Copaiba oleoresins are exuded from the trunks of trees of the Copaifera species (Leguminosae-Caesalpinoideae). This oleoresin is a solution of diterpenoids, especially, mono- and di-acids, solubilized by sesquiterpene hydrocarbons. The sesquiterpenes and diterpenes (labdane, clerodane and kaurane skeletons) are different for each Copaifera species and have been linked to several reported biological activities, ranging from anti-tumoral to embriotoxic effects. This review presents all the substances already described in this oleoresin, together with structures and activities of its main terpenoids.

Óleos de copaíba são importantes produtos naturais que têm sido amplamente utilizados por suas atividades cicatrizantes e anti-inflamatórias. Constituídos de sesquiterpenos e diterpenos, estes óleos apresentam composição química variável que, segundo a literatura pode ser originada por diversos fatores bióticos e abióticos. Com o objetivo de analisar a relação entre a composição química e fatores abióticos como sazonalidade, diâmetro à altura do peito (DBH) e composição do solo, dezesseis amostras de óleo-resina de Copaifera multijuga Hayne, provenientes da Reserva Florestal Ducke (Manaus-AM, Brasil), foram analisadas por cromatografia gasosa com detector de ionização de chama (GC-FID) e acoplada à espectrometria de massas (GC-MS). Trinta e cinco substâncias foram identificadas e os resultados avaliados por técnicas de análise multivariada (análises de agrupamento hierárquico (HCA) e a análise de componentes principais (PCA)), permitindo a diferenciação das amostras em dois grupos com composições distintas. Um deles apresentou como substância majoritária b-cariofileno enquanto o outro apresentou o óxido de cariofileno, essa variação na composição parece depender do tipo de solo. Outros fatores, anteriormente descritos como essenciais para a definição da composição química dos óleos de copaíba, como sazonalidade e DBH, não mostraram influência significativa sobre a composição química dos óleos-resina desta espécie.Copaiba oils are important medicinal products used primarily for their healing and antiinflammatory activities. Consisting of sesquiterpenes and diterpenes, these oils have variable composition which, according to the literature, may originate from several factors. In order to analyze the relationship between chemical composition and abiotic factors such as seasonality, diameter at breast height (DBH) and soil composition, sixteen of oilresin samples of Copaifera multijuga Hayne, from the Ducke Forest Reserve (Manaus City, Amazon State, Brazil), were analyzed by gas chromatography with flame ionization detection (GC-FID) and coupled with mass spectrometry (GC-MS). Thirty-five compounds were identified and the results evaluated by multivariate analysis (hierarchical cluster analysis (HCA) and principal component analysis (PCA)), allowing differentiation of the samples into two groups with different compositions. One of them presented b-caryophyllene as the major constituent, while the other presented caryophyllene oxide. This variation in composition appears to depend on soil type. Other factors previously described as essential for defining the chemical composition of copaiba oils, such as seasonality and DBH, showed no significant influence on the chemical composition of oils of this species.Keywords: oilresins, chemical variability, multivariate analysis, seasonal influence, diameter at breast height, soil type Influence of Abiotic Factors on the Chemical Composition of Copaiba Oil (Copaifera multijuga Hayne) J. Braz. Chem. Soc. 1824 IntroductionThe genus Copaifera belongs to the family Fabaceae,...

Oils of various species of Copaifera are commonly found in pharmacies and on popular markets and are widely sold for their medicinal properties. However, the chemical variability between and within species and the lack of standardization of these oils have presented barriers to their wider commercialization. With the aim to recognize patterns for the chemical composition of copaiba oils, 22 oil samples of C. multijuga Hayne species were collected, esterified with CH2 N2 , and characterized by GC-FID and GC/MS analyses. The chromatographic data were processed using hierarchical cluster analysis (HCA) and principal component analysis (PCA). In total, 35 components were identified in the oils, and the multivariate analyses (MVA) allowed the samples to be divided into three groups, with the sesquiterpenes β-caryophyllene and caryophyllene oxide as the main components. These sesquiterpenes, which were detected in all the samples analyzed in different concentrations, were the most important constituents in the differentiation of the groups. There was a prevalence of sesquiterpenes in all the oils studied. In conclusion, GC-FID and GC/MS analyses combined with MVA can be used to determine the chemical composition and to recognize chemical patterns of copaiba oils.

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