Synthesis and biological evaluation of polyhydroxycurcuminoids

Venkateswarlu, Somepalli; Ramachandra, Marellapudi S.; Subbaraju, Gottumukkala V.

doi:10.1016/j.bmc.2005.06.050

Cited by 113 publications

(70 citation statements)

References 25 publications

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“…Thus, compound 5 was identified as 1-(4-hydroxyphenyl)-7-(3, 4-dihydroxyphenyl)-1, 6-heptadiene-3, 5-dione. This is the first report of 5 from a natural source; however, Venkateswarlu [22] and Abas [23] had synthesized this compound. Its 13 C NMR data is reported here for the first time (Table 2).…”

Section: Resultsmentioning

confidence: 85%

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

Wang

Feng

et al. 2009

Magnetic Reson in Chemistry

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Thirteen curcuminoids (1-13) were isolated from the rhizomes of Curcuma longa. Among them, 1,5-dihydroxy-1,7-bis(4-hydroxyphenyl)-4,6-heptadiene-3-one (1), 1,5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-4,6-heptadiene-3-one (2), 1,5-dihydroxy-1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-4,6-heptadiene-3-one (3), and 3-hydroxy-1,7-bis-(4-hydroxyphenyl)-6-heptene-1,5-dione (4) are new compounds, and 1-(4-hydroxyphenyl)-7-(3, 4-dihydroxyphenyl)-1, 6-heptadiene-3, 5-dione (5) is isolated from natural sources for the first time. The structures of these compounds were elucidated by extensive spectroscopic analyses, especially 1D and 2D NMR spectroscopy. The (13)C NMR data and complete (1)H and (13)C NMR assignments of some known compounds are reported for the first time. In addition, the errors of (1)H and (13)C assignments reported in the literature were corrected.

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Section: Resultsmentioning

confidence: 85%

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

Wang

Feng

et al. 2009

Magnetic Reson in Chemistry

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“…Synthetic Curcumin Analogues. Similarly, a variety of curcumin analogues have been synthesized for the purpose of increasing water solubility, deterring degradation/modification (Ferrari et al, 2009;Liang et al, 2009;Wan et al, 2010;Abdel Aziz et al, 2012;Gagliardi et al, 2012;Kulkarni et al, 2012), and improving therapeutic and chemopreventive efficacy Ohtsu et al, 2002;Venkateswarlu et al, 2005;Tamvakopoulos et al, 2007a;Fuchs et al, 2009;Liang et al, 2009). A schematic overview of synthetic curcumin analogues that are both more stable in aqueous media at neutral pH and pharmacologically equally or more effective than curcumin in different cancer cell lines is provided in Fig.…”

Section: •-mentioning

confidence: 99%

The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancer

Golen²,

et al. 2013

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“…[4][5][6][7][8] Inhibition of arachidonic acid metabolism by curcumin has been suggested to be a key mechanism for its anticarcinogenic action. The enzyme cyclooxygenase (COX) catalyzes the first two steps in the biosynthesis of prostaglandins (PGs) from the substrate arachidonic acid.…”

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confidence: 99%

“…[1][2][3] Furthermore, it also exhibits anti-inflammatory, antioxidant, antiviral, and anti-infectious activities and wound healing properties. [4][5][6][7][8] Inhibition of arachidonic acid metabolism by curcumin has been suggested to be a key mechanism for its anticarcinogenic action. The enzyme cyclooxygenase (COX) catalyzes the first two steps in the biosynthesis of prostaglandins (PGs) from the substrate arachidonic acid.…”

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confidence: 99%

Synthesis of Novel Curcumin Analogues and Their Evaluation as Selective Cyclooxygenase-1 (COX-1) Inhibitors

et al. 2007

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Curcumin (diferuloyl methane, Chart 1) is a major constituent found in the spice tumeric, which is a dried powder from the rhizomes of Curcuma longa L. Several in vitro and in vivo studies demonstrated suppression, retardation, or inversion of carcinogenesis.1-3) Furthermore, it also exhibits anti-inflammatory, antioxidant, antiviral, and anti-infectious activities and wound healing properties. [4][5][6][7][8] Inhibition of arachidonic acid metabolism by curcumin has been suggested to be a key mechanism for its anticarcinogenic action. The enzyme cyclooxygenase (COX) catalyzes the first two steps in the biosynthesis of prostaglandins (PGs) from the substrate arachidonic acid. At least two forms of this enzyme exist. 9,10) One of these forms, COX-1, is constitutively expressed and is responsible for maintaining normal physiologic function and the PGs produced by this enzyme play a protective role. The other known form of the enzyme, cyclooxygenase-2 (COX-2), is an inducible form and its expression is affected by various stimuli such as mitogens, oncogenes, tumor promoters, and growth factors. 10) COX-2 has been detected in various tumors and its role in carcinogenesis and angiogenesis has been well documented. Therefore, COX-2 is thought to be a promising therapeutic target for cancer. However, current clinical studies of a COX-2-selective inhibitor, rofecoxib (Vioxx), for preventing recurrence of colorectal polyps in patients with a history of colorectal adenomas were discontinued and the drug was withdrawn from the market because its use was associated with an increased incidence of cardiovascular events, such as heart attack and stroke. 11)Very recently, experimental results have also indicated a possible involvement of the other isoform of COX, COX-1, in angiogenesis, thereby providing the rationale for the development of selective COX-1 inhibitors.12,13) These data were also confirmed by in vitro studies in isolated ovine COX-1 and COX-2 enzymes which showed that curcumin and its analogues tetrahydrocurcumin and trimethoxydibenzoylmethane had significantly higher inhibitory effects on the peroxidase activity of COX-1 than that of COX-2.2) Furthermore, a recent report by Gupta et al. 14) has also indicated that COX-1 is overexpressed in a significant number of ovarian cancers. We therefore investigated whether novel curcumin analogues might achieve an even better and more selective COX-1 inhibition than curcumin. Thus, seven analogues of curcumin were synthesized using standard chemical methods. Each analogue (except the intermediate 2) was then tested for COX-1 and COX-2 inhibition in an in vitro model and the resulting inhibition values compared with that of the clinically established selective COX-2 inhibitor celecoxib. Also molecular docking studies were performed to investigate the ligand-protein interactions responsible for the biological data found. Results and DiscussionThe chemical synthesis of the curcumin analogues was carried out following two known pathways. Their basic principle is the same, b...

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Synthesis and biological evaluation of polyhydroxycurcuminoids

Cited by 113 publications

References 25 publications

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancer

Synthesis of Novel Curcumin Analogues and Their Evaluation as Selective Cyclooxygenase-1 (COX-1) Inhibitors

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