Essential Oils from Fruits and Leaves of Siparuna guianensis (Aubl.) Tulasne from Southeastern Brazil

Abstract

The essential oils from leaves and fruits of Siparuna guianensis collected in southeastern Brazilian cerrado were analyzed by GC and GC/MS. The main constituents found in the leaf oil were decanoic acid (46.6%) and 2-undecanone (31.7%). The fruit oil consisted mainly of 2-undecanone (32.5%), β-pinene (19.6%) and limonene (13.6%).

Key Word Index

Siparuna guianensis, Siparunaceae, essential oil composition, 2-undecanone, decanoic acid, β-pinene, limonene.

Plant Name

Siparuna guianensis (Aubl.) Tulasne. Local name: Limão-Bravo, capitu, vulnerária-das-guianas.

Previous Work

The oil composition of S. guianensis collected in the Brazilian Amazon Region (Acre and Pará) and along the Canal Zone in Panama has been the subject of previous studies (1,2,3). The main components of fresh and dried leaves collected in Rio Branco (AC-Brazil) were γ-cadinene (21.8%), bergamotenal (14.2%) and β-caryophyllene (15.1%) and siparunone (23.3%), γ-cadinene (12.7 %) and isogermacrenone (12.2%), respectively (1). The oils from three different specimens obtained from different locations were compared; one contained mainly epi-α-bisabolol (25.1%) and spathulenol (15.7%), the second contained spathulenol (22.0%), selin-ll-en-4α-ol (19.4%), β-eudesmol (10.0%) and elemol (10.0%) and the third contained germacrone (23.2%), germacrene D (10.9%), bicyclogermacrene (8.6%), germacrene B (8.0%) andatractylone (31.4%) (2). The main constituents of S. guianensis leaf oil of Panamanian origin were curzerenone (25.64%), curzerenone types and/or products of degradation of curzerenone (42.31%) and myristicin (7.93%) (3). Furthermore, the oxoaporphine alkaloids liriodenine and cassamedine have been isolated from the trunk wood of S. guianensis (4).

Experimental

Plant material: The fruits and leaves of fertile S. guianensis specimens were collected in October 2000 at the Experimental Reserve of the Botanical Institute of São Paulo, in Mogi-Guaçu (SP). Voucher specimens (Fischer3-SPF) have been deposited in the Herbarium of the Institute of Biosciences from University of São Paulo University.

oils from fresh fruits (243 g) andleaves (214 g) were obtained by hydrodistillation for 3 h using a Clevenger-type apparatus to yield 0.53 g (0.22%) and 1.08 g (0.49%), respectively.

Component identification: The volatile oils were submitted to GC and GC/MS analysis. GC analysis was performed in a Chromatograph (Shimadzu GC-17A) equipped with Shimadzu GC 10 software, using a fused silica capillary column (30 m × 0.25 mm, 0.25 µm film thickness, coated with DB-5), and a flame ionization detector. Injector and detector temperatures were set at 220°C and 250°C, respectively; the oven temperature was programmed from 60°-300°C at 3°C/min and helium was employed as carrier gas (1 mIVmin). The percentage compositions were obtained from electronic integration measurements using flame ionization detection without taking into account relative response factors.

The sample was analyzed by GC/MS, using a Shimadzu capillary GC-quadrupole MS system (QP 5000) operating at 70 eV in the same conditions as described above. The identification of the compounds performed by comparing retention indices (determined relatively to the retention times of a series of n-alkanes) and mass spectra with those of authentic samples authentic and with literature data (5,6).

Results and Discussion

The oil constituents of fruits and leaves are presented in Table I and II, respectively. The main constituents found in the fruit oil were 2-undecanone (32.5%), β-pinene (19.6%) and limonene (13.6%), accounting for nearly 65% of the oil constituents. All other substances contributed less than 10% ofthe oil composition. The leaf oil contained fewer components than the fruit oil. The major compounds were decanoic acid (46.6%) and 2-undecanone (31.7%). The specimen analyzed was collected from the so-called "Brazilian cerrado" (a savannah-like area), which is a completely diverse biome from those previously investigated. The oil composition of S. guianensis samples from the Amazon region (1,2) and the one from Panama (3) possessed sesquiterpenes as major components, while the one from cerrado contained a methylketone and a fatty acid as main compounds.

References

1. L.M.C Rebouças, Terpenos de Siparuna guianensis: aldeídos via epoxidação de duplas terminais. MSc. Thesis, Curso de Pós-Graduação em Química, Universidade Federal do Ceará, Fortaleza, 116 pp (1984).

2. M.G.B. Zohgbi, E.H.A. Andrade, A.S. Santos, M.H.L. Suva and J.G.S. Maia, Essential oils of Siparuna guianensis Aubl. J. Essent. oil Res., 10, 543-546(1998).

3. T.M. Antonio, G.R. Waller and CJ. Mussinan, Composition of Essential Oil from the Leaves of Siparuna guianensis (Monimiaceae). Chem. Ind., 14, 514-515 (1984).

4. R. Braz-Filho, SJ. Gabriel, C.M.R. Gomes, O.R. Gottlieb, M.G.A. Bichara and J.G.S. Maia, Oxoaporphine alkaloids from Fusea longifolia and Siparuna guianensis. Phytochemistry, 15, 1187-1188 (1976).

5. R.P. Adams, Identification of essential oil components by gas chromatography/ion trap mass spectrometry. Allured Pub., Carol Stream, IL (1995).