1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (E,E)-/DEMETHOXYCURCUMIN,BIS/Bis(p-hydroxycinnamoyl)methane/Bisdemethoxycurcumin/1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione/p,p'-Dihydroxydicinnamoylmethane/(1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione/CURCUMIN 3/bis demethoxycurcumin/(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione/Bisdemethoxycucurmin/bisdemetoxycurcumin/curcumin III/bisdesmethoxycurcumin/Didemethoxycurcumin/1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-
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Turmeric (Curcuma longa L, Zingiberaceae) rhizomes exhibit versatile biological activities including the significant anti-cancer property. As an herbal medicine, the therapeutic effects of turmeric may be expressed by multi-components which have complicated integration effects on multi-targets. Therefore, having previously found three A549 cell-binding curcuminoids (curcumin, Cur; demethoxycurcumin, DMcur; bisdemethoxycurcumin, BMcur) from turmeric, studies were undertaken in this paper to determine the anti-cancer mechanism and integration effects of these curcuminoids by using chemical markers’ knockout and UHPLC-LTQ Orbitrap MS-based metabolomics. Four curcuminoid-containing fractions including a mixture of 3 cell-binding curcuminoids (CE), and three individual curcuminoids with natural proportion in turmeric were prepared by chemical markers’ knockout method. CE, Cur, DMcur and BMcur fractions showed significant anti-cancer activity on A549 cells. The activities of CE, Cur and BMcur fractions were comparative with the turmeric crude extract (TcE). In the metabolomics study, CE and three individual curcuminoid fractions changed the expression of 25 metabolites in A549 cells, which were involved in glycerophospholipid catabolism, sphingolipid metabolism and fatty acid metabolism, etc. Among them, glycerophospholipid catabolism was disordered greatly in CE group, while sphingolipid metabolism was suggested to be closely related to DMcur and BMcur activity. Furthermore, the metabolomics data showed that three curcuminoids existed synergistic and antagonistic actions and the use of multi-curcuminoids is more powerful than use of single curcuminoid on the metabolic alterations of A549 cells.
Copyright © 2019 Elsevier B.V. All rights reserved.
Anti-cancer integration effects; Chemical markers’ knockout; Curcuminoids; Turmeric; UHPLC-LTQ Orbitrap MS-based metabolomics
Chemical markers' knockout coupled with UHPLC-HRMS-based metabolomics reveals anti-cancer integration effects of the curcuminoids of turmeric (Curcuma longa L.) on lung cancer cell line.
Zhou JL1, Zheng JY2, Cheng XQ3, Xin GZ2, Wang SL4, Xie T5.
2019 Oct 25
A fast and reliable ultra-performance liquid chromatography-diode array detection method was developed and validated for the quantitative assessment of turmeric extracts from different geographical locations. Acclaim RSLC PolarAdvantage II column (2.2 μm, 2.1 × 100 mm) was used to analyze individual curcuminoids (curcumin, demethoxycurcumin and bisdemethoxycurcumin) from turmeric samples. The detection was done on ultraviolet absorbance at 425 nm and the column temperature was maintained at 45 °C. A mobile phase consisting of acetonitrile and water was found to be suitable for separation, at a flow rate of 1 mL/min with linear gradient elution. Linearity, specificity, precision, recovery and robustness were measured to validate the method and instrument. Under the described conditions, curcuminoids were collected within one minute. The calibration curve of each curcuminoid showed good linearity (correlation coefficient > 0.999). The relative standard deviations (RSD) of intra-day, inter-day precision and repeatability were less than 0.73%, 2.47% and 2.47%, respectively. In the recovery test, the accuracy ranged from 98.54%-103.91% with RSD values of less than 2.79%. The developed method was used for quantification of individual curcuminoids of turmeric samples. Analysis of turmeric samples from Nepal and South Korea revealed that curcuminoid content was related to geographical location. Turmeric cultivated in warmer climates were found to have higher curcumionoid content than turmeric samples from cooler climates, the southern part of Nepal was found to have two times higher content of curcuminoids than turmeric from the north.
UPLC-DAD; curcuminoids; turmeric; validation
Geographical Discrimination in Curcuminoids Content of Turmeric Assessed by Rapid UPLC-DAD Validated Analytical Method.
Poudel A1,2, Pandey J3, Lee HK4.
2019 May 10
Curcuminoids, mainly present in the plant rhizomes of turmeric (Curcuma longa), consist of mainly three forms (curcumin (CUR), bisdemethoxycurcumin (BDMC) and demethoxycurcumin (DMC)). It has been reported that different forms of curcuminoids possess different biological activities. However, the mechanisms associated with these differences are not well-understood. Recently, our laboratory found differences in the cellular uptake of these curcuminoids. Therefore, it has been inferred that these differences contribute to the different biological activities.
In this study, we investigated the mechanisms of differential cellular uptake of these curcuminoids.
Based on our previous study, we hypothesized the differential cellular uptake is caused by (I) polarity, (II) transporters, (III) metabolism rate of curcuminoids and (IV) medium components. These four hypotheses were each investigated by (I) neutralizing the polarities of curcuminoids by encapsulation into poly(lactic-co-glycolic) acid nanoparticles (PLGA-NPs), (II) inhibition of polyphenol-related absorption transporters, (III) analysis of the cellular curcuminoids and their metabolites by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and (IV) use of different mediums in cell study.
The differential cellular uptake was not affected by (I-III). However, when investigating (IV), not only CUR but also BDMC and DMC were incorporated into cells when serum free media was used. Furthermore, when we used the serum free medium containing bovine serum albumin (BSA), only CUR was taken up but BDMC and DMC were not. Therefore, we identified that the differential cellular uptake of curcuminoids is caused by the medium components, especially BSA. Also, the fluorescence quenching study suggested that differential cellular uptake is due to the different interaction between BSA and each curcuminoid.
The differential cellular uptake of curcuminoids was caused by the different interaction between curcuminoids and BSA. The results from this study might give clues on the mechanisms by which curcuminoids exhibit different physiological activities.
Copyright © 2019. Published by Elsevier GmbH.
Albumin; Cellular uptakes; Curcuminoids; High-performance liquid chromatography (HPLC); Protein drug interaction
The differential cellular uptake of curcuminoids in vitro depends dominantly on albumin interaction.
Itaya M1, Miyazawa T2, Zingg JM3, Eitsuka T1, Azzi A4, Meydani M4, Miyazawa T5, Nakagawa K6.