Chemistry and Biological Activities of Terpenoids from Copaiba (Copaifera spp.) Oleoresins

Leandro, Lidiam Maia; Vargas, Fabiano de Sousa; Barbosa, Paula Cristina Souza; Neves, Jamilly Kelly Oliveira; Silva, José Alexsandro da; Veiga, Valdir Florêncio da

doi:10.3390/molecules17043866

Cited by 210 publications

(206 citation statements)

References 134 publications

Supporting

Mentioning

146

Contrasting

Unclassified

Order By: Relevance

“…Thus, the results from physicochemical analysis reinforce the fact that it is imperative to include the analysis of copaiba oil which will ensure the quality of commercialized products. On the other hand, the similarity of sample A1 with in natura copaiba oil was confi rmed by GC-MS analysis with α-copaene, β-caryophyllene, Z-α-bergamotene, α-humulene and β-bisabolene (Table 5) being among the main sesquiterpenes of copaiba oleoresins (Leandro et al, 2012). The antimicrobial fi ndings associated to variable quality of samples representing products from Copaifera spp.…”

Section: Discussionmentioning

confidence: 95%

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

Fonseca

Barros

Apel

et al. 2015

Acta Sci Pol Technol Aliment

View full text Add to dashboard Cite

Background. The copaiba oil is a common natural product used in cosmetic industry and as a nutraceutical product. However, lack of quality control and scarce knowledge about its antimicrobial activity is a point of concern. The proposal of this study was to investigate the physicochemical properties and the antimicrobial activity of fi ve commercial brands of copaiba oil. Material and methods. Acidity and ester index, refractory index, solubility in alcohol, and thin layer chromatography were performed to verify the physicochemical properties of fi ve commercial copaiba oils sold in local pharmacies. Ultra performance liquid chromatography coupled with diode-array detection and electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-DAD/ESI-Q-TOF-MS) was used to investigate diterpene acids while the volatile compounds were analysed by gas chromatography-mass spectrometry (GC-MS). Antibacterial and antifungal activities were also evaluated by agar diffusion technique; and minimal inhibitory concentration and maximal bactericidal concentration were defi ned for each sample and bacteria. Results. The physical-chemical analysis revealed heterogeneity between all samples analysed. The A1 sample showed characteristics of copaiba oil and was mainly composed by hydrocarbon sesquiterpenes (29.95% β-bisabolene, 25.65% Z-α-bergamotene and 10.27% β-cariophyllene). Among diterpene acids, the UPLC-DAD/ESI-Q-TOF-MS data are compatible with presence of copalic and/or kolavenic acid (m/z 305 [M + H]

show abstract

Section: Discussionmentioning

confidence: 95%

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

Fonseca

Barros

Apel

et al. 2015

Acta Sci Pol Technol Aliment

View full text Add to dashboard Cite

show abstract

“…As many structurally diverse antileishmanial compound show activity against amstigotes at 0.06 to 14.00 µmol/L [42]. Maytansine, taxol and the electrophiles block the growth of L. donovani amastigote like form in vitro at low (<1 µmol/L) concentration [43,44] . The activity of methanolic crude extract is similar but their concentration was higher compared to pure compounds.…”

Section: Discussionmentioning

confidence: 99%

Cyanobacteria, Lyngbya aestuarii and Aphanothece bullosa as antifungal and antileishmanial drug resources

Kumar

Tripathi

Srivastava

et al. 2013

Asian Pacific Journal of Tropical Biomedicine

View full text Add to dashboard Cite

“…Entretanto, os sesquiterpenos têm despertado maior interesse das industrias de perfumaria, farmacêuticas e de cosméticos. De acordo com Leandro et al, 28 esse interesse nos sesquiternos tem elevado o seu valor e o concentrado destes compostos pode chegar a 600 vezes o valor do óleo-resina. Nessa perspectiva, este trabalho propõe a concentração destes compostos por meio da destilação molecular.…”

Section: Composição De Terpenosunclassified

Sesquiterpenes Recovery of Copaiba Oil-Resin From Molecular Distillation

Galúcio¹,

Benites²,

Rodrigues³

et al. 2016

Química Nova

View full text Add to dashboard Cite

publicado na web em 06/06/2016 SESQUITERPENES RECOVERY OF COPAIBA OIL-RESIN FROM MOLECULAR DISTILLATION. Copaiba oil-resin has aromatic characteristics and pharmacological activities attributed to sesquiterpenes compounds. These purified compounds present application in perfume, pharmaceutical and cosmetic industries. Therefore, the objective of this work was to use molecular distillation to recover and purify sesquiterpenes of the copaiba oil-resin with purity high. The parameters evaporator temperature (TEV) from 45 to 100 ºC and feed flow rate (Q) between 15 and 30 ml min -1 were evaluated through design of experiments (2 2 with center points). The results showed that it was possible to recover sesquiterpenes with 98.12% purity in the distillate stream. Increased in TEV and reduction in Q were the effects observed experimentally and through the response surface. The best experimental condition was TEV of 100 °C and Q of 15 mL min -1 . Collor differences were noticed between distillate streams (colorless) and residue (brown). These can be used as parameters for separation of sesquiterpenes and diterpenes. The molecular distillation proved to be an efficient processo to both recovery and purification of sesquiterpenes from the copaiba oil-resin.Keywords: short path; Copaifera genus; sesquiterpenes purification; bioactive compounds. INTRODUÇÃOO óleo-resina de copaíba pode ser extraído sustentavelmente a partir do tronco das árvores do gênero Copaifera. Este é constituído de sesquiterpenos (óleo essencial) e diterpenos (resina) que apresentam variações no teor mesmo sendo da mesma espécie. Entretanto, alguns destes compostos ocorrem com mais frequência e apresentam comprovada propriedade medicinal. Dentre eles, o β-cariofileno é o sesquiterpeno mais comum e destaca-se por sua atividade anti--inflamatória. Para o óleo essencial de copaíba também se reporta a atividade antifúngica e antipsoríase. [1][2][3][4][5] Umas das características observadas para o óleo-resina é a variação de cor. De acordo com Rigamonte-Azevedo et al., 6 estes podem apresentar-se incolor, amarelo claro, amarelo médio, amarelo dourado e acastanhado. Os motivos podem ser fatores sazonais e ambientais. Diferenças no conteúdo de óleo essencial e resina também são apontadas como responsáveis nas mudanças de cor no óleo-resina de copaíba. Amostras com maior teor de óleos essenciais apresentam coloração mais clara. A confirmação destas características é muito importante e as análises cromatográficas estão entre as técnicas analíticas mais eficientes para determinação da composição dos terpenos do óleo-resina de copaíba. Geralmente, estes são identificados por meio da combinação de duas técnicas cromatográficas: cromatografia em fase gasosa equipada com detector seletivo de massas (GC-MS) e cromatografia em fase gasosa com detector de ionização de chama (GC-FID). 2,7 O método comumente empregado para a obtenção do óleo essencial é a hidrodestilação. 8,9 Este método caracteriza-se por ser um procedimento simples e de baixo custo. Porém, a exposição d...

show abstract

Chemistry and Biological Activities of Terpenoids from Copaiba (Copaifera spp.) Oleoresins

Cited by 210 publications

References 134 publications

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

Cyanobacteria, Lyngbya aestuarii and Aphanothece bullosa as antifungal and antileishmanial drug resources

Sesquiterpenes Recovery of Copaiba Oil-Resin From Molecular Distillation

Contact Info

Product

Resources

About