Effect of Anthraquinone Derivatives on Lipid Peroxidation in Rat Heart Mitochondria: Structure-Activity Relationship

Lipid peroxidation was induced in rat heart mitochondria with FeSO4 and the inhibitory effects of various anthraquinone derivatives were compared. Oxygen consumption and malondialdehyde formation were used to quantitate the amount of lipid peroxidation. Emodin [2], alizarin [13], and alizarin comple...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1995-09, Vol.58 (9), p.1365-1371
Main Authors: Huang, Shiang-Suo, Yeh, Sheau-Farn, Hong, Chuang-Ye
Format: Article
Language:English
Subjects:
Animals
ANTHRAQUINONE
ANTHRAQUINONES
Anthraquinones - chemistry
Anthraquinones - pharmacology
Antioxidants - chemistry
Antioxidants - pharmacology
ANTRAQUINONAS
BIOASSAYS
CHEMICAL COMPOSITION
COEUR
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
CORAZON
DOSAGE BIOLOGIQUE
DRUG PLANTS
ENSAYO BIOLOGICO
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
HEART
In Vitro Techniques
LIPID PEROXIDATION
Lipid Peroxidation - drug effects
Male
MEDICINAL PROPERTIES
MITOCHONDRIA
Mitochondria, Heart - drug effects
Mitochondria, Heart - metabolism
MITOCHONDRIE
MITOCONDRIA
MOLECULAR CONFORMATION
MOLECULAR STRUCTURE
PEROXIDACION LIPIDICA
PEROXYDATION DES LIPIDES
PLANTAS MEDICINALES
PLANTE MEDICINALE
POLYGONACEAE
POLYGONUM
POLYGONUM MULTIFLORUM
PROPIEDADES MEDICINALES
PROPRIETE PHARMACOLOGIQUE
RAT
RATA
RATS
Rats, Sprague-Dawley
Structure-Activity Relationship
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Summary:Lipid peroxidation was induced in rat heart mitochondria with FeSO4 and the inhibitory effects of various anthraquinone derivatives were compared. Oxygen consumption and malondialdehyde formation were used to quantitate the amount of lipid peroxidation. Emodin [2], alizarin [13], and alizarin complexone [14] significantly inhibited lipid peroxidation; their potency as inhibitors of lipid peroxidation was higher than that of alpha-tocopherol. Structure-activity analysis showed that two hydroxyl groups arranged in either the ortho- or meta-position in the C ring of the anthraquinone nucleus are required for such derivatives to inhibit lipid peroxidation. The diphenyl-p-picrylhydrazyl test showed that alizarin [13] and alizarin complexone [14] are free-radical scavengers while emodin [2] is not. The mechanism for emodin [2] to inhibit lipid peroxidation is most likely due to inhibition on the propagation of lipid peroxyl radicals in the mitochondrial membrane.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50123a005