Activation of human neutrophils by dotriacontane from Tynanthus micranthus Corr. Méllo (Bignoniaceae) for the production of superoxide anions
DOI:
https://doi.org/10.5902/2179460X41253Keywords:
Tynanthus micranthus, Bignoniaceae, Dotriacontane, Neutrophhil Activation.Abstract
The species Tynanthus micranthus Corr. Méllo, is popularly known as "Cipó Cravo" or "Craveiro", and is usually used as a stimulant and aphrodisiac, and found in the north of the State of Paraná - Brazil. The isolate the alkane dotriacontane from T. micranthus and to verify its action on the activation of human neutrophils to produce superoxide anions by the nitroblue tetrazolium reduction method (NBT), in comparison with the activation obtained by commercial dotriacontane. The ethanolic extract dried leaves was prepared by modified Soxhlet apparatus. Then the ethanolic extract was fractionated with n-hexane to obtain the hexane fraction which was submitted to the chromatographic column to obtain the compound dotriacontane. The substance was identified by 1H and 13C NMR spectroscopy. Isolated and commercial dotriacontane were evaluated by the NBT assay for verification of the activation of human neutrophils. The isolated and commercial dotriacontane activated neutrophils (10.0 μg/mL) when compared to phorbol myristate acetate (PMA) (10.0 μg/mL). In the quantitative test commercial dotriacontane induced significant activation when compared to PMA (10.0 μg/mL). The substance dotriacontane, first time identified in the genus Tynanthus. The dotriacontane was shown to be important to confirm the activation of human neutrophils to produce superoxide anions.
Downloads
References
References
Abreu, J.S., Marzocchi-Machado, C.M., Urbaczek, A.C., Fonseca, L.M., Urbinati, E.C. Leukocytes respiratory burst and lysozyme level in pacu (Piaractus mesopotamicus Holmberg, 1887). Braz. J. Biol. 2009; (69): 1133-1139.
Agaiby, A.D., Dyson, M. Immuno-inflammatory cell dynamics during cutaneous wound healing. J. Anat. 1999; (195): 531-542.
Akesson, C., Pero, R.W., Ivars, F. C-Med 100, a hot water extract of Uncaria tomentosa, prolongs lymphocyte survival in vivo. Phytomedicine. 2003; (10): 23-33.
Arruda, A.L.A., Souza, D.G., Vieira, C.J.B., Oliveira, R.F., Pavan, F.R., Fujimura, C.Q.L., Resende, U.M., Castilho, R.O. Análise fitoquímica e atividade antimicobacteriana de extratos metanólicos de Jacaranda cuspidifolia Mart. (Bignoniaceae). Rev. Bras. Plan. Med. 2012; (14): 276-281.
Balla, A.K., Doi, E.M., Lerner, M.R., Bales, W.D., Archer, L.T., Wunder, P.R., Wilson, M.F., Brackett, D.J. Dose-response effect of in vivo administration o endotoxin on polymorphonuclear leukocytes oxidative burst. Shock. 1996; (5): 357-361.
Balla, A.K., Doi, E.M., Wunder, P.R., Ogle, J.D., Debault, L.E. Human polymorphonuclear leukocyte (PMN) priming/activation by acute ethanol intoxication. Drugs of Abuse, Immunity, and AIDS. 1993; (335): 165-168.
Bin-Hafeez, B., Ahmad, I., Haque, R., Raisuddin, S. Protective effect of Cassia occidentalis L. on cyclophosphamide-induced suppression of humoral immunity in mice. J. Ethnopharmacol. 2001; (75): 13-18.
Bordoloi, M., Saikia, S., Bordoloi, P.K., Kolita, B., Dutta, P.P., Bhuyan, P.D., Dutta, S.C., Rao, P.G. Isolation, characterization and antifungal activity of very long chainalkane derivatives from Cinnamomum obtusifolium, Elaeocarpuslanceifolius and Baccaurea sapida. Journal of Molecular Structure. 2017; (1142); 200-210.
Cansian, F.C., Lima, C.P., Zortéa, F.M., Miguel, O.G., Miguel, M.D. Potencial alelopático de Tynanthus micranthus Corr. Mello ex. Schum. (Bignoniaceae) sobre diásporos de Lactuca sativa L. Rev. Ciênc. Farm. Bás. Apl., 2013; (34): 137-140.
Cansian, F.C., Merino, F.J.Z., Amaral, V.L.L., Salvador, R.A., Campos, P.M., Montrucchio, D.P., Miguel, O.G., Miguel, M.D. Aphrodisiac properties of Tynanthus micranthus Corr. & Mello ex. Schum in male mice. Afr. J. Pharm. Pharmacol. 2014; (8): 1200-1204.
Cansian, F.C., Miguel, M.D., Miguel, O.G., Miyasaki, C.M.S., Lima, C.P., Kalegari, M., Merino, F.J.Z., Souza, A.M., Cogo, L.L. Phytochemical, toxicity and microbiological activity study of Tynanthus micranthus Corr. Mello ex Schum. (Bignoniaceae). Lat. Am. J. Pharm. 2012; (31): 487-491.
Cansian, F.C., Silva, C.B., Lima, C.P., Merino, F.J.Z., Rech, K.S., Otuki, M.F., Campos, P.M., Miguel, O.G., Miguel, M.D. Tynanthus micranthus: An efficient antioxidant and tyrosinase activity inductor. Afr. J. Pharm. Pharmacol. 2014; (8): 651-657.
Carvalho, J.L.S, Cunico, M.M., Dias, J.F.G., Miguel, M.D., Miguel, O.G. Termoestabilidade de processos extrativos de Nasturtium officinale R. Br., Brassicaceae por sistema Soxhlet modificado. Quím Nova. 2009; (32): 1031-1035.
Correa, M.P. Dicionário das plantas úteis do brasil e das exóticas cultivadas. 1.ed. Rio de Janeiro: IBDF, 1974. 687 p.
Corrêa, M.F.P., Melo, G.O., Costa, S.S. Substâncias de origem vegetal potencialmente úteis na terapia da asma. Rev. Brasil. de Farmacog. 2008; (18): 785-797.
Costa-Silva, T.A., Grecco, S.S., Sousa, F.S., Lago, J.H., Martins, E.G., Terrazas, C.A., Varikuti, S., Owens, K.L., Beverley, S.M., Satoskar, A.R., Tempone, A.G. Immunomodulatory and antileishmanial activity of phenylpropanoid dimers isolated from Nectandra leucantha. J. Nat. 2015; (78): 653-657.
Cruvinel, W.M., Júnior, D.M., Araújo, J.A.P., Catelan, T.T.T., Souza, A.W.S., Silva, N.P., Andrade, L.E.C. Sistema Imunitário – Parte I: Fundamentos da imunidade inata com ênfase nos mecanismos moleculares e celulares da resposta inflamatória. Rev. Bras. Reumatol. 2010; (50): 434-461.
Custódio, D.L., Burgo, R.P., Moriel, B., Barbosa, A.M., Rezende, M.I., Daniel, J.F.S., Pinto, J.P., Bianchini, E., Faria, T.J. Antimicrobial activity of essential oils from Pimenta pseudocaryophyllus and Tynanthus micranthus. Braz. Arch. Biol. Technol. 2010; (53): 1363-1369.
Davis, L., Kuttan, G. Immunomodulatory activity of Withania somnifera. J. Ethnopharmacol. 2000; (71): 193-202.
Dove, H., Mayes, R.W. The use of plant wax alkanes as marker substances in studies of the nutrition of herbivores: a review. Aust. J. Agric. Res. 1991; (42): 913-952.
Dulbecco, R., Vogt, M. Plaque formation and isolation of pure lines with poliomyelitis viruses. The Journal of Experimental Medicine. 1954; (99): 167-182.
Ferreira, D.F. Sisvar: a computer statistical analysis system. Ciência e Agrotecnologia. 2011; (35): 1039-1042.
Ferrier, J. Ethnobotany, pharmacology, and metabolomics of antidiabetic plants used by the Eeyou Istchee Cree, Lukomir Highlanders, and Q’eqchi’ Maya. Canada. [Dissertation of master degree. Faculty of Graduate and Postdoctoral Studies. University of Ottawa]. 2014. 193 p.
Ghule, B.V., Murugananthan G., Nakhat, P.D., Yeole, P.G. Immunostimulant effects of Capparis zeylanica Linn. leaves. J. Ethnopharmacol. 2006; (108): 311-315.
Ghule, B.V., Yeole, P.G. In vitro and in vivo immunomodulatory activities of iridoids fraction from Barleria prionitis Linn. J. Ethnopharmacol. 2012; (141): 424-431.
Glasser, L., Fiederlein, R.l. The effect of various cell separation procedures on assays of neutrophil function. American Journal of Clinical Pathology. 1990; (93): 662-669.
Gormann, R., Schreiber, L., Kolodziej, H. Cuticular wax profiles of leaves of some traditionally used african Bignoniaceae. Z. Naturforsch. 2004; (59): 9-10.
Higuchi, C.T., Sannomiya, M., Pavan, F.R., Leite, S.R.A., Sato, D.N., Franzblau, S.G., Sacramento, L.V.S., Vilegas, W., Leite, C.Q.F., 2011. Byrsonima fagifolia Niedenzu apolar compounds with antitubercular activity. J. Evid. Based Complementary Altern. Med. 2011; 1-5.
Jafar, N., Edriss, H., Nugent, K. The effect of short-term hyperglycemia on the innate immune system. Am. J. Med. Sci. 2016; (351), 201-211.
Javid, A., Zlotnikov, N., Pětrošová, H., Tang, T.T., Zhang, Y., Bansal, A.K., Ebady, R., Parikh, M., Ahmed, M., Sun, C., Newbigging, S., Kim, Y.R., Sosa, M.S., Glogauer, M., Moriarty, T.J.,. Hyperglycemia impairs neutrophil-mediated bacterial clearance in mice infected with the Lyme disease pathogen. PLoS ONE. 2016; 1-20.
Johansson, S., Göransson, U., Luijendijk, T., Backlund, A., Claeson, P., Bohlin, L. A neutrophil multitarget functional bioassay to detect anti-inflammatory Natural Products. J. Nat. Prod. 2002; (65), 32-41
Kalegari, M., Miguel, M.D., Dias, J.F.G., Lordello, A.L.L., Lima, C.P., Miyazaki, C.M.S., Warumby, S.M.Z., Verdam, M.C.S., Miguel, O.G. Phytochemical constituents and preliminary toxicity evaluation of leaves from Rourea induta Planch. (Connaraceae). Braz. J. Pharm. Sci. 2011; (47), 635-642.
Kang, S., Min, H. Ginseng, the “Immunity Boost”: The Effects of Panax ginseng on Immune System. J. Ginseng Res. 2012; (36), 354-368.
Kanjwani, D.G., Marathe, T.P., Chiplunkar, S.V., Sathaye, S.S. Evaluation of immunomodulatory activity of methanolic extract of Piper betel. J. Immunol. 2008; (67), 589-593.
Levinsky, R.J., Harvey, B.A.M., Rodeck, C.H., Soothill, J.F. Phorbol myristate acetate stimulated NBT test: a simple method suitable for antenatal diagnosis of chronic granulomatous disease. Clinical & Experimental Immunology. 1983; (54), 595-598.
Li, C., Yu, J. Chemical Composition and Antimicrobial Activity of Essential Oils of Stems of Macleaya cordata (Willd) R. Br. Asian Journal of Chemistry. 2014; (26), 7741-7745.
Lograda, T., Ramdani, M., Chalard, P., Figuered, G., Khalfoune, K., Silini, H. Phytochemistry, antibacterial activity and chromosome number of Centaurea solstitialis L. grown in Algeria. Global J. Res. Med. Plants and Indigen. Med. 2013; (2), 675-684.
Lopes, M. M. M., Carvalho-Okano, R.M., Souza, A.L., Paiva, H.N. Crescimento de mudas de Cipó-Cravo (Tynanthus fasciculatus Miers), uma Liana com potencial medicinal. Revista Árvore. 2008; (32), 211-216.
Lundqvist-Gustafsson, H., Bengtsson, T. Activation of the granule pool of the NADPH oxidase accelerates apoptosis in human neutrophils. Journal of Leukocyte Biology. 1999; (65), 196-204.
Markert, M., Andrews, P.C., Babior, B.M. Measurement of O2- production by human neutrophils. The preparation and assay of NADPH oxidase-containing particles from human neutrophils. Methods in Enzymology. 1984; (105), 358-365.
Muñoz, V., Sauvain, M., Bourdy, G., Callapa, J., Rojas, I., Vargas, L., Tae, A., Deharo, E. The search for natural bioactive compounds through a multidisciplinary approach in Bolivia. Part II. Antimalarial activity of some plants used by Mosetene Indians. J. Ethnopharm. 2000; (69), 139-155.
Nagori, K., Singh, M.K., Alexander, A., Kumar, T., Dewangan, D., Badwaik, H., Tripathi, D.K. Piper betle L.: A review on its ethnobotany, phytochemistry, pharmacological profile and profiling by new hyphenated technique DART-MS (Direct Analysis in Real Time Mass Spectrometry). J.Pharm. Res. 2011; (4), 2991-2997.
Park, B.H., Fikrig, S.M., Smithwick, E.M. Infection and nitroblue-tetrazolium reduction by neutrophils. A diagnostiv acid. Lancet. 1968; (7), 532-534.
Park, H.H., Good, R.A. N.B.T. test stimulated. Lancet. 1970; (19), 616.
Parmar, V.S., Jain, S.C., Gupta, S., Talwar, S., Rajwanshi, V.K., Kumar, R., Azim, A., Malhotra, S., Kumar, N., Jains, R., Sharma, N.K., Tyagi, O.D., Lawrie, S.J., Errington, W., Howarth, O.W., Olsen, C.E., Singh, S.K., Wengel, J. Polyphenols and alkaloids from Piper species. Phytochem. 1998; (49), 1069-1078.
Pearson, R.D., Steigbigel, R.T. Phagocytosis and killing of the protozoan Leishmania donovani by human polymorphonuclear leukocytes. Journal of Immunology. 1981; (127), 1438-1443.
Plaza, A., Montoro, P., Benavides, A., Pizza, C., Piacente, S. Phenylpropanoid Glycosides from Tynanthus panurensis: Characterization and LC-MS Quantitative Analysis. J. Agric. Food Chem. 2005; ( 53), 2853-2858.
Rocha, J.L.L., Baggio, H.C.C., Cunha C.A., Niclewicz, E.A., Leite, S.A.O., Baptista, M.I.D.K. Aspectos relevantes da interface entre Diabetes mellitus e infecção. Arq. Bras. Endocrinol. Metab. 2002; (46), 221-229.
Roy, P., Amdekar, S., Kumar, A., Singh, V. Preliminary study of the antioxidant properties of flowers and roots of Pyrostegia venusta (Ker Gawl) Miers. BMC Complement Altern Med. 2011; (11), 69.
Santos, A.A., Araújo, E.G. The effect of PKC activation on the survival of rat retinal ganglion cells in culture. Brain Research. 2000; (853), 338-343.
Scapini, P., Lapinet-Vera, J.A., Gasperini, S., Calzetti, F., Bazzoni, F., Cassatella, M.A. The neutrophil as a cellular source of chemokines. Immunology Review. 2000; (177), 195-203.
Sharma, M.L., Singh, B., Chandan, B.K., Khajuria, A., Kaul, A., Bani, S., Banerjeee, S.K., Gambhir, S.S. Actions of some flavonoids on specific and non-specific immune mechanisms. Phytomedicine. 1996; (3), 191-195.
Sharma, U., Bala, M., Kumar, N., Singh, B., Munshi, R., Bhalerao, S. Immunomodulatory active compounds from Tinospora cordifolia. Journal of Ethnopharmacology. 2012; (141), 918-926.
Tayade, A.B., Dhar, P., Kumar, J., Sharma, M., Chauhan, R.S., Chaurasia, O.P., Srivastava, R.B. Chemometric Profile of Root Extracts of Rhodiola imbricata Edgew. with Hyphenated Gas Chromatography Mass Spectrometric Technique. PloS One. 2013; (8), e52797.
Tessmann, D., Dianese, J.C. Hentriacontane: a leaf hydrocarbon from Syzygium jambos with stimulatory effects on the germination of urediniospores of Puccinia psidii. Fitopatol. Bras. 2002; (27), 538-542.
Verhoef, Jan. Phagocytosis. In: Roitt, I. M., Delves, P. J. (Ed) Encyclopedia of Immunology. Academic Press Limited. 1992; 1220-1222.
Wunder, P.R., Waner, J.L., Balla, A.K. Alcohol, neutrophils, and viral infections. In: Advances in the Biosciences. Pergamon Press Ltd. 1993; (86), 449-455.
Zychlinsky, A., Weinrauch, Y., Weiss, J. Forum in immunology. Introduction: forum in immunology on neutrophils. Microbes and Infection. 2003; (5), 1289-1291.
Published
Versions
- 2022-04-06 (2)
- 2020-05-11 (1)
How to Cite
Issue
Section
License
To access the DECLARATION AND TRANSFER OF COPYRIGHT AUTHOR’S DECLARATION AND COPYRIGHT LICENSE click here.
Ethical Guidelines for Journal Publication
The Ciência e Natura journal is committed to ensuring ethics in publication and quality of articles.
Conformance to standards of ethical behavior is therefore expected of all parties involved: Authors, Editors, Reviewers, and the Publisher.
In particular,
Authors: Authors should present an objective discussion of the significance of research work as well as sufficient detail and references to permit others to replicate the experiments. Fraudulent or knowingly inaccurate statements constitute unethical behavior and are unacceptable. Review Articles should also be objective, comprehensive, and accurate accounts of the state of the art. The Authors should ensure that their work is entirely original works, and if the work and/or words of others have been used, this has been appropriately acknowledged. Plagiarism in all its forms constitutes unethical publishing behavior and is unacceptable. Submitting the same manuscript to more than one journal concurrently constitutes unethical publishing behavior and is unacceptable. Authors should not submit articles describing essentially the same research to more than one journal. The corresponding Author should ensure that there is a full consensus of all Co-authors in approving the final version of the paper and its submission for publication.
Editors: Editors should evaluate manuscripts exclusively on the basis of their academic merit. An Editor must not use unpublished information in the editor's own research without the express written consent of the Author. Editors should take reasonable responsive measures when ethical complaints have been presented concerning a submitted manuscript or published paper.
Reviewers: Any manuscripts received for review must be treated as confidential documents. Privileged information or ideas obtained through peer review must be kept confidential and not used for personal advantage. Reviewers should be conducted objectively, and observations should be formulated clearly with supporting arguments, so that Authors can use them for improving the paper. Any selected Reviewer who feels unqualified to review the research reported in a manuscript or knows that its prompt review will be impossible should notify the Editor and excuse himself from the review process. Reviewers should not consider manuscripts in which they have conflicts of interest resulting from competitive, collaborative, or other relationships or connections with any of the authors, companies, or institutions connected to the papers.
