- Study on the Synthesis of Methylated Reference and Their Application in the Quantity of Curcuminoids Using Single Reference Liquid Chromatography Based on Relative Molar Sensitivity
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We report on the recommendation of the simple and versatility of methylated reference (MR) to improve applications in the single reference (SR)-LC based on relative molar sensitivity (RMS). Three curcuminoids (Curs) such as curcumin, demethoxycurcumin and bisdemethoxycurcumin in turmeric products were determined using authentic standards and methylated curcumin. In addition, high-speed countercurrent chromatography (HSCCC) purification is necessary to separate Curs for indicating the RMS. For HSCCC separation, a biphasic solvent system was used to obtain these fractions, which were then subjected to 1H quantitative NMR to determine their contents in each test solution. Using these solutions, the RMS of Curs are calculated from slopes ratios of calibration curves (three ranges from 0-100μmol/L, r2>0.998). The averaged RMS of Curs were 8.92 (relative standard deviation (RSD), 1.17%), 8.97 (2.18%), and 9.61 (0.77%), respectively. Cur concentrations in turmeric products can be determined using RMS, peak area, and MR content added in these samples. This proposed method, which is based on chemical methylation and the SR-LC assay has been successfully applied for the simple and reliable estimation of Curs in turmeric products.
- Inoue, Koichi,Masumoto, Naoko,Morimoto, Koji,Nishizaki, Yuzo,Sato, Kyoko,Sugimoto, Naoki,Takahashi, Miki
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- A PERSONAL CARE COMPOSITION
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Disclosed is a personal care composition and a method of providing antiperspirant and anti-inflammation using certain curcuminoid derivatives. The composition comprises: (i) a compound of the Formula 1 Ar-CHnCHn-X.C(R)2-X.CHnCHn-Ar (Formula 1) wherein Ar is a substituted or unsubstituted phenyl group; R is H or CH3; X is CH(OH) group or C=O group; n has the value 1 or 2; and, (ii) a topically acceptable base comprising at least 0.1% of a fragrance wherein, when n=1, the compound of (Formula 1) is 1E,6E)-1,7-bis(3,4- dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione (Formula 2), and when n=2, the compound of (Formula 1) is 1,7-bis(4-hydroxy-3- methoxyphenyl) heptane-3,5-diol (Formula 4) or is 1,7-bis (3,4-dimethoxyphenyl)-4,4-dimethylheptane-3,5-diol (Formula 5).
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Page/Page column 16; 17
(2018/09/18)
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- Design, synthesis, and evaluation of curcumin derivatives as Nrf2 activators and cytoprotectors against oxidative death
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Activation of nuclear factor erythroid-2-related factor 2 (Nrf2) has been proven to be an effective means to prevent the development of cancer, and natural curcumin stands out as a potent Nrf2 activator and cancer chemopreventive agent. In this study, we synthesized a series of curcumin analogs by introducing the geminal dimethyl substituents on the active methylene group to find more potent Nrf2 activators and cytoprotectors against oxidative death. The geminally dimethylated and catechol-type curcumin analog (compound 3) was identified as a promising lead molecule in terms of its increased stability and cytoprotective activity against the tert-butyl hydroperoxide (t-BHP)-induced death of HepG2 cells. Mechanism studies indicate that its cytoprotective effects are mediated by activating the Nrf2 signaling pathway in the Michael acceptor- and catechol-dependent manners. Additionally, we verified by using copper and iron ion chelators that the two metal ion-mediated oxidations of compound 3 to its corresponding electrophilic o-quinone, contribute significantly to its Nrf2-dependent cytoprotection. This work provides an example of successfully designing natural curcumin-directed Nrf2 activators by a stability-increasing and proelectrophilic strategy.
- Tu, Zhi-Shan,Wang, Qi,Sun, Dan-Dan,Dai, Fang,Zhou, Bo
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- Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents
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Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2′-azinobis(3-ethylbenzothiazoline-6- sulfonic acid) radical cation (ABTS.+), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS.+-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.
- Bayomi, Said M.,El-Kashef, Hassan A.,El-Ashmawy, Mahmoud B.,Nasr, Magda N. A.,El-Sherbeny, Magda A.,Badria, Farid A.,Abou-Zeid, Laila A.,Ghaly, Mariam A.,Abdel-Aziz, Naglaa I.
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p. 1147 - 1162
(2013/04/10)
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- CURCUMIN ANALOGS AS DUAL JAK2/STAT3 INHIBITORS AND METHODS OF MAKING AND USING THE SAME
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Curcumin analogues and methods of making and using the same are disclosed.
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Page/Page column 5; 14-15
(2010/11/04)
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