Cited by 167Sesquiterpenes and Asteraceae StudiesNatural Compounds in Disease TreatmentPhytochemistry and Biological Activities

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Effect of two active compounds obtained from the essential oil of Cordia verbenacea on the acute inflammatory responses elicited by LPS in the rat paw

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Medeiros, R, Passos, G F, Vitor, C E, Koepp, J, Mazzuco, T L, Pianowski, L F, Campos, M M, Calixto, J B·2007·British Journal of Pharmacology

DOI 10.1038/sj.bjp.0707270PMC PMC2013990

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Abstract

BACKGROUND AND PURPOSE: alpha-Humulene and trans-caryophyllene are sesquiterpene compounds identified in the essential oil of Cordia verbenacea which display topical and systemic anti-inflammatory effects in different experimental models. However, the molecular mechanisms through which they exert their anti-inflammatory activity still remain unclear. Here, we evaluate the effects of alpha-humulene and trans-caryophyllene on the acute inflammatory responses elicited by LPS. EXPERIMENTAL APPROACH: The biological activities of alpha-humulene and trans-caryophyllene were investigated in a model of acute inflammation in rat paw, induced by LPS and characterized by paw oedema, neutrophil recruitment, cytokine production, activation of MAP kinases and NF-kappaB and up-regulated expression of kinin B(1) receptors. KEY RESULTS: Treatment with either alpha-humulene or trans-caryophyllene effectively reduced neutrophil migration and activation of NF-kappaB induced by LPS in the rat paw. However, only alpha-humulene significantly reduced the increase in TNF-alpha and IL-1beta levels, paw oedema and the up-regulation of B(1) receptors following treatment with LPS. Both compounds failed to interfere with the activation of the MAP kinases, ERK, p38 and JNK. CONCLUSIONS AND IMPLICATIONS: Both alpha-humulene and trans-caryophyllene inhibit the LPS-induced NF-kappaB activation and neutrophil migration, although only alpha-humulene had the ability to prevent the production of pro-inflammatory cytokines TNF-alpha and IL-1beta and the in vivo up-regulation of kinin B(1) receptors. These data provide additional molecular and functional insights into the beneficial effects of the sesquiterpenes alpha-humulene and trans-caryophyllene isolated from the essential oil of Cordia verbenacea as agents for the management of inflammatory diseases.

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Dalavaye, N., Nicholas, M., Pillai, M., Erridge, S., & Sodergren, M. H. (2024) · Planta Medica · doi:10.1055/a-2307-8183 · Cited by 39
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Abd‐ElGawad, A. M., Elgamal, A. M., El-Amier, Y. A., Mohamed, T. A., Gendy, A. E. G. E., & Elshamy, A. I. (2021) · Plants · doi:10.3390/plants10071294 · Cited by 32
“[60] described that trans-caryophyllene showed p tent anti-inflammatory in rats by significa tly decreasing the migrat on of neutrophils as well as increasi g the NF-κB-induced stimulation by lipopolysaccharides.”
Background
Essential Oil from the Leaves of Chromolaena odorata, and Sesquiterpene Caryophyllene Oxide Induce Sedative Activity in Mice
Dougnon, G., & Ito, M. (2021) · Pharmaceuticals · doi:10.3390/ph14070651 · Cited by 32
Suppression of lipopolysaccharide-stimulated inducible nitric oxide synthase (iNOS) expression by a novel humulene derivative in macrophage cells
Min, H., Kim, M. S., Jang, D. S., Park, E., Seo, E. K., & Lee, S. K. (2009) · International Immunopharmacology · doi:10.1016/j.intimp.2009.03.005 · Cited by 33
Comparative analysis of essential oil composition and oil containing glands in Ocimum sanctum L. (Holy basil) under ambient and supplemental level of UV-B through gas chromatography–mass spectrometry and scanning electron microscopy
Kumari, R., & Agrawal, S. B. (2010) · Acta Physiologiae Plantarum · doi:10.1007/s11738-010-0637-0 · Cited by 30
“Medeiros et al. (2007) reported that a-humulene and (-)-trans-caryophyllene might be useful as important tools for the management and/or treatment of inflammatory diseases. a-humulene also has antitumorous property (Tundis et al. 2009). b-selinene has antimalarial, antiinfertility, antidementia,…”
Background
Chemical composition of essential oil from Varronia curassavica Jacq. accessions in different seasons of the year
Marques, A. P. S., Bonfim, F. P. G., Dantas, W. F. C., Puppi, R. J., & Marques, M. O. M. (2019) · Industrial Crops and Products · doi:10.1016/j.indcrop.2019.111656 · Cited by 30
Distribution of local plant knowledge in a recently urbanized area (Campeche District, Florianópolis, Brazil)
Gandolfo, E. S., & Hanazaki, N. (2014) · Urban Ecosystems · doi:10.1007/s11252-014-0345-4 · Cited by 30
“…as Polydoro et al. (2004) and Kadarian et al. (2002) for A. satureoides, Coelho-de-Souza et al. (2004) for P. catleyanum, and Sertie et al. (1991), Medeiros et al. (2007) and Passos et al. (2007) for V. curassavica (formerly Cordia verbenaceae); the latter known widely along the Brazilian coast…”
Antiprotozoal activity of essential oils derived fromPiperspp. grown in Colombia
Pinto, S. M. L., Pino-Benitez, N., Stashenko, E. E., Martı́nez, J. R., & Escobar, P. (2013) · Journal of Essential Oil Research · doi:10.1080/10412905.2013.820669 · Cited by 30
“It is an important chemical component of many EOs from some aromatic plants such as Cordia verbenacea (31), Copaiba tree (32), Syzygium aromaticum (33) and Piper spp.”
Background
Patents of drugs extracted from Brazilian medicinal plants
Balbani, A. P. S., Silva, D. H. S., & Montovani, J. C. (2009) · Expert Opinion on Therapeutic Patents · doi:10.1517/13543770902824180 · Cited by 29
Review of Recent Studies and Research Analysis for Anti-oxidant and Anti-aging Materials
Na, E. J., Jang, H. H., & Kim, G. R. (2016) · Asian Journal of Beauty and Cosmetology · doi:10.20402/ajbc.2016.0107 · Cited by 28
Citrus hystrix Extracts Protect Human Neuronal Cells against High Glucose-Induced Senescence
Pattarachotanant, N., & Tencomnao, T. (2020) · Pharmaceuticals · doi:10.3390/ph13100283 · Cited by 28
The genotoxic, cytotoxic and growth regulatory effects of plant secondary metabolite β-caryophyllene on polyphagous pest Spodoptera litura (Fabricius) (Lepidoptera: Noctuidae)
Mahajan, E., Singh, S., Diksha, Kaur, S., & Sohal, S. K. (2022) · Toxicon · doi:10.1016/j.toxicon.2022.09.016 · Cited by 27
Monitoring of biotransformation of hop aroma compounds in an in vitro digestion model
Heinlein, A., & Buettner, A. (2012) · Food & Function · doi:10.1039/c2fo30061c · Cited by 27
Differential Expression of Inflammation-Related Genes in Children with Down Syndrome
Silva, C. R. S., Biselli, J. M., Zampieri, B. L., Silva, W. A., de Souza, J. E. S., Bürger, M. C., Goloni‐Bertollo, E. M., & Pavarino, É. C. (2016) · Mediators of Inflammation · doi:10.1155/2016/6985903 · Cited by 27
Development and validation of a quantification method for α-humulene and trans-caryophyllene in Cordia verbenacea by high performance liquid chromatography
Gomes, M. V. D. S., da Silva, J. D., Ribeiro, A. F., Cabral, L. M., & de Sousa, V. P. (2019) · Revista Brasileira de Farmacognosia · doi:10.1016/j.bjp.2019.01.009 · Cited by 24
Essential oils of Psidium cattleianum Sabine leaves and flowers: Anti-inflammatory and cytotoxic activities
Elsayed, H. E., El-Deeb, E. M., Taha, H., Taha, H. S., Elgindi, M. R., & Moharram, F. A.-E. (2023) · Frontiers in Chemistry · doi:10.3389/fchem.2023.1120432 · Cited by 24
“It possessed different biological effects such as anti-inflammatory (Medeiros et al., 2007) and anticarcinogenic (Langhasova et al.”
In Vivo Up-Regulation of Kinin B1 Receptors after Treatment with Porphyromonas gingivalis Lipopolysaccharide in Rat Paw
Dornelles, F. N., Santos, D. S., Dyke, T. E. V., Calixto, J. Β., Júnior, E. L. B., & Campos, M. M. (2009) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.109.155762 · Cited by 24
“The induction of this receptor has been associated with generation of inflammatory cytokines, neutrophil migration, and activation of several signaling pathways (Passos et al., 2004; Medeiros et al., 2007).”
Background
Antifertility potential of hydroalcoholic extract of Cordia dichotoma G Forst. leaves: A folklore medicine used by Meena community in Rajasthan state in India
Sharma, P., Manjusha, Rani, S., Malhotra, H., nitesh, N., Deswal, S., & Singh, S. (2015) · Asian Pacific Journal of Reproduction · doi:10.1016/s2305-0500(15)30004-x · Cited by 23
Metabolic Profiling of Varronia curassavica Jacq. Terpenoids by Flow Modulated Two-Dimensional Gas Chromatography Coupled to Mass Spectrometry
Facanali, R., Marques, M. O. M., & Hantao, L. W. (2020) · Separations · doi:10.3390/separations7010018 · Cited by 22
Biologia floral e sistema reprodutivo da erva-baleeira (Varronia curassavica Jacq.)
Brandão, D. S., Mendes, A. D. R., dos Santos, R. R. Q., Rocha, S. M., Leite, G. L. D., & Martins, E. R. (2015) · Revista Brasileira de Plantas Medicinais · doi:10.1590/1983-084x/14_011 · Cited by 22
Utilization of UPLC-PDA and GC–MS/MS coupled with metabolomics analysis to identify bioactive metabolites in medicinal turmeric at different ages for the quality assurance
Pantharos, P., Sukcharoen, P., Phadungrakwittaya, R., Akarasereenont, P., Booranasubkajorn, S., & Lumlerdkij, N. (2022) · Phytomedicine · doi:10.1016/j.phymed.2022.154157 · Cited by 20
Therapeutic Potential of Essential Oils Against Ulcerative Colitis: A Review
Li, J., Zhang, X., Luan, F., Duan, J., Zou, J., Sun, J., Shi, Y., Guo, D., Wang, C., & Wang, X. Q. (2024) · Journal of Inflammation Research · doi:10.2147/jir.s461466 · Cited by 20
Preparation and Characterization of Liposomal β-Caryophyllene (Rephyll) by Nanofiber Weaving Technology and Its Effects on Delayed Onset Muscle Soreness (DOMS) in Humans: A Randomized, Double-Blinded, Crossover-Designed, and Placebo-Controlled Study
Amalraj, A., Jacob, J., C., K. V. A., & Gopi, S. (2020) · ACS Omega · doi:10.1021/acsomega.0c03456 · Cited by 20
EVALUATION FOR ANTIBACTERIAL EFFECTS OF VOLATILE FLAVORS FROM CHRYSANTHEMUM INDICUM AGAINST FOOD‐BORNE PATHOGENS AND FOOD SPOILAGE BACTERIA
LEE, J. H., Jang, M., Seo, J., & Kim, G. (2011) · Journal of Food Safety · doi:10.1111/j.1745-4565.2010.00277.x · Cited by 20
Anti-inflammatory effects of α-humulene on the release of pro-inflammatory cytokines in lipopolysaccharide-induced THP-1 cells
Becker, L., & Holtmann, D. (2024) · Cell Biochemistry and Biophysics · doi:10.1007/s12013-024-01235-7 · Cited by 19
Cordia verbenacea and secretion of mast cells in different animal species
de Oliveira, D. M. C., Luchini, A. C., Seito, L. N., Gomes, J. C., Lopez, M. E. C., & Stasi, L. C. D. (2011) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2011.03.046 · Cited by 19
“In this latter oil, the anti-inflammatoryproperty wasmainly attributed to -humulene and (−)-trans-caryophyllene (Fernandes et al., 2007; Medeiros et al., 2007; Passos et al., 2007).”
BackgroundInfluential
Toxicity of Varronia curassavica Jacq. Essential Oil to Two Arthropod Pests and Their Natural Enemy
Andrade, F. P., Venzon, M., das Dôres, R. G. R., Franzin, M. L., Martins, E. F., de Araújo, G. J., & Fonseca, M. C. M. (2021) · Neotropical Entomology · doi:10.1007/s13744-021-00906-x · Cited by 18
Novel Insights into the Immunomodulatory Effects of Caryophyllane Sesquiterpenes: A Systematic Review of Preclinical Studies
Gullì, M., Percaccio, E., Giacomo, S. D., & Sotto, A. D. (2022) · Applied Sciences · doi:10.3390/app12052292 · Cited by 17
GC-TOF-MS-based metabolomics correlated with bioactivity assays unveiled seasonal variations in leaf essential oils of two species in Garcinia L.
Lin, F., & Long, C. (2023) · Industrial Crops and Products · doi:10.1016/j.indcrop.2023.116356 · Cited by 19
Combination of Taurine and Black Pepper Extract as a Treatment for Cardiovascular and Coronary Artery Diseases
Swiderski, J., Sakkal, S., Apostolopoulos, V., Zulli, A., & Gadanec, L. K. (2023) · Nutrients · doi:10.3390/nu15112562 · Cited by 18
Factors Influencing the Production and Chemical Composition of Essential Oils in Aromatic Plants from Brazil
Boaro, C. S. F., Vieira, M. A. R., Campos, F. G., Ferreira, G., De‐la‐Cruz‐Chacón, I., & Marques, M. O. M. (2019) · Springer eBooks · doi:10.1007/978-3-030-16546-8_2 · Cited by 18
In Silico Study of Anti-Insomnia Mechanism for Suanzaoren Prescription
Gao, J., Wang, Q., Huang, Y., Tang, K., Yang, X. L., & Cao, Z. (2019) · Frontiers in Pharmacology · doi:10.3389/fphar.2019.00925 · Cited by 18
Technical and economic evaluation of cultivation and obtaining of Varronia curassavica Jacq. essential oil
Tonial, C. H., Rodrigues, M. F. F., Bosse, M. A., Sousa, I. M. D. O., de Lima, J. D., da Cunha, M. A. A., Foglio, M. A., Marques, M. O. M., & Marchese, J. A. (2020) · Industrial Crops and Products · doi:10.1016/j.indcrop.2020.112650 · Cited by 18
Anti-inflammatory and antiulcerogenic activities of leaf extracts and sesquiterpene fromTeucrium ramosissimum(Lamiaceae)
Sghaïer, M. B., Harizi, H., Louhichi, T., Krifa, M., Ghedira, K., & Ghédira, L. C. (2011) · Immunopharmacology and Immunotoxicology · doi:10.3109/08923973.2011.558903 · Cited by 18
“Anti-inflammatory activity of the tested extracts may be ascribed to polyphenols, flavonoids, and sesquiterpene.((25)) For example, it has been clearly established that flavonoids such as kaempferol act as regulators of NO synthase expression and NO release by concanavalin A (ConA)-stimulated splenocytes.”
Background
Using Varronia curassavica (Cordiaceae) essential oil for the biocontrol of Phytomonas serpens
Silva, K. P., SANTOS, T. A. D. C., Moutinho, B. L., da Silva, R. S., Pinto, V. S. D. S. C., Blank, A. F., Corrêa, C. B., Scher, R., & Fernandes, R. P. M. (2019) · Industrial Crops and Products · doi:10.1016/j.indcrop.2019.111523 · Cited by 17
3D Printed Bigel: A Novel Delivery System for Cannabidiol-Rich Hemp Extract
Gościniak, A., Kocaj, F., Stasiłowicz-Krzemień, A., Szymański, M., Karpiński, T. M. M., & Cielecka‐Piontek, J. (2024) · Gels · doi:10.3390/gels10120770 · Cited by 17
Evaluation of the in vitro release and permeation of Cordia verbenacea DC essential oil from topical dosage forms
da Silva, J. D., Gomes, M. V. D. S., Cabral, L. M., & de Sousa, V. P. (2019) · Journal of Drug Delivery Science and Technology · doi:10.1016/j.jddst.2019.101173 · Cited by 16
Polygonum minus essential oil modulates cisplatin-induced hepatotoxicity through inflammatory and apoptotic pathways
Rashid, N. A., Hussan, F., Hamid, A., Ridzuan, N. R. A., Halim, S. A. S. A., Jalil, N. A. A., Najib, N. H. M., Teoh, S. L., & Budin, S. B. (2020) · EXCLI journal · doi:10.17179/excli2020-2355 · Cited by 16
“In addition, α-caryophyllene and β-caryophyllene were found to inhibit the lipopolysaccharide (LPS)-induced NF-kB activation and neutrophil migration in animal models of inflammation (Medeiros et al., 2007).”
Background
Beta Caryophyllene-Loaded Nanostructured Lipid Carriers for Topical Management of Skin Disorders: Statistical Optimization, In Vitro and Dermatokinetic Evaluation
Ghazwani, M., Hani, U., Alqarni, M. H., & Alam, A. (2023) · Gels · doi:10.3390/gels9070550 · Cited by 15
“Anti-inflammatory [2], anti-carcinogenic [3], anti-bacterial [4], anti-oxidative [5], and analgesic [6] properties are amongst its reported biological effects.”
Background
Antioxidative and Antimicrobial Activities of Methanol Extract from Rosmarinus officinalis L. and Their Fractions
Yu, M.-H., Chae, I.-G., Jung, Y.-T., Jeong, Y.-S., Kim, H.-I., & Lee, I. (2011) · Journal of Life Science · doi:10.5352/jls.2011.21.3.375 · Cited by 13
Reguladores vegetais e substratos no enraizamento de estacas de erva-baleeira (Varronia curassavica Jacq.)
Mendes, A. D. R., Lacerda, T. H. S., Rocha, S. M., & Martins, E. R. (2014) · Revista Brasileira de Plantas Medicinais · doi:10.1590/s1516-05722014000200015 · Cited by 13
In vitro propagation, histochemistry, and analysis of essential oil from conventionally propagated and in vitro-propagated plants of Varronia curassavica Jacq
Santos, A. V., Defaveri, A. C. A. E., Bizzo, H. R., Gil, R. A. D. S. S., & Sato, A. (2013) · In Vitro Cellular & Developmental Biology - Plant · doi:10.1007/s11627-013-9528-6 · Cited by 13
“…Janeiro 22290-240 Rio de Janeiro, Brazil e-mail: alicesato@unirio.br of cancer cells as well as strong antioxidant activity (Fernandes et al. 2007; Medeiros et al. 2007; Quispe-Condori et al. 2007; Roldão et al. 2008; Michielin et al. 2009, 2011) Based on its active component, the sesquiterpene…”
BackgroundMethodInfluential
Chemical composition, antioxidant and anticancer activity of the essential oil from myric rubra leaves
Yin, J., Li, X., Huang, F. F., Lu, M.-Q., Yang, J., & Zhu, L. (2019) · IOP Conference Series Earth and Environmental Science · doi:10.1088/1755-1315/346/1/012085 · Cited by 13
Chemical composition, antinociceptive and anti-inflammatory effects in mice of the essential oil of Psidium cattleyanum Sabine leaves
Silva, V. B. G., da Fonsêca, B. M. B., de Aguiar, J. C. R. D. O. F., Navarro, D. M. D. A. F., de Oliveira, A. M., Napoleão, T. H., Correia, M. T. D. S., Lima, V. L. D. M., Costa, W. K., & da Silva, M. V. (2023) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2023.116443 · Cited by 12
Fermentative α-Humulene Production from Homogenized Grass Clippings as a Growth Medium
Langsdorf, A., Drommershausen, A., Volkmar, M., Ulber, R., & Holtmann, D. (2022) · Molecules · doi:10.3390/molecules27248684 · Cited by 12
Phytochemical characterization by HPLC and evaluation of antibacterial and aminoglycoside resistance-modifying activity of chloroform fractions of Cordia verbenacea DC leaf extracts
Matias, E. F. F., Alves, E. F., Silva, M. K. D. N., Carvalho, V. R. D. A., Medeiros, C. R., dos Santos, F. A. V., Bitu, V. D. C. N., de Souza, C. E. S., Figueredo, F. G., de Menezes, I. R. A., et al. (2015) · European Journal of Integrative Medicine · doi:10.1016/j.eujim.2015.03.007 · Cited by 12
Preliminary Study on Phytochemical Constituents and Biological Activities of Essential Oil from Myriactis nepalensis Less.
Fu, J., Gao, Y., & Xing, X. (2022) · Molecules · doi:10.3390/molecules27144631 · Cited by 11
“In addition, both of these compounds were found to exhibit anti-inflammatory [33,34], analgesic [26,35], antifungal [36,37], and antibacterial activities [28,38,39].”
Background

Authors: Medeiros, R., Passos, G. F., Vitor, C. E., Koepp, J., Mazzuco, T. L., Pianowski, L. F., Campos, M. M., & Calixto, J. B.
Affiliations: Universidade Federal de Santa Catarina (BR)
Pontifícia Universidade Católica do Rio Grande do Sul (BR)
ORCID: Medeiros, R
Passos, G F
Mazzuco, T L
Campos, M M
Venue: British Journal of Pharmacology
Publisher: Wiley
Published: 2007-07
Volume: 151
Issue: 5
Pages: 618-627
ISSN: 0007-1188 (ISSN-L)
1476-5381
DOI: 10.1038/sj.bjp.0707270
PMC: PMC2013990
OpenAlex: W1984871487
Cited by: 167
References: 46
Citations by year: 2026: 3 · 2025: 8 · 2024: 7 · 2023: 11 · 2022: 10 · 2021: 12 · 2020: 12 · 2019: 11 · 2018: 11 · 2017: 6 · 2016: 9 · 2015: 16 · 2014: 8 · 2013: 6 · 2012: 6
FWCI: 2.23
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 578 d)
Locations: British Journal of Pharmacology (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina
Topics: Physical Sciences › Chemistry › Organic Chemistry › Sesquiterpenes and Asteraceae Studies
Health Sciences › Medicine › Complementary and alternative medicine › Natural Compounds in Disease Treatment
Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
Keywords: Cordia verbenacea, α-humulene, β-caryophyllene, sesquiterpenes, essential oils, anti-inflammatory activity, acute inflammation, lipopolysaccharide, paw edema, neutrophil migration, NF-κB, mitogen-activated protein kinase, TNF-α, IL-1β, kinin B1 receptor, inflammatory cytokines
MeSH terms: Polycyclic Sesquiterpenes, Animals, Anti-Inflammatory Agents, Non-Steroidal, Cell Nucleus, Cytosol, Edema, Foot, Lipopolysaccharides, Male, Peroxidase, Neutrophils, Oils, Volatile, Sesquiterpenes, Tumor Necrosis Factor-alpha, Blotting, Western, Up-Regulation, NF-kappa B, Rats, Wistar, Reverse Transcriptase Polymerase Chain Reaction, Neutrophil Infiltration, Mitogen-Activated Protein Kinases, Electrophoretic Mobility Shift Assay, Cordia, Receptor, Bradykinin B1, Rats, Interleukin-1beta

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Effect of two active compounds obtained from the essential oil of Cordia verbenacea on the acute inflammatory responses elicited by LPS in the rat paw

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