Studies On The Preparation And Bioactivity Of Naringenin Inclusion Compound And Metal Complexes

The flavonoid naringenin(4',5,7-trihydroxy flavanone),has numerous pharmacological activities such as antioxidant activity,effective eliminating the reactive oxygen species(ROS),inhibition of monoamine oxidase generation,effective prevention and treatment of cancer.Nar can dissolve in organic solvents including methanol,ether and benzene,and can not dissolve in water.Also,Nar has tendencies to oxidation and isn't steady in water and in the air.Therefore,despite its various pharmacological activities,the shortcomings of oxidation and poor solubility in water limits the application of Nar in medicine.In this article,we firstly prepared naringenin-sulfobutyl ether-beta-cyclodextrin(Nar-SBE-?-CD)inclusion complex.The ultraviolet detection,IR,XRD and TG have been applied to characterize and verify the formation of this complex.The phase solubility studies verified the formation of a 1:1 inclusion complex between Nar and SBE-(3-CD,and the solubility of Nar increased 32 times due to the inclusion associations.The optimum preparation condition for the inclusion complex were established as follows:the weight ratio of Nar and SBE-P-CD was 1:23.49,concentration of methanol was 100%,temperature was 30? and the time of preparation was 2h.of For three batches of Nar-SBE-beta-CD inclusion complex,the encapsulation efficiency was 68.73%,71.26%,69.68%respectively,and the average encapsulation efficiency was 69.89%,RSD is 1.83%.Naringenin-copper(Nar-Cu(II))complex and naringenin-zinc(Nar-Zn(II))complex also were prepared in the second part.The maximum absorption peak of the coordination compound in UV(293nm,298nm)significantly shifted compared with naringenin(289 nm).The result of elemental analysis showed that the 2:1 complexes containing three water had been formed between ligand and the metal,and the complex formulation is M(C15H11O5)2·3H2O(M=Cu,Zn).IR and TG also were used to verify the formation of inclusion complexes.Free radical scavenging tests showed that Nar-Cu(?)complex(IC50 = 0.293?mol/mL)have the strongest scavenging activity of 02-,but Nar-SBE-?-CD and the physical mixture did not show significant scavenging activity.Nar-SBE-?-CD showed the strongest scavenging activity of ABTS and the order of ABTS scavenging activity is,Nar-SBE-?-CD inclusion complex>physical mixture>Vitamin C>Nar-Cu(?)>Nar-Zn(?)>Nar.Finally,three strains of C.elegans had been used as model organism to evaluate the toxicities biological activities of Nar-SBE-?-CD,Nar-Cu(?),and Nar-Zn(?).The results showed that Nar-Cu(?)had significant suppressed over activated Ras pathway.The survival curves showed that Nar-Cu(?)significantly increased the survival rate,mean life span and the maximum life span of C.elegans.These results indicated that the Nar-Cu(?)maybe a potential anti-tumor and anti-aging drug candidate.