Demethoxycurcumin-Metal Complexes: Fragmentation and Comparison with Curcumin-Metal Complexes, as Studied by ESI-MS/MS

Ostrowski, Wojciech; Śniecikowska, Lidia; Hoffmann, Marcin; Frański, Rafał

doi:10.1155/2013/749641

Cited by 5 publications

(3 citation statements)

References 49 publications

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“…This finding might be related to the asymmetrical nature of DMCM in contrast to CM and BDCM. In DMCM the two oxygen atoms at the aliphatic chain (O-3 and O-5) are not chemically identical and form a predominant tautomer B2 [ 78 ]. The o -methoxy group influences the electron density on the central keto-enol group, which in turn might affect its binding ability to ATPase proteins.…”

Section: Discussionmentioning

confidence: 99%

Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life

et al. 2016

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P-type ATPases catalyze the active transport of cations and phospholipids across biological membranes. Members of this large family are involved in a range of fundamental cellular processes. To date, a substantial number of P-type ATPase inhibitors have been characterized, some of which are used as drugs. In this work a library of natural compounds was screened and we first identified curcuminoids as plasma membrane H+-ATPases inhibitors in plant and fungal cells. We also found that some of the commercial curcumins contain several curcuminoids. Three of these were purified and, among the curcuminoids, demethoxycurcumin was the most potent inhibitor of all tested P-type ATPases from fungal (Pma1p; H+-ATPase), plant (AHA2; H+-ATPase) and animal (SERCA; Ca2+-ATPase) cells. All three curcuminoids acted as non-competitive antagonist to ATP and hence may bind to a highly conserved allosteric site of these pumps. Future research on biological effects of commercial preparations of curcumin should consider the heterogeneity of the material.

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Section: Discussionmentioning

confidence: 99%

Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life

et al. 2016

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“…In this context, the MS/MS data of the class of compounds under study play a key role . The gas‐phase fragmentation reactions of a series of protonated and deprotonated β‐diketone curcuminoids have been previously investigated . However, in the case of the MKCs, data on their fragmentation are still scarce.…”

Section: Introductionmentioning

confidence: 99%

Electrospray ionization tandem mass spectrometry of monoketone curcuminoids

Vieira

Orenha

Crevelin

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Although monoketone curcuminoids (MKCs) have been largely investigated due to their biological activities, data on the gas‐phase fragmentation reactions of protonated MKCs under collision‐induced dissociation (CID) conditions are still scarce. Here, we combined electrospray ionization tandem mass spectrometry (ESI‐MS/MS) data, multiple‐stage mass spectrometry (MSn), deuterium exchange experiments, accurate‐mass data, and thermochemical data estimated by computational chemistry to elucidate and to rationalize the fragmentation pathways of eleven synthetic MKCs. Methods The MKCs were synthesized by Claisen‐Schmidt condensation under basic (1–9) or acidic (10–11) conditions. ESI‐CID‐MS/MS analyses and deuterium‐exchange experiments were carried out on a triple quadrupole mass spectrometer. MSn analyses on an ion trap mass spectrometer helped to elucidate the fragmentation pathways. Accurate‐mass data and thermochemical data, obtained at the B3LYP/6–31+G(d,p) level of theory, were used to support the ion structures. Results The most intense product ions were the benzyl ions ([C7H2R1R2R3R4R5]+) and the acylium ions ([M + H − C8H3R1R2R3R4R5]+), which originated directly from the precursor ion as a result of two competitive hydrogen rearrangements. Product ions [M + H – H2O]+ and [M + H − C6HR1R2R3R4R5]+, which are formed after Nazarov cyclization, were also common to all the analyzed compounds. In addition, •Br and •Cl eliminations were diagnostic for the presence of these halogen atoms at the aromatic ring, whereas •CH3 eliminations were useful to identify the methyl and methoxy groups attached to this same ring. Nazarov cyclization in the gas phase occurred for all the investigated MKCs and did not depend on the presence of the hydroxyl group at the aromatic ring. However, the presence and the position of a hydroxyl group at the aromatic rings played a key role in the Nazarov cyclization mechanism. Conclusions Our results reinforce some aspects of the fragmentation pathways previously published for 1,5‐bis‐(2‐methoxyphenyl)‐1,4‐pentadien‐3‐one and 1,5‐bis‐(2‐hydroxyphenyl)‐1,4‐pentadien‐3‐one. The alternative fragmentation mechanism proposed herein can explain the fragmentation of a wider diversity of monoketone curcuminoids.

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“…Among several natural products, as an active constituent of Curcuma longa , curcumin (bis[4‐hydroxy‐3‐methoxyphenyl]‐1,6‐heptadiene‐3,5‐dione) is used as a precursor for developing various drugs . Moreover, curcumin is a yellow spice which is well‐known for its anti‐oxidant, anti‐inflammatory, and anti‐cancer activities . Curcumin has been shown to inhibit diethylnitrosamine‐induced liver tumours and to have a dose‐dependent chemopreventive effect in rodent models of colon, duodenal, gastric, esophageal, and oral cancer .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and electrochemistry studies of iron(III) complex with curcumin ligand

Özbolat

Yegani

Tuli

2018

Clin Exp Pharma Physio

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Iron overload is a serious clinical condition for humans and is a key target in drug development. The aim of this study was to investigate the coordination of iron(III) ions with curcumin ligand that may be used in the treatment of iron overload. Iron(III) complex of curcumin was synthesized and structurally characterized in its solid and solution state by FT-IR, UV-Vis, elemental analysis, and magnetic susceptibility. Electrochemical behaviour of the ligand and the complexes were examined using cyclic voltammetry. The cytotoxic activities of the ligand and the iron(III) complex were evaluated by the MTT assay. Curcumin reacted with iron in high concentrations at physiological pH at room temperature. Subsequently, a brown-red complex was formed. Data regarding magnetic susceptibility showed that the complexes with a 1:2 (metal/ligand) mole ratio had octahedral geometry. The complex showed higher anti-oxidant effect towards the cell line ECV304 at IC values of 4.83 compared to curcumin. The complex exhibited very high cytotoxic activity and showed a cytotoxic effect that was much better than that of the ligand. The potentials for redox were calculated as 0.180 V and 0.350 V, respectively. The electrochemistry studies showed that Fe /Fe couple redox process occurred at low potentials. This value was within the range of compounds that are expected to show superoxide dismutase activity. This finding indicates that the iron complex is capable of removing free radicals. The observed cytotoxicity could be pursued to obtain a potential drug. Further studies investigating the use of curcumin for this purpose are needed.

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Demethoxycurcumin-Metal Complexes: Fragmentation and Comparison with Curcumin-Metal Complexes, as Studied by ESI-MS/MS

Cited by 5 publications

References 49 publications

Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life

Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life

Electrospray ionization tandem mass spectrometry of monoketone curcuminoids

Synthesis, characterization and electrochemistry studies of iron(III) complex with curcumin ligand

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