| Turmeric is an important traditional Chinese medicine. The curcuminoids and turmeric oil posessing many bioactivities are its main components, which have wide application prospects in medical industry and food industry. Extraction of curcumin, demethoxycurcumin and bisdemethoxycurcumin was studied with ionic liquids microwave assisted extraction (ILs-MAE), which provided a new way of plant active components. In order to realize ecological utilization of turmeric residue, the turmeric feed additive was prepared, which not only increased economic benefits of enterprise and decreased enviromental pollution, but also overcomed side influence on food safety and human health due to use of drug additive.The application of curcumin is limited due to poor solubility in water, and poor stability.The inclusion of curcumin and (3-CD derivatives and properties of complexes were studied, which provided theoretical basis for development of water-solubility preparation of curcumin.Structure modification is an effective approach to improve bioactivity of drug. Curcumin was used as lead compound to design and synthesize curcumin analogues. Bioactivities and structure-activity relationship of curcumin analogues were studied, and new compounds possessing obvious antibacterial activity was obtained, which provided scientific foundation for research of curcumin antimicrobial agents.In the present work, the study results can summerized as following aspects:(1) Extraction of curcumin, demethoxycurcumin and bisdemethoxycurcumin using ILs-MAEHPLC analysis of curcumin, demethoxycurcumin and bisdemethoxycurcumin was established.The regression models of extraction yield for curcumin, demethoxycurcumin and bisdemethoxycurcumin using ILs-MAE were obtained by Box-Behnken experiment design and Design-Expert. The regression model of extraction yield for curcumin was Y1=2.30+0.048×A+0.039×B+0.051×C+0.050×A×-0.025×A×C+0.027×B×C-0.075×A2-0.097×-0.087×C2, the regression model of extraction yield for demethoxycurcumin was Y2=0.86+0.024×A+0.026×B+0.020×C+0.033×B+0.01×B×C-0.017×A2-0.027×B2-0.035×C2, and the regression model of extraction yield for bisdemethoxycurcumin was Y3=0.70+0.024×A+0.032xB+0.00625×C-0.018×B×C-0.019xA2-0.057×B2+0.011×C2.The optimization extraction technologies of curcumin, demethoxycurcumin and bismethoxycurcumin were obtained. The predicted extraction yield of curcumin model was 2.29% under optimization extraction conditions of extraction time 15 min, ratio of liquid to material 17.44:1 and extraction temperature 62.29?, the predicted extraction yield of demethoxycurcumin model was 0.90% under optimization extraction conditions of extraction time 15 min, ratio of liquid to material 19.98:1 and extraction temperature 66.40?, and the predicted extraction yield of bisdemethoxycurcumin model was 0.725% under extraction conditions of extraction time 15 min, ratio of liquid to material 15:1 and extraction temperature 70?. The extraction yields showed good reproducibility with the predicted values under optimized extraction conditions.Comparison of three extraction methods was carried out. The results showed that ILs-WAE was better than solvent extraction and microwave-assisted extraction.(2) Inclusion of curcumin and ?-cyclodextrin derivatives and the properties of complexesThe inclusion of curcumin and ?-CD derivatives was investigated by spectrophoto-metry. The results showed a 1:1 complex was formed between curcumin and ?-CD derivatives, the apparent formation constants decreased with the increase of temperature for curcumin-?-CD complex and curcumin-DM-?-CD complex, and the apparent formation constants increased with the increase of temperature for curcumin-RM-?-CD-m complex, and the optimization pH of inclusion process was 3.The main driving force for complex formation of curcumin and ?-CD derivatives was revealed from thermodynamics parameters. The formation of curcumin-?-CD complex and curcumin-DM-?-CD complex was a spontaneous and exothermic process, the main driving force was enthalpy, and lowering temperature was beneficial to inclusion process. However, the formation of curcumin-RM-?-CD-m complex was a spontaneous and endothermic process, the main driving force was entropy, and raising temperature was beneficial to inclusion process. The formation of complex was confirmed by IR and TGA.The embedding rate of curcuminoids was 87.34% under optimization conditions of inclusion temperature 50?, inclusion time 1.5 h and Wcurcuminoids: wp_cD=1:30. Afer embedded, the solubility of curcuminoids was 3.0 mg/mL, and thermal stability, photostability and oxidative resistance of curcuminoids were improved.(3) Synthesis and bioactivities of curcumin derivativesMonomethyl fumarate, monoethyl fumarate, monobutyl fumarate and monopentyl fumarate were synthesized, and their yields were 85.8%,91.3%, 65.6% and 69.4% respectively under the optimization conditions. Their structures were confirmed by IR and EA.Four acylchloridizing products of monomethyl fumarate, monoethyl fumarate, monobutyl fumarate and monopentyl fumarate with thionyl chloride were obtained, and their yields were 83.64%,86.37%,81.50% and 85.41% respectively under the optimization conditions.The curcumin-fumarate derivatives, Cur-MMF, Cur-MEF, Cur-MBF and Cur-MPF, were synthesized, and their yields were 80.5%,83.7%,81.2% and 85.4%respectively under optimization conditions. Their structures were characterized by IR, 1H NMR and 13C NMR. Four compounds were not reported.The antioxidation experiment results showed Cur-MMF,Cur-MEF,Cur-MBF and Cur-MPF possessed antioxidant activity, IC50 of four compounds for scavenging DPPH-were 164.14,166.98,171.97 and 175.10 ?g/mL respectively, and antioxidant activity slighly decreased with prolongation of fumarate alkyl carbon chain.The antibacterial experiment results showed that Cur-MMF, Cur-MEF, Cur-MBF and Cur-MPF possessed good antibacterial activity. The MIC of four compounds was determined for aureus staphylococcus, escherichia coli, penicillium sp and aspergilluse Niger. The MIC of Cur-MMF was 1.5,1.5,0.5 and 1.0 g/L respectively, the MIC of Cur-MEF was 1.5,1.5,0.5 and 1.0 g/L respectively, the MIC of Cur-MBF was 1.0,1.0,0.25 and 1.0 g/L respectively, and the MIC of Cur-MPF was 0.5 v 0.5? 0.25 and 1.0 g/L respectively. The, ?-unsaturated carbonyl group unit was the antibacterial function domain of these compounds, and the antibacterial activity increased with prolongation of fumarate alkyl carbon chain.(4) Synthesis of curcumin analogues containing chalcone unit and its bioactivities13 curcumin analogues containing chalcone unit and 3 chalcone derivatives were synthsized and their structures were confirmed by 1H NMR and 13C NMR. Compounds 2,3,4,6,8,9,10,12 and 13 were not reported.The inhibitory activities of curcumin analogues against white rot fungus, aureus staphylococcus, escherichia coli were deterimned. The results showed that curcumin analogues possessed significant inhibitory activity for white rot fungus, and IC50 of compounds 2,11,13 against white rot fungus were 15.61,15.35 and 12.43?g/mL respectively. The inhibitory effect of compound 11 was the best for aureus staphylococcus, and its IC50 was 105.38?g/mL.The DPPH-scavenging activity of curcumin analogues was determined. The results indicated that the DPPH-scavenging activity of compound 13 was the best, and its IC50 was 90.51?g/mL.(5) Preparation and application effect of turmeric feed additiveThe turmeric feed additive was prepared with turmeric residue, ginseng residue and tea residue.After the turmeric feed additive added to basal diet, the apparent and true metabolic rate of crude protein and amino acid, and their utilization ratio increased. The apparent metabolic rate in 4%turmeric residue group (69.16%) was highest, and very significantly higher than that of control group and the other groups.After the turmeric additive was added to basal diet, T3 and T4 content of broiler serum increased. T3 content of broiler serum in 4% turmeric residue group (1.28 ng/mL) was significantly higher that of control group (0.67 ng/mL). GH content of broiler in 4% turmeric residue group (0.50 ng/mL) was the highest, and significantly higher than that of control group. The turmeric feed additive decreased TG and CHO of broiler serum, and TG content of broiler serum in 7 test groups was very significantly lower than that of control group. The turmeric feed additive increased TP and ALB content of broiler serum at different degree. TP content of 4% turmeric residue group and ALB content of 4% compound ? was significantly higher than that of control group in broiler serum. GGT, ALT and AST of broiler serum in 7 test groups were significantly lower than that of control group, and there was no significant effect for GLU.The test group with turmeric feed additive could improve growth performance of broiler at different degree, and decrease ratio of feed to gain. Compaered with that of control group, ratio of feed to gain of 4% turmeric group was 2.47, and decreased by 4.63%. The growth performance of compound I was better than that of compound II at same level.The turmeric feed additive could improve slaughter performance of broiler at diffe-rent degree. The slaughter performance of 7 test groups was better than that of control group, and content of fat and amino acid increased in breast muscle and leg muscle.The turmeric feed additive regulated metabolism of protein and fat by regulating secretion of T3, T4, GH, TG and CHO, and increased conversion rate of feed, then improved growth performance of broiler. |
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