دورية أكاديمية
Cyclodextrin inclusion complex of a multi-component natural product by hot-melt extrusion.
العنوان: | Cyclodextrin inclusion complex of a multi-component natural product by hot-melt extrusion. |
---|---|
المؤلفون: | de Oliveira Nonato R; Laboratory of Nanosystems and Drug Delivery Devices (NanoSYS), School of Pharmacy, Universidade Federal de Goiás (UFG), Setor Leste Universitário, Rua 240, Goiânia, GO, 74605-170, Brazil., Krawczyk-Santos AP; Laboratory of Nanosystems and Drug Delivery Devices (NanoSYS), School of Pharmacy, Universidade Federal de Goiás (UFG), Setor Leste Universitário, Rua 240, Goiânia, GO, 74605-170, Brazil., Cardoso G; Laboratory of Nanosystems and Drug Delivery Devices (NanoSYS), School of Pharmacy, Universidade Federal de Goiás (UFG), Setor Leste Universitário, Rua 240, Goiânia, GO, 74605-170, Brazil., Kogawa AC; School of Pharmacy, Universidade Federal de Goiás (UFG), Goiânia, GO, Brazil., Ricommini K; Pharmaceutical Application Laboratory, Ashland Specialty Ingredients, São Paulo, SP, Brazil., de Lima ÁAN; Pharmacy Department, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil., Heimfarth L; Department of Physiology (DFS), Laboratory of Neuroscience and Pharmacological Assays (LANEF), Universidade Federal de Sergipe, São Cristóvão, SE, Brazil., Quintans-Júnior LJ; Department of Physiology (DFS), Laboratory of Neuroscience and Pharmacological Assays (LANEF), Universidade Federal de Sergipe, São Cristóvão, SE, Brazil., Cunha-Filho M; Laboratory of Food, Drug, and Cosmetics (LTMAC), School of Health Sciences, Universidade de Brasilia, Brasília, DF, Brazil., Taveira SF; Laboratory of Nanosystems and Drug Delivery Devices (NanoSYS), School of Pharmacy, Universidade Federal de Goiás (UFG), Setor Leste Universitário, Rua 240, Goiânia, GO, 74605-170, Brazil., Marreto RN; Laboratory of Nanosystems and Drug Delivery Devices (NanoSYS), School of Pharmacy, Universidade Federal de Goiás (UFG), Setor Leste Universitário, Rua 240, Goiânia, GO, 74605-170, Brazil. ricardomarreto@ufg.br. |
المصدر: | Drug delivery and translational research [Drug Deliv Transl Res] 2023 Apr; Vol. 13 (4), pp. 1140-1152. Date of Electronic Publication: 2022 Dec 23. |
نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
اللغة: | English |
بيانات الدورية: | Publisher: Springer Country of Publication: United States NLM ID: 101540061 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 2190-3948 (Electronic) Linking ISSN: 2190393X NLM ISO Abbreviation: Drug Deliv Transl Res Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: New York : Springer |
مواضيع طبية MeSH: | Cyclodextrins*/chemistry, 2-Hydroxypropyl-beta-cyclodextrin/chemistry ; Catechols ; Solubility |
مستخلص: | This study aimed to investigate whether hot-melt extrusion (HME) processing can promote molecular encapsulation of a multi-component natural product composed of volatile and pungent hydrophobic substances (ginger oleoresin (OR)) with cyclodextrins. 6-Gingerol and 6-shogaol, the biomarkers of ginger OR, were quantified by HPLC. Phase-solubility studies were performed using β-cyclodextrin (βCD) and hydroxypropyl-β-cyclodextrin (HPβCD) for ginger OR complexation. Solid complexes were then prepared by thermal (HME)- and solvent (slurry (SL))-based methods. Morphology, thermal behavior, solubility, in vitro dissolution, and in vivo anti-inflammatory activity were evaluated. HPβCD gave rise to AL-type complexes with ginger OR, whereas βCD led to materials with limited solubility. Ginger OR was complexed with HPβCD by HME without significant change in gingerol and shogaol content. Additionally, thermogravimetric analysis (TGA) suggested higher volatile retention in HME complexes than in SL ones. Shogaol and gingerol solubility and dissolution significantly increased from SL and HME complexes compared with ginger OR. In turn, 1:2 OR/HPβCD HME complex showed higher 6-shogaol solubility than SL, associated with a gradual release. The carrageenan-induced pleurisy test showed that the anti-inflammatory activity of ginger OR was maintained after complexation with HPβCD. The complexes significantly decrease the levels of IL-1β and inhibit cell migration. HME complex showed performance equivalent to the positive control and superior to the SL material. Taken together, these results indicate that HME can be useful for promoting the molecular encapsulation of complex natural products that contain volatile and thermolabile substances. HME complexes showed better in vivo and in vitro performance than complexes prepared using the solvent-based method. (© 2022. Controlled Release Society.) |
References: | Srinivasan K. Ginger rhizomes (Zingiber officinale): a spice with multiple health beneficial potentials. PharmaNutrition. 2017;5:18–28. (PMID: 10.1016/j.phanu.2017.01.001) de Souza EPBSS, Gomes MVLD, dos Santos Lima B, Silva LAS, Shanmugan S, Cavalcanti MD, et al. Nerolidol-beta-cyclodextrin inclusion complex enhances anti-inflammatory activity in arthritis model and improves gastric protection. Life Sci. 2021;265. Wang S, Zhang C, Yang G, Yang Y. Biological properties of 6-gingerol: a brief review. Nat Prod Commun. 2014;9:1027–30. (PMID: 25230520) Lantz RC, Chen GJ, Sarihan M, Sólyom AM, Jolad SD, Timmermann BN. The effect of extracts from ginger rhizome on inflammatory mediator production. Phytomedicine. 2007;14:123–8. (PMID: 10.1016/j.phymed.2006.03.00316709450) Harimurti N, Nhestricia N, Subardjo SY, Yuliani S. Effect of oleoresin concentration and composition of encapsulating materials on properties of the microencapsulated ginger oleoresin using spray drying method. Indones J Agric. 2011;4:33–9. Bhattarai S, Van Tran H, Duke CC. The stability of gingerol and shogaol in aqueous solutions. J Pharm Sci. 2001;90:1658–64. (PMID: 10.1002/jps.111611745724) Bhattarai S, Tran VH, Duke CC. Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluids. J Pharm Biomed Anal. 2007;45:648–53. (PMID: 10.1016/j.jpba.2007.07.00617706909) Pais JM, Pereira B, Paz FAA, Cardoso SM, Braga SS. Solid γ-cyclodextrin inclusion compound with gingerols, a multi-component guest: preparation, properties and application in yogurt. Biomolecules. 2020;10. Li R, Bao R, Yang QX, Wang QL, Adu-Frimpong M, Wei QY, et al. [6]-Shogaol/β-CDs inclusion complex: preparation, characterisation, in vivo pharmacokinetics, and in situ intestinal perfusion study. J Microencapsul [Internet]. Taylor & Francis; 2019;36:500–12. Available from: https://doi.org/10.1080/02652048.2019.1649480 . Carneiro SB, Duarte FÍC, Heimfarth L, Quintans JDSS, Quintans-Júnior LJ, Júnior VFDV, et al. Cyclodextrin-drug inclusion complexes: in vivo and in vitro approaches. Int J Mol Sci. 2019;20:1–23. (PMID: 10.3390/ijms20030642) da Silva JA, Sampaio PA, Dulcey LJL, Cominetti MR, Rabello MM, Rolim LA. Preparation and characterization of [6]-gingerol/β-cyclodextrin inclusion complexes. J Drug Deliv Sci Technol. 2021;61. de Almeida Magalhães TSS, de Oliveira Macedo PC, da Costa ÉCP, de Aragão Tavares E, da Silva VC, Guerra GCB, et al. Increase in the antioxidant and anti-inflammatory activity of Euterpe oleracea Martius oil complexed in β-cyclodextrin and hydroxypropyl-β-cyclodextrin. Int J Mol Sci. 2021;22. Thiry J, Krier F, Ratwatte S, Thomassin JM, Jerome C, Evrard B. Hot-melt extrusion as a continuous manufacturing process to form ternary cyclodextrin inclusion complexes. Eur J Pharm Sci [Internet]. Elsevier B.V.; 2017;96:590–7. Available from: https://doi.org/10.1016/j.ejps.2016.09.032 . Fukuda M, Miller DA, Peppas NA, McGinity JW. Influence of sulfobutyl ether β-cyclodextrin (Captisol ® ) on the dissolution properties of a poorly soluble drug from extrudates prepared by hot-melt extrusion. Int J Pharm. 2008;350:188–96. (PMID: 10.1016/j.ijpharm.2007.08.03817920217) Malaquias LFB, Sá-Barreto LCL, Freire DO, Silva ICR, Karan K, Durig T, et al. Taste masking and rheology improvement of drug complexed with beta-cyclodextrin and hydroxypropyl-β-cyclodextrin by hot-melt extrusion. Carbohydr Polym [Internet]. Elsevier; 2018;185:19–26. Available from: https://doi.org/10.1016/j.carbpol.2018.01.011 . Marreto RN, Cardoso G, dos Santos Souza B, Martin-Pastor M, Cunha-Filho M, Taveira SF, et al. Hot melt-extrusion improves the properties of cyclodextrin-based poly(pseudo)rotaxanes for transdermal formulation. Int J Pharm [Internet]. Elsevier; 2020;586:119510. Available from: https://doi.org/10.1016/j.ijpharm.2020.119510 . Higuchi T, Connors KA. Phase-solubility techniques advances in analytical chemistry and instrumentation. 1965. de Oliveira AM, Conserva LM, de Souza Ferro JN, de Almeida Brito F, Lyra Lemos RP, Barreto E. Antinociceptive and anti-inflammatory effects of octacosanol from the leaves of Sabicea grisea var. grisea in mice. Int J Mol Sci. 2012;13:1598–611. Vinegar R, Truax JF, Selph JL. Some quantitative temporal characteristics of carrageenin-induced pleurisy in the rat. Proc Soc Exp Biol Med. 1973;143:711–4. (PMID: 10.3181/00379727-143-373974719457) Balachandran S, Kentish SE, Mawson R, Ashokkumar M. Ultrasonic enhancement of the supercritical extraction from ginger. Ultrason Sonochem. 2006;13:471–9. (PMID: 10.1016/j.ultsonch.2005.11.00616423551) Cheng XL, Liu Q, Peng YB, Qi LW, Li P. Steamed ginger (Zingiber officinale): changed chemical profile and increased anticancer potential. Food Chem [Internet]. Elsevier Ltd; 2011;129:1785–92. Available from: https://doi.org/10.1016/j.foodchem.2011.06.026 . Kou X, Li X, Rahman MRT, Yan M, Huang H, Wang H, et al. Efficient dehydration of 6-gingerol to 6-shogaol catalyzed by an acidic ionic liquid under ultrasound irradiation. Food Chem [Internet]. Elsevier Ltd; 2017;215:193–9. Available from: https://doi.org/10.1016/j.foodchem.2016.07.106 . Salmon CNA, Bailey-Shaw YA, Hibbert S, Green C, Smith AM, Williams LAD. Characterisation of cultivars of Jamaican ginger (Zingiber officinale Roscoe) by HPTLC and HPLC. Food Chem. Elsevier Ltd; 2012;131:1517–22. Available from: https://doi.org/10.1016/j.foodchem.2011.09.115 . Varakumar S, Umesh KV, Singhal RS. Enhanced extraction of oleoresin from ginger (Zingiber officinale) rhizome powder using enzyme-assisted three phase partitioning. Food Chem. Elsevier Ltd; 2017;216:27–36. Available from: https://doi.org/10.1016/j.foodchem.2016.07.180 . Jambhekar SS, Breen P. Cyclodextrins in pharmaceutical formulations II: solubilization, binding constant, and complexation efficiency. Drug Discov Today. Elsevier Ltd; 2016;21:363–8. Available from: https://doi.org/10.1016/j.drudis.2015.11.016 . Haiyee ZA, Saim N, Said M, Illias RM, Mustapha WAW, Hassan O. Characterization of cyclodextrin complexes with turmeric oleoresin. Food Chem. Elsevier Ltd; 2009;114:459–65. Available from: https://doi.org/10.1016/j.foodchem.2008.09.072 . de Almeida Magalhães TSS, de Oliveira Macedo PC, Pacheco SYK, da Silva SS, Barbosa EG, Pereira RR, et al. Development and evaluation of antimicrobial and modulatory activity of inclusion complex of Euterpe oleracea Mart oil and β-cyclodextrin or HP-β-cyclodextrin. Int J Mol Sci. 2020;21. Ozdemir N, Pola CC, Teixeira BN, Hill LE, Bayrak A, Gomes CL. Preparation of black pepper oleoresin inclusion complexes based on beta-cyclodextrin for antioxidant and antimicrobial delivery applications using kneading and freeze drying methods: a comparative study. LWT - Food Sci Technol. Elsevier; 2018;91:439–45. Available from: https://doi.org/10.1016/j.lwt.2018.01.046 . Pinheiro JG de O, Tavares E de A, da Silva SS, Silva JF, de Carvalho YMBG, Ferreira MRA, et al. Inclusion complexes of copaiba (Copaifera multijuga Hayne) oleoresin and cyclodextrins: physicochemical characterization and anti-inflammatory activity. Int J Mol Sci. 2017;18. Marreto RN, Almeida EECV, Alves PB, Niculau ES, Nunes RS, Matos CRS, et al. Thermal analysis and gas chromatography coupled mass spectrometry analyses of hydroxypropyl-β-cyclodextrin inclusion complex containing Lippia gracilis essential oil. Thermochim Acta. 2008;475:53–8. (PMID: 10.1016/j.tca.2008.06.015) Pires FQ, Pinho LA, Freire DO, Silva ICR, Sa-Barreto LL, Cardozo-Filho L, et al. Thermal analysis used to guide the production of thymol and Lippia origanoides essential oil inclusion complexes with cyclodextrin. J Therm Anal Calorim. Springer International Publishing; 2019;137:543–53. Available from: https://doi.org/10.1007/s10973-018-7956-6 . Mašková E, Kubová K, Raimi-Abraham BT, Vllasaliu D, Vohlídalová E, Turánek J, et al. Hypromellose – a traditional pharmaceutical excipient with modern applications in oral and oromucosal drug delivery. J Control Release. Elsevier; 2020;324:695–727. Available from: https://doi.org/10.1016/j.jconrel.2020.05.045 . Jog R, Gokhale R, Burgess DJ. Solid state drug-polymer miscibility studies using the model drug ABT-102. Int J Pharm. Elsevier B.V.; 2016;509:285–95. Available from: https://doi.org/10.1016/j.ijpharm.2016.05.068 . Fröde TS, Souza GEP, Calixto JB. The modulatory role played by TNF-α and IL-1β in the inflammatory responses induced by carrageenan in the mouse model of pleurisy. Cytokine. 2001;13:162–8. (PMID: 10.1006/cyto.2000.081611161459) Loram LC, Fuller A, Fick LG, Cartmell T, Poole S, Mitchell D. Cytokine profiles during carrageenan-induced inflammatory hyperalgesia in rat muscle and hind paw. J Pain. 2007;8:127–36. (PMID: 10.1016/j.jpain.2006.06.01016949880) Barreto RSS, Quintans JSS, Amarante RKL, Nascimento TS, Amarante RS, Barreto AS, et al. Evidence for the involvement of TNF-α and IL-1β in the antinociceptive and anti-inflammatory activity of Stachys lavandulifolia Vahl. (Lamiaceae) essential oil and (-)-α-bisabolol, its main compound, in mice. J Ethnopharmacol. Elsevier; 2016;191:9–18. Available from: https://doi.org/10.1016/j.jep.2016.06.022 . Lima B dos S, Campos C de A, da Silva Santos ACR, Santos VCN, Trindade G das GG, Shanmugam S, et al. Development of morin/hydroxypropyl-β-cyclodextrin inclusion complex: enhancement of bioavailability, antihyperalgesic and anti-inflammatory effects. Food Chem Toxicol. Elsevier; 2019;126:15–24. Available from: https://doi.org/10.1016/j.fct.2019.01.038 . Loram LC, Fuller A, Cartmell T, Mitchell B, Mitchell D. Behavioural, histological and cytokine responses during hyperalgesia induced by carrageenan injection in the rat tail. Physiol Behav. 2007;92:873–80. (PMID: 10.1016/j.physbeh.2007.06.01517692348) ALmohaimeed HM, Mohammedsaleh ZM, Batawi AH, Balgoon MJ, Ramadan OI, Baz HA, et al. Synergistic anti-inflammatory and neuroprotective effects of Cinnamomum cassia and Zingiber officinale alleviate diabetes-induced hippocampal changes in male albino rats: structural and molecular evidence. Front Cell Dev Biol. 2021;9:727049. Bischoff-Kont I, Fürst R. Benefits of ginger and its constituent 6-shogaol in inhibiting inflammatory processes. Pharmaceuticals. 2021;14:1–19. (PMID: 10.3390/ph14060571) Ha SK, Moon E, Ju MS, Kim DH, Ryu JH, Oh MS, et al. 6-Shogaol, a ginger product, modulates neuroinflammation: a new approach to neuroprotection. Neuropharmacology. Elsevier Ltd; 2012;63:211–23. Available from: https://doi.org/10.1016/j.neuropharm.2012.03.016 . |
فهرسة مساهمة: | Keywords: Cyclodextrin; Ginger; Gingerols; Hot-melt extrusion; Oleoresin; Shogaols |
المشرفين على المادة: | 83DNB5FIRF (shogaol) 0 (Cyclodextrins) 1I96OHX6EK (2-Hydroxypropyl-beta-cyclodextrin) 925QK2Z900 (gingerol) 0 (Catechols) |
تواريخ الأحداث: | Date Created: 20221223 Date Completed: 20230306 Latest Revision: 20230324 |
رمز التحديث: | 20230327 |
DOI: | 10.1007/s13346-022-01280-w |
PMID: | 36564661 |
قاعدة البيانات: | MEDLINE |
تدمد: | 2190-3948 |
---|---|
DOI: | 10.1007/s13346-022-01280-w |