New functions of glucosamine as a scavenger of the lipid peroxidation product malondialdehyde.
Direct reaction between malondialdehyde (MDA) and glucosamine (GlcN) was studied using high-performance liquid chromatography, liquid chromatography/mass spectrometry, spectrophotometry, and spectrofluorometry. The results indicated that GlcN reacted readily with MDA at supraphysiological conditions to form different products, such as a nonfluorescent enamine with an absorption peak at 281 nm (product 1) and a lipofuscin-like fluorescent (Ex. 392 nm/Em. 454 nm) 1,4-dihydropyridine (product 2). GlcN also greatly inhibited the formation of lipofuscin-like fluorescence induced by MDA reacted with bovine serum albumin. The reaction of GlcN with MDA suggested a novel anticarbonylation function of GlcN in pathophysiological situations related to aging-related diseases and provided insight into the reaction mechanism of GlcN in protecting proteins against carbonyl stress.
Fang
Chui
C
Key Laboratory of Protein Chemistry and Developmental Biology of the Ministry of Education, College of Life Sciences, Hunan Normal University, Changsha 410081, Hunan, China.
Peng
Mijun
M
Li
Guolin
G
Tian
Jinzhou
J
Yin
Dazhong
D
D002851:Chromatography, High Pressure Liquid; D005453:Fluorescence; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology*; D005944:Glucosamine / Q000737:chemistry / Q000494:pharmacology*; D006863:Hydrogen-Ion Concentration; D015227:Lipid Peroxidation / Q000187:drug effects*; D008315:Malondialdehyde / Q000737:chemistry* / Q000378:metabolism; D013058:Mass Spectrometry; D015394:Molecular Structure; D050050:Protein Carbonylation / Q000187:drug effects; D013050:Spectrometry, Fluorescence; D017392:Thiobarbituric Acid Reactive Substances / Q000737:chemistry / Q000378:metabolism
D016166:Free Radical Scavengers; D017392:Thiobarbituric Acid Reactive Substances; D008315:Malondialdehyde; D005944:Glucosamine