Potent antioxidant activity of a dithiocarbamate-related compound from a marine hydroid.
Recently, we discovered a novel class of natural products, named the tridentatols, in a marine hydroid. Close examination of their molecular structures suggested that they may have antioxidant activity. This observation prompted us to evaluate in vitro the capacity of one of these tridentatols, viz. tridentatol A, to inhibit lipid peroxidation using human low density lipoprotein (LDL) as an experimental model. LDL was incubated with 5 microM cupric chloride (Cu2+) in the absence and presence of tridentatol A or a reference antioxidant standard, i.e. vitamin E. The onset of rapid formation of conjugated lipid hydroperoxides was delayed in a concentration-dependent manner by tridentatol A. More specifically, LDL incubated with Cu2+ had a lag-phase time (the elapsed time before the onset of rapid formation of conjugated lipid hydroperoxides) of 150 min. However, when 0.5 microM tridentatol A was present during incubation, the lag phase time was extended to 225 min. With 1 microM tridentatol A, the lag phase time was 300 min. The same concentrations of vitamin E produced noticeably lower lag phase times. Thus, compared with vitamin E, tridentatol A better protected against the formation of conjugated lipid hydroperoxides in LDL. Direct colorimetric measurements of both lipid hydroperoxides and thiobarbituric acid-reactive substances confirmed the greater potency of tridentatol A relative to vitamin E. Furthermore, tridentatol A negated the Cu2+-induced increase in electrophoretic mobility of LDL to a greater extent than vitamin E. In conclusion, tridentatol A is a powerful antioxidant against lipid peroxidation of LDL and is significantly more potent than vitamin E in this regard.
Johnson
M K
MK
Department of Nutrition and Foodservice Systems, School of Human Environmental Sciences, University of North Carolina at Greensboro, 27412, USA.
Alexander
K E
KE
Lindquist
N
N
Loo
G
G
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D003063:Cnidaria / Q000737:chemistry*; D004050:Ditiocarb / Q000494:pharmacology*; D005260:Female; D006801:Humans; D066298:In Vitro Techniques; D008077:Lipoproteins, LDL / Q000378:metabolism; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology*; D014810:Vitamin E / Q000494:pharmacology
D000975:Antioxidants; D008077:Lipoproteins, LDL; D010636:Phenols; C121186:tridentatol A; D014810:Vitamin E; D004050:Ditiocarb