Chemical composition of the volatile oil of Cardiopetalum calophyllum collected in the Cerrado area

Composição química do óleo volátil de Cardiopetalum calophyllum coletada em área de Cerrado

ABSTRACT:

TheAnnonaceae family consists of ~135 genera with diverse species and a large number of chemical compounds arising from the secondary metabolism. However, the chemical composition of the essential oil of several species of the family such asCardiopetalum calophyllum has not been completely determined. In this study, the essential oils extracted from the leaves, flowers, and fruits ofC. calophyllum , collected in typical areas of the Cerrado of Goiás, were characterized. The essential oil was extracted by hydrodistillation for 4h using a Clevenger apparatus. The chemical analysis was carried out by gas chromatography-mass spectrometry (GC-MS), and the constituents were identified by comparing the spectra and retention index obtained with those available in the literature. Twenty three compounds were identified in the essential oil of leaves; the oxygenated sesquiterpene, spathulenol (28.78%), was the major compound. Twenty five compounds were identified in the flowers, mainly comprising sesquiterpene hydrocarbons, germacrene-D (37.03%) and germacrene-B (13.72%). Seventeen compounds were reported in fruits, mainly comprising sesquiterpene hydrocarbons, germacrene-D (28.19%) and germacrene-B (20.90%), and an oxygenated sesquiterpene, spathulenol (11.53%). This is the first report on the chemical composition of the essential oils from leaves, flowers, and fruits of C. calophyllum.

Key words:
essential oil; Annonaceae ; chemical composition; imbirinha

RESUMO:

A famíliaAnnonaceae é constituída por cerca de 135 gêneros, com uma diversidade extensa de espécies com grande quantidade de compostos químicos diversificados, advindos do metabolismo secundário. Entretanto, as informações sobre a composição química de óleo essencial de várias espécies da família ainda são incipientes, como é o caso daCardiopetalum calophyllum . O trabalho teve como objetivo caracterizar quimicamente o óleo essencial extraído de folhas, flores e frutos daC. calophyllum , coletadas em áreas típicas do Cerrado goiano. A extração do óleo essencial se deu pelo método de hidrodestilação em aparelho de clevenger por um período de 4 horas. A análise química do óleo essencial foi realizada por cromatografia gasosa acoplada à espectrometria de massas (CG-MS) e a identificação dos constituintes pela comparação dos espectros obtidos com os espectros disponíveis na literatura e pelo cálculo do índice de retenção (IR). Foram identificados 23 compostos no óleo essencial das folhas, em que o composto majoritário foi o sesquiterpeno oxigenado espatulenol (28,78%); nas flores, foram identificados 31 compostos com predominância dos sesquiterpenos hidrocarbonados germacreno-D (37,03%) e germacreno-B (13,72%); e, nos frutos, 17 compostos com predominância dos sesquiterpenos hidrocarbonados germareno-D (28,19%) e germacreno-B (20,90%) e do sesquiterpeno oxigenado espatulenol (11,53%). Este trabalho descreve pela primeira vez a composição química do óleo essencial das folhas, flores e frutos da C. calophyllum , contribuindo significativamente para o conhecimento químico da espécie.

Palavras-chave:
óleo essencial; Annonaceae ; composição química; imbirinha

INTRODUCTION:

The Annonaceae family consists of ~2500 species, grouped in 135 genera, with a pantropical distribution. In Brazil, 386 species belonging to 29 genera exist. The Cerrado is home to 10 genera and 47 species, none of which is endemic to the area, even though some of the genera and species are quite common, such as Annona crassiflora , Duguetia furfuracea , Xylopia aromatica , and Cardiopetalum calophyllum (LOPES & MELLO-SILVA, 2014). According to ISHARA & MAIMONI-RODELLA (2011), the Annonaceae family occupies the 13^th place with respect to the number of species per family in the Cerrado.

Some genera are chemically well-documented, such as Xylopia , where significant concentrations of caryophyllene oxide, α-pinene, α-terpinene, limonene, spathulenol, germacrene-D, trans-β-guaiene, and β-caryophyllene are present in the essential oils extracted from the leaves and fruits (SANTOS, et al. 2004; PONTES et al., 2007; VALTER et al., 2008).Annona genus has also been well-characterized; caryophyllene, camphene, α-pinene, and β-pinene have been identified in the essential oil extracted from the leaves (BANDEIRA et al., 2011; CAMPOS et al., 2014). However, the active substances present in the plants of this family are still investigated (NASCIMENTO et al., 2003; SILVA, 2007; NUNES et al., 2012; ALMEIDA et al., 2014; KRINSKI et al., 2014).C. calophyllum is a semideciduous species flowering between the months of August and October, with the peak flowering in September and fruiting between the months of January and April (SILVA et al., 2009; ELIAS, 2010). C. calophyllum is represented by trees and shrubs with heights ranging from 1.5 to 12m, commonly known as imbira, imbirinha, coast pepper, red pepper, among others (FECHINE et al., 2002; SILVA et al., 2009). Several communities use C. calophyllum to treat some diseases such as bronchitis, sinusitis, dysmenorrhea, and fever, and as a carminative, both in the form of syrup and tea (NASCIMENTO et al., 2003; COELHO et al., 2009; COSTA, 2011; COSTA et al., 2013).

Biological studies of C. calophyllum have shown diverse potential applications. FOURNET et al. (1994) reported the leishmanicidal effect of ethanol extract of leaves of C. calophyllum on Leishmania amazonensis , the etiological agent of cutaneous leishmaniasis. COSTA (2011) reported the biocidal effect of methanol extract of fruits of C. calophyllum in Aedes aegypti larvae on the third stage of development. SILVA et al. (2008) evaluated the action of eight organic extracts from various organs of C. calophyllum on the in vitro mycelial growth of six pathogenic fungi; the ethanol and hexane extracts of the stem bark inhibited growth.

Chemical composition of essential oil of C. calophyllum has not been reported. The aim of this study was to compare the chemical composition of volatile oils extracted from leaves, flowers, and fruits of C. calophyllum collected in Cerrado areas.

MATERIALS AND METHODS:

Plant material

Leaves, flowers, and fruits of C. calophyllum were collected in March, September, and December 2014, respectively, in the city of Rio Verde, state of Goiás, a native Cerrado area in the Universidade de Rio Verde (UniRV). Species was identified by biologists Odirlei Simões and Marcelo Nogueira, and the exsiccatae were deposited in the herbarium of the Universidade Estadual de Montes Claros (UNIMONTES), record number 3815. The material was transferred to the Natural Products Chemistry Laboratory of the Instituto Federal de Ciência, Educação e Tecnologia de Goiás, Rio Verde campus, where it was screened and the damaged material was discarded.

Extraction of volatile oil

The oil was obtained by hydrodistillation for 4h, following the method described by SIQUEIRA et al. (2011). The essential oil was extracted from the hydrolat with dichloromethane, and trace water was removed using anhydrous sodium sulfate. Salt was removed by filtration, and the solvent was removed by evaporation at room temperature. The essential oil was stored at -4°C until the analysis.

Identification of the chemical components

The essential oils were analyzed by coupled gas chromatography-mass spectrometry (GC-MS, Shimadzu QP-5000). A capillary column DB-5 (30.0m×0.25mm×0.25µm) was used as follows: injector at 220°C, detector at 240°C, split injection (1:20), volume of injection: 1µL, temperature gradient from 60°C to 300°C, with an increment of 3°C min^-1.

Compounds were identified by comparing their mass spectra with a database (NIST 11 library) and also by comparing their retention indices (RI) with those reported in the literature (ADAMS, 2007). The RI were determined using the calibration curve of a series of n-alkanes (C10-C29) injected under the same chromatographic conditions as the samples.

RESULTS AND DISCUSSION:

This is the first report on the chemical composition of the essential oil of leaves, flowers, and fruits of C. calophyllum , thus contributing significantly, to the knowledge of the species. The list of special metabolites identified in the essential oil extracted from the leaves, flowers, and fruits of C. calophyllum , their relative amounts, and IR spectral data are shown in table 1. From the GC-MS data, 23 compounds were identified in the essential oil of leaves, where the major compound was spathulenol (28.78%). Twenty five compounds were identified in the flowers, mainly comprising germacrene-D (37.03%) and germacrene-B (13.72%). Seventeen compounds were identified in the fruits, mainly comprising germacrene-D (28.19%), germacrene-B (20.90%), and spathulenol (11.53%).

Table 1
Compounds identified in the essential oil of the leaves, flowers, and fruits of C. calophyllum , collected in a typical area of Cerrado in the city of Rio Verde in 2014.

• RI: retention index.

The sesquiterpenes represent the majority of the compounds identified in different organs of C. calophyllum (Table 1), as observed in other species of the Annonaceae family. FEITOSA et al. (2009) characterized the essential oil present in the branches of Rollinia leptopetala , lacking monoterpenes, whereas sesquiterpenes, particularly oxygenated sesquiterpenes, were abundantly present. PONTES et al. (2007) evaluated the acaricidal activity of the essential oil obtained from the leaves of Xylopia sericea ; ~95% of the oil comprised of a complex mixture of sesquiterpenes. CAMPOS et al. (2014) also reported a predominance of sesquiterpenes in the essential oils of Annona emarginata and Annona squamosa .

PEREIRA & TEIXEIRA (1999) attributed the presence of sesquiterpenes in secondary metabolites to the adaptation of the plant species to the environment, i.e., against herbivores, pathogens, and encrusting organisms. In a study that focused on the essential oil of Duguetia furfuracea , VALTER et al. (2008) noted that the presence of oxygenated sesquiterpenes is not common in Cerrado species because of the specific conditions of the biome. However, this was not observed in the essential oil of C. calophyllum , where spathulenol was observed in high concentrations in more than one organ.

Spathulenol has been reported as the major compound in the essential oil extracted from the leaves of the other species of the Annonaceae family, such as Guatteria schomburgkiana (TRIGO et al., 2007), Annona vepretorum (COSTA et al., 2012), Rollinia leptopetala (COSTA et al., 2008) and Duguetia furfuracea (VALTER et al., 2008), among others. High concentrations of spathulenol have also been reported in the essential oil of the species of the genera Annona , Artabotrys , Cleistopholis , Goniothalamus , Piptostigma , Uvaria , and Xylopia (TRIGO et al., 2007). Moreover, spathulenol was observed in high concentrations (11.53%) in the fruit of C. calophyllum . Because of this predominance of spathulenol, LIMA et al. (2004) and SIQUEIRA et al. (2011) recommended the use of spathulenol as a chemical marker of the Annonaceae family.

Germacrene-D is also common in other species of the Annonaceae family. VALTER et al. (2008) reported the presence of significant concentrations of germacrene-D in Duguetia furfuracea . CASTRO et al. (2006) and SOUZA et al. (2007) suggested that pollinators were attracted to these plants because of the presence of germacrene-D, because its chemical backbone mimics the sex pheromones of insects, explaining the high concentration of germacrene-D in the essential oils of the flowers and fruits of C. calophyllum .

Other less abundant sesquiterpenes, with known biological activities, were also identified in the essential oil of the three organs (leaf, flower, and fruit) of C. calophyllum in different concentrations (Table 1). Copaene exhibits deterrent activity against insects and has a great industrial value because of its characteristic aroma (PEREIRA et al., 2008). Caryophyllene exhibits several biological activities such as spasmolytic, anti-inflammatory, and anesthetic activities (LIMBERGER et al., 2004). Further, humulene is described in the literature as an insecticide, antimicrobial, antioxidant, and anticancer compound (ALMEIDA et al., 2011).

CONCLUSION:

Essential oil of leaves, flowers, and fruits of C. calophyllum consists of a complex mixture of mono and sesquiterpenes, with a predominance of the latter. The major constituents identified were spathulenol (28.78%) in essential oil of leaves, germacrene-D (37.03%) and germacrene-B (13.72%) in flowers, and germacrene-D (28.19%), germacrene-B (20.90%), and spathulenol (11.53%) in essential oil of fruits.

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• 1
  CR-2015-0371.R3

Publication Dates

• Publication in this collection
  2 Feb 2016
• Date of issue
  May 2016

History

• Received
  13 Mar 2015
• Accepted
  19 Oct 2015
• Reviewed
  16 Dec 2015