Química Nova
Print version ISSN 0100-4042
Quím. Nova vol.37 no.6 São Paulo July 2014
http://dx.doi.org/10.5935/0100-4042.20140163
ARTIGO
Volatile constituents of Aristolochia trilobata L. (Aristolochiaceae): a rich source of sulcatyl acetate
Darlisson de Alexandria SantosI; Péricles Barreto AlvesI,*; Emmanoel Vilaça CostaI; Clovis Roberto Pereira FrancoII; Angelita NepelIII; Andersson BarisonIII
IDepartamento de Química, Universidade Federal do Sergipe, Av. Marechal Rondon, S/N, Campus Universitário, 49100-000 São Cristóvão - SE, Brasil
IIDepartamento de Biologia, Universidade Federal do Sergipe, Av. Marechal Rondon, S/N, Campus Universitário, 49100-000 São Cristóvão - SE, Brasil
IIIDepartamento de Química, Universidade Federal do Paraná, 81530-900 Curitiba - PR, Brasil
ABSTRACT
Analysis of the volatile fraction of Aristolochia trilobata stem led to the identification of 6-methyl-5-hepten-2-yl acetate (23.31 ± 0.28%), limonene (15.43 ± 0.030%), linalool (8.70 ± 0.29%), p-cymene (7.81 ± 0.12%), bicyclogermacrene (4.21 ± 0.11%), and spathulenol (4.17 ± 0.14%) as the major constituents of the essential oil. Linalool (29.51 ± 0.49%), 6-methyl-5-hepten-2-ol (19.54 ± 0.82%), 6-methyl-5-hepten-2-yl acetate (8.92 ± 0.16%), and a-terpineol (4.62 ± 0.05%) were identified as major constituents of the hydrolate. The compound 6-methyl-5-hepten-2-yl acetate was isolated for the first time from this plant and was identified as the major component of the volatile fraction.
Keywords: Aristolochia trilobata; essential oil; 6-methyl-5-hepten-2-yl acetate.
INTRODUCTION
The genus Aristolochia consists of ~500 species distributed mainly in Asia, Africa, South America, and North America.1 In recent studies, many of these plants have shown diuretic, analgesic, anti-inflammatory, and anti-cancer activity.2
Several species of Aristolochia, which present similarities both in terms of their botanical characteristics and their properties, can be found in Brazil. The species most commonly used in folk medicine are A. triangularis, A. esperanzae, A. ridicula, A. brasiliensis, A. arcuate, and A. gigantea. Considering the above-mentioned similarities, these species share the same common names in Brazil, which include jarrinha, cipó-mil-homens, mil-homens, milone, papo-de-peru, erva-de-urubu, and jiboinha.3
Extensive research has been carried out on the plants of this genus, mainly on extracts of the leaves, stems, and roots. A variety of activities have been attributed to them, these include bactericidal, anti-inflammatory, anti-trypanosomal, and anti-tumoral.4-7
Chemical compounds that have been identified in these plants, both in the essential oils and in organic solvent extracts, include aporphines, amides, quinolines, lignanes, diphenyl ethers, flavonoids, benzenoids, steroids, and terpenoids.1
The essential oils of the species belonging to the genus Aristolochia are comprised mainly of monoterpenes and sesquiterpenes, the commonly occurring terpenes being germacrene and caryophyllene, which are the major compounds in most cases.
Aristolochia trilobata L. is a species of Aristolochia found in Central and South America, and has several applications in traditional medicine in these regions.8
One such medicinal use in treating injured dogs has been reported by Lans et al.,9 who carried out a study on hunters in Trinidad and Tobago. According to this study, species of the genus Aristolochia, in particular A. trilobata and A. rugosa, are widely used in treatment for dogs that have been bitten by snakes or scorpions.9 In the same country, A. trilobata is used for treating stomach ache, colic, poisoning, and diabetes in human patients, as well as to facilitate the removal of the placenta and abortion.10-12
The use of this plant for treating snake bites is not restricted to Trinidad and Tobago. Studies have revealed that A. trilobata has also been used for this purpose in Brazil and Nicaragua.13,14 In Brazil, it has been reported that A. trilobata is also used as a fungicide.15
Studies reveal that A. trilobata is used as an antimalarial agent in French Guiana.16 In Dominica, this plant is used for treating intestinal problems.17
An infusion (tea) or a plant extract of A. trilobata is used in folk medicine. One study determined the chemical composition of the methanolic extracts of the root and stem; four aristolochic acids and one aristolactam were identified.18
The stem is found in markets and fairs in Aracaju, Sergipe State, Brazil, and is commonly used by the population in cachaça (sugar cane spirit) infusions and ingested in this form.
In this paper, the first study on the chemical composition of the essential oil of the stem of A. trilobata is reported. The analysis of the hydrolate is also reported.
