SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL STUDIES OF SOME DIVALENT METAL(II) COMPLEXES DERIVED FROM 1-[(4-IODO-PHENYLIMINO)-METHYL]-NAPHTHALEN-2-OL SCHIFF BASE
DOI:
https://doi.org/10.33003/fjs-2021-0503-681Keywords:
Schiff base, Complexes, azomethine, 4-Iodoaniline, 2-hydroxy-1-naphthaldehydeAbstract
Schiff base derived from condensation of 2-hydroxy-1-naphthaldehyde and 4-iodoaniline was synthesized and used for the preparation of Co(II) and Ni(II) complexes. The complexes were characterized by IR, Powder-XRD, Solubility test, thermal analysis, conductivity measurement, magnetic susceptibility and elemental micro analysis. IR study indicated a strong band in the spectra of the Schiff base at 1603 cm-1 assigned to azomethine v(C=N) stretching vibration. It shifted to new frequency regions (1618 - 1622 cm-1) in the spectra of the complexes indicating the formation of the desired complexes. The decomposition temperatures of the complexes are in the range of (260-265) oC , molar conductance values are in the range of (4.51 -11.31) Ohm-1cm2 mol-1, indicating non electrolytic nature of the synthesized complexes in DMF. Magnetic susceptibility measurement indicated that Co(II) and Ni(II) complexes are paramagnetic and exhibit magnetic moment in the range of 2.92-3.24 BM, the values correspond to the square planar geometry. The Powder x-ray diffraction analysis showed the patterns of the metal(II) complexes were different from the reactants, signifying that reactants were changed to product. The CHN analysis results show the formation of 1:2 metal to ligand ratio. The synthesized compounds have been studied for antimicrobial activity using pathogenic bacteria and fungal pathogens by disc diffusion method. The results indicated that metal complexes (10 – 15 mm inhibition zone) are more active compared to Schiff base (8 – 12 mm inhibition zone) against the test organisms.
References
Adebona, M. B., Ogunsua, A. O. and Ologunde, M. O. (1988). Development of Conophor nut-based cereal snack food 1-Biscuits. J Food and Agric, 2: 123-136.
Ajaiyeoba, E. O. and Fadare, D. A. (2006). Antimicrobial potential of extracts and fractions of the African walnut–Tetracarpidium conophorum. African Journal of Biotechnology, 5(22): 2322-2325.
Akomolafe, S. F., Oboh, G., Akindahunsi, A. A. and Afolayan, A. J. (2015). Antiperoxidative Activity of Tetracarpidium conophorum Leaf Extract in Reproductive Organs of Male Rats. Evid Based Compl. & Altern, Med, Volume 2015, Article ID 798491, 8 Pages.
Akomolafe, S. F., Oboh, G., Oyeleye, S. I. and Olasehinde, T. A. (2017). Toxicological Effects of Aqueous Extract from African Walnut (Tetracarpidium conophorum) Leaves in Rats. J Evid-Based Compl & Altern Med, 22(4): 919-925.
Akpan, O. U. and Anietie, A. A. (2014). Aqueous extract of Tetracarpidium conophorum increases FSH and LH plasma levels and impairs sperm indices in albino Wistar rats. Intl J Biomed Res, 5(10), 631-635.
Amaeze, O. U., Ayoola, G. A., Sofidiya, M. O., Adepoju-Bello, A. A., Adegoke, A. O. and Coker, H. A. B. (2011). Evaluation of Antioxidant Activity of Tetracarpidium conophorum (Mull. Arg) Hutch & Dalziel Leaves. Oxid. Med Cellul. Longevity, Article ID 976701, 7 pages.
Anosike, C. A., Abonyi, O. and Etaduovie, S. E. (2015). Effect of Methanol Extract of Tetracarpidium conophorum Seed on Indomethacin-Induced Ulcer in Rats. Glob Veterinaria, 14(6): 848-852.
Awe, I. S. and Sodipo, O. A. (2001). Purification of saponins of root of Bhlighia sapida KOENIG HOLL. Nig J Biochem & Mol. Biol (Proceedings Supplement), 16:201s-204s.
Ayodele, O. B. (2003). Nutrition in Nigeria, Ibadan, Catoon Publishers. IRJP, 5: 28-17.
Ayoola, P. B., Onawumi, O. O. and Faboya O. O. P. (2011). Chemical evaluation and nutritive values of Tetracarpidium conophorum (Nigerian walnut) seeds. J Pharm. and Biomed Sci, 11(5): 1 – 5.
Bello, O. S., Olaifa, F. E., Emikpe, B. O. and Ogunbanwo, S. T. (2013). Potentials of walnut [Tetracarpidum conophorum Mull. Arg] leaf and onion [Allium cepa Linn] bulb extracts as antimicrobial agents for fish. Afr J Microbiol Res, 7(19): 2027–2033.
Bogdanis, G. C. (2012). Effect of Physical Activity and Inactivity on Muscle Fatigue. Frontiers in Physiol, 3: 142.
Brooks, G. A. (1986). The lactate shuttle during exercise and recovery. Med Sci Sports Exerc, 18: 360–368.
Brunner, J. H. (1984). Direct spectrophotometer determination of saponin. Anal Chem, 34: 1314-1326.
Carvalho, J. F., Masuda, M. O. and Pompeu, F. A. (2005). Method for diagnosis and control of aerobic training in rats based on lactate threshold. Comp Biochem Phys, A140, 409–413.
Chae, S. W., Mitsunaga, F., Jung, S. J., Ha, K. C., Hong-Sig, H. S., Jang, S. H. and Nakamura, S. (2015). Mechanisms Underlying the Antifatigue Effects of the Mycelium Extract of Cordyceps (Paecilomyces hepiali, CBG-CS-2) in Mice in the Forced Swimming Test. Food and Nutrition Sciences, 6: 287-298.
Chang, Q., Miao, X., Ju, X., Zhu, L., Huang, C., Huang, T., Zuo, X. and Gao, C. (2013). Effects of Pulse Current on Endurance Exercise and Its Anti-Fatigue Properties in the Hepatic Tissue of Trained Rats. PLoS ONE, 8(10): e75093.
Chikezie, U. (2017). Phytochemical and Proximate Compositions of Tetracarpidium Conophorum (African Walnut) Seeds. Intl J of Res Studies in Biosci (IJRSB), 5(10): 25-31.
Cigremis, Y., Turel, H. and Adiguzel, K. (2009). The effects of acute acetaminophen toxicity on hepatic mRNA expression of SOD, CAT, GSH-Px, and levels of peroxynitrite, nitric oxide, reduced glutathione, and malondialdehyde in rabbit. Mol Cellul Biochem, 323(1-2): 31-38.
Coyle, E. F., Hagberg, J. M. and Hurley, B. F. (1983). Carbohydrate feeding during prolonged strenuous exercise can delay fatigue. J Appl Physiol, 55(1 Pt 1), 230.
Dada, E. O. and Ogundolie, O. O. (2016). In vivo Antiplasmodial Activity of Raw Ethanolic Seed Extract of Tetracarpidium conophorum in Swiss Albino Mice Infected with Plasmodium berghei. J Adv Med Pharm Sci, 9(2): 1-8.
Dalziel, J. M. (1937). The useful plants of West Tropical Africa. Whitefriars Press, London; Pp 164.
Edem, C. A. A., Dosunmu, M. I. and Bassey, F. I. (2009). Determination of proximate composition, ascorbic acid and heavy metal content of African walnut (Tetracarpidium conophorum). Pakis J Nutri, 8(3): 225-226.
Ezealisiji, K. M., Omotosho, A. E., Udoh, R. and Agbo, M. O. (2014a). Wound healing activity of n-hexane and methanol extracts of Tetracarpidium conophorum (Mull. Arg.) Hutch (African walnut) in wistar rats. Malaysian J Pharm Sci, 12(1): 79–88.
Ezealisiji, K. M., Stanley, C. N. and Ekanem, E. S. (2016). Evaluation of Anti-Cholesterol Activity of Ethyl Acetate and N-Hexane Extracts of Tetracarpidium conophorum (Mull. Arg.) Hutch and Dalziel (African Walnut) Towards Hypercholesterolemic Rats. Intl J Pharmacog Phytochem Res, 8(8): 1372-1376.
Ezealisiji, M. A., Ijeomah, S. C. and Agbo, M. O. (2014b). Anti-ulcer activity of African walnut ‘Tetracarpidium conophorum’ nuts against gastric ulcers in rats. Asia Pac J Trop Dis, 4(1): 671-674.
Fang, L., Ren, D., Cui, L., Liu, C., Wang, J., Liu, W., Min, W. and Liu, J. (2018). Antifatigue, Antioxidant and Immunoregulatory Effects of Peptides Hydrolyzed from Manchurian Walnut (Juglans mandshurica Maxim.) on Mice. Grain & Oil Science and Technology, 1(1): 44-52.
Fang, Y. F., Miao, Y. L., Lao, Q. Y., Chen, M. L. and Song, W. D. (2011). Three enzyme hydrolysis process optimization of long oyster meat and the anti-fatigue test of its hydrolysate. Chin. Pharm J, 46: 579–584.
Feng, Z. H., Bai, L. Y., Yan, J., Li, Y. and Shen, W. L. (2011). Mitochondrial dynamic remodeling in strenuous exercise-induced muscle and mitochondrial dysfunction: regulatory effects of hydroxytyrosol. Free Radical Bio Med, 50: 1437–1446.
Finsterer, J. (2012). Biomarkers of Peripheral Muscle Fatigue during Exercise. BMC Musculoskeletal Disorders, 13: 218.
Freitag, E., Edgecombe, G., Baldwin, I., Cottier, B. and Heland, M. (2010). Determination of body weight and height measurement for critically ill patients admitted to the intensive care unit: A quality improvement project. Aust Crit Care, 23(4): 197-207.
Gadekar, R., Chaurasiya, P. K. and Pawar, R. S. (2010). A potential of some medical plants as antiulcer. Pharmacog Rev, 4(8): 136-146.
Gandevia, S. C. (2001). Spinal and Supraspinal Factors in Human Muscle Fatigue. Physiol Rev, 81: 1725-1789.
Gbadamosi, S. O., Abiose, S. H. and Aluko, R. E. (2012). Solubilization, amino acid composition and electrophoretic characterization of Conophor nut. Intl Food Res J, 19(2): 651-656.
Gbile, Z. O. and Adesina, S. K. (1981). Endangered species of the Nigerian Flora. Nig. J Forestry, 8(1): 14-20.
GRIN, (Germplasm Resources Information Network), Plukenetia conophora Mull. Arg. Germplasm Resources Information Network (GRIN) Taxonomy for Plants. United States Department of Agriculture (USDA) and Agricultural Research Services (ARS), Beltsville area 2010; http://www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl? 400342. Accessed 18/08/16. 2010.
Harborne, J. B. (1989). Phytochemical Methods: A Guide to Modern Technology of Plant Analysis, 3rd Edn, Champman and Hall, New York, USA, 1989, Pp:88-185.
Ikarashi, N., Fukazawa, Y., Toda T., Ishii, M., Ochiai, W., Usukura, M. and Sugiyama, K. (2013). Effect of Conclevan on endurance capacity in mice. Biol Pharm Bull, 35(2): 231-238.
Jakobsen, L. K. (2009). Quantitative Determination of Blood Glucose Using Glucose Oxidase and Peroxidase. Scandinavian J Clin Lab Invest, 12(1): 76-79.
Jiang, D. Q., Guo, Y., Xu, D. H., Huang, Y. S., Yuan, K. and Lv, Z. Q. (2013). Antioxidant and anti-fatigue effects of anthocyanins of mulberry juice purification (MJP) and mulberry marc purification (MMP) from different varieties mulberry fruit in China. Food Chem Toxicol, 59, 1–7.
Jin, S. L. and Yin, Y. G. (2012). In vivo antioxidant activity of total flavonoids from indocalamus leaves in aging mice caused by D-galactose. Food Chem Toxicol, 50: 3814–3818.
Kanu, A. M., Kalu, J. E. and Okorie, A. C. (2015). Nutritional and health values of African walnut (Tetracarpidium conophorum). Int’l J Sci & Tech Res, 4(9): 215-220.
Kim, D. I. and Kim, K. S. (2013). Walnut extract exhibits anti-fatigue action via improvement of exercise tolerance in mice. Lab Anim Res, 29(4): 190-195.
Kim, H., Park, S., Han, D. S. and Park, T. (2003). Octacosanol supplementation increases running endurance time and improves biochemical parameters after exhaustion in trained rats. J Med Food, 6: 345–351.
Kohler, N., Gansera, L. and Holze, S. (2014). Cancer-related fatigue in patients before and after radical prostatectomy. Results of a prospective multi-centre study. Supportive Care in Cancer, 22(11): 2883-2889.
Mainasara, M. M., Aliero, B. L., Aliero, A. A. and Yakubu, M. (2012). Phytochemical and antibacterial properties of root and leaf extract of Calotropis procera. Nig J Basic Appl Sci, 20(1): 1-6.
Makkar, H. P. S., Baker, K., Abel, H. and Pawelzik, E. (1997). Nutrient content, rumen protein degradability and nutritional factors in some colour-and-white flowering cultivars of Vicia faba beans. J Sci Food Agric, 75: 11-520.
Matsumoto, K., Ishihara, K., Tanaka, K., Inoue, K. and Fushiki, T. (1996). An adjustable current swimming pool for the evaluation of endurance capacity of mice. J Appl Physiol, 81: 1843–1849.
Nozawa, Y., Yamada, K. and Okabe, Y. (2009). The anti-fatigue effects of the low-molecular weight fraction of bonito extract in mice. Biol Pharm Bulletin, 32(3): 468-474.
Nwabunnia, E. and Otogbor, C. C. (2015). Microflora of the shells of ready-to-eat Conophor (Tetracarpidium conophorum) nuts on retail sale in Owerri. Nig J. Microbiol, 2964-2971.
Nwaichi, E. O., Osuoha, J. O. and Monanu, M. O. (2017). Nutraceutical Potential of Tetracarpidium conophorum and Buccholzia coriacea in Diet-induced Hyperlipidemia. J Chem Health Risks, 7(3): 157–170.
Obadoni, B. O. and Ochuko, P. O. (2001). Phytochemical studies and comparative efficacy of the crude extracts of some homeostatic plants in Edo and Delta States in Nigeria. Global J Pure Appli Sci, 8b: 203-208.
Obianime, A. V. and Uche, F. I. (2010). The effects of aqueous extract of Tetracarpidium conophorum seeds on the hormonal parameters of male guinea pigs. Asian J Trop Med, 21-24.
Odebiyi, A. and Sofowora, A. E. (1978). Phytochemical screening of Nigerian medicinal plant. Part III, Lloydia, 41: 234-246.
Ogbolu, D. O. and Alli, A. O. T. (2012). In-vitro antimicrobial activity of aqueous and methanol extracts of Tetracarpidium conophorum on some susceptible and multi-resistant bacteria. Afr J Microbiol Res, 6(13):3354 -3359.
Ogunsua, A. O. and Adebona, M. B. (1983). Chemical composition of Tetracarpiduim conophorum. J. Food Chem, 10: 173–177.
Ojobor, C. C., Anosike, C. A. and Ani, C. C. (2015). Studies on the phytochemical and nutritional properties of Tetracarpidium conophorum (Black walnut) seeds. J Global Biosci, 4(2): 1366-1372.
Onwuli, D. O., Brown, H. and Ozoani, H. A. (2014). Antihyperglycaemic effect of Tetracarpidium conophorum nuts in alloxan-induced diabetic rats. ISRN Endocrinol, 1-4.
Oriakhi, K. and Uadia, P. O. (2016). In vivo anti-hyperlipidemic activity of Tetracarpidium conophorum (African walnut) oil. J Glycomics Lipidomics, 6:3 (Suppl), 2016.
Oyedemi, S. O., Bradley, G. and Afolayan, A. J. (2010). In-vitro and in-vivo antioxidant activities of aqueous extract of Strychnos henningsii Gilg. Afr J Pharm Pharmacol, 4: 70-78.
Ren, J., Zhao, M., Wang, H., Cui, C. and You, L. (2011). Effects of Supplementation with Grass Carp Protein versus Peptide on Swimming Endurance in Mice. Nutrition, 27: 789-795.
Robergs, R. A., Ghiasvand, F. and Parker, D. (2004). Biochemistry of exercise-induced metabolic acidosis. Am J Physiol Regul Integr Comp Physiol, 287(3): R502-R516.
Saurez, J., Herreta, M. D. and Marhuenda, E. (1993). Hesperidine and Neohesperidine Dihydrochalcone on different experimental models of induced gastric ulcer. Phytotherapy Res, 10: 616-618.
Shao, J. T., Wang, M. Y. and Zheng, L. B. (2013). Antifatigue Effect of Gracilaria eucheumoides in Mice. Exp Therap Med, 6: 1512-1516.
Sofowora, A. (1993). Medicinal Plants and Traditional Medicine in Africa. 2nd Edition, Spectrum Books, Ibadan, Nigeria, 26-100.
Swain, T. (1979). Tannins and Lignins. In: G. A. Rosenthal and D. H. Janzen, eds. Herbivores: Their interaction with secondary plant metabolites, Academic Press, New York, Pp. 657-682.
Tan, W., Yu, K. Q., Liu, Y. Y., Ouyang, M. Z., Yan, M. H., Luo, R. and Zhao, X. S. (2012). Anti-fatigue activity of polysaccharide extract from Radix Rehmanniae. Preparata, Int J Biol Macromol, 50: 59–62.
Tharakan, B., Dhanasekaran, M. and Manyam, B. V. (2005). Antioxidant and DNA protecting properties of anti-fatigue herb Trichopus zeylanicus. Phytother Res, 19(8): 669-673.
Tietz, N. W., Pruden, E. L. and Siggaard-Anderson, O. (1994). In: Burtis CA, Ashwood ER, editor. Tietz Textbook of Clinical Chemistry. London: W.B. Saunders Company, Pp 1354-74.
Trease, G. E. and Evans, M. C. (1983). A textbook of Pharmacognosy, 1983. 12th ed. Bailliere-Tindall Ltd, London. Pp. 343-383.
Udedi, S. C., Ani, O. N., Anajekwu, B. N., Igwilo, I. O., Ononamadu, C. J., Adindu, C. S. and Okafor, U. M. (2013). Comparative Proximate Analyses of Raw and Cooked Tetracarpidium conophorum (African Walnut) Found in Awka, Anambra State, Nigeria. The Bioscientist, 1(2): 114-118.
Usman, H. and Osuji, J. C. (2007). Phytochemical and in vitro antimicrobial assay of the leaf extract of Newbouldia laevis. Afr. J. Tradit. Compliment. Altern. Med, 4: 476-480.
Walls, M. E., Wani, M. C., Brown, D. M. and Fullas, F. (1996). Effect of tannins on screening of plant extracts for enzyme inhibitory activity and techniques for their removal. Phytomedicine, 3: 281–285.
Wang, L., Zhang, H. L. and Lu, R. (2008). The decapeptide CMS001 enhances swimming endurance in mice. Peptides, 29(7): 1176-1182.
Wei, W., Zheng, L., Yu, M., Jiang, N., Yang, Z. and Luo, X. (2010). Anti fatigue activities of extract from submerged fermentation of Ganoderma lucidum using Radix astragali as substrate. J Anim Plant Sci, 6: 677-684.
Willis, L. M., Shukitt-Hale, B., Cheng, V. and Joseph, J. A. (2009). Dose dependent effects of walnuts on motor and cognitive function in aged rats. British Journal of Nutrition, 101: 1140-1144.
Wroblewski, F. and La-Due, J. S. (1955). Lactate dehydrogenase activity in blood. Proc Soc Exp Biol Med, 90: 210.
Yadav, R. N. S. and Agarwala, M. (2011). Phytochemical analysis of some medicinal plants. J Phytology, 3(12): 10–19.
Yan, B. and Wang, Z. B. (2010). Effects of Ginkgo biloba extract on free radical metabolism of liver in mice during endurance metabolism, Afr J Tradit Complem, 7: 291–295.
Yan, F., Wang, B. and Zhang, Y. (2014). Polysaccharides from Cordyceps sinensis mycelium ameliorate exhaustive swimming exercise-induced oxidative stress. Pharm Biol, 52: 157-161.
You, L., Zhao, M., Regenstein, J. M. and Ren, J. (2011). In vitro antioxidant activity and in vivo anti-fatigue effect of loach (Misgurnus anguillicaudatus) peptides prepared by papain digestion. Food Chem, 124: 188–194.
Zhang, X. L., Ren, F. and Huang, W. (2010). Anti-fatigue activity of extracts of stem bark from Acanthopanax senticosus. Molecules, 16(1): 28-37.
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