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Terpenes and derivatives as a new perspective for pain treatment: a patent review

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Ksenija Rutnik, Maša Knez Hrnčič & Iztok Jože Košir. (2022) Hop Essential Oil: Chemical Composition, Extraction, Analysis, and Applications. Food Reviews International 38:sup1, pages 529-551.
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Mariia Nesterkina, Sergii Smola & Iryna Kravchenko. (2019) Effect of esters based on terpenoids and GABA on fluidity of phospholipid membranes. Journal of Liposome Research 29:3, pages 239-246.
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Tamiris Alves Rocha, Danielle Feijó de Moura, Marllyn Marques da Silva, Talita Giselly dos Santos Souza, Maria Aparecida da Conceição de Lira, Dayane de Melo Barros, Alexandre Gomes da Silva, Rafael Matos Ximenes, Emerson Peter da Silva Falcão, Cristiano Aparecido Chagas, Francisco Carlos Amanajás de Aguiar Júnior, Noêmia Pereira da Silva Santos, Marcia Vanusa da Silva & Maria Tereza dos Santos Correia. (2019) Evaluation of cytotoxic potential, oral toxicity, genotoxicity, and mutagenicity of organic extracts of Pityrocarpa moniliformis. Journal of Toxicology and Environmental Health, Part A 82:3, pages 216-231.
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Janaina Kieling Fröhlich, Taciane Stein, Layzon Antônio da Silva, Maique Weber Biavatti, Carlos Rogério Tonussi & Elenara Lemos-Senna. (2017) Antinociceptive and anti-inflammatory activities of the Jatropha isabellei dichloromethane fraction and isolation and quantitative determination of jatrophone by UFLC-DAD. Pharmaceutical Biology 55:1, pages 1215-1222.
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Heitor G. Araújo-Filho, Jessica Deise Santos Dias, Lucindo J. Quintans-Júnior, Márcio R. V. Santos, Pollyanna A. S. White, Rosana S. S. Barreto, André S. Barreto, Charles S. Estevam, Silvan S. Araujo, Jackson R. G. S. Almeida, Irwin R. A. Menezes, Henrique D. M. Coutinho & Jullyana S. S. Quintans. (2016) Phytochemical screening and analgesic profile of the lyophilized aqueous extract obtained from Chrysobalanus icaco leaves in experimental protocols. Pharmaceutical Biology 54:12, pages 3055-3062.
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Michele Fraga de Santana, Adriana Gibara Guimarães, Danielle Oliveira Chaves, Juliane Cabral Silva, Leonardo Rigoldi Bonjardim, Waldecy de Lucca Júnior, Jamylle Nunes de Souza Ferro, Emiliano de Oliveira Barreto, Flávia Evangelista dos Santos, Milena Botelho Pereira Soares, Cristiane Flora Villarreal, Jullyana de Souza Siqueira Quintans & Lucindo José Quintans-Júnior. (2015) The anti-hyperalgesic and anti-inflammatory profiles of p-cymene: Evidence for the involvement of opioid system and cytokines. Pharmaceutical Biology 53:11, pages 1583-1590.
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Miriana Kfoury, Ramona Balan, David Landy, Denisa Nistor & Sophie Fourmentin. (2015) Investigation of the complexation of essential oil components with cyclodextrins. Supramolecular Chemistry 27:9, pages 620-628.
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GB de Oliveira Makson, Adriana G Guimarães, AS Araújo Adriano, SS Quintans Jullyana, Márcio RV Santos & Lucindo J Quintans-Júnior. (2015) Cyclodextrins: improving the therapeutic response of analgesic drugs: a patent review. Expert Opinion on Therapeutic Patents 25:8, pages 897-907.
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Kurati Sony Priya, Bothsa Sruthi Sri, Kimariyo Patrick F, Guruvelli Sangeeta, Perupogu Suvarna B & Muthyala Murali Krishna K. Synthesis and screening of clerodane diterpene analogues from 16 hydroxycleroda 3,13(14)-Z-diene 15,16-olide for potential anti-mycobacterial activity. Natural Product Research 0:0, pages 1-9.
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Adrian Łukowski, Radosław Jagiełło, Piotr Robakowski, Dawid Adamczyk & Piotr Karolewski. (2022) Adaptation of a simple method to determine the total terpenoid content in needles of coniferous trees. Plant Science 314, pages 111090.
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Parul Kaushik, Priyanka Ahlawat, Kuldeep Singh & Raman Singh. (2021) Chemical constituents, pharmacological activities, and uses of common ayurvedic medicinal plants: a future source of new drugs. Advances in Traditional Medicine.
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Vincent Maida, Runjie Bill Shi, Francesco Gabriele Tatangelo Fazzari & Lydia Zomparelli. (2021) Topical cannabis‐based medicines – A novel adjuvant treatment for venous leg ulcers: An open‐label trial. Experimental Dermatology 30:9, pages 1258-1267.
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Wensu Ji & Xiaoyue Ji. (2021) Comparative Analysis of Volatile Terpenes and Terpenoids in the Leaves of Pinus Species—A Potentially Abundant Renewable Resource. Molecules 26:17, pages 5244.
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Rayane da Cruz Albino, Marcelle Magalhães Braz, Humberto Ribeiro Bizzo, Raquel Vieira Santana da Silva, Suzana Guimarães Leitão & Danilo Ribeiro de Oliveira. (2021) Amazonian medicinal smokes: Chemical analysis of Burseraceae pitch (breu) oleoresin smokes and insights into their use on headache. Journal of Ethnopharmacology 276, pages 114165.
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Paco Noriega. 2021. Terpenes and Terpenoids - Recent Advances. Terpenes and Terpenoids - Recent Advances.
Mohammad Abbas Sheikholeslami, Shiva Ghafghazi, Siavash Parvardeh, Sheida Koohsari, Saeed Haji Aghajani, Ramin Pouriran & Leila Alipour Vaezi. (2021) Analgesic effects of cuminic alcohol (4-isopropylbenzyl alcohol), a monocyclic terpenoid, in animal models of nociceptive and neuropathic pain: Role of opioid receptors, L-arginine/NO/cGMP pathway, and inflammatory cytokines. European Journal of Pharmacology 900, pages 174075.
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Nader Tanideh, Alireza Ameri, Akram Jamshidzadeh, Pedram Keshavarz, Romina Tanideh, Omid Farshad, Nazanin Pouya, Cambyz Irajie, Aida Iraji & Shahdab Dehshahri. (2021) Comparative Evaluation of the Analgesic Effects of Pistacia atlantica Leaves, Gum, and Fruit Extracts in Rats. Shiraz E-Medical Journal 22:5.
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Mohammad Zarei, Davoud Ahmadimoghaddam & Saeed Mohammadi. (2021) Artemisia biennis Willd.: Anti-Nociceptive effects and possible mechanisms of action. Journal of Ethnopharmacology 268, pages 113604.
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Ilaria Chiocchio, Manuela Mandrone, Paola Tomasi, Lorenzo Marincich & Ferruccio Poli. (2021) Plant Secondary Metabolites: An Opportunity for Circular Economy. Molecules 26:2, pages 495.
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Vincent Maida, Runjie B. Shi, Francesco G. T. Fazzari & Lydia Zomparelli. (2020) Topical cannabis‐based medicines – A novel paradigm and treatment for non‐uremic calciphylaxis leg ulcers: An open label trial. International Wound Journal 17:5, pages 1508-1516.
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Luana Heimfarth, Klécia Santos dos Anjos, Yasmim Maria Barbosa Gomes de Carvalho, Bruno Lucena dos Santos, Mairim Russo Serafini, Antônio Guilherme de Carvalho Neto, Paula Santos Nunes, José Ivo Araújo Beserra Filho, Sara Pereira da Silva, Alessandra Mussi Ribeiro, Daniel Pereira Bezerra, Ricardo Neves Marreto, Jullyana de Souza Siqueira Quintans, Adriano Antunes de Souza Araújo, Henrique Douglas Melo Coutinho, Marcus T. Scotti, Luciana Scotti & Lucindo José Quintans-Júnior. (2020) Characterization of β-cyclodextrin/myrtenol complex and its protective effect against nociceptive behavior and cognitive impairment in a chronic musculoskeletal pain model. Carbohydrate Polymers 244, pages 116448.
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Eden Arazi, Galit Blecher & Noam Zilberberg. (2020) A regulatory domain in the K2P2.1 (TREK-1) carboxyl-terminal allows for channel activation by monoterpenes. Molecular and Cellular Neuroscience 105, pages 103496.
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Eden Arazi, Galit Blecher & Noam Zilberberg. (2020) Monoterpenes Differently Regulate Acid-Sensitive and Mechano-Gated K2P Channels. Frontiers in Pharmacology 11.
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Taejoon Kim, Bokyeong Song, Kyoung Sang Cho & Im-Soon Lee. (2020) Therapeutic Potential of Volatile Terpenes and Terpenoids from Forests for Inflammatory Diseases. International Journal of Molecular Sciences 21:6, pages 2187.
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Weilin Zheng, Jiayi Wu, Jiangyong Gu, Heng Weng, Jie Wang, Tao Wang, Xuefang Liang & Lixing Cao. (2020) Modular Characteristics and Mechanism of Action of Herbs for Endometriosis Treatment in Chinese Medicine: A Data Mining and Network Pharmacology–Based Identification. Frontiers in Pharmacology 11.
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Fernanda O. Carvalho, Érika R. Silva, Paula S. Nunes, Fernanda A. Felipe, Karen P. P. Ramos, Luiz Augusto S. Ferreira, Viviane N. B. Lima, Saravanan Shanmugam, Alan Santos Oliveira, Sílvia S. Guterres, Enilton A. Camargo, Tassia Virginia Cravalho Olivera, Ricardo Luiz C. de Albuquerque Júnior, Waldecy de Lucca Junior, Lucindo José Quintans-Júnior & Adriano A. S. Araújo. (2019) Effects of the solid lipid nanoparticle of carvacrol on rodents with lung injury from smoke inhalation. Naunyn-Schmiedeberg's Archives of Pharmacology 393:3, pages 445-455.
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Khushbu Sharma, Amol Tayade, Jashbir Singh & Suresh Walia. 2020. Functional Foods and Nutraceuticals. Functional Foods and Nutraceuticals 543 593 .
S. M. Ezzat, A. M. Khattaby, Shimaa Abdelmageed & Marwa A. Abd Elaal. (2019) Cytotoxicity, antioxidant, anti-inflammatory activity, and GC-MS analysis of Egyptian propolis. Comparative Clinical Pathology 28:6, pages 1589-1598.
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Wagner B.R. Santos, Marlange A.O. Melo, Rafael S. Alves, Renan G. de Brito, Thallita K. Rabelo, Lindaura da S. Prado, Virginia K. dos S. Silva, Daniel P. Bezerra, José E.R. de Menezes-Filho, Diego S. Souza, Carla M.L. de Vasconcelos, Luciana Scotti, Marcus Tullius Scotti, Waldecy de Lucca Júnior, Lucindo J. Quintans-Júnior & Adriana G. Guimarães. (2019) p-Cymene attenuates cancer pain via inhibitory pathways and modulation of calcium currents. Phytomedicine 61, pages 152836.
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Daniele Nascimento Gouveia, Adriana Gibara Guimarães, Wagner Barbosa da Rocha Santos & Lucindo José Quintans-Júnior. (2019) Natural products as a perspective for cancer pain management: A systematic review. Phytomedicine 58, pages 152766.
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Tine van de Donk, Marieke Niesters, Mikael A. Kowal, Erik Olofsen, Albert Dahan & Monique van Velzen. (2018) An experimental randomized study on the analgesic effects of pharmaceutical-grade cannabis in chronic pain patients with fibromyalgia. Pain 160:4, pages 860-869.
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Alexandra M.S. Carvalho, Luana Heimfarth, Klécia A. Santos, Adriana G. Guimarães, Laurent Picot, Jackson R.G.S. Almeida, Jullyana S.S. Quintans & Lucindo J. Quintans-Júnior. (2019) Terpenes as possible drugs for the mitigation of arthritic symptoms – A systematic review. Phytomedicine 57, pages 137-147.
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Laura Hévila I. Leite, Gerlânia O. Leite, Bruno Anderson F. da Silva, Sacha Aubrey A.R. Santos, Francisco Ernani A. Magalhães, Paula P. Menezes, Mairim R. Serafini, Claudener S. Teixeira, Renan G. Brito, Priscila L. Santos, José Galberto M. da Costa, Adriano A.S. Araújo, Lucindo J. Quintans-Júnior, Irwin R.A. de Menezes, Henrique Douglas M. Coutinho & Adriana Rolim Campos. (2019) Molecular mechanism underlying orofacial antinociceptive activity of Vanillosmopsis arborea Baker (Asteraceae) essential oil complexed with β-cyclodextrin. Phytomedicine 55, pages 293-301.
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Joana Pinto, Ana Sofia Oliveira, Paulo Lopes, Isabel Roseira, Miguel Cabral, Maria de Lourdes Bastos & Paula Guedes de Pinho. (2019) Characterization of chemical compounds susceptible to be extracted from cork by the wine using GC-MS and 1H NMR metabolomic approaches. Food Chemistry 271, pages 639-649.
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Priscila L. Santos, João Pedro S.C.F. Matos, Laurent Picot, Jackson R.G.S. Almeida, Jullyana S.S. Quintans & Lucindo J. Quintans-Júnior. (2019) Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food and Chemical Toxicology 123, pages 459-469.
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Jullyana S.S. Quintans, Saravanan Shanmugam, Luana Heimfarth, Adriano Antunes S. Araújo, Jackson R.G.da S. Almeida, Laurent Picot & Lucindo J. Quintans-Júnior. (2019) Monoterpenes modulating cytokines - A review. Food and Chemical Toxicology 123, pages 233-257.
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Pollyana S. Siqueira-Lima, Fabiolla R.S. Passos, Angélica M. Lucchese, Irwin R.A. Menezes, Henrique D.M. Coutinho, Adley A.N. Lima, Gokhan Zengin, Jullyana S.S. Quintans & Lucindo J. Quintans-Júnior. (2019) Central nervous system and analgesic profiles of Lippia genus. Revista Brasileira de Farmacognosia 29:1, pages 125-135.
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Corey W. Meadows, Florence Mingardon, Brett M. Garabedian, Edward E. K. Baidoo, Veronica T. Benites, Andria V. Rodrigues, Raya Abourjeily, Angelique Chanal & Taek Soon Lee. (2018) Discovery of novel geranylgeranyl reductases and characterization of their substrate promiscuity. Biotechnology for Biofuels 11:1.
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Xingxing Dai, Ran Wang, Zhimin Wu, Shujuan Guo, Chang Yang, Lina Ma, Liping Chen, Xinyuan Shi & Yanjiang Qiao. (2018) Permeation-enhancing effects and mechanisms of borneol and menthol on ligustrazine: A multiscale study using in vitro and coarse-grained molecular dynamics simulation methods. Chemical Biology & Drug Design 92:5, pages 1830-1837.
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Marcus Blümel, Shota Nagasawa, Katherine Blackford, Stephanie R. Hare, Dean J. Tantillo & Richmond Sarpong. (2018) Rearrangement of Hydroxylated Pinene Derivatives to Fenchone-Type Frameworks: Computational Evidence for Dynamically-Controlled Selectivity. Journal of the American Chemical Society 140:29, pages 9291-9298.
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Renan Guedes Brito, Priscila Laise Santos, Marlange Almeida Oliveira, Lícia Tairiny Santos Pina, Angelo Roberto Antoniolli, Jackson Roberto Guedes da Silva Almeida, Laurent Picot, Gokhan Zengin, Jullyana Souza Siqueira Quintans & Lucindo José Quintans Júnior. 2018. Discussions of Unusual Topics in Fibromyalgia. Discussions of Unusual Topics in Fibromyalgia.
Lucindo J. Quintans-Júnior, Renan G. Brito, Jullyana S. S. Quintans, Priscila L. Santos, Zaine T. Camargo, Péricles A. Barreto, Maria F. Arrigoni-Blank, Waldecy Lucca-Júnior, Luciana Scotti, Marcus T. Scotti, Sandra J. Kolker & Kathleen A. Sluka. (2017) Nanoemulsion Thermoreversible Pluronic F127-Based Hydrogel Containing Hyptis pectinata (Lamiaceae) Leaf Essential Oil Produced a Lasting Anti-hyperalgesic Effect in Chronic Noninflammatory Widespread Pain in Mice. Molecular Neurobiology 55:2, pages 1665-1675.
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Melanie-Jayne R. Howes. 2018. Immunity and Inflammation in Health and Disease. Immunity and Inflammation in Health and Disease 363 388 .
Mónia A.R. Martins, Liliana P. Silva, Olga Ferreira, Bernd Schröder, João A.P. Coutinho & Simão P. Pinho. (2017) Terpenes solubility in water and their environmental distribution. Journal of Molecular Liquids 241, pages 996-1002.
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Pollyana S. Siqueira-Lima, Renan G. Brito, Heitor G. Araújo-Filho, Priscila L. Santos, Angélica Lucchesi, Adriano A.S. Araújo, Paula P. Menezes, Luciana Scotti, Marcus T. Scotti, Irwin R.A. Menezes, Henrique D.M. Coutinho, Gokhan Zengin, Abdurrahman Aktumsek, Angelo R. Antoniolli, Lucindo J. Quintans-Júnior & Jullyana S.S. Quintans. (2017) Anti-hyperalgesic effect of Lippia grata leaf essential oil complexed with β-cyclodextrin in a chronic musculoskeletal pain animal model: Complemented with a molecular docking and antioxidant screening. Biomedicine & Pharmacotherapy 91, pages 739-747.
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Luciane Corbellini Rufatto, Denis Amilton dos Santos, Flávio Marinho, João Antonio Pêgas Henriques, Mariana Roesch Ely & Sidnei Moura. (2017) Red propolis: Chemical composition and pharmacological activity. Asian Pacific Journal of Tropical Biomedicine 7:7, pages 591-598.
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José de Maria de Albuquerque de Melo Júnior, Marina de Barros Mamede Vidal Damasceno, Sacha Aubrey Alves Rodrigues Santos, Talita Matias Barbosa, João Ronielly Campêlo Araújo, Antonio Eufrásio Vieira-Neto, Deysi Viviana Tenazoa Wong, Roberto César Pereira Lima-Júnior & Adriana Rolim Campos. (2017) Acute and neuropathic orofacial antinociceptive effect of eucalyptol. Inflammopharmacology 25:2, pages 247-254.
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Jullyana de Souza Siqueira Quintans, Rafael dos Santos Alves, Darlisson de Alexandria Santos, Mairim Russo Serafini, Péricles Barreto Alves, Emmanoel Vilaça Costa, Gokhan Zengin, Lucindo José Quintans-Júnior & Adriana Gibara Guimarães. (2017) Antinociceptive effect of Aristolochia trilobata stem essential oil and 6-methyl-5-hepten-2yl acetate, its main compound, in rodents . Zeitschrift für Naturforschung C 72:3-4, pages 93-97.
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Luana Torres Melo, Mariana Araújo Braz Duailibe, Luciana Moura Pessoa, Flávio Nogueira da Costa, Antonio Eufrásio Vieira-Neto, Ana Paula de Vasconcellos Abdon & Adriana Rolim Campos. (2016) (−)-α-Bisabolol reduces orofacial nociceptive behavior in rodents. Naunyn-Schmiedeberg's Archives of Pharmacology 390:2, pages 187-195.
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Changling Qiu, Jonathan Smuts & Kevin A. Schug. (2017) Analysis of terpenes and turpentines using gas chromatography with vacuum ultraviolet detection. Journal of Separation Science 40:4, pages 869-877.
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Zou Huibin, Hui Liu, Elhussiny Aboulnaga, Huizhou Liu, Tao Cheng & Mo Xian. 2017. Industrial Biotechnology. Industrial Biotechnology 473 504 .
Antonio Germano, Andrea Occhipinti, Francesca Barbero & Massimo E. Maffei. (2017) A Pilot Study on Bioactive Constituents and Analgesic Effects of MyrLiq®, a Commiphora myrrha Extract with a High Furanodiene Content . BioMed Research International 2017, pages 1-11.
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Pollyana S.S. Lima, Angélica M. Lucchese, Heitor G. Araújo-Filho, Paula P. Menezes, Adriano A.S. Araújo, Lucindo J. Quintans-Júnior & Jullyana S.S. Quintans. (2016) Inclusion of terpenes in cyclodextrins: Preparation, characterization and pharmacological approaches. Carbohydrate Polymers 151, pages 965-987.
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Xingxing Dai, Qianqian Yin, Guang Wan, Ran Wang, Xinyuan Shi & Yanjiang Qiao. (2016) Effects of Concentrations on the Transdermal Permeation Enhancing Mechanisms of Borneol: A Coarse-Grained Molecular Dynamics Simulation on Mixed-Bilayer Membranes. International Journal of Molecular Sciences 17:8, pages 1349.
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Patrícia de Brum Vieira, Nícolas Luiz Feijó Silva, Gloria Narjara Santos da Silva, Denise Brentan Silva, Norberto Peporine Lopes, Simone Cristina Baggio Gnoatto, Márcia Vanusa da Silva, Alexandre José Macedo, Jaume Bastida & Tiana Tasca. (2016) Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis. Bioorganic & Medicinal Chemistry Letters 26:9, pages 2229-2236.
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Yosra Lozon, Ahmed Sultan, Stuart J. Lansdell, Tatiana Prytkova, Bassem Sadek, Keun-Hang Susan Yang, Frank Christopher Howarth, Neil S. Millar & Murat Oz. (2016) Inhibition of human α7 nicotinic acetylcholine receptors by cyclic monoterpene carveol. European Journal of Pharmacology 776, pages 44-51.
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Heitor G. Araújo-Filho, Lucindo J. Quintans-Júnior, André S. Barreto, Jackson R. G. S. Almeida, Rosana S. S. Barreto & Jullyana S. S. Quintans. (2015) Neuroprotective Effect of Natural Products on Peripheral Nerve Degeneration: A Systematic Review. Neurochemical Research 41:4, pages 647-658.
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Hua Song, Jianhong Lin, Xuan Zhu & Qing Chen. (2016) Developments in high-speed countercurrent chromatography and its applications in the separation of terpenoids and saponins. Journal of Separation Science 39:8, pages 1574-1591.
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Lucindo J. Quintans-Júnior, Adriano A.S. Araújo, Renan G. Brito, Priscila L. Santos, Jullyana S.S. Quintans, Paula P. Menezes, Mairim R. Serafini, Gabriel F. Silva, Flavio M.S. Carvalho, Nicole K. Brogden & Kathleen A. Sluka. (2016) β-caryophyllene, a dietary cannabinoid, complexed with β-cyclodextrin produced anti-hyperalgesic effect involving the inhibition of Fos expression in superficial dorsal horn. Life Sciences 149, pages 34-41.
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Renan G. Brito, Priscila L. dos Santos, Jullyana S.S. Quintans, Waldecy de Lucca Júnior, Adriano A.S. Araújo, Shanmugam Saravanan, Irwin R.A. Menezes, Henrique D.M. Coutinho & Lucindo J. Quintans-Júnior. (2015) Citronellol, a natural acyclic monoterpene, attenuates mechanical hyperalgesia response in mice: Evidence of the spinal cord lamina I inhibition. Chemico-Biological Interactions 239, pages 111-117.
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Yenny BUENO-DUARTE & Stelia Carolina MENDEZ-SÁNCHEZ. (2015) Linalool effect on mitochondrial bioenergetics rat liver. Revista Vitae 22:1.
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Leila Gholami Mahtaj, Azadeh Feizpour, Majid Kianmehr, Mohammad Soukhtanloo & Mohammad Hossein Boskabady. (2015) The effect of carvacrol on systemic inflammation in guinea pigs model of COPD induced by cigarette smoke exposure. Pharmacological Reports 67:1, pages 140-145.
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Adriana Gibara Guimarães, Marlange Almeida Oliveira, Rafael dos Santos Alves, Paula dos Passos Menezes, Mairim Russo Serafini, Adriano Antunes de Souza Araújo, Daniel Pereira Bezerra & Lucindo José Quintans Júnior. (2015) Encapsulation of carvacrol, a monoterpene present in the essential oil of oregano, with β-cyclodextrin, improves the pharmacological response on cancer pain experimental protocols. Chemico-Biological Interactions 227, pages 69-76.
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