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The Effects of Some Bis - 1, 2, 4 - Triazole Containing Aminomethyl Derivatives on MDA Levels and Vitamins in Tissues of Rats.

Byline: Naci Omer Alayunt, Mustafa Karatepe, Akif Evren Parlak, Mustafa Ulas, Semra Turkoglu, Sevgi Durna Dastan, Metin Koparir and Sait Celik

Summary: It was reported that the 1, 2, 4-triazole and the derivatives of this compound demonstrate numerous activities in a pharmacological point of view. 1, 2, 4-Triazole moieties were employed in an extensive range of drug candidates, which are therapeutically promising and include anti - inflammatories, anti-anxiety compounds, sedatives, CNS stimulants, antimicrobial agents, and antimycotic ones such as intraconazole, fluconazole and voriconazole. In the current investigation, several aminomethyl derivatives, which contain bis-1, 2, 4-triazole, were newly synthesized and their impacts on the levels of antioxidant vitamins (A, C and E) and malondialdehyde (MDA) we re examined in serum, kidney and liver of rats.

The investigation of the levels of the vitamins (A, C and E) and malondialdehyde (MDA) were performed by calculations in HPLC system. In the study, the observed antioxidant activity revealed that all the analyzed compounds, have promising antioxidant activities, which may be the result of the presence of benzylpiperazine and dipropylamine, and a methylpiperidine moiety as well as the allyl group. Therefore, it was concluded that ample scope exists for further studies.

Keywords: Aminomethyl derivatives; 1,2,4 - triazole; Kidney; Liver; Malondialdehyde (A, E and C) Vitamins.

Introduction

Throughout the recent decades, 1, 2, 4-triazoles' chemical characteristics and derivatives of them, which are fused and heterocyclic, took a significant notice due to the effective and synthetic biological significances they possess. The moieties of 1, 2, 4-Triazole were included in a considerable range of drug candidates, which are therapeutically promising and include anti-inflammatories, anti-anxiety compounds, sedatives, CNS stimulants, anti-microbial [1-3] and anti-mycotic agents (e.g intraconazole, fluconazole and voriconazole) [4, 5]. Several drugs on the market contain the 1, 2, 4-triazole group, such as alprazolam, triazolam, furacilin and etizolam [6-8].

The aim of this paper is to evaluate the levels of antioxidant vitamins (A, C and E) and MDA in the serum, kidney and liver of the rats within experimental and control groups and analyze the data by comparing the other aminomethyl derivatives, which contain bis-1, 2, 4-triazole, with the data obtained from the control group. Additionally, liver and kidney tissues and blood samples were taken from rats with in vivo method, and then the effects of these compounds on antioxidant vitamins A, E, C, and MDA were examined. When Mannich compounds with triazole ring show high levels of biological activity, they may prove important for further research on the pharmaceutics industry. On the other hand, introducing this subject to the literature is also important.

Experimental

Animal Treatment

The following experiments in this study were approved by the Ethical Committee of Firat University for the care and use of laboratory animals. The experiments were carried out on male Long Evans rats, which weigh 200-240 g and 6-8 weekly. The rats were permitted free access to water and food supplies. In the experiment, a 12-hour light-dark cycle was adopted while the room temperature was maintained at 22 +- 1AdegC. Rats were obtained from Firat University Experimental Research Center (FUDAM), and experiments were carried out in the same center. Rats were fed in specially prepared cages in a ventilated environment and the bottoms of the cages were cleaned every day. Feeds were given in special steel pots and water was given in feeding bottles with stainless steel balls. Used animals in the experiments were fed with rat feeds in the form of pellets specially prepared in Elazig feed factory. Care of the rats was continued in this manner through the duration of the experiments.

None of the experiment subjects died for any reason in the course of the study.

Creating groups and implementations

The rats were divided into groups of 5, which constituted 1 control and 4 experimental groups.

The rats were randomly chosen and divided into groups of five, which formed five groups as Control (DMSO), L1 (DMSO + 5,5'-butane-1,4-diylbis{2-[(4-benzylpiperazin-1-yl)methyl]-4-allyl-2,4-dihydro-3H-1,2,4-triazole-3-thione), L2 (DMSO + 5,5'-butane-1,4-diylbis[4-allyl-2-(pyrrolidin-1-ylmetil)-2,4-dihydro-3H-1,2,4-triazole-3-thione), L3 (DMSO + 5,5'-butane-1,4-diylbis{4-allyl-2-[(dipropylamino)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione), L4 (DMSO + 5,5'-butane-1,4-diylbis{4-allyl-2-[(4-methylpiperidin-1-yl)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione) (Figure 1 and Table-1). Aminomethyl derivatives, which contain bis-1, 2, 4-triazole were diluted by using corn oil. Because dimethyl sulfoxide (DMSO) was dissolved in the process as well, the amount was kept below 10% [9]. DMSO, following the dilution with corn oil only, was administered subcutaneously to the control group.

For the derivatives groups, 25 mg/kg including 0.5 ml DMSO was subcutaneously administered for a period of 30 days while implementing three-day intervals throughout the experiment [10].

Table-1: UIPAC Nomenclature of derivatives.

L1###5,5'-butane-1,4-diylbis{2-[(4-benzylpiperazin-1-yl)methyl]-4-allyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

L2###5,5'-butane-1,4-diylbis[4-allyl-2-(pyrrolidin-1-ylmetil)-2,4-dihydro-3H-1,2,4-triazole-3-thione

L3###5,5'-butane-1,4-diylbis{4-allyl-2-[(dipropylamino)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione

L4###5,5'-butane-1,4-diylbis{4-allyl-2-[(4-methylpiperidin-1-yl)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione

The treatments were maintained for 30 days. Then, each rat from the experimental group was anesthetized and decapitated. The blood samples were harvested and placed in storage at -20 0C before the biochemical analysis was conducted. Additionally, the samples of blood were stored in tubes. The samples of blood were subjected to centrifugation process at 4500 x g for 10 minutes. Then, the serum was extracted to be used for the investigation of serum MDA and vitamins. Furthermore, the kidneys and livers were extracted to be analyzed for vitamins and MDA. Samples of 300 mg liver and 300 mg kidney tissues were homogenized in tubes which contain 3 mL acetonitrile/methanol/isopropyl alcohol (2: 1: 1, v/v/v) and the samples were subjected to vortex process for 30 seconds and they were centrifuged at 6000 x g for 10 min. After these practices, the supernatants were placed to auto sampler vials to be used in the HPLC system.

Chemicals

In implementations, Bis-1, 2, 4-triazole which contains derivatives of aminomethyl were used. Inspired by the ligand term, coding was applied on the compounds in the form of L1-4. These compounds were synthesized and characterized by the researchers of Firat University Faculty of Science, Department of Organic Chemistry [11]. The synthesized compounds bearing bis-1,2,4-triazole ring were characterized by elemental analysis, IR, 1H and 13C NMR spectral data. The IR spectra were measured with Perkin-Emler spectrum one FT-IR spectrophotometer. Electronic spectral studies were conducted on a Shimadzu model UV-1700 spectrophotometer in the wavelength 1100-200 nm. The 1H and 13C spectra were taken on Bruker AC-300 and Bruker AC-400 NMR spectrometer operating at 400 MHz for 1H, 100 MHz for 13C NMR.All solvents used in the study were analytical grade reagents.

Bis-1, 2, 4-triazole which contains derivatives of aminomethyl employed in the practices were synthesized and their characteristics were determined by Koparir et al. [11]. The derivatives' structures and IUPAC Nomenclature were presented below (Fig. 1 and Table-1).

Analytical Methods

The liquid chromatography system (Shimadzu) adopted in the study had two LC-20AD pumps, a Sil20A auto sampler, a DGU-20A5 degasser, an SPD-M20A DAD system, an RF-10AXL FLD system and a CTO-10As VP column oven. The connection of the two detectors was established in series.

Determination of MDA and Vitamin C levels of Tissues

0.3 grams of kidney and liver tissue samples were extracted and they were homogenized in a mixture of 1.5 ml distilled water and 1.5 ml of HClO4 (0.5 M). Following this process, the tissue samples were subjected to centrifugation at 4500 RPM for 25 min. Following the centrifugation of the mixture, samples amounting to 20 ul were extracted from the supernatants carefully. Then, they were transferred into the HPLC system by injections. For vitamin C and MDA, the analysis was conducted at 254 nm. The acquired results were calculated as nmol MDA/g tissue and ug/g for vitamin C [12].

Determination of the levels of Vitamin A and E of Tissues

Samples of 0.3 grams of kidney and liver tissues were extracted and combined with 4 ml of ethyl alcohol, which contains 1% H2SO4, in order to precipitate the proteins. Following the vortexes, the samples were subjected to centrifugation at 4500 RPM for 25 min. Following the centrifugation of the mixture, the n-hexane amounting to 0.3 ml was included and the tubes were subjected to vortex and centrifugation again. When the centrifugation process was concluded, the hexane phase was carefully extracted to a glass tube. Then, the n-hexane amounting to 0.3 ml was included and the mixture was subjected to centrifugation again. The Hexane phase was evaporated by using nitrogen flow. Then, the residue was dissolved in 100 uL of methanol and 20 ul of the sample was transferred into the HPLC system by injection. The analysis was conducted at 296 nm for vitamin E, and at 326 nm for vitamin A. The acquired results were expressed as ug/g [12].

Determination of Serum MDA levels and Vitamin C

A sample of 0.3 ml of serum was extracted. Then, 0.3 mL of 0.5 M HClO4 was included in the mixture in order to precipitate the proteins. Afterward, the mixture was vortexed and the process was completed by adding pure water to a total volume of 1 ml. After 15 minutes, the mixture was centrifuged at 2500 RPM/minute and 20 ul of the sample was carefully extracted from the supernatants and transferred into the HPLC system by injection. The analysis was conducted at 254 nm for MDA and vitamin C. The acquired results were expressed as ug/mL for MDA and vitamin C [13].

Determination of Serum Vitamin E and A levels

Samples of 0.3 ml of serum were extracted and included in 0.3 ml of ethyl alcohol, which contains 1%H2SO4, in order to precipitate the proteins. After the samples were vortexed, they were subjected to centrifugation at 2500 RPM for 5 minutes. Following the centrifugation, 250 ul of n-hexane was included in the mixture. Then, the tubes were subjected to vortex and centrifugation again. When the centrifugation process concluded, the hexane phase was carefully extracted to a glass tube. Then, a 250 ul of n-hexane was included and the mixture was subjected to centrifugation again. The Hexane phase was evaporated by using nitrogen flow. A 100 ul of methanol was used to dissolve the residue and a sample of 20 ul was transferred to the HPLC system by injection. The analysis was conducted at 296 nm for vitamin E and 326 nm for vitamin A. The acquired results were expressed as ug/mL for vitamin A and E [14, 15].

Statistical Analysis

In this study, SPSS 15.0 software was adopted for the statistical analysis process. The results of the experiments were expressed as mean +- S.D. The comparisons conducted among the control group and the experimental groups were performed by using the Tukey and ANOVA tests.

Results and Discussion

In the current study, antioxidant vitamins and MDA were investigated in the serum, kidney and liver tissues acquired from the healthy tissues of rats by using the HPLC system. In the liver tissue, it was observed that the vitamin C level was elevated in the L1 group and similar values were obtained in L3 and L4 groups compared to the control group. Additionally, vitamin C level was observed to be decreased in L2 group. It was concluded that L2 group demonstrated a statistically meaningful difference compared to the control and the other experimental groups. It was also observed that Levels of vitamin A and E were observed to be similar in all groups, except in L2 group, compared to the data of the control group. It was also noted that the L2 group had significantly decreased levels. Thus, it was concluded that L2 group demonstrated a statistically significant difference compared to the control and other groups.

MDA levels were observed to be decreased in L1 group and similar values were observed in L4 and L5 groups. Furthermore, it was observed that MDA level increased in the L2 group. Thus, it was concluded that all of the groups demonstrated statistically meaningful differences compared to each other and the control group (Table-2).

In the examined kidney tissue, it was observed that the level of vitamin C was elevated in the L1 group and similar values were obtained in L3 and L4 groups compared to the control group. Additionally, vitamin C level was observed to be significantly decreased in L2 group. Thus, it was concluded that L2 group demonstrated a statistically significant difference compared to the control and other experimental groups. Furthermore, the level of vitamin A was observed to be increased in the L1, L3 and L4 group. Nevertheless, in the observation of L2 group, vitamin A level was observed to be decreased. Vitamin E levels were observed to be similar in all of the groups, except in L2 group, comparison to the data of the control group. Furthermore, it was noted that the levels were significantly decreased in the L2 group. Thus, it was concluded that L2 group demonstrated a statistically significant difference compared to the control and other groups.

Moreover, the level of MDA was observed to be elevated in the L2 group and this condition indicated that there was a statistically meaningful difference compared to the other groups. Additionally, MDA level was observed to be similar in the L1, L3 and L4 groups compared to control group. However, this state did not pose a statistically meaningful difference in the experimental groups (Table-3).

In the evaluation of the serum samples, it was observed that vitamin C levels were increased in the L1, L3 and L4 group. However, it was decreased in the L2 group in comparison to the data of the control group. Additionally, the level of vitamin C was observed to be decreased significantly in L2 group. Thus, it was concluded that L2 group demonstrated a statistically significant difference in comparison to the control and other groups. It was also observed that the levels of Vitamin E and A were elevated by similar values in all of the groups, except in the L2 group in comparison to the data of the control group. It was observed that the level decreased significantly in the L2 group and this state indicated a statistically meaningful difference compared to the control and other groups. Furthermore, it was observed that the MDA level was elevated in the L2 group and MDA levels were observed to be similar in the L4 group.

Additionally, it was observed that MDA levels increased in the L1 and L3 groups compared to the data of the control group. Thus, this state indicated a statistically meaningful difference in control and experimental groups (Table-4).

Table-2: The contents of vitamins (A,C,E) and MDA levels in the liver tissue of experimental and control group rats. Results are given as mean +- standard deviation (SD), n=5.

Parameters###Control###L1###L2###L3###L4###P

C Vitamin (ug/g)###14,20+-2,27ab###17,98+-2,00a###9,30+-2,74b###15,58+-1,37ab###15,32+-1,08ab###*

MDA (nmol/g)###5,26+-0,60b###4,30+-0,32b###10,24+-0,55a###5,10+-0,74b###5,06+-0,94b###***

A Vitamin (ug/g)###0,21+-0,01a###0,19+-0,01a###0,12+-0,01b###0,19+-0,02a###0,19+-0,02a###***

E Vitamin (ug/g)###0,62+-0,08a###0,63+-0,09a###0,23+-0,05b###0,62+-0,04a###0,62+-0,04a###**

Table-3: The contents of vitamins (A,C,E) and MDA levels in the kidney tissue of experimental and control group rats. Results are given as mean +- standard deviation (SD), n=5.

Parameters###Control###L1###L2###L3###L4###P

C Vitamin###10,40+-2,16ab###14,36+-1,84ab###6,58+-0,79b###11,88+-0,39ab###10,68+-3,22ab###*

MDA (nmol/g)###4,00+-0,42b###3,28+-0,67b###6,83+-0,22a###3,68+-0,59b###3,86+-0,88b###**

A Vitamin###0,18+-0,01ab###0,23+-0,03a###0,11+-0,02b###0,24+-0,03a###0,25+-0,02a###***

E Vitamin###0,68+-0,04a###0,68+-0,02a###0,38+-0,06b###0,71+-0,06a###0,69+-0,07a###**

Table-4: The contents of vitamins (A,C,E) and MDA levels in the serum tissue of experimental and control group rats. Results are given as mean +- standard deviation (SD), n=5.

Parameters###Control###L1###L2###L3###L4###P

C Vitamini###3,80+-0,22a###3,96+-0,30a###2,43+-0,30b###3,95+-0,08a###3,90+-0,23a###***

MDA (nmol/g)###0,54+-0,02ab###0,37+-0,06bc###0,73+-0,01a###0,37+-0,10bc###0,52+-0,03abc###***

A Vitamini###0,56+-0,02a###0,59+-0,02a###0,31+-0,09b###0,52+-0,06a###0,55+-0,02a###**

E Vitamini###3,39+-0,26ab###3,42+-0,23a###2,49+-0,17b###3,45+-0,23a###2,97+-0,27ab###*

According to these results, it was inferred that among all of the synthesized derivative compounds, L1 with benzylpiperazine moiety demonstrated the most favorable biological activity compared to the others. Thus, it was determined that the presence of benzylpiperazine moiety was fundamental for high biological activity. Among the observed compounds, L2 with pyrrolidine moiety demonstrated no antioxidant activity; on the contrary, it demonstrated an oxidant activity. It was observed that L2 increased MDA level and decreased vitamin levels. Thus, it was concluded that L2 compound increased the free radical formation.

In the study carried out by Turkoglu et al. (2006), the impact of schiff bases on fatty acids and lipophilic vitamins in several tissues (kidney, liver, heart and testis tissues) of rats were investigated and it was reported that no notable difference existed (p>0.05) in the amount of K2, retinol vitamin, and cholesterol among the examined groups. Vitamin K1 and vitamin D2 amounts were reported to be elevated (p< 0.05) in the Ni and Mn complex groups considerably compared to the data of the control group. Furthermore, it was reported that the [alpha]-tocopherol amount was elevated in both the Ni and Co complex groups in comparison to the control group. However, this elevation was parallel with the amounts in the same groups (p<0.05). Moreover, it was reported that the amount of D3 was decreased in the Ni, Co and Zn complex groups in comparison to the control group. Nevertheless, this decrease was observed to be parallel to the amounts in the same groups (p<0.05).

Amounts of Vitamin K1 were reported to be decreased (p< 0.05) in the ligand, Cu complex groups compared to the other groups while the [alpha]-tocopherol amount was reported to be decreased (p< 0.05) in the ligand, Zn and Mn complex groups compared to the other groups. In the examination of the amount of ergosterol, it was reported that the amount was decreased (p<0.05) in the Cu, Ni and Co complex groups in comparison to the other groups [16].

It was reported on the examination of the control group values and the results of the compounds, it was noted that the compound L2 decreased the level of vitamins A, E, C significantly compared to the data of the control group and other compounds. In the groups where other test compounds were implemented, the values obtained were found to be close to the control group values. Thus, no statistically notable difference was determined. On the other hand, considering the effects on MDA, statistically notable differences were found in the test groups of L1, L3, and L4, where MDA levels were determined as close to the control. The compound L2 was determined to increase MDA levels significantly.

In another study, when they evaluate the results in tissue and blood samples, it is seen that MDA levels increased significantly relative to the control in the group where the test compound L2 was implemented. The L2 compound also decreased the levels of the vitamins. Generally, in other test groups, while there was an activity that increased MDA levels compared to the control group, levels were close to the control group in terms of vitamins [17].

According to the results of other groups and derivatives, the increase in free radical formation causes an increase in MDA levels while causing a decrease in vitamin E levels [18-20]. In another study where researchers [21] gave antioxidant substances (naringin and probucol) to rabbits with diet, they observed that these substances did not affect plasma MDA and the level of vitamin A while increasing the level of vitamin E by decreasing its use. Accordingly, in our study, it can be put forward that the compound L2 increases MDA by showing the radical effect on the tissue. Therefore, vitamins decrease by consumption. On the contrary, it can be suggested that the other test compounds also decreased MDA by showing fairly antioxidant effects, and therefore, their use decreased as the vitamins were not consumed. Hence, this resulted in values that were close to the control or slightly higher.

Conclusion

In conclusion, the results of the study indicate the successful synthesis and demonstration of the biological activity of new bis-1, 2, 4-triazole containing aminomethyl derivatives. In the study, the observed antioxidant activity revealed that all the analyzed compounds, except L2, have promising antioxidant activities, which may be the result of the presence of benzylpiperazine and dipropylamine, and a methylpiperidine moiety as well as the allyl group. Therefore, it was concluded that ample scope exists for further studies.

References

1. N. D. Heindel and J. R Reid, 4-Amino-3-mercapto-4H-1, 2, 4-triazoles and propargyl aldehydes: A new route to 3-R-8-aryl-1, 2, 4-triazolo[3, 4-b]-1, 3, 4-thiadiazepines, J Heterocycl Chem. 17, 1087 (1980).

2. B. S. Holla, B. Kalluraya, K. R. Sridhar, E. Drake, L. M. Thomas, K. K. Bhandary and M. S. Levine, Synthesis, structural characterization, crystallographic analysis and antibacterial properties of some nitrofuryl triazolo [3, 4-b]-1, 3, 4-thiadiazines, Eur J Med Chem. 29, 301 (1994).

3. V. Mathew, J. Keshavayya and V. P. Vidya, Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activities of some substituted 1, 2, 4-triazolo[3, 4-b]-1, 3, 4-thiadiazoles, Eur J Med Chem. 41, 1048 (2006).

4. The Merck Index, 12rd Ed., Merck Co. Inc., USA, (1996).

5. J. Haber, Present status and perspectives on antimycotics with systemic effects, Cas. Lek. Cesk. 140, 596-604 (2001).

6. A. Brucato, A. Coppola, S. Gianguzza and P. M Provenzano, Triazolam: characteristics of its depressive action, Boll Soc Ital Biol Sper. 54, 1051 (1978).

7. D. L. Coffen and R. I. Fryer, U.S. Patent, 3, 849 434 (1974); Chem Abstr. 82, 73044v (1975).

8. M. Shiroki, T. Tahara, and K. Araki, Jap, Patent 75100096 (1975); Chem Abstr. 84, 59588k. (1976).

9. A. Varvaresou, A. Tsantili-Kakoulidou, T. Siatra-Papastaikoudi, et al. Synthesis and Biological Evaluation of Indole Containing Derivatives of Thiosemicarbazide and Their Cyclic 1, 2, 4-Triazole and 1, 3, 4-Thiadiazole Analogs, Arzneimittel forschung. 50, 48 (2000).

10. N. Cesur, S. Birteksoz and G. Otuk, Synthesis and biological evaluation of some new thiosemicarbazide, 4-thiazolidinone, 1, 3, 4-oxadiazole and 1, 2, 4-triazole-3-thione derivatives bearing imidazole [1, 2-a]pyridine moiety, Acta Pharm Turcica. 44, 23 (2002).

11. M. Koparir and C. Orek, Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2, 4-dihydro-3H-1, 2, 4-triazole-3-thiones, Chem Sci Trans. 2, 181 (2013).

12. N. Cetinkaya and H. Ozcan, Postpartum relationship of beta carotene and vitamin A between placenta, blood and colostrum in cows and their newborns, Comp, Biochem, Physiol. A Comp. Physiol. 100, 1003 (1991).

13. M. Karatepe, Simultaneous determination of ascorbic acid and free malondialdehyde on human serum by HPLC-UV, LC-GC North America. 22, 362 (2004).

14. G. L Catignani and J. G. Bieri, Simultaneous determination of retinol and alpha-tocopherol in serum or plasma by liquid chromatography, Clin. Chem. 29, 708 (1983).

15. S. M. Henning, M. E. Swendseid, B. T. Ivandic and F. Liao, Vitamins C, E and A and heme oxygenase in rats fed methyl/folate-deficient diets, Free Radic, Biol. Med. 23, 936 (1997).

16. S. Turkoglu, A. E. Parlak, I. Yildirim, Y. Karagozoglu, N. O. Alayunt, The Effects Hydroxyurea Derivative Schiff Bases on Fatty Acids and Lypophilic Vitamins in Liver of Rats, Digest J. Nano. Biostructures. 9, 159 (2014).

17. A. E. Parlak, S. Celik, M. Karatepe, S. Turkoglu, N. O. Alayunt, S. D. Dastan, M. Ulas, S. Sandal, S. Tekin and M. Koparir, Investigation of biological effects of some Mannich Bases containing Bis-1, 2, 4-Triazole, Cell. Mol. Biol. 62, 46 (2016).

18. A. B. Bott and M. A. Green, Effect of Glutation Depletion on The Biodistribution of Cu (PTSM) in Rats, Int. J. Rad. Appl. Inst. 18, 865 (1991).

19. A. T. Diplock, Antioxdant Nutrients and Disease Prevention: An Overview. Am, J. Chim. Nutr. 53, 1895 (1991).

20. E. L. Novelli, A. M. Silva, P. J. Monterio, L. B. Sacomani and J. L. Novellif, Free Radical Production by Azomethine H: Effectson Pancreatic and Hepatic Tissues, Free Radic, Res. 26, 319 (1997).

21. J Seon-Min, J Song-Hae, J Moon-Kyoo, K Yeon-Hee, N Kyung-Tak, J Tae-Sook, et al., Comparison of antioxidant effects of naringin and probucol in cholesterol-fed rabbits, Clin. Chim. Acta. 17, 181 (2003).
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