Vanillin and ferulic acid: not the major degradation products of curcumin

Gordon, Odaine N.; Schneider, Claus

doi:10.1016/j.molmed.2012.04.011

Cited by 86 publications

(89 citation statements)

References 10 publications

(22 reference statements)

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“…Compounds 1-7 and 9 are novel products of the autoxidation of curcumin that are formed in addition to the previously identified bicyclopentadione isomers 8a-8c (20,21,31,32). The newly identified products are highly polar (1-4) and/or unstable at acidic pH (6 and 7), which might explain why they have not been described as products before.…”

Section: Isolation and Characterization Of Curcumin Autoxidationmentioning

confidence: 85%

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Unraveling Curcumin Degradation

Gordon

Luis

Sintim

et al. 2015

Journal of Biological Chemistry

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135

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Background:The bioactive metabolites of curcumin are not well defined. Results: Using [14 C]curcumin as tracer, degradation products and unstable reaction intermediates were isolated and identified. Conclusion: The spontaneous degradation of curcumin is an autoxidation that yields electrophilic and nucleophilic products. Significance: The unexpected chemical diversity of its metabolites may explain the polypharmacology of curcumin.

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Section: Isolation and Characterization Of Curcumin Autoxidationmentioning

confidence: 85%

“…Autoxidative transformation is the major pathway of degradation of curcumin at physiological pH in vitro (21). Biological relevance for this transformation was found in the topoisomerase poisoning activity of curcumin (22,23).…”

mentioning

confidence: 99%

Unraveling Curcumin Degradation

Gordon

Luis

Sintim

et al. 2015

Journal of Biological Chemistry

Self Cite

135

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“…Dissolution with RPMI60 cell culture media containing 10% FBS raised the half-life of curcumin to ~8hr [37] and so ~ 90% of curcumin would oxidise in 24hr in the presence of culture media. It has been proposed that the anticancer activity of curcumin is due partly to one or more of its auto-oxidation products [38,39].…”

Section: Curcumin and 5-azacytidine Decrease Lncap Cell Viabilitymentioning

confidence: 99%

Curcumin restores glutathione-S-transferase activity for LNCaP prostate cancer cells

Dubey¹,

Owusu‐Apenten²

2014

pacs

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Prostate cancer is a leading cause of death in males aged fifty and over. Glutathione transferase (GST) activity is depressed in prostate cancer cells. The aim of this study was to assess GST reactivation in LNCaP prostate cancer cells treated with curcumin or 5-azacitidine (5-Aza) which is a known hypomethylation agent. GST activity was determined using monochlorobimane (MCB). Cell viability was assessed with resazurin (Vision blue TM) or 3-(4, 5-Dimethylthiazol-2-yl)-2, 5-di-phenyltetrazolium-bromide (MTT). From the results, treatment with >5 μM of curcumin or 5-Aza for 3 or 6 days depressed LNCaP cell viability. The concentrations of curcumin leading to 50% reduction of LNCaP cell viability (IC50) was 10-25 μM or 2-3 μM for 3 days or 6 days of treatment, respectively. The IC50 with 5-Aza was 17-23 μM (3 days) or 50-52 μM (6 days). Combination treatment using curcumin and 5-Aza showed complimentary interactions affecting cell viability. Low levels of curcumin or 5-Aza had no effect on GST activity. By contrast, cytotoxic doses of curcumin or 5-Aza increased GST activity by 450-750 % (3days) or 161-2800 % (6days). In conclusion, GST reactivation was feasible but only when LNCaP prostate cancer cells were treated with cytotoxic doses of curcumin or 5-azacytidne. 62Vaibhav Dubey and Richard Owusu-Apenten

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“…A radical chain reaction leads to incorporation of oxygen into curcumin, resulting in dioxygenated bicyclopentadione products. 9,12,13 Oxidation was also catalysed by recombinant cyclooxygenase-2 and the rate was increased ∼10-fold by the addition of H 2 O 2 . 9 An enzymatic or autoxidative mechanism proposing hydrogen abstraction from a phenolic hydroxyl resulting in a quinone methide and a delocalized radical in the heptadiene chain that then undergoes 5-exo cyclisation and oxygenation.…”

Section: Introductionmentioning

confidence: 99%

“…9 An enzymatic or autoxidative mechanism proposing hydrogen abstraction from a phenolic hydroxyl resulting in a quinone methide and a delocalized radical in the heptadiene chain that then undergoes 5-exo cyclisation and oxygenation. 12 Hydration of the quinone methide and rearrangement with loss of water gives the final dioxygenated bicyclopentadione product.…”

Section: Introductionmentioning

confidence: 99%

Photodegradation of methoxy substituted curcuminoids

Ŝket¹,

Galer²

2015

ACSi

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Dedicated to the memory of Prof. Dr. Jurij V. Bren~i~. AbstractPhotodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-dimethoxy and the longest for the 2,5-dimethoxy derivative. For the 3,5-dimethoxy curcuminoid, the major degradation products were 3,5-dimethoxybenzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxycinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, products with the molecular formula C 23 H 24 O 6 and C 23 H 22 O 6 attributed to the reaction of intramolecular [2 + 2] cycloaddition of the dimethoxy curcuminoid, and the dioxygenated bicyclopentadione derivative (C 23 H 24 O 8 ) derived from autoxidative transformation of the dimethoxy curcuminoid.

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Vanillin and ferulic acid: not the major degradation products of curcumin

Cited by 86 publications

References 10 publications

Unraveling Curcumin Degradation

Unraveling Curcumin Degradation

Curcumin restores glutathione-S-transferase activity for LNCaP prostate cancer cells

Photodegradation of methoxy substituted curcuminoids

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