Antinociceptive activity of Copaifera officinalis Jacq. L oil and kaurenoic acid in mice

Dalenogare, Diéssica Padilha; Ferro, Paula Ronsani; Prá, Samira Dal Toé De; Rigo, Flávia Karine; Antoniazzi, Caren Tatiane de David; Almeida, Amanda Spring de; Damiani, Adriani Paganini; Strapazzon, Giulia; Sardinha, Thanielly Thais de Oliveira; Galvani, Nathália Coral; Boligon, Aline Augusti; Andrade, Vanessa Moraes de; Brum, Evelyne da Silva; Oliveira, Sara Marchesan; Trevisan, Gabriela

doi:10.1007/s10787-019-00588-3

Cited by 20 publications

(18 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Both kaurenic acid and hinokinin produced the greatest antinociceptive activity at the highest dose evaluated in the formalin test. Previous studies have reported the analgesic activity of kaurenoic acid, a diterpene, in thermal-induced pain (tail-flick test), as well as in chemical-induced pain such as the intraplantar administration of capsaicin [29]. The mechanism of action of kaurenoic acid is by inhibiting proinflammatory cytokines and the activation of the NO-cyclic GMP-ATP-K + channels signaling pathway [30,31].…”

Section: Discussionmentioning

confidence: 99%

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

et al. 2020

View full text Add to dashboard Cite

Aristolochia odoratissima L. is employed for the treatment of pain and as an antidote against the poison of venomous animals in traditional medicine. However, reports have not been found, to our knowledge, about the evaluation of the antinociceptive activity of extracts nor about the presence of compounds associated with this activity. Thus, the purpose of this work was to evaluate the antinociceptive activity of extracts and compounds isolated from the stems of Artistolochia odoratissima L. The extracts were obtained with solvents of increasing polarity and the compounds were isolated and characterized by column chromatography, HPLC, and NMR. The antinociceptive activity was carried out by the formalin test in mice. Ethyl acetate (AoEA) and methanolic (AoM) extracts decreased the paw licking in both phases of the formalin test. The isolated compounds (kaurenoic acid and hinokinin) from AoEA showed the highest antinociceptive activity in both phases of the formalin test. These results confirmed the analgesic effect of this specie described in traditional medicine and provided a base for a novel analgesic agent. They also allowed an approach for the development of standardized plant extracts with isolated metabolites.

show abstract

Section: Discussionmentioning

confidence: 99%

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The chemical compositions of oleoresin from different Copaifera species may vary according to several factors, including the genetic background of the plant, seasonality, and environmental conditions (Cascon and Gilbert, 2000; Santos et al, 2008a; Barbosa et al, 2012; Arruda et al, 2019); and as we pointed before the acid diterpenes appear to be responsible for most of the biological effects observed in oleoresin of different Copaifera species (Abrão et al, 2015; Vargas et al, 2015; Kian et al, 2018; Trindade et al, 2018; Arruda et al, 2019; Dalenogare et al, 2019). The sesquiterpene β-caryophyllene is largely found in both species (Santos et al, 2008b; Trindade et al, 2018; Arruda et al, 2019), and has been related to the anti-inflammatory activity of the Copaifera oil volatile fraction (Veiga Junior et al, 2007).…”

Section: Discussionmentioning

confidence: 79%

“…Overall, a mixture of sesquiterpenes (volatile fraction) and acid diterpenes (non-volatile resin fraction) was found in copaiba oil from different Copaifera species (Santos et al, 2008b; Trindade et al, 2018; Arruda et al, 2019). Moreover, many of the biological activities of copaiba oil from different Copaifera species have been attributed to the acid diterpene content (Abrão et al, 2015; Vargas et al, 2015; Kian et al, 2018; Trindade et al, 2018; Arruda et al, 2019; Dalenogare et al, 2019). Particularly, kaurenoic acid, hardwickiic acid and copalic acid have been described as main acid diterpene of C. officinalis oleoresin (Santos et al, 2008b; Trindade et al, 2018; Arruda et al, 2019; Dalenogare et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, many of the biological activities of copaiba oil from different Copaifera species have been attributed to the acid diterpene content (Abrão et al, 2015; Vargas et al, 2015; Kian et al, 2018; Trindade et al, 2018; Arruda et al, 2019; Dalenogare et al, 2019). Particularly, kaurenoic acid, hardwickiic acid and copalic acid have been described as main acid diterpene of C. officinalis oleoresin (Santos et al, 2008b; Trindade et al, 2018; Arruda et al, 2019; Dalenogare et al, 2019). In light of these data, we performed a mass spectral analyses of the copaiba oil and confirmed the presence of copalic acid [ EIMS m/z 305.24 (M+)] , kaurenoic acid [EIMS m/z 341.26 (M + K)] , and hardwickiic acid [EIMS m/z 317.22 (M+)] (Supplementary Figure S1).…”

Section: Resultsmentioning

confidence: 99%

“…The sesquiterpene β-caryophyllene is largely found in both species (Santos et al, 2008b; Trindade et al, 2018; Arruda et al, 2019), and has been related to the anti-inflammatory activity of the Copaifera oil volatile fraction (Veiga Junior et al, 2007). Regarding acid diterpenes, the copalic acid (ranging from 1.1 to 11.0% of the total terpene content) was the main component in C. multijuga (Santos et al, 2008b; da Silva et al, 2017; Trindade et al, 2018); on the other hand, copalic (13.9% of the total terpene content), hardwickiic (30.7% of the total terpene content) and kaurenoic (13.8% of the total terpene content) acids have been reported in C. officinalis (Santos et al, 2008b; Dalenogare et al, 2019).…”

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Hydrogel Containing Oleoresin From Copaifera officinalis Presents Antibacterial Activity Against Streptococcus agalactiae

et al. 2019

View full text Add to dashboard Cite

Streptococcus agalactiae or Group B Streptococcus (GBS) remains a leading cause of neonatal infections worldwide; and the maternal vaginal-rectal colonization increases the risk of vertical transmission of GBS to neonates and development of infections. This study reports the in vitro antibacterial effect of the oleoresin from Copaifera officinalis Jacq. L. in natura (copaiba oil) and loaded into carbomer-hydrogel against planktonic and sessile cells of GBS. First, the naturally extracted copaiba oil was tested for the ability to inhibit the growth and metabolic activity of planktonic and sessile GBS cells. The time-kill kinetics showed that copaiba oil exhibited a dose-dependent bactericidal activity against planktonic GBS strains, including those resistant to erythromycin and/or clindamycin [minimal bactericidal concentration (MBC) ranged from 0.06 mg/mL to 0.12 mg/mL]. Copaiba oil did not inhibit the growth of different Lactobacillus species, the indigenous members of the human microbiota. The mass spectral analyses of copaiba oil showed the presence of diterpenes, and the kaurenoic acid appears to be one of the active components of oleoresin from C. officinalis related to antibacterial activity against GBS. Microscopy analyses of planktonic GBS cells treated with copaiba oil revealed morphological and ultrastructural alterations, displaying disruption of the cell wall, damaged cell membrane, decreased electron density of the cytoplasm, presence of intracellular condensed material, and asymmetric septa. Copaiba oil also exhibited antibacterial activity against established biofilms of GBS strains, inhibiting the viability of sessile cells. Low-cost and eco-friendly carbomer-based hydrogels containing copaiba oil (0.5% – CARB-CO 0.5; 1.0% – CARB-CO 1.0) were then developed. However, only CARB-CO 1.0 preserved the antibacterial activity of copaiba oil against GBS strains. This formulation was homogeneous, soft, exhibited a viscoelastic behavior, and showed good biocompatibility with murine vaginal mucosa. Moreover, CARB-CO 1.0 showed a slow and sustained release of the copaiba oil, killing the planktonic and sessile (established biofilm) cells and inhibiting the biofilm formation of GBS on pre-coated abiotic surface. These results indicate that carbomer-based hydrogels may be useful as topical systems for delivery of copaiba oil directly into de vaginal mucosa and controlling S. agalactiae colonization and infection.

show abstract

Kauranes as Anti-inflammatory and Immunomodulatory Agents: An Overview of In Vitro and In Vivo Effects

Mijares

Martínez

Sanctis

2022

Plant Secondary Metabolites

View full text Add to dashboard Cite

Antinociceptive activity of Copaifera officinalis Jacq. L oil and kaurenoic acid in mice

Cited by 20 publications

References 54 publications

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

Hydrogel Containing Oleoresin From Copaifera officinalis Presents Antibacterial Activity Against Streptococcus agalactiae

Kauranes as Anti-inflammatory and Immunomodulatory Agents: An Overview of In Vitro and In Vivo Effects

Contact Info

Product

Resources

About