Constituents of the Essential Oil of Capraria biflora from Northeast Brazil

Journal of Essential Oil Research: JEOR, Mar/Apr 2006 by Fonseca, Aluísio M, Pessoa, Otília D L, Lemos, Telma L G, Nascimento, Ronaldo F

Abstract

The essential oil from the fresh leaves of Capraria biflora (Scrophulariaceae), obtained by hydrodistillation piOcesss, was analyzed by GC and GC/MS. Nine compounds were characterized representing 91.1% of compounds present in the oil. The major components present were the sesquiterpenes β-caryophyllene (29.6%) and γ-muurolene (32.6%).

Key Word Index

Capraria biflora, Scrophulariaceae, essential oil composition, γ-muurolene, β-caryophyllene.

Plant Name

Capraria biflora (Scrophulariaceae). Local name: cha-dorio, chá-de calçada (1).

Source

Plant material was collected in Fortaleza, Ceará, Brazil in February 2003. Plant identification was done by Edson P. Nunes and voucher specimens # 30848 and 30849 have been deposited at the Herbario Frisco Bezerra of the Departamento de Biologia, Universidade Federal do Ceará, Brazil.

Plant Part

The fresh leaves (500 g) were submitted to hydrodistillation in a Clevenger-type apparatus for 3 h. The oil obtained was dried over anhydrous sodium sulfate to yield 443 mg; 0.09% (v/v) and stored at 4°-6°C.

Previous Work

Capraria biflora L. (Scropulariaceae) is a perenial herb widely distributed in several countries of Tropical America (1). Previous phytochemical investigation have allowed the characterization of orifto-naphthoquinone identified as biflorin having antimicrobial properties against Gram-positive bacteria (2-4), besides sesquiterpenes characterized as caprariolides with insecticidal activity (5) and iridoides (6). Recently our group made aphytochemical reinvestigation of this species and identified one ortho-naphthoquinone dimernamed bis-biflorin, manitol and β-sitosterol (7,8). The leaves of C. biflora have pharmacological significance in folk medicine and have been used for treatment of fever, influenza, indigestion, diarrhea and several dermal disorders such as scabies, itching and other skin diseases (9). As far as we know there is no report about chemical constituents of the oils from Capraria biflora.

Present work

GC: Analytical GC-FID was carried out on a Shimadzu GC-17A gas chromatograph using dimethylpolysiloxane DB-5 fused silica capillary column (30 m x 0.25 mm, film thickness 0.25 µm). H^sub 2^ was used as carrier gas at a flow rate 1 mL/min and 30 psi inlet pressure; split, 1:30; temperature program: 35°-180°C at 4°C/min, then heated at a rate of 17°C/min to 280°C and held isothermal for 10 min; injector temperature, 250°C; detector used FID, detector temperature, 250°C.

GC/MS: Analysis of the oils was performed on a Hewlett-Packard 5971 GC/MS instrument employing the following conditions: dimethylpolysiloxane DB-1 fused silica capillary column (30 m x 0.25 mm, 0.1 µm film thickness); carrier gas: He (1 mL/min); injector temperature: 250°C; detector temperature: 200°C; column temperature: 35°-180°C at 4°C/min, then 180°-250°C at 10°C/min; mass spectra: electronic impact 70 eV. Individual components were identified by two computer library MS searches using retention indices as a preselection routine (10) and visual inspection of the mass spectra from literature for confirmation (11). Nine compounds were identified representing 91.1%ofthe total components detected. The chemical composition of the oil is represented in Table I.

Acknowledgments

The authors thank CAPES/CNPQ for the fellowships and financial support.

References

1. R. Braga, Plantas do Nordeste: Especialmente do Ceará. Coleção Mossoroense: Natal-RN, p 186 (1960).

2. O.G. Lima, W. Keller-Schierleinand V. Prelog, Über das biflorin. Helv. Chim. Acta., 41, 1386-1390 (1958).

3. J. Comin, O.G. Lima, H. Grant, LM. Jachman, W. Keller-Schierlein and V. Prelog, Über die Konstitution des Biflorins, eines o-Chinons der DiterpenenReihe. Helv. Chim. Acta, 46, 409-415 (1963).

4. I.L.D.Albuquerque, M.C.P. Navair and O.G. Lima, Novo Método de Extração e Purificação de Biflorina com Possibilidade Industrial. Rev. Inst. Ant., 4, 79-81 (1962).

5. D.O. Collins, W.A. Gallimore, W.F. Reynolds, L.A.D. Willians, and P.B. Reese, New Skeletal Sesquiterpenoids, Caprariolides A-D, from Capraria biflora and their Insecticidal Activity. J. Nat. Prod., 63, 1515-1518 (2000).

6. M. Heinnch and H. Rimpler, Harpagide and 8-o-Benzoylharpagide from the Mixe Medicinal Plant Capraria biflor. Planta Med., 55, 622 (1989).

7. A.M. Fonseca, O.D.L. Pessoa, E.R. Silveira, FJ.Q. Monte, R. Braz-Filho and T.L.G. Lemos, Total assignments of the ^sup 1^H and ^sup 13^C NMR spectra of biflorin andbis-biflorin from Caprana biflora. Magn. Res. Chem., in press (2003).

8. A.M. Fonseca, Estudo Fitoquimico dos Constitutes fixos e volátais de Caprana biflora. Dissertação de Mestrado, UFC, Fortaleza-Ceará (2002).

9. A.A.Craveiro, F.J.A. Matos and J.W. Alencar, Kovats Indices as a preselection routine in mass spectra library search of volatiles. J. Nat. Prod., 47, 890-892 (1984).

10. E. Stenhagen, S. Abrahamson and F.W. MoLafferty, Registry of Mass Spectra Data. John. Willey & Sons, New York, NY (1974).

11. R.P. Adams, Identification of Essential Oils Components by Gas Chromatogrphy/TrapMassSpectrometry, Allured Publ. Corp., Carol Steam, IL (2001).


 

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