Structures and biological activity of cuprophyllins
Keywords:
cuprophyllins, chlorophyllin, chlorophyllipt, biological activity, chemical structureAbstract
Chlorophylls (a, b) are the porphyrin compounds and most common chemical in the plant’s world. In fact, these compounds are an obligatory intermediate product both in energy metabolism and in plant catabolism. At the same time, currently there are few pharmaceutical preparations on the pharmaceutical market based on chlorophylls. Dyes based on hydrolyzed chlorophyll are successfully used in the food industry. Commercial chlorophylline is a copper complex of hydrolyzed chlorophylls. As shown earlier in TLC, the chlorophyllin mixture contains a large number of different compounds. It is like water-soluble saponified derivatives in the form of sodium-magnesium complexes, and similar structures in the form of a complex with copper. The latter are more brightly colored, soluble in water and widely used as coloring agents in cooking. In this case, if the initial chlorophyll was not found to have a pronounced biological activity, the substituted derivatives in the form of copper complexes possessed a number of new unique biological properties. Non-hydrolyzed hydrophobic cuprophylline obtained from eucalyptus leaves possessed high antimicrobial activity to most strains of staphylococci, inclusion resistant to antimicrobials and multiresistant strains. This drug is called Chlorophyllipt, it is allowed to be used as a medicinal product and is one of the oldest antibacterial drugs from plants on the market. It is marketed as ethanoic and oily solutions for topical use, and as an alcohol solution for intravenous injections. Its main purpose is the fight against staphylococcal infections. Recently, found that the oral administration of chlorophyllipt activates cellular immunity and indirectly exhibits antiviral activity. Another compound of cuprophyllin is water-soluble chlorophyllin. Some authors show the variability of the structure and biological activity of cuprophyllins. Different derivatives of chlorophyll have different biological activity. Hydrophilic cuprophyllin chlorophyllin very good studied and have good profile of toxicity and uses in cooking as colorant. Chlorophyllin have such biological effects: antiatherosclerotic, antiviral, antimicrobial, immunomodulating, antimutagenic and anticancerogenic, antioxidant. Most of the studies were carried out as in vitro and in vivo with statistically trustworth results. Derivatives of chlorophyll are very perspective candidates for fight with multiresistant strains of mnicroorganisms and viral infections. Derivatives of chlorophyll must be more studied for using as active pharmaceutical ingredients for development a new drugs in the form of injection, tablets, ointments.
References
Sato M., Fujimoto I., Sakai T.et al. Effect of sodium copper chiorophyllin on lipid peroxidation. IX. On the antioxidative components in commercial preparations of sodium copper chlorophyllin// Chem. Pharm. Bull. 1986. Vol. 34. P. 2428-2434.
Nadtokova VL The domestic antibacterial drug chlorophyllipt // Antibiotics. 1970. N. 10. P. 888-892.
Nadtoka V.L. Chlorophyllipt. Experimental-clinical research // Avtoref. Diss. For the competition Degree of Doct. M. Sciences. - Kharkov, 1970. - 23 p.
Olefir Yu. V., Luttseva AI, Gunar O V. et al. Experimental evaluation of methods for determining the antimicrobial activity of chlorophylliptine preparations// Statements of the scientific center of expertise of means of medical application. 2015. Vol. 4. P. 47-50.
Elizarova V.E.. Chlorophyllipt as an effective antiseptic in the treatment of periodontitis// Stomatol. Children. Age and prevention. 2003. Vol. 1-2. P. 17-18.
Young R. W., Beregi J. S. Use of chlorophyllin in the care of geriatric patients// Journal of the American Geriatrics Society.1980. Vol. 28. N. 1.P. 46-47.
Nelson R.L. Chlorophyllin, an antimutagen, acts as a tumor promoter in the rat-dimethylhydrazine colon carcinogenesis model// Anticancer Res. 1992. Vol. 12. P. 737-740.
Wall M.E. Preparation of chlorophyll derivatives for industrial and pharmaceutical use// US Agricultural and Chemistry Bureau.1951. Vol. 299. P. 1- 6
Eddy W.H. Chlorophyll, Strong Cobb and Co., Inc., Lake Worth, Florida. 1953. P. 1-60
Kephart J.C. Chlorophyll derivatives: their chemistry, commercial preparation and uses// Econ Bot. 1955. Vol. 0. P.3-38.
Chernomorsky S.A. Chiorophyllin copper complex: quality control// J. Soc. 1993. Vol. 44. P. 235-238.
Kurnygina V.T., Nikitina T.V. Effect of metal-chlorophyll complexes on pancreatic lipase activity. 1981. Biol Nauki. Vol. 6. P. 31-34.
Sato M., Fujimoto I., Sakai T., et al. Effect of sodium copper chiorophyllin on lipid peroxidation, IX, On the antioxidative components in commercial preparations of sodium copper chlorophyllin// Chem. Pharm. Bull. 1986. Vol. 34. P. 2428-2434.
Spikes J.D., Bommer J.C. Chlorophyll and related pigments as photosensitizers in biology and medicine, in: H. Scheer (Ed.), Chlorophylls, CRC Press, London. 1990. P. 1185-1189.
Garcia-Rodriguez M. C., Morales-Ramirez P., Altamirano-Lozano M. Effects of chlorophyllin on mouse embryonic and fetal development in vivo// Teratog Carcinog Mutagen. 2002. Vol. 22. N. 6. P. 461–471. https://doi.org/10.1002/tcm.10042
Chlorophyll-Copper-complex. Material Safety Data Sheet according to Regulation (EC) No. 1907/2006 (REACH) Revision Date 16.11.2015
Yun C. H., Jeon Y. J., Yang Y., Ju H. R., Han S. H. Chlorophyllin suppresses interleukin-1 beta expression in lipopolysaccharide-activated RAW 264.7 cells// Int Immunopharmacol. 2006. Vol.6. N. 2. P. 252–259. https://doi.org/10.1016/j.intimp.2005.08.012
Nagai H., Nishiyori T., Daikoku M., Koda A.. Immunopharmacological studies of sodium copper chlorphyllin (SCC)// Jpn J Pharmacol. 1983. Vol.33. N. 4. P. 819–828. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/6195383
Sharma D., Kumar S. S., Sainis K. B.. Antiapoptotic and immunomodulatory effects of chlorophyllin// Mol Immunol. 2007.Vol. 44. N.4). P. 347–359. https://doi.org/10.1016/j.molimm.2006.02.031
Yin L. M., Jiang H. F., Wang X. et al.. Effects of sodium copper chlorophyllin on mesenchymal stem cell function in aplastic anemia mice// Chin J Integr Med. 2013. Vol. 19. N. 5. P. 360–366. https://doi.org/10.1007/s11655-012-1210-z
Yun C. H., Son C. G., Chung D. K., Han S. H.. Chlorophyllin attenuates IFN-gamma expression in lipopolysaccharide-stimulated murine splenic mononuclear cells via suppressing IL-12 production// Int Immunopharmacol. 2005. Vol. 5. N. 13–14. P. 1926–1935. https://doi.org/10.1016/j.intimp.2005.06.014
Pimentel E., Cruces M. P., Zimmering S.. On the persistence of the radioprotective effect of chlorophyllin (CHL ) in somatic cells of Drosophila// Mutat Res. 1999. Vol. 446. N. 2. Vol. 189–192. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/10635341
Olvera O., Arceo C., Zimmering S.. The effect of treating Drosophila females with chlorophyllin on the yield of dominant lethals recovered from irradiated sperm// Mutat Res. 2003). Vol.534. N. 1–2. P. 201–202. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/12504769
Tajmir-Riahi H. A., Neault J. F., Diamantoglou S.. DNA adducts with chlorophyll and chlorophyllin as antimutagenic agents: synthesis, stability, and structural features// Methods Mol Biol.2004. Vol 274. P. 159–171. https://doi.org/10.1385/1-59259-799-8:159
Pimentel E., Cruces M. P., Zimmering S.. Evidence that chlorophyllin (CHL ) may behave as an inhibitor or a promoter of radiation-induced genetic damage in somatic cells of drosophila// Mutat Res. 2000. Vol. 472, N. 1–2. P. 71–74. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/11113699
Krikun B. L., Chernomorskii S. A., Gurinovich L. K.. Study of the antiviral properties of chlorophyllin sodium preparations. Bulletin of Experimental Biology and Medicine. 1969. Vol. 68. N. 5. P. 1271–1273.
Azizullah A., Rehman Z. U., Ali I., et al. Chlorophyll derivatives can be an efficient weapon in the fight against dengue//Parasitol Res. 2014. Vol.113. N. 12. P. 4321–4326. https://doi.org/10.1007/s00436-014-4175-3
https://www.mysciencework.com/publication/show/d9bd0ae1a11b10e498ff05752e689953
Ito A., Tsuneki A., Yoshida Y., et al. In Vitro Inhibition of Cytopathic Effect of Influenza Virus and Human Immunodeficiency Virus by Bamboo Leaf Extract Solution and Sodium Copper Chlorophyllin// Yonago acta medica. 2016. Vol. 59. N. 1. P. 61.
Guo H., Pan X., Mao R., et al. Alkylated porphyrins have broad antiviral activity against hepadnaviruses, flaviviruses, filoviruses, and arenaviruses// Antimicrobial agents and chemotherapy. 2011.Vol. 55. N.2.P. 478-486.
Botelho M. V. J., Orlandi J. M., Melo F. L., et al. Chlorophyllin protects HEp‐2 cells from nuclear fragmentation induced by poliovirus// Letters in applied microbiology. 2004. Vol.39. N.2.P.174-177.
Mowbray S. The antibacterial activity of chlorophyll// Br Med J. 1957. Vol.1. N. 5013P. 268–270.
Rajalakshmi K., Banu N. Antimicrobial activity of natural chlorophyllin from endangered medicinal plant Mimosa pudica l// Int J Farm & Farm Sci. 2016. Vol.8, N.4.
Maekawa L.E., Lamping R., Marcacci D. et al. Chlorophyll-solution presents effective antimicrobial activity on C. albicans but did not present any activity on E. faecalis// RSBO. 2007. Vol.4. P.37-40.
Park S. J., Park Y. M. Eco-dyeing and antimicrobial properties of chlorophyllin copper complex extracted from Sasa veitchii //Fibers and Polymers. 2010. Т. 11. №. 3. С. 357-362
Miller J. M., Jackson D. A., Collier C. S. The inhibition of the coagulase of the Staphylococcus aureus by the water-soluble derivatives of sodium-copper chlorophyllin// Am J Surg. 1959. Vol.97. N. 3. P. 321–323. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/13627357
Daly S., Heller G., Schneider E. Effect of Chlorophyll Derivatives and Related Compounds on the Growth of M. tuberculosis// Experimental Biology and Medicine. 1939. Vol. 42. N. 1. P. 74-78
Krasovskiy V. V., Nadtoka V. L., Pokhil S. I. Listeria bacterial carriage: a method for sanative treatment// Zhurnal mikrobiologii, epidemiologii, i immunobiologii. 1999. Vol .3. P. 18-20.
Vlad M., Bordas E., Caseanu E., et al. Effect of cuprofilin on experimental atherosclerosis// Biological trace element research. 1995. Vol. 48. N. 1. P. 99.
Kapiotis S., Hermann M., Exner M., et al. Copper-and magnesium protoporphyrin complexes inhibit oxidative modification of LDL induced by hemin, transition metal ions and tyrosyl radicals. Free radical research. 2005. Vol. 39. N. 11. P. 1193-1202.
Mohamed H. R. H. Attenuation of nano-TiO2 induced genotoxicity, mutagenicity and apoptosis by chlorophyllin in mice cardiac cells// Int J Sci Res. 2014. Vol.3. N.6. P. 2625-2636.
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