GC–MS profiling of the phytochemical constituents of the oleoresin from Copaifera langsdorffii Desf. and a preliminary in vivo evaluation of its antipsoriatic effect

Gelmini, Fabrizio; Beretta, Giangiacomo; Anselmi, Cecilia; Centini, Marisanna; Magni, Paolo; Ruscica, Massimiliano; Cavalchini, Alberto; Facino, Roberto Maffei

doi:10.1016/j.ijpharm.2012.08.021

Cited by 92 publications

(59 citation statements)

References 23 publications

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“…4,5,34 Despite their importance, many reports concerning the valuable properties of these balsams have not provided the proper botanical identification and/or a complete chemical characterization. As mentioned before, most of the previous reported studies had just carried out the chemical characterization of the volatile constituents, 2,[16][17][18][19][20] and have described the presence of more than 70 sesquiterpenes.…”

Section: Resultsmentioning

confidence: 99%

Development and Validation of a Rapid and Reliable RP-HPLC-PDA Method for the Quantification of Six Diterpenes in Copaifera duckei, Copaifera reticulata and Copaifera multijuga Oleoresins

Carneiro¹,

Bianchi²,

Silva³

et al. 2017

J. Braz. Chem. Soc.

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Oleoresins from Copaifera species are extensively used in folk medicine in Brazil, which are employed mainly in the production of cosmetic formulations in Brazil, North America and Europe. Considering the lack of validated analytical methods for the analyses of diterpenes in Copaifera oleoresins, it was developed a validated and reliable reversed-phase high-performance liquid chromatography with photodiode array detection (RP-HPLC-PDA) method for the analysis of six diterpenes, including: (-)-polyalthic acid; (13E)-ent-labda-7, 13-dien-15-oic acid; ent-8(17)-labden-15,18-dioic acid; (-)-copalic acid; (-)-3β-acetoxycopalic acid and (-)-3β-hydroxycopalic acid. These compounds were isolated from C. duckei, C. reticulata and C. multijuga oleoresins by chromatographic means. The analytical curves were linear with regression coefficients (r 2 ) between 0.9903 and 0.9999. The limits of detection (LOD) and quantification (LOQ) values were 0.35 to 3.09 µg mL -1 and 1.05 to 9.36 µg mL -1, respectively. The method also displayed good precision and accuracy. The developed analytical method is reliable and a useful tool for the analysis of Copaifera oleoresin and its products.Keywords: Copaifera spp., oleoresins, diterpenes, RP-HPLC-PDA IntroductionThe Copaifera genus (Leguminoseae) consists of approximately 72 species, from which 16 of them occur only in Brazil, mainly in Northern region in the states of Amazonas, Pará and Ceará.1,2 These trees are popularly known as "copaiba", "copaibeiras" or "pau d'óleo", and the oleoresins obtained from their trunks are extensively used in folk medicine due to their antiinflammatory, analgesic, wound healing, antimicrobial, antileishmanial and antitumoral properties.2,3 Such ethnopharmacological relevance has stimulated several researchers to investigate their biological activities, which corroborated their pharmacological potential. [4][5][6][7][8] In addition to their pharmaceutical properties, these balsams are also largely used as dietary supplement, employed in the production of flavoring agents, and extensively commercialized as crude oil in Brazil. Moreover, these natural products are exported to Europe and North America, to be used mainly in cosmetic formulations. 2,9 Despite the great relevance of these oleoresins for pharmaceutical and cosmetic industries, most of these commercial balsams have not been authenticated, and their chemical profile has not been well established, thus hindering their industrial and biomedical applications, as well as impairing the quality and economic value of such products. 9,10 Chemically, the oleoresins of copaiba are predominantly composed by a mixture of volatile and non-volatile compounds comprising mainly sesquiterpenes and acid diterpenes. Acid diterpenes stands out for a wide range of the biological properties reported for these oleoresins, such as: antimicrobial, antitumoral, antinociceptive and anti-inflammatory, among others. 3,4,6,[11][12][13][14][15] Despite this fact, most of the studies reporting the chemical identification and quan...

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Section: Resultsmentioning

confidence: 99%

Development and Validation of a Rapid and Reliable RP-HPLC-PDA Method for the Quantification of Six Diterpenes in Copaifera duckei, Copaifera reticulata and Copaifera multijuga Oleoresins

Carneiro¹,

Bianchi²,

Silva³

et al. 2017

J. Braz. Chem. Soc.

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“…Na parte inferior é constituída da correntes de saída (destilado e resíduo). Os compostos com maior massa molar ou que não evaporaram são obtidos na corrente de resíduo (4). Os compostos com menor massa molar (voláteis), que evaporam, atingem o condensador e são obtidos na corrente de destilado (5).…”

Section: Matéria-primaunclassified

“…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.…”

Section: Introductionunclassified

Sesquiterpenes Recovery of Copaiba Oil-Resin From Molecular Distillation

Galúcio¹,

Benites²,

Rodrigues³

et al. 2016

Química Nova

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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...

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“…O seuà leoà e aà e ele teà pa aà aà u aà deà feridas, porque nem mesmo restam vestígios deà i at izes ,à dizà eleà p gi aà .à Ga ielà Soares de Sousa 60 oà o side avaà u à leoà sa tíssi o à ta à usadoà pa aà f ialdades,à dores de barriga e po tadasà deà f io à p gi aà 164). Para Gândavo 49 ,antiinflamatória [261][262][263][264][265][266][267] , antileishmania [268][269][270][271] , na endometriose 272 , na urolitíase 273 , na acne 274 , na psoríase 275 , no controle do mosquito Aedes aegypti [276][277][278] , no controle de ácaros 279 e em infecções ginecológicas. 280 O óleo da copaíba também reduz os níveis séricos de ureia e creatinina em ratos submetidos à síndrome de isquemia e reperfusão.…”

Section: Graças a Essas Duas Instituiçõesunclassified

Production of Phytotherapeutics in Brazil: History, Problems and Perspectives

Alves¹

2013

Revista Virtual De Química

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GC–MS profiling of the phytochemical constituents of the oleoresin from Copaifera langsdorffii Desf. and a preliminary in vivo evaluation of its antipsoriatic effect

Cited by 92 publications

References 23 publications

Development and Validation of a Rapid and Reliable RP-HPLC-PDA Method for the Quantification of Six Diterpenes in Copaifera duckei, Copaifera reticulata and Copaifera multijuga Oleoresins

Development and Validation of a Rapid and Reliable RP-HPLC-PDA Method for the Quantification of Six Diterpenes in Copaifera duckei, Copaifera reticulata and Copaifera multijuga Oleoresins

Sesquiterpenes Recovery of Copaiba Oil-Resin From Molecular Distillation

Production of Phytotherapeutics in Brazil: History, Problems and Perspectives

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