Antioxidant, Free Radical Scavenging and Anti-Inflammatory Effects of Aloesin Derivatives in Aloe vera

Abstract

Antioxidant components in Aloe vera were examined for lipid peroxidation using rat liver microsomal and mitochondrial enzymes. Among the aloesin derivatives examined, isorabaichromone showed a potent antioxidative activity. The DPPH radical and superoxide anion scavenging activities were determined. As one of the most potent components, isorabaichromone together with feruloylaloesin and p-coumaroylaloesin showed potent DPPH radical and superoxide anion scavenging activities. Electron spin resonance (ESR) using the spin trapping method suggested that the potent superoxide anion scavenging activity of isorabaichromone may have been due to its caffeoyl group. As A. vera has long been used to promote wound healing, the inhibitory effects of aloesin derivatives for cyclooxygenase (Cox)-2 and thromboxane (Tx) A₂ synthase were examined and the participation of p-coumaroyl and feruloyl ester groups in the aloesin skeleton was demonstrated. These findings may explain, at least in part, the wound healing effects of A.vera.

Abbreviations

ADP:adenosine diphosphate

ASA:ascorbic acid

BHT:butylated hydroxytoluene

BSA:bovine serum albumin

DMPO:5,5-dimethyl-1-pyrroline N-oxide

DPPH:1,1-diphenyl-2-picrylhydrazyl

EDTA:edetic acid

HEPES:N-(2-hydroxyethyl)-piperazine-N-2′-ethane-sulfonic acid

NADH:reduced nicotinamide adenine dinucleotide

NADPH:reduced nicotinamide adenine dinucleotide phosphate

NBT:nitroblue tetrazolium

Pg:prostaglandin

SOD:superoxide dismutase

TBA:thiobarbituric acid

TCA:trichloroacetic acid

XOD:xanthine oxidase

Aloe vera - Asphodelaceae - isorabaichromone - antioxidants - free radical - ESR - anti-inflammatory

References

• 1 Yagi A, Haraguchi H. Protective effect of terpenoids against oxidative stresses. In: Pandarai SG. editor Resent research development in phytochemistry. Vol.1 India; Research Signpost 1997: 11-24
• 2 Lee K Y, Weintraub S T, Yu B P. Isolation and identification of a phenolic antioxidant from Aloe barbadensis .  Free Radical Biological & Medicines. 2000;  28 261-5
• 3 Yagi A, Kanbara T, Morinobu N. Inhibition of mushroom tyrosinase by Aloe extract.  Planta Medica. 1987;  53 515-7
• 4 Okamura N, Hine N, Harada S, Fujioka T, Mihashi K, Yagi A. Three chromone components from Aloe vera leaves.  Phytochemistry. 1996;  43 495-8
• 5 Okamura N, Asai M, Hine N, Yagi A. High-performance liquid chromatograpic determination of phenolic compounds in Aloe species.  Journal of Chromatography A.. 1996;  746 225-31
• 6 Davis R H. Aspirin and Aloe, Aloe vera - a scientific approach. New York; Vantage Press 1997: 226-62
• 7 Hutter J A, Salman M, Stavinoha W B, Satsangi N, Williams R F, Streeper R T, Weintraub S T. Anti-inflammatory C-glycosyl chromone from Aloe barbadensis .  Journal of Natural Products. 1996;  59 541-3
• 8 Reynolds T, Dweck A C. Aloe vera leaf gel: a review update.  Journal of Ethnopharmacology. 1999;  68 3-37
• 9 Okamura N, Hine N, Tateyama Y, Nakazawa M, Fujioka T, Mihashi K, Yagi A. Three chromones of Aloe vera leaves.  Phytochemistry. 1997;  45 1511-3
• 10 Johnson D, Lardy H. Isolation of the liver and kidney mitochondria. In: Estabrook RW, Pullman M. editors Methods in Enzymology. New York:; Academic Press 1967 10: 94-6
• 11 Liu G, Zhang T, Wang B, Wang Y. Protective action of seven natural phenolic compounds against peroxidative damage to biomembrane.  Biochemical Pharmacology. 1992;  43 147-52
• 12 Wills E D. Lipid peroxidation in microsomes. General consideration.  Biochemical Journal. 1969;  113 315-24
• 13 Blois M S. Antioxidant determination by the use of a stable free radical.  Nature. 1958;  182 1199-200
• 14 Halliwell B. Use of desferrioxamine as a ”probe” for iron-dependent formation of hydroxyl radicals.  Biochemical Pharmacology. 1985;  34 229-33
• 15 Mitsuya K, Mizuta Y, Kohno M, Mori A. The application of ESR spin trapping technique to the evaluation of SOD-like activity of biological substances.  Bulletin of Chemical Society of Japan. 1990;  63 187-91
• 16 Riendeau D, Charleson S, Cromlish W, Mancini J A, Wong E, Guay J. Comparison of the cyclooxygenase-1 inhibitory properties of non-steroidal anti-inflammatory drugs and selective Cox-2 inhibitors, using sensitive microsomal and platelet assays.  Canadian Journal Physiological Pharmacology. 1997;  75 1088-95
• 17 Borsch-Haubold A G, Pasquet S, Watson S P. Direct inhibition of cyclooxygenase-1 and -2 by the kinase inhibitors SB 203 580 and PD 98 059. SB also inhibits thromboxane synthase.  Journal Biological Chemistry. 1998;  273 28 766-72
• 18 Janzen E G, Stronks H J, Dubose C M, Poyer J L, McCay P B. Chemistry and biology of spin trapping radicals associated with halocarbon metabolism in vitro and in vivo .  Enviromental Health Perspectives. 1985;  64 151-70
• 19 Heggers J P, Roboson M C. Eicosanoids in wound healing. In: Prostaglandins in clinical practice. Watkins WD, Fletcher JR, Stubbs DF, Peterson MB editors New York; Raven Press 1989: 183-94
• 20 Mac Claudy R L, Hing D N, Robson M C, Heggers J P. Frostbite injuries: a rational approach based on the pathophysiology.  Journal of Trauma. 1983;  23 143-7