journal article·2022-12-21Open access

Production and Characterization of a β-Cyclodextrin Inclusion Complex with Platonia insignis Seed Extract as a Proposal for a Gastroprotective System

Juliana Lima Nascimento, Angélica Gomes Coelho, Ytallo Samuel Oliveira Barros, Irisdalva Sousa Oliveira, Francilene Vieira da Silva, Ana Flávia Seraine Custódio Viana, Bruno Quirino Araújo, Márcio dos Santos Rocha, Francisco das Chagas Pereira de Andrade, Celma de Oliveira Barbosa, Hélio de Barros Fernandes, Anderson Nogueira Mendes, Joaquim Soares da Costa-Júnior, Rita de Cássia Meneses Oliveira, Massimo Lucarini, Alessandra Durazzo, Daniel Dias Rufino Arcanjo, Antônia Maria das Graças Lopes Citó

Applied Sciences· Volume 13· Issue 1

Abstract

Platonia insignis Mart, Clusiaceae, known as bacuri, is a species native to Brazil that, in studies with extract of the seed of its fruit, showed antioxidant activity against free radicals. Products with such properties may be of great importance in the treatment of peptic ulcers since this pathology may be associated with the inflammatory process caused by the action of free radicals. Cyclodextrins are molecules capable of forming inclusion complexes with other molecules, affecting their physicochemical properties and improving their pharmacokinetic characteristics. Thus, this work aimed to produce, characterize, and evaluate the gastroprotective effect of the inclusion complex of β-cyclodextrin (β-CD) with the bacuri seeds hexanic extract (BSHE). In the characterization of the inclusion complex, an apparent stability constant (Kc) of 416 mol/L was obtained in the solubility study; the BSHE:β-CD m/m (g) complexation ratios at 1:9, 2:8, and 3:7 were 5.51%, 21.46%, and 20.11%, respectively. The formation of the BSHE:β-CD inclusion complex was observed by FTIR technique, indicating the disappearance of bands characteristic of BSHE (2960 cm−1 and 1755 cm−1) when in the complex, compared to the spectra of pure BSHE or in physical mixture with β-CD, and by X-ray diffraction, which indicated a loss of crystallinity, typical signals of pure β-CD, and presentation of intense amorphization, characteristic of BSHE, incorporated in the β-CD pockets. In the evaluation of gastroprotective activity, through absolute ethanol-induced gastric lesions in mice, both BSHE and BSHE:β-CD reduced gastric lesions, with 100 mg/kg dose of the complex having the greatest gastroprotective effect. BSHE:β-CD was also able to reduce gastric lesions from ischemia and reperfusion, with the 50 mg/kg dose being the most effective. BSHE:β-CD, also at this dose, reduced the MDA levels of the gastric mucosa, indicating a possible antioxidant activity in its gastroprotective effect. Thus, it was concluded that inclusion complex formation between β-CD and BSHE is possible, and that this formulation enhanced the gastric protective activity.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Phytochemistry Medicinal Plant Applications · Phytochemistry and biological activity of medicinal plants · Phytochemicals and Antioxidant Activities

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Laboratório de Geoquímica Orgânica, LAGO, Universidade Federal do Piauí, Teresina, Piauí 64049-550, Brazil

Departamento de Biofísica e Fisiologia, Universidade Federal do Piauí, Teresina, Piauí 64049-550, Brazil

Núcleo de Pesquisas em Plantas Medicinais, NPPM, Universidade Federal do Piauí, Teresina, Piauí 64049-550, Brazil

Departamento de Química, Instituto Federal de Educação, Ciência e Tecnologia do Piauí, Teresina, Piauí 64000-040, Brazil

CREA—Research Centre for Food and Nutrition, 00178 Rome, Italy

References (100+)

Show source-provided references
1. NuBBEDB: An updated database to uncover chemical and biological information from Brazilian biodiversity10.1038/s41598-017-07451-x ↗
2. Ramadan, M.F., Durazzo, A., and Lucarini, M. (2021). Advances in Research on Food Bioactive Molecules and Health. Molecules, 26.10.3390/molecules26247678 ↗
3. Figueiredo, A., Hugueney, P., and Durazzo, A. (2022). Recent Advances in Plant Metabolomics: From Metabolic Pathways to Health Impact. Biology, 11.10.3390/biology11020238 ↗
4. Durazzo, A., and Lucarini, M. (2021). Environmental, Ecological and Food Resources in the Biodiversity Overview: Health Benefits. Life, 11.10.3390/life11111228 ↗
5. The historical development of pharmacopoeias and the inclusion of exotic herbal drugs with a focus on Europe and Brazil10.1016/j.jep.2019.111891 ↗
6. The role of natural products in modern drug discovery10.1590/0001-3765201920190105 ↗
7. Studies on the volatile fraction composition of three native Amazonian-Brazilian fruits: Murici (Byrsonima crassifolia L., Malpighiaceae), bacuri (Platonia insignis M., Clusiaceae), and sapodilla (Manilkara sapota L., Sapotaceae)10.1016/j.foodchem.2016.09.098 ↗
8. Platonia insignis Mart., a Brazilian Amazonian Plant: The Stem Barks Extract and Its Main Constituent Lupeol Exert Antileishmanial Effects Involving Macrophages Activation10.1155/2017/3126458 ↗
9. Investigation of biological activities of dichloromethane and ethyl acetate fractions of Platonia insignis Mart. seed10.1111/j.1742-7843.2012.00924.x ↗
10. Bioactive compounds and antioxidant capacities of 18 non-traditional tropical fruits from Brazil10.1016/j.foodchem.2010.01.037 ↗
11. Biological evaluation and quantitative analysis of antioxidant compounds in pulps of the Amazonian fruits bacuri (Platonia insignis Mart.), ingá (Inga edulis Mart.), and uchi (Sacoglottis uchi Huber) by UHPLC-ESI-MS/MS10.1111/jfbc.12455 ↗
12. Emulgel based on amphotericin B and bacuri butter (Platonia insignis Mart.) for the treatment of cutaneous leishmaniasis: Characterization and in vitro assays10.1080/03639045.2018.1492610 ↗
13. Behavioral and neurochemical studies in mice pretreated with garcinielliptone FC in pilocarpine-induced seizures10.1016/j.pbb.2014.05.021 ↗
14. Immunomodulatory and toxicological evaluation of the fruit seeds from Platonia insignis, a native species from Brazilian Amazon Rainforest10.1016/j.bjp.2015.05.014 ↗
15. The regulatory mechanism and biological significance of the Snail-miR590-VEGFR-NRP1 axis in the angiogenesis, growth and metastasis of gastric cancer10.1038/s41419-020-2428-x ↗
16. Helicobacter pylori-induced adrenomedullin modulates IFN-γ-producing T-cell responses and contributes to gastritis10.1038/s41419-020-2391-6 ↗
17. Kalange, M., Nansunga, M., Kasozi, K.I., Kasolo, J., Namulema, J., Atusiimirwe, J.K., Ayikobua, E.T., Ssempijja, F., Munanura, E.I., and Matama, K. (2020). Antimalarial combination therapies increase gastric ulcers through an imbalance of basic antioxidative-oxidative enzymes in male Wistar rats. BMC Res. Notes, 13.10.1186/s13104-020-05084-4 ↗
18. Pumpkin Oil-Based Nanostructured Lipid Carrier System for Antiulcer Effect in NSAID-Induced Gastric Ulcer Model in Rats10.2147/IJN.S247252 ↗
19. Comparison of Antioxidant Effects of the Proton Pump-Inhibiting Drugs Omeprazole, Esomeprazole, Lansoprazole, Pantoprazole, and Rabeprazole10.1159/000506232 ↗
20. Oxidative free radicals scavenging activity (in vitro and in vivo assay) of standardized fractions from the seeds of Argyreia speciosa (Ghav-patta) a traditional Indian medicine
21. Crosstalk Between DNA Damage and Inflammation in the Multiple Steps of Gastric Carcinogenesis
22. Role of NRF2 in protection of the gastrointestinal tract against oxidative stress10.3164/jcbn.17-139 ↗
23. Carneiro, J.G., Holanda, T.D.B.L., Quinderé, A.L.G., Frota, A.F., Soares, V.V.M., Sousa, R.S., Carneiro, M.A., Martins, D.S., Gomes Duarte, A.S., and Benevides, N.M.B. (2018). Gastroprotective Effects of Sulphated Polysaccharides from the Alga Caulerpa mexicana Reducing Ethanol-Induced Gastric Damage. Pharmaceuticals, 11.10.3390/ph11010006 ↗
24. Oseltamivir and S-Adenosyl-L-Methionine Combination as Effective Therapeutic Strategy for Suppression of Oxidative Damage in Lung Caused by Influenza Virus Infection in Mice10.1055/a-1147-8824 ↗
25. Effect of carotenoid encapsulation on antioxidant activities: A protocol for systematic review10.1097/MD.0000000000019772 ↗
26. Toxicity of different forms of antimony to rice plants: Effects on reactive oxidative species production, antioxidative systems, and uptake of essential elements10.1016/j.envpol.2020.114544 ↗
27. Durazzo, A., Lombardi-Boccia, G., Santini, A., and Lucarini, M. (2021). Dietary Antioxidants and Metabolic Diseases. Int. J. Mol. Sci., 22.10.3390/ijms222212558 ↗
28. Oxyl radicals, redox-sensitive signalling cascades and antioxidants10.1016/j.cellsig.2007.04.009 ↗
29. Free radicals and antioxidants in normal physiological functions and human disease10.1016/j.biocel.2006.07.001 ↗
30. Reactive oxygen species and antioxidant defense in human gastrointestinal diseases10.1016/j.imr.2016.07.004 ↗
31. Study to explore the mechanism to form inclusion complexes of β-cyclodextrin with vitamin molecules10.1038/srep35764 ↗
32. Nanoparticle loaded hydrogel for the light-activated release and photothermal enhancement of antimicrobial peptides10.1021/acsami.9b22587 ↗
33. Enhanced dissolution, permeation and oral bioavailability of aripiprazole mixed micelles: In vitro and in vivo evaluation10.1016/j.ijpharm.2020.119361 ↗
34. Synthesis, characterization of α-terpineol-loaded PMMA nanoparticles as proposed of therapy for melanoma10.1016/j.mtcomm.2019.100762 ↗
35. Encapsulation of Piper cabralanum (Piperaceae) nonpolar extract in poly(methyl methacrylate) by miniemulsion and evaluation of increase in the effectiveness of antileukemic activity in K562 cells10.2147/IJN.S134756 ↗
36. Souto, E.B., Silva, G.F., Dias-Ferreira, J., Zielinska, A., Ventura, F., Durazzo, A., Lucarini, M., Novellino, E., and Santini, A. (2020). Nanopharmaceutics: Part I-Clinical Trials Legislation and Good Manufacturing Practices (GMP) of Nanotherapeutics in the EU. Pharmaceutics, 12.10.3390/pharmaceutics12020146 ↗
37. Souto, E.B., Silva, G.F., Dias-Ferreira, J., Zielinska, A., Ventura, F., Durazzo, A., Lucarini, M., Novellino, E., and Santini, A. (2020). Nanopharmaceutics: Part II-Production Scales and Clinically Compliant Production Methods. Nanomaterials, 10.10.3390/nano10030455 ↗
38. Big impact of nanoparticles: Analysis of the most cited nanopharmaceuticals and nanonutraceuticals research10.1016/j.crbiot.2020.04.002 ↗
39. Garcinielliptone FC, a polyisoprenylated benzophenone from Platonia insignis Mart., promotes vasorelaxant effect on rat mesenteric artery10.1080/14786419.2014.889136 ↗
40. Phase solubility techniques
41. Coelho, L.N. (2001). Estudo da Inclusão de Filtros Solares em Ciclodextrinas e suas Aplicações em Dermocosmética. [Master’s Thesis, Faculdade de Farmácia do Rio de Janeiro].
42. Evaluation of effects of dichloromethane fraction from Platonia insignis on pilocarpine-induced seizures10.1590/S0102-695X2011005000163 ↗
43. Anti-inflammatory phloroglucinols and terpenoids from Garcinia subelliptica10.1021/np049811x ↗
44. Novel and anti-inflammatory constituents of Garcinia subelliptica10.1002/chem.200204535 ↗
45. Cytoprotection by prostaglandins in rats. Prevention of gastric necrosis produced by alcohol, HCl, NaOH, hypertonic NaCl, and thermal injury10.1016/0016-5085(79)90002-7 ↗
46. (−)-Myrtenol accelerates healing of acetic acid-induced gastric ulcers in rats and in human gastric adenocarcinoma cells10.1016/j.ejphar.2019.04.025 ↗
47. Acid secretagogues induce Ca2+ mobilization coupled to K+ conductance activation in rat parietal cells in tissue culture10.1016/0167-4889(89)90105-5 ↗
48. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction10.1016/0003-2697(79)90738-3 ↗
49. The mechanism of bensulfuron-methyl complexation with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin and effect on soil adsorption and bio-activity10.1038/s41598-018-38234-7 ↗
50. Injectable inclusion complex composed of α-cyclodextrin and hydrophobically modified poly(vinyl alcohol) as a cerebral aneurysm embolization material10.1038/s41428-020-0321-1 ↗
51. Real, D.A., Bolaños, K., Priotti, J., Yutronic, N., Kogan, M.J., Sierpe, R., and Donoso-González, O. (2021). Cyclodextrin-Modified Nanomaterials for Drug Delivery: Classification and Advances in Controlled Release and Bioavailability. Pharmaceutics, 13.10.3390/pharmaceutics13122131 ↗
52. Cyclodextrin-enabled green environmental biotechnologies10.1007/s11356-021-18176-w ↗
53. Inclusion of terpenes in cyclodextrins: Preparation, characterization and pharmacological approaches10.1016/j.carbpol.2016.06.040 ↗
54. Prodea, A., Mioc, A., Banciu, C., Trandafirescu, C., Milan, A., Racoviceanu, R., Ghiulai, R., Mioc, M., and Soica, C. (2022). The Role of Cyclodextrins in the Design and Development of Triterpene-Based Therapeutic Agents. Int. J. Mol. Sci., 23.10.3390/ijms23020736 ↗
55. Structural and energetic investigation on the host/guest inclusion process of benzyl isothiocyanate into β-cyclodextrin using dispersion-corrected DFT calculations10.1016/j.carres.2020.107980 ↗
56. Physicochemical characterization of cyclodextrin-drug interactions in the solid state and the effect of water on these interactions10.1002/jps.24319 ↗
57. Fast-dissolving electrospun gelatin nanofibers encapsulating ciprofloxacin/cyclodextrin inclusion complex10.1016/j.colsurfb.2019.02.059 ↗
58. Cyclodextrins and ternary complexes: Technology to improve solubility of poorly soluble drugs10.1590/S1984-82502011000400003 ↗
59. Inclusion complexation of imidazolium-based ionic liquid and β-cyclodextrin: A detailed spectroscopic investigation10.1016/j.molliq.2020.112530 ↗
60. Gao, S., Jiang, J.-Y., Liu, Y.-Y., Fu, Y., Zhao, L.X., Li, C.Y., and Ye, F. (2019). Enhanced Solubility, Stability, and Herbicidal Activity of the Herbicide Diuron by Complex Formation with β-Cyclodextrin. Polymers, 11.10.3390/polym11091396 ↗
61. Antifungal activity of econazole nitrate/cyclodextrin complex: Effect of pH and formation of complex aggregates10.1016/j.ijpharm.2019.118896 ↗
62. Cyclodextrins as solubilizers: Formation of complex aggregates10.1002/jps.21861 ↗
63. Cyclodextrins as pharmaceutical solubilizers10.1016/j.addr.2007.05.012 ↗
64. Curcumin loaded poly (amidoamine) dendrimer-plamitic acid core-shell nanoparticles as anti-stress therapeutics10.1080/03639045.2020.1724132 ↗
65. A cyclodextrin polymer membrane-based passive sampler for measuring triclocarban, triclosan and methyl triclosan in rivers10.1016/j.scitotenv.2018.08.151 ↗
66. Aspectos biofarmacêuticos da formulação de medicamentos para neonatos: Fundamentos da complexação de indometacina com hidroxipropil-b-ciclodextrina para tratamento oral do fechamento do canal arterial10.1590/S1516-93322005000300002 ↗
67. Avaliação da atividade antioxidante in vitro do extrato hexânico da semente do bacuri (Platonia insignis Mart.) e de seu complexo de inclusão com β-ciclodextrina
68. Complexation of the local anesthetic pramoxine with hydroxypropyl-beta-cyclodextrin can improve its bioavailability10.1016/j.jddst.2019.101475 ↗
69. Aqueous solubility of kinase inhibitors: II the effect of hexadimethrine bromide on the dovitinib/γ-cyclodextrin complexation10.1016/j.jddst.2019.101463 ↗
70. Preparation and characterization of phloretin by complexation with cyclodextrins10.1039/C9NJ06228A ↗
71. Cyclodextrin solubilization and complexation of antiretroviral drug lopinavir: In silico prediction; Effects of derivatization, molar ratio and preparation method10.1016/j.carbpol.2019.115287 ↗
72. Nystatin complexation with β-cyclodextrin: Spectroscopic evaluation of inclusion by FT-Raman, photoacoustic spectroscopy, and 1H NMR10.1016/j.matchemphys.2019.122117 ↗
73. Case to case study for exploring inclusion complexes of an anti-diabetic alkaloid with α and β cyclodextrin molecules for sustained dischargement10.1016/j.molstruc.2019.126988 ↗
74. Formulation and evaluation of β-cyclodextrin-mediated inclusion complexes of isoniazid scaffolds: Molecular docking and in vitro assessment of antitubercular properties10.1039/C9NJ06351J ↗
75. Hydrocortisone/cyclodextrin complex electrospun nanofibers for a fast-dissolving oral drug delivery system10.1039/C9MD00390H ↗
76. Preparation of sulfobutylether β-cyclodextrin-silica hybrid monolithic column, and its application to capillary electrochromatography of chiral compounds10.1016/j.chroma.2020.460932 ↗
77. Inclusion complexation of novel synthesis amino acid based ionic liquids with β-cyclodextrin10.1016/j.molliq.2019.112204 ↗
78. Infrared-based protocol for the identification and categorisation of ginseng and its products10.1016/j.foodres.2006.11.009 ↗
79. Complexation of a cationic pyrene derivative with sulfobutylether substituted β-cyclodextrin: Towards a stimulus-responsive supramolecular material10.1016/j.molliq.2020.112840 ↗
80. Combined computational and experimental study on the inclusion complexes of β-cyclodextrin with selected food phenolic compounds10.1007/s11224-019-01347-4 ↗
81. A theoretical investigation on the encapsulation process of mepivacaine into β-cyclodextrin10.1016/j.cplett.2019.137060 ↗
82. DFT investigation of host–guest interactions between α-Terpineol and β-cyclodextrin10.1007/s10847-019-00940-8 ↗
83. Host–guest interaction between 20(S)-protopanaxatriol and three polyamine-modified β-cyclodextrins: Preparation, characterization, inclusion modes, and solubilization10.1007/s10847-020-00992-1 ↗
84. Maltosyl-β-cyclodextrin mediated Supramolecular Host-Guest inclusion complex used for enhancing baicalin antioxidant activity and bioavailability10.1016/j.jddst.2019.101346 ↗
85. Inclusion complex of emodin with hydroxypropyl-β-cyclodextrin: Preparation, physicochemical and biological properties10.1016/j.molliq.2019.111151 ↗
86. X-ray crystal structures of α-cyclodextrin–5-hydroxypentanoic acid, β-cyclodextrin–5-hydroxypentanoic acid, β-cyclodextrin–ε-caprolactone, and β-cyclodextrin–ε-caprolactam inclusion complexes10.1007/s10847-019-00953-3 ↗
87. Physicochemical properties and fungicidal activity of inclusion complexes of fungicide chlorothalonil with β-cyclodextrin and hydroxypropyl-β-cyclodextrin10.1016/j.molliq.2019.111513 ↗
88. Enhanced physicochemical properties and herbicidal activity of an environment-friendly clathrate formed by β-cyclodextrin and herbicide cyanazine10.1016/j.molliq.2020.112858 ↗
89. β-Cyclodextrin encapsulation of nortriptyline HCl and amitriptyline HCl: Molecular insights from single-crystal X-ray diffraction and DFT calculation10.1016/j.ijpharm.2019.118899 ↗
90. Encapsulation of boswellic acid with β- and hydroxypropyl-β-cyclodextrin: Synthesis, characterization, in vitro drug release and molecular modelling studies10.1016/j.molstruc.2017.10.061 ↗
91. Solid-state characterization and dissolution properties of Naproxen–Arginine–Hydroxypropyl-β-cyclodextrin ternary system10.1016/j.ejpb.2004.05.005 ↗
92. Preparation of budesonide/γ-cyclodextrin complexes in supercritical fluids with a novel SEDS method10.1002/jps.20702 ↗
93. Physical–chemical characterization of binary systems of metformin hydrochloride with triacetyl-β-cyclodextrin10.1016/j.jpba.2007.07.018 ↗
94. Effect of allantoin on experimentally induced gastric ulcers: Pathways of gastroprotection10.1016/j.ejphar.2017.12.052 ↗
95. Antiulcerogenic activity of Scutia buxifolia on gastric ulcers induced by ethanol in rats10.1016/j.apsb.2014.05.001 ↗
96. Protective action of ethanolic extract of Rosmarinus officinalis L. in gastric ulcer prevention induced by ethanol in rats10.1016/j.fct.2012.12.038 ↗
97. Evaluation of antiulcer activity of the main phenolic acids found in Brazilian Green Propolis10.1016/j.jep.2008.09.015 ↗
98. Use of plant oils from the southwestern Amazon for the control of maize weevil10.1016/j.jspr.2015.07.002 ↗
99. Medicinal plants from the Brazilian Amazonian region and their antileishmanial activity: A review10.1016/j.joim.2018.04.004 ↗
100. Evaluation of possible antioxidant and anticonvulsant effects of the ethyl acetate fraction from Platonia insignis Mart. (Bacuri) on epilepsy models10.1016/j.yebeh.2011.09.021 ↗