Abstract
Two novel naphthohydroquinone dimers with unprecedented skeletons, rubialatins A (1) and B (2), were isolated from the herbal plant Rubia alata together with their precursor, mollugin (3). The structures were elucidated on the basis of NMR spectra and crystal X-ray diffraction. Compound 1, a racemate, was separated by chiral column chromatography, and the absolute configurations of the enantiomers were determined by the computational methods. Cytotoxicity of 1-3 was evaluated as well as the effect on the NF-κB pathway. Compound (+)-1 showed cytotoxicity and could inhibit NF-κB pathway. Meanwhile, 2 showed cytotoxicity and a synergistic effect with TNF-α on NF-κB activation.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry*
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Antineoplastic Agents, Phytogenic / pharmacology*
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Cell Line, Tumor
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Humans
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Hydroquinones / chemistry*
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Hydroquinones / isolation & purification
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Hydroquinones / pharmacology*
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Hydroquinones / toxicity*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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NF-kappa B / chemistry*
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NF-kappa B / drug effects*
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Plant Extracts / chemistry*
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Plant Extracts / pharmacology*
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Plant Roots / chemistry*
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Pyrans / chemistry*
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Pyrans / isolation & purification
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Rubia / chemistry*
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Stereoisomerism
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Tumor Necrosis Factor-alpha / chemistry*
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Tumor Necrosis Factor-alpha / drug effects*
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Tumor Necrosis Factor-alpha / metabolism
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X-Ray Diffraction
Substances
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Antineoplastic Agents, Phytogenic
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Hydroquinones
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NF-kappa B
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Plant Extracts
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Pyrans
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Tumor Necrosis Factor-alpha
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rubialatin A
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rubialatin B
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rubimaillin
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1,4-naphthohydroquinone