ArticleJournal of natural products2018
A Curcumin Degradation Product, 7-Norcyclopentadione, Formed by Aryl Migration and Loss of a Carbon from the Heptadienedione Chain.
Article in Journal of natural products, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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0 citing papers in PubMed, 3 citations in OpenAlex.
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3 authors at 1 institution in 1 country.
Funding
Abstract
Evidence that anti-inflammatory and other biological effects of curcumin may at least in part be mediated by its metabolites underscores the importance of identifying novel transformation products. Spontaneous degradation of curcumin in buffer pH 7.5 results mainly in dioxygenated products with a characteristic cyclopentadione ring composed of carbons 2 through 6 of the former heptadienedione chain. When analyzing degradation reactions of 4'- O-methylcurcumin, a product was identified missing one of the terminal carbons of the heptadienedione moiety while containing a cyclopentadione ring and adjacent hydroxy group typical of curcumin degradation products. Analysis of curcumin autoxidation reactions showed formation of an analogous compound, 7-norcyclopentadione, a degradation product exhibiting net loss of a carbon and gain of an oxygen atom. Removal of the carbon is proposed to occur via a peroxide-linked curcumin dimer in conjunction with radical-mediated 1,2-aryl migration of a guaiacol moiety. Oxidation reactions of demethoxycurcumin gave demethoxy-7-norcyclopentadione, whereas an analogous product was not observed from bis-demethoxycurcumin. Incubation of RAW264.7 macrophage-like cells with curcumin showed the presence of 7-norcyclopentadione, the formation of which was not increased upon activation of the cells with 12- O-tetradecanoylphorbol-13-acetate . 7-Norcyclopentadione is a novel type of degradation product that is most likely formed via autoxidative processes when cells are incubated with curcumin.
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