Category: 33171-05-0

Impact of Conventional and Sustainable Solvents on the Yield, Selectivity, and Recovery of Curcuminoids from Turmeric was written by Kisanthia, Rattikon;Hunt, Andrew J.;Sherwood, James;Somsakeesit, La-or;Phaosiri, Chanokbhorn. And the article was included in ACS Sustainable Chemistry & Engineering in 2022.COA of Formula: C19H16O4 The following contents are mentioned in the article:

Extraction of pharmaceutically important curcuminoid platform mols. has been achieved from turmeric with ultrasound-assisted greener solvent extraction, demonstrating excellent performance and product recovery. Extraction of curcuminoids from turmeric was undertaken with both conventional and potentially bio-based solvents. Sustainable solvents, namely, Et acetate, ethanol, Cyrene, and deep eutectic solvent (DES-B5, 1:6 ChCl:1,4-butanediol) demonstrated high extraction yields of curcuminoids, including 24.36 ± 3.10, 25.30 ± 4.58, 23.51 ± 2.56, and 27.40 ± 3.80 mg/g of curcumin, resp. In contrast, curcumin extracted in lower polarity solvents such as hexane, toluene, and tetramethyloxolane was low at less than 7.0 mg/g, whereas 2-MeTHF, DMF, and THF represented moderate extraction yields of 13.80 ± 3.90, 14.43 ± 4.46, and 15.17 ± 2.08 mg/g, resp. DES-B5 with 10% water extracted the greatest yield of curcumin (46.70 ± 0.55 mg/g), bisdemethoxycurcumin (46.14 ± 0.82 mg/g), and demethoxycurcumin (10.63 ± 0.35 mg/g), followed by a simple and low energy product recovery method through the addition of water and precipitation COSMOtherm calculations suggested that the extraction efficiency was related to solvent interactions with the cell walls of the biomass, rather than the solubility of the curcuminoids. In addition, the application of ultrasound in extraction in combination with DES-B5 enabled the strong destruction of the plant matrix that was confirmed by SEM. The sustainability, efficiency, and toxicity of the proposed extraction methodologies were evaluated through the CHEM21 green metrics toolkit. The methods utilizing ethanol, Et acetate, and Cyrene in this work demonstrate a significant improvement over those previously published by 3-10 times of process mass intensity total, and DES-B5 also performed well under the green metrics assessment. Because of its high yields, low toxicity, being a bio-based solvent, inexpensive, and readily available, DES-B5 with 10% water is recommended as the greenest solvent for curcuminoid extraction under ultrasonication. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0COA of Formula: C19H16O4).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.COA of Formula: C19H16O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A combination index and glycoproteomics-based approach revealed synergistic anticancer effects of curcuminoids of turmeric against prostate cancer PC3 cells was written by Wei, Meng-Meng;Zhao, Shu-Juan;Dong, Xue-Man;Wang, Yong-Jie;Fang, Can;Wu, Pu;Song, Gao-Qian;Gao, Jun-Na;Huang, Zhi-Hui;Xie, Tian;Zhou, Jian-Liang. And the article was included in Journal of Ethnopharmacology in 2021.Product Details of 33171-05-0 The following contents are mentioned in the article:

Herbal medicines (HMs) often exert integration effects, including synergistic, additive and antagonistic effects, in such ways that they act on multiple targets and multiple pathways on account of their multiple components. Turmeric, made from the rhizome of Curcuma longa L., is a well-known HM prescribed in the polyherbal formulas for cancer treatment in traditional Chinese medicines (TCMs). However, neither the multiple anticancer compounds of turmeric nor the integration effects of these components are fully known. This work aims to develop a systematic approach to reveal the integration effect mechanisms of multiple anticancer compounds in turmeric against prostate cancer PC3 cells. Combination index and omics technologies were applied to profile the integration effect mechanisms of bioactive compounds in proportions naturally found in turmeric. PC3 cell line (a prostate cancer cell line) fishing and high resolution mass spectrometry were employed to screen and identify the anticancer compounds from turmeric. The combinations which contain different cell-bound compounds in natural proportions were prepared for further evaluation of anti-cancer activity by using cell viability assays, and assessment of cell apoptosis and cell cycle anal. Combination index anal. was applied to study the integration effects of the anticancer compounds in their natural proportions. Finally, quant. glycoproteomics/proteomics and Western blot were implemented to reveal the potential synergistic effect mechanisms of the anticancer compounds based on their natural proportions in turmeric. Three curcuminoids (curcumin, CUR; demethoxycurcumin, DMC; bisdemethoxycurcumin, BDMC) in turmeric were discovered and shown to possess significant synergistic anticancer activities. Combination index anal. revealed an additive effect of CUR combined with DMC or BDMC and a slight synergistic effect of DMC combined with BDMC in natural proportions in turmeric, while a combination of all three curcuminoids (CUR, DMC and BDMC) at a ratio of 1:1:1 yielded superior synergistic effects. Interestingly, the presence of BDMC and DMC are essential for synergistic effect. Glycoproteomics and proteomics demonstrated that different curcuminoids regulate various protein pathways, such as ribosome, glycolysis/gluconeogenesis, biosynthesis of amino acids, and combination of CUR + DMC + BDMC showed the most powerful effects on down-regulation of protein expression. Our anal. approach provides a systematic understanding of the holistic activity and integration effects of the anti-cancer compounds in turmeric and three curcuminoids of turmeric showed a synergistic effect on PC3 cells. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Product Details of 33171-05-0).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 33171-05-0

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Virtual screening of functional foods and dissecting their roles in modulating gene functions to support post COVID-19 complications was written by Afroz, Sharmin;Fairuz, Shadreen;Joty, Jahanara Alam;Uddin, Nazim Md.;Rahman, Atiar Md. And the article was included in Journal of Food Biochemistry in 2021.Formula: C19H16O4 The following contents are mentioned in the article:

COVID-19 has become the focal point since 2019 after the outbreak of coronavirus disease. Many drugs are being tested and used to treat coronavirus infections; different kinds of vaccines are also introduced as preventive measure. Alternative therapeutics are as well incorporated into the health guidelines of some countries. This research aimed to look into the underlying mechanisms of functional foods and how they may improve the long-term post COVID-19 cardiovascular, diabetic, and respiratory complications through their bioactive compounds The potentiality of nine functional foods for post COVID-19 complications was investigated through computational approaches. A total of 266 bioactive compounds of these foods were searched via extensive literature reviewing. Three highly associated targets namely troponin I interacting kinase (TNNI3K), dipeptidyl peptidase 4 (DPP-4), and transforming growth factor beta 1 (TGF-β1) were selected for cardiovascular, diabetes, and respiratory disorders, resp., after COVID-19 infections. Best docked compounds were further analyzed by network pharmacol. tools to explore their interactions with complication-related genes (MAPK1 and HSP90AA1 for cardiovascular, PPARG and TNF-alpha for diabetes, and AKT-1 for respiratory disorders). Seventy-one suggested compounds out of one-hundred and thirty-nine (139) docked compounds in network pharmacol. recommended 169 Gene Ontol. (GO) items and 99 Kyoto Encyclopedia of Genes and Genomes signaling pathways preferably AKT signaling pathway, MAPK signaling pathway, ACE2 receptor signaling pathway, insulin signaling pathway, and PPAR signaling pathway. Among the chosen functional foods, black cumin, fenugreek, garlic, ginger, turmeric, bitter melon, and Indian pennywort were found to modulate the actions. Results demonstrate that aforesaid functional foods have attenuating roles to manage post COVID-19 complications. Practical applications : Functional foods have been approaching a greater interest due to their medicinal uses other than gastronomic pleasure. Nine functional food resources have been used in this research for their traditional and ethnopharmacol. uses, but their directive-role in modulating the genes involved in the management of post COVID-19 complications is inadequately studied and reported. Therefore, the foods types used in this research may be prioritized to be used as functional foods for ameliorating the major post COVID-19 complications through appropriate science. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Formula: C19H16O4).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Formula: C19H16O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Triple role of sodium salicylate in solubilization, extraction, and stabilization of curcumin from Curcuma longa was written by Degot, Pierre;Huber, Verena;El Maangar, Asmae;Gramueller, Johannes;Rohr, Lea;Touraud, Didier;Zemb, Thomas;Gschwind, Ruth M.;Kunz, Werner. And the article was included in Journal of Molecular Liquids in 2021.Recommanded Product: Bisdemethoxycurcumin The following contents are mentioned in the article:

Solubility, extraction and stabilization of curcumin extracted from Curcuma longa are still a challenge. Either the solubility power of the extracting solvent mixture is not at its optimum or non-sustainable solvents are used or the curcumin instability against oxidation is a problem. In order to tackle these problems, we consider here a promising alternative solvent medium, which is a ternary system composed of water/sodium salicylate (an anionic, preservative hydrotrope)/ethyl acetate. The effects of the structuring of the system are also studied. The position of the new critical point and the orientation of tie-lines in the liquid/liquid area were determined and further examined via interfacial tension and diffusion ordered spectroscopy (DOSY NMR) measurements. The critical point between the mono-phasic region and the liquid/liquid area is a classical one, around which no special nano-structuring is found, in contrast to some other ternary mixtures with hydrotropes. The system was investigated in terms of its curcumin solubility and its extraction power thereof. Good extraction yields (∼90% of the Soxhlet reference) could be achieved in the area of best solubility Surprisingly, the hydrophobic curcumin shows a significant solubility in systems that contain a significant amount of water in presence of sodium salicylate. These mixtures are far from the critical point but show significant structuring. The solubility is even higher than in pure Et acetate. At the point of highest solubility (water/sodium salicylate/ethyl acetate 7/13/80 weight/weight/w) 15.48 mg of curcuminoids per g Curcuma longa are successfully extracted The partition coefficient in the lower liquid/liquid two-phasic region was determined for a subsequent purification of curcumin by precipitation Surprisingly, curcumin accumulates at the “oil-water” interface in the more polar phase. Sodium salicylate could be removed from the precipitated curcumin by washing it with water (no trace of sodium salicylate has been detected with NMR after the washing process). The preservative effect of salicylate against the oxidative effect of light on curcumin was found to be significant. A better stabilization of curcumin was observed far away from the critical point and was most efficient in the region, where aggregates could be detected. So, extraction, solubilization, and chem. stabilization of a light sensitive substance could be performed using an anti-oxidative hydrotrope. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Recommanded Product: Bisdemethoxycurcumin).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Recommanded Product: Bisdemethoxycurcumin

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Curcuma longa enhances IFN-gamma secretion by natural killer cells through cytokines secreted from macrophages was written by Seo, Sang Gwon;Ahn, Young Je;Jin, Mu Hyun;Kang, Nae Gyu;Cho, Ho Song. And the article was included in Journal of Food Science in 2021.Name: Bisdemethoxycurcumin The following contents are mentioned in the article:

Interferon-gamma (IFN-gamma) regulates the human immune system. To study the interaction between macrophages and natural killer (NK) cells, we established a THP-1 macrophage-conditioned media. Among the 58 natural plant extracts tested, Curcuma longa exerted the strongest IFN-gamma-enhancing effect in NK-92 cells through THP-1 macrophages. C. longa extract (CLE) enhanced IFN-gamma secretion 2.3- and 4.2-fold at 50 and 100 mug/mL, resp. Therefore, we evaluated its IFN-gamma-enhancing effect in vitro. Although NK-92 cells did not produce IFN-γ following treatment with C. longa, enhanced IFN-gamma secretion was observed after treatment with THP-1 macrophage-conditioned media. We hypothesized that the cytokines secreted by the CLE-treated THP-1 macrophages are responsible for stimulating NK-92 cells. Cytokine array results show upregulation of cytokines, including MIP-1alpha, CXCL-1, IL-1beta, PAI-1, and TNF-alpha, in CLE-treated THP-1 macrophages. To determine the cytokines responsible for augmenting IFN-gamma secretion, NK-92 cells were stimulated with MIP-1alpha, CXCL-1, IL-1beta, or PAI-1. ELISA results show that all cytokines induced IFN-gamma production, although the dose response was somewhat varied. High-performance liquid chromatog. anal. of CLE revealed the concentrations of three active curcuminoids, curcumin, demethoxycurcumin, and bisdemethoxycurcumin, as 6.70%, 1.00%, and 0.95%, resp. Their mixture (with concentrations comparable to their occurrence in CLE) exerted an effect similar to that of the whole CLE. Our findings reveal that CLE indirectly stimulated NK-92 cells to secrete IFN-gamma, which is mediated by cytokines produced from THP-1 macrophages. Further, we identified three curcuminoids partly responsible for this IFN-gamma-enhancing effect. Therefore, C. longa can be used as a functional food ingredient owing to its immune-boosting ability. This study demonstrates that CLE stimulates THP-1 macrophages to secrete cytokines, which can in turn stimulate IFN-gamma production by NK-92 cells. A mixture of three curcuminoids present in the extract exerted effects similar to whole CLE, demonstrating that the curcuminoids are partly responsible for the IFN-gamma-enhancing effect of C. longa. Since IFN-gamma is a key regulator of human immune system, these results suggest the potential use of C. longa as an immune-boosting functional food ingredient. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Name: Bisdemethoxycurcumin).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Name: Bisdemethoxycurcumin

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Polyphenolic HRMS Characterization, Contents and Antioxidant Activity of Curcuma longa Rhizomes from Costa Rica was written by Quiros-Fallas, Maria Isabel;Vargas-Huertas, Felipe;Quesada-Mora, Silvia;Azofeifa-Cordero, Gabriela;Wilhelm-Romero, Krissia;Vasquez-Castro, Felipe;Alvarado-Corella, Diego;Sanchez-Kopper, Andres;Navarro-Hoyos, Mirtha. And the article was included in Antioxidants in 2022.Recommanded Product: 33171-05-0 The following contents are mentioned in the article:

Curcuma longa constitutes an important source of secondary metabolites that have been associated with multiple health benefits. For instance, curcumin, demethoxycurcumin and bisdemethoxycurcumin, have been found to perform important biol. activities, such as anti-inflammatory, antioxidant, anticancer, antimicrobial, antihypertensive and anticoagulant. These promising results prompted this research to evaluate the polyphenols of C. longa rhizomes in Costa Rica. The present work reports a comprehensive study on the polyphenolic profile and the contents of the three main curcuminoids as well as the antioxidant activity of extracts from C. longa rhizomes (n = 12) produced in Costa Rica. Through UPLC-QTOF-ESI MS, a total of 33 polyphenols were identified, grouped in eight types of structures. In addition, our findings on the main curcuminoids using UPLC-DAD show all rhizomes complying with total curcuminoids (TC) content established by the USP (USP). At an individual level, samples NW-3 and NE-1 show the higher contents (118.7 and 125.0 mg/g dry material), representing more than twice the average values of the lowest samples. These samples also exhibit the highest Folin-Ciocalteu (FC) reducing capacity results as well as the best DPPH (IC50 15.21 and 16.07μg extract/mL) and NO (IC50 between 52.5 and 54.3μg extract/mL) antioxidant values. Further, Pearson correlation anal. findings indicated pos. correlation (p < 0.05) between TC, CUR with FC results (r = 0.833 and r = 0.867 resp.) and neg. correlation (p < 0.05) between CUR, TC and FC with DPPH results (r = -0.898, r = -0.911, and r = -0.890, resp.) and between NO results and DPPH (r = -0.805, p < 0.05). Finally, results for Principal Component Anal. (PCA) showed composition variability associated with their region of origin with products from the Northeastern (NE) region exhibiting higher average values for FC, TC and antioxidant activities. Further, PCA confirmed that two samples, namely NE-1 and NW-3, stand out by presenting the highest PC1 due to their particularly high TC, CUR and antioxidant activities. Consequently, our findings agree with previous results indicating the importance of C. longa extracts to elaborate products with potential benefits for health, while delivering extracts with higher levels of curcuminoids than previous reports and exhibiting high antioxidant activity. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Recommanded Product: 33171-05-0).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Recommanded Product: 33171-05-0

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem