Constituintes químicos de Lippia sidoides (Cham.) Verbenaceae

Costa, Sônia Maria O.; Lemos, Telma Leda G.; Pessoa, Otília Deusdênia L.; Assunção, João Carlos C.; Braz-Filho, Raimundo

doi:10.1590/S0102-695X2002000300032

Resumo

Thirteen compounds, 3-O-acetyloleanolic acid (1), methyl 3,4-dihydroxy benzoate (2), lapachenol (3), tecomaquinone (4), tectoquinone (5), tectol (6), acetilated tectol (7), quercetin (8), luteolin (9), glucoluteolin (10), lippisidoquinone (11), taxifolin (12) and isolariciresinol (13), were isolated from ethanol extract of Lippia sidoides. Their structures were assigned unambiguously by a combination of 1D and 2D NMR, IR and EIMS spectral data analysis and comparison with the published data for structurally related compounds. In brazilian traditional medicine the aerial parts of this specie are used as anti-infective agent, particularly as antiseptic.

Constituintes químicos de Lippia sidoides (Cham.) Verbenaceae

Sônia Maria O.Costa^I; Telma Leda G. Lemos^I,^* * tlemos@dqoi.ufc.br ; Otília Deusdênia L. Pessoa^I; João Carlos C. Assunção^I; Raimundo Braz-Filho^II

^ILaboratório de Química de Produtos Naturais-Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, CP 12 200, 60455-970, Fortaleza, CE

^IISetor de Química de Produtos Naturais-LCQUI-CCT, Universidade Estadual do Norte Fluminense, Campos, RJ, Brasil

ABSTRACT

Thirteen compounds, 3-O-acetyloleanolic acid (1), methyl 3,4-dihydroxy benzoate (2), lapachenol (3), tecomaquinone (4), tectoquinone (5), tectol (6), acetilated tectol (7), quercetin (8), luteolin (9), glucoluteolin (10), lippisidoquinone (11), taxifolin (12) and isolariciresinol (13), were isolated from ethanol extract of Lippia sidoides. Their structures were assigned unambiguously by a combination of 1D and 2D NMR, IR and EIMS spectral data analysis and comparison with the published data for structurally related compounds. In brazilian traditional medicine the aerial parts of this specie are used as anti-infective agent, particularly as antiseptic.

Texto completo disponível apenas em PDF.

Full text available only in PDF format.

Agradecimentos

Os autores agradecem as bolsas de pesquisador concedidas pelo CNPq, além do apoio financeiro recebido das Instituições CNPq, CAPES e FUNCAP.

1 Lacoste E, Chaumont JP, Mandin D, Plumel MM, Matos FJA. Lęs Propriétés Antiseptiques de I'huile essentielle de Lippia sidoides Cham. Application ŕ la microflore cutanée. Annais Pharmaceutics Françaises 1996; 54: 228-30
2 Lemos TLG, Matos FJA, Alencar JW, Craveiro AA, Antimicrobial activity of essential oils of brazilian plants. Phytoterapy Research 1990; 4: 82-4
3 Matos FJA. Lippia sidoides Cham. - Farmacognosia, química e farmacologia. Revista Brasileira de Farmácia 1996; 77: 65-7
4 Chang CWJ, Flament I, Matson JA, Nishida T, Ohloff G, Wehrli FW, Weinhheimer AJ. Progress in the chemistry of organic natural products. New York. 1979; 96-7
5 Harrison LJH, Sia GL, Sim K Y, Tan HTW, Connolly JD, Lavaude C, Massiots G. A Ferulic acid ester of sucrose and other constituents of Bhesa paniculata Phytochemistry 1995; 38:1497-500
6 Gonzalez AG, Barroso JT, Cardona RJ, Medina JM, Luis FR. Química de las rubiáceas. Anales de Quimica. 1976; 73: 538-45
7 Lemos TLG, Costa SMO, Pessoa ODL., Braz-Filho R. Total Assignment of ¹H and ¹³C NMR spectra of tectol and tecomaquinone I. Magnetic Resonance in Chemistry 1999; 37:908-11
8 Pouchert CJ, Bennke J. The Aldrich Library of ¹³C and 1H NMR spectra USA: 1993: 912 e 1258
9 Agrawal PK. Carbon-13 NMR of flavanoids elsevier Science Publishers B. V., Amsterdam. Netherlands. 1989,118, 134, 154, 320
10 Costa SMO, Lemos TLG, Pessoa ODL, Braz-Filho R. Chemical Constituents from Lippia sidoides and Cytotoxic Activity. Journal of Natural Products. 2001 (in press).
11 Urones JG, Pascoal Teresa J, Sanchez Marcos I, Diez Martín D. Ent - Isolariciresinol in Reseda suffruticosa Phytochemistry 1987; 26: 1540-1

*

tlemos@dqoi.ufc.br

Datas de Publicação

Publicação nesta coleção
05 Out 2009
Data do Fascículo
2002

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

[1] 1 Lacoste E, Chaumont JP, Mandin D, Plumel MM, Matos FJA. Lęs Propriétés Antiseptiques de I'huile essentielle de Lippia sidoides Cham. Application ŕ la microflore cutanée. Annais Pharmaceutics Françaises 1996; 54: 228-30

[2] 2 Lemos TLG, Matos FJA, Alencar JW, Craveiro AA, Antimicrobial activity of essential oils of brazilian plants. Phytoterapy Research 1990; 4: 82-4

[3] 3 Matos FJA. Lippia sidoides Cham. - Farmacognosia, química e farmacologia. Revista Brasileira de Farmácia 1996; 77: 65-7

[4] 4 Chang CWJ, Flament I, Matson JA, Nishida T, Ohloff G, Wehrli FW, Weinhheimer AJ. Progress in the chemistry of organic natural products. New York. 1979; 96-7

[5] 5 Harrison LJH, Sia GL, Sim K Y, Tan HTW, Connolly JD, Lavaude C, Massiots G. A Ferulic acid ester of sucrose and other constituents of Bhesa paniculata Phytochemistry 1995; 38:1497-500

[6] 6 Gonzalez AG, Barroso JT, Cardona RJ, Medina JM, Luis FR. Química de las rubiáceas. Anales de Quimica. 1976; 73: 538-45

[7] 7 Lemos TLG, Costa SMO, Pessoa ODL., Braz-Filho R. Total Assignment of ¹H and ¹³C NMR spectra of tectol and tecomaquinone I. Magnetic Resonance in Chemistry 1999; 37:908-11

[8] 8 Pouchert CJ, Bennke J. The Aldrich Library of ¹³C and 1H NMR spectra USA: 1993: 912 e 1258

[9] 9 Agrawal PK. Carbon-13 NMR of flavanoids elsevier Science Publishers B. V., Amsterdam. Netherlands. 1989,118, 134, 154, 320

[10] 10 Costa SMO, Lemos TLG, Pessoa ODL, Braz-Filho R. Chemical Constituents from Lippia sidoides and Cytotoxic Activity. Journal of Natural Products. 2001 (in press).

[11] 11 Urones JG, Pascoal Teresa J, Sanchez Marcos I, Diez Martín D. Ent - Isolariciresinol in Reseda suffruticosa Phytochemistry 1987; 26: 1540-1