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Benzophenones from Hypericum carinatum

Ana Paula M. Bernardi,^† Alexandre B. F. Ferraz,^† Daniela V. Albring,^† Sérgio A. L. Bordignon,^† Jan Schripsema,^‡ Raquel Bridi,^§ Carlos Severo Dutra-Filho,^§ Amélia T. Henriques,^† and Gilsane Lino von Poser*^†

Programa de Ps Graduao em Cincias Farmacuticas, UFRGS, Avenida Ipiranga, 2752, 90610-000 Porto Alegre, RS, Brazil, Grupo Metabolmica, LCQUI/CCT, Universidade Estadual do Norte Fluminense, Avenida Alberto Lamego, 2000, 28015-620 Campos dos Goytacazes, RJ, Brazil, and Departamento de Bioqumica, Instituto de Cincias Bsicas da Sade, Universidade Federal do Rio Grande do Sul, Rua Ramiro Barcelos, 2600, 90035-003 Porto Alegre, RS, Brazil

J. Nat. Prod., 2005, 68 (5), pp 784–786

DOI: 10.1021/np040149e

Publication Date (Web): April 19, 2005

†

Programa de Pós Graduação em Ciências Farmacêuticas, UFRGS.

‡

Universidade Estadual do Norte Fluminense.

Instituto de Ciências Básicas da Saúde, UFRGS.

To whom correspondence should be addressed. Tel: 55-51-3316-5456. Fax: 55-51-3316-5456. E-mail: gilsane@farmacia.ufrgs.br.

Abstract

Two new benzophenones were isolated from the leaves of Hypericum carinatum. Their structures were established on the basis of 2D NMR spectroscopic analyses and mass spectrometry as cariphenone A (6-benzoyl-5,7-dihydroxy-2,2,8-trimethyl-2H-chromene) (1) and cariphenone B (8-benzoyl-5,7-dihydroxy-2,2,6-trimethyl-2H-chromene) (2). Five known compounds, the phloroglucinol derivative uliginosin B (3), 1-eicosanol, sitosterol, stigmasterol, and campesterol, were also characterized. Compounds 1−3 were evaluated for their total antioxidant capacity through a total radical-trapping parameter assay. Only compound 1 showed moderate antioxidant activity, exhibiting inhibition of chemiluminescence similar to that of quercetin at the same concentration.

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Published In Issue May 27, 2005
Received July 6, 2004

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Benzophenones from Hypericum carinatum