Abstract
A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithiolane 1-oxides, brugierol (2) and isobrugierol (3) were isolated from the flowers of Bruguiera gymnorrhiza. With stably-transfected HepG2 cells, the three isolates activated antioxidant response element (ARE) luciferase activation with (EC(50)) values of 56.7, 3.7 and 1.8 microM, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-kappaB (nuclear factor-kappaB) luciferase activity with IC (50) values of 85.0 and 14.5 microM, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC(50) value of 6.1 microM. The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / administration & dosage
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Antioxidants / chemistry
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Antioxidants / pharmacology*
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Antioxidants / therapeutic use
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Cell Line, Tumor / drug effects
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Crystallography, X-Ray
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Cyclooxygenase Inhibitors / administration & dosage
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Cyclooxygenase Inhibitors / chemistry
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Cyclooxygenase Inhibitors / pharmacology
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Cyclooxygenase Inhibitors / therapeutic use
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Flowers
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Humans
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Inhibitory Concentration 50
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Luciferases / metabolism
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NF-kappa B / antagonists & inhibitors
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Phytotherapy*
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Plant Extracts / administration & dosage
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Plant Extracts / chemistry
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Plant Extracts / pharmacology*
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Plant Extracts / therapeutic use
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Rhizophoraceae*
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Thiosulfonic Acids / administration & dosage
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Thiosulfonic Acids / chemistry
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Thiosulfonic Acids / pharmacology*
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Thiosulfonic Acids / therapeutic use
Substances
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Antioxidants
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Cyclooxygenase Inhibitors
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NF-kappa B
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Plant Extracts
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Thiosulfonic Acids
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bruguiesulfurol
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Luciferases