In silico prediction of antiviral activity and evaluation of pharmacokinetic and toxicological characteristics of compounds present in the essential oil of Petiveria alliacea L.
Keywords:
Antivirals; Pharmaceutical Chemistry; Petiveria tetrandra; volatile oils.Abstract
The computational prediction of pharmacological activity allows the selection of components considered promising at the beginning of scientific research. New trends are considered for the use of in silico methodologies. Objective to carry out an in silico evaluation of the pharmacokinetics, toxicological parameters and antiviral activity of compounds present in the essential oil of Petiveria alliacea L. Free programs such as: Way2Drug, ACD/ChemSketch Freeware 14.01, Marvin Sketch 6.2.2, PreADMET2.0 were used. and OSIRIS Property Explorer. The compounds used were selected through a literature review of the phytochemical studies of Petiveria, and they were the ones that had isolated and identified substances derived from sulfur. It was notable the scarcity of scientific material on the topic addressed, in particular, of works that used essential oil as an object of study. On the other hand, the in vivo research found showed some viral activity against species of the Flaviviridae family such as hepatitis C virus (HCV) and dengue, as well as the prediction performed. Activity was also observed against the immunodeficiency virus, but without effects for Herpes Simplex type 1, Poliovirus type 1, Adenovirus serotype 7. Through the in silico study, it was possible to observe that the compounds isolated from Petiveria presented satisfactory values for the antiviral activity against some species and also in the other parameters, opening the possibility for the metabolites to become phytopharmaceuticals or even to be modified for such.
Downloads
References
BENEVIDES, P.J. Antifungal polysulphides from Petiveria alliaceae L. Phytochemisrty, v. 57, n. 743, 2001.
BERGER, I. Plants used in guatemala for the treatment of protozoal infections: II Activity of extracts and fractions of five Guatemalean plants againt Trypanosoma cruzy.
BLAINSKI, A.; PICCOLO, V. K.; MELLO, J. C. P.; OLIVEIRA, R. M. W. Dual effects of crude extracts obtained from Petiveria alliacea L. (Phytolaccaceae) on experimental anxiety in mice. Journal of Ethnopharmacology, v. 128, p. 541–544, 2010.
BURGESS, A & HYNYNEN, K. Noninvasive and targeted drug delivery to the brain using focused ultrasound. ACS chemical neuroscience, v. 4, n. 4, p. 519–526, 2013.
CÁCERES, A. Plants used in Guatemala for the treatment of dermatophytic infections. I. Screening for antimycotic activity of 44 plant extracts. J. Ethnopharmacol, v. 31, n. 263, 1979.
CÁCERES, A. Plants used in Guatemala for the treatment of protozoal infections. I.
Chemotherapy, v. 48, n. 144, 2002.
D’ÁVILA, A. M. M. N et al. Interações medicamentosas: fitoterápicos utilizados na Odontologia e fármacos de uso contínuo dos pacientes. Arch Health Invest, vol. 10, p. 468–473, 2021.
DA COSTA NUNES, I. K. A Importância do Estudo do Metabolismo nos Estágios Iniciais de Desenvolvimento de Fármacos. Revista Virtual de Química, v. 7, n. 2, p. 649-662, 2015.
DE SOUSA, J. R.; DEMUNER, A. J.; PINHEIRO, J. A.; BREITMAIER, E.; CASSELS, B. K: Dibenzyl trisulphide and trans-N-methyl-4-methoxyproline from Petiveria alliacea. Phytochemistry, v. 29, p. 3653–3655. 1990.
DELLE MONACHE, F.; MENICHINI, F.; SUAREZ, L. E. C: Petiveria alliacea. II. Further flavonoids and triterpenes. Gazz Chim Ital, v. 126, p. 275-78, 1996.
DOLABELA, M. F.; SILVA, A. R. P. D.; OHASHI, L. H.; BASTOS, M. L. C.; SILVA, M. C. M. D.; VALE, V. V. Estudo in silico das atividades de triterpenos e iridoides isolados de Himatanthus articulatus (Vahl) Woodson. Revista Fitos, v. 12, n. 3, p. 227-242, 2018.
DRUZHILOVSKIY, D.S.; RUDIK, A.V.; FILIMONOV, D.A. et al. Computational platform Way2Drug: from the prediction of biological activity to drug repurposing. Russ Chem Bull, v. 66, p. 1832–1841, 2017. https://doi.org/10.1007/s11172-017-1954-x
FERRER, J. I. Principales referencias etnomédicas sobre el anamú (Petiveria alliacea Linn) y principios activos encontrados en la planta: un acercamiento al tema.
HENRY, I. C.; LOWE.; NGEH, J.; TOYANG.; SANJIT, R.; CHARAH, T.; WATSON & JOSEPH L. BRYANT2. Inhibition of the Human Hepatitis C Virus by Dibenzyl Trisulfide from Petiveria alliacea L (Guinea Hen Weed). British Microbiology Research Journal, v. 12, n. 1, p. 1-6, 2016
HERNÁNDEZ, J. F.; URUEÑA, C. P.; CIFUENTES, M. C.; SANDOVAL, T. A.; POMBO, L. M.; CASTAÑEDA, D, et al. Petiveria alliacea standardized fraction induces breast adenocarcinoma cell death by modulating glycolytic metabolism. J Ethnopharmacol, v. 153, n. 3, p. 641-9, 2014.
J. Ethnopharmacol, v. 62, n. 107, p. 25, 1998.
JING, Y.; EASTER, A.; PETERS, D.; KIM, N.; ENYDY I. J. In silico prediction of hERG inhibition. Future medicinal chemistry, v. 7, n. 5, p. 571-586, 2015.
JOHNSON, L.; WILLIAMS, L.A.D.; ROBERTS, E.V. An Insecticidal and Acaricidal Polysulfide Metabolite from the Roots of Petiveria alliacea. Pestic.Sci., v.50, p. 228- 232, 1997.
KUBEC, R., MUSAH, R.A. Cysteine sulfoxide derivatives in Petiveria alliacea. Phytochemistry v.58, p.981–985, 2001.
LEYSSEN, P.; DE CLERCQ, E.; NEYTS J. Perspectives for the treatment of infections with flaviviridae. Clin Microbiol Rev 2000;13:67–82.
LORENZI, H.; SOUZA, H. M. Plantas ornamentais no Brasil: arbustivas, herbáceas e trepadeiras. 4 ed. Nova Odessa/ São Paulo: Instituto Plantarum da Estudos da Flora LTDA, 2008, 1088p.
LOWE, H. I. C.; NGEH, J.; TOYANG, A. H, KENNETH, N. N.; CHARAH, T. WATSON1 & BRYANT, J. Petiveria alliacea L. (Guinea Hen Weed) and Its Major Metabolite Dibenzyl Trisulfide Demonstrate HIV-1 Reverse Transcriptase Inhibitory Activity. European Journal of Medicinal Plants, v. 5, n. 1, p. 88-94, 2015.
LOWE, H. I.; FACEY, C. O.; TOYANG, N. J.; BRYANT, J. L. Specific RSK kinase inhibition by dibenzyl trisulfide and implication for therapeutic treatment of cancer. Anticancer Res, v. 34, n. 4, p. 1637-41, 2014.
MATOS, Karina Silvia.Estudos computacionais e experimentais da permeabilidade celular de candidatos a fármacos. 2017. Tese (Doutorado em Física Aplicada) -Instituto de Física de São Carlos, University of São Paulo, São Carlos, 2017. Doi:10.11606/T.76.2017.tde-11052017-140338. Acesso em: 2020-07-18.
MISAS, C.A.J. The biological assessment of cuban plants III. Rev. Cub. Med. Trop, v. 31, n. 21, 1990.
MONACHE, F. D.; SUAREZ, L. E. C. 6-C-formyl and 6-C-hydroxymethyl flavonones from Petiveria alliacea. Phytochemistry 1992;31:2481–2482.
OLIVEIRA, NS.; ARRUDA, EL. Estudos in silico sobre as atividades anticancerígenas do Eugenol no Cravo-da-índia (Syzygium aromaticum). Pesquisa, Sociedade e Desenvolvimento , [S. l.] , v. 10, n. 4, pág. e27910414165, 2021. DOI: 10.33448/rsd-v10i4.14165. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/14165. Acesso em: 23 jul. 2022.
plants. J. Ethnopharmacol, v. 62, n. 195, 1998.
POGODIN, P.V et al. PASS Targets: Sistema computacional multi-alvo baseado em ligantes baseado em dados públicos e abordagem Bayes ingênua. SAR e QSAR em Pesquisa Ambiental, v. 26, n. 10, p. 783-793. 2015.
POROIKOV, V.V, et al. Previsão auxiliada por computador de espectros de atividade biológica para compostos orgânicos: as possibilidades e limitações. Russo. Química Bul., v. 68, n. 12, p. 2143-2154, 2019.
PURCELL, R. H: Hepatitis C virus; in Webster RG, Granoff A (eds): Encyclopedia of Virology.London, Bath Press, 1994, vol 2, pp 569–574.
Revista CENIC Ciencias Biológicas, v. 38, n. 1, 2007.
ROSA, R.L. et al. Investigação do uso de plantas medicinais no tratamento de indivíduos com diabetes melito na cidade de Herval D' Oeste - SC. Rev. bras. plantas medicinais, v.14, n.2, p. 306-310, 2012.
RUFFA, M.J.; PERUSINA, M.; ALFONSO, M.L.; WAGNERB, M.; SURIANO, B C.; VICENTE, R.; CAMPOSA, L. Cavallaroa Antiviral Activity of Petiveria alliacea against the Bovine Viral Diarrhea Virus. Chemotherapy, v. 48, p. 144–147, 2002.
SANTOS, R. C. Etal.Modificação molecular incremental: análise de parâmetros físico-químicos, farmacocinéticos e toxicológicos in sílico de fármacos inibidores seletivos da recaptação de serotonina (ISRSS). Boletim Informativo Geum, v. 9, n. 2, 2018.
SILVA CHAGAS, CK; ROLIM, CEL.; MARTINS, HP dos S.; DOLABELA, M. F. Estudo in silico de compostos fenólicos isolados de Inga laurina. Pesquisa, Sociedade e Desenvolvimento , [S. l.] , v. 11, n. 2, pág. e24511225592, 2022. DOI: 10.33448/rsd-v11i2.25592. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/25592. Acesso em: 23 jul. 2022.
ŠMELCEROVIĆ, A., TOMOVIĆ, K., ŠMELCEROVIĆ, Ž., PETRONIJEVIĆ, Ž., KOCIĆ, G., TOMAŠIČ, T., JAKOPIN, Z., & ANDERLUH, M. Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity. European journal of medicinal chemistry, v. 135, p. 491-516, 2017.
SOSA, H. M., SOSA, Y. J., PHANSALKAR, S., & STIEGLITZ, K. A. Structural Analysis of Flavonoid/Drug Target Complexes: Natural Products as Lead Compounds for Drug. Development.Nat Prod Chem Res, v. 5, n. 254, p.2, 2017.
SOUZA, M. V. N. Fármacos Inibidores de Fusão: uma Nova Estratégia no Combate à Replicação do Vírus VIH. Rio de Janeiro: Acta Farm. Bonaerense, v. 24, n. 2, p. 291-9, 2010.
THIEL, H. J.; PLAGEMANN, P.G.W.; MOENNING, V: Pestivirus; in Fields BF, Knipe DM, Howley PM (eds): Fields Virology, ed 3. Philadelphia, Lippincott- Raven, 1996, vol 1, pp 1059 1073.
TIMBRELL, J. A. Principles of Biochemistry Toxicology. Nova Iorque. Editora Informa Heathcare, 2009.
TISSERAND, R. Aromaterapia para todos. Belo Horizonte: Ed Laszlo, 2017. 252 p.
VIEIRA, G. D & SOUSA, C. M. Aspectoscelulares e fisiológicos da Barreira Hematoencefálica e a sua relação com as doenças neurodegenerativas. Journal of Health & Biological Sciences, v. 1, n. 4, p. 166-170, 2013.
VIEIRA, G. D & SOUSA, C. M. Aspectoscelulares e fisiológicos da Barreira Hematoencefálica e a sua relação com as doenças neurodegenerativas. Journal of Health & Biological Sciences, v. 1, n. 4, p. 166-170, 2013.
WAGNER, H.; BLADT, S: Plant Drugs Analysis. A Thin Layer Chromatography Atlas, ed 2. Berlin, Springer Verlag, 1996, pp 349–354.
WOLFFENBUTTEL, A. N. Bases químicas dos óleos essenciais e aromaterapia: Abordagens técnica e científica. Belo Horizonte: Ed. Laszlo, 2016. 494 p.
YAKAIAH, C.; SNEHA, T.; SHALINI, T.; SRINIVAS, C.; ANAND, K. D.; NIRANJANA, K. A.; SRINIVAS K. V. N. S.; SARFARAZ A.; KOTESH K. J.; FEROZ K.; ASHOK T., P. G. Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity. European Journal of Medicinal Chemistry, v. 93, p. 564-573, 2015.
YEE, S. In vitro permeability in Caco-2 (colonic) cells may predict absorption in vivo (small intestine) in humans -fact or myth. Pharm Res.v. 14, p. 763-766, 1997.
ZOGHBI, M. G. B.; ANDRADE, E. H. A.; MAIA, J. G. S. Volatile constituents from
Adenocalymma alliaceum Miers and Petiveria alliacea L., two medicinal herbs of the
Amazon. Flavour and Frangrance Journal, v. 17, p. 133-135, 2002.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Camila Cristina da Silva Miranda, Victor Alexandre Cardoso Salazar, Angélica Gomes Coelho
This work is licensed under a Creative Commons Attribution 4.0 International License.
Português (Brasil)
English
Español (España)