; D008981:Molsidomine / Q000031:analogs & derivatives / Q000494:pharmacology; D010084:Oxidation-Reduction; D015125:Oxyquinoline / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry; D011804:Quinolines / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D017392:Thiobarbituric Acid Reactive Substances
D000470:Alkaloids; D000578:Amidines; D000975:Antioxidants; D053299:Apolipoprotein B-100; D001055:Apolipoproteins B; D001713:Biphenyl Compounds; D002614:Chelating Agents; D016166:Free Radical Scavengers; D008077:Lipoproteins, LDL; D010851:Picrates; D011804:Quinolines; D017392:Thiobarbituric Acid Reactive Substances; C049535:2,8-dihydroxyquinoline; C002385:linsidomine; D015125:Oxyquinoline; C046728:2,2'-azobis(2-amidinopropane); D003300:Copper; D008981:Molsidomine; C004931:1,1-diphenyl-2-picrylhydrazyl