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Food and Chemical Toxicology 46 (2008) 2770–2775

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Concentrations of p-synephrine in fruits and leaves of Citrus species (Rutaceae) and the acute toxicity testing of Citrus aurantium extract and p-synephrine
M.D. Arbo a, E.R. Larentis a, V.M. Linck a, A.L. Aboy a,A.L. Pimentel b, A.T. Henriques a, E. Dallegrave c, S.C. Garcia d, M.B. Leal b, R.P. Limberger a,*
Programa de Pós-Graduação em Ciências Farmacêuticas, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga, 2752, Cep: 90610-000, Porto Alegre, RS, Brazil b Departamento de Farmacologia, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, RuaSarmento Leite, 500/202, Cep: 90050-170, Porto Alegre, RS, Brazil c Centro de Informações Toxicológicas do Rio Grande do Sul, Fundação Estadual de Produção e Pesquisa em Saúde, Rua Domingos Crescêncio, 8° andar, Cep: 90650-090, Porto Alegre, RS, Brazil d Departamento de Análises Clínicas e Toxicológicas, Universidade Federal de Santa Maria C.P. 5061, Campus Universitário, Cep: 97110-970, SantaMaria, RS, Brazil

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Dietary supplements containing bitter orange unripe fruit extract/p-synephrine are consumed worldwide for lose weight. This study were conducted to determine the concentration of p-synephrine in unripe fruits and leaves from Citrus aurantium Lin, C. sinensis Osbeck, C. deliciosa Ten, C. limon Burm and C. limonia Osbeck, collected inSouthern Brazil, and to evaluate the acute toxicity of C. aurantium extract and p-synephrine. A high performance liquid chromatographic method with diode array detector (HPLCDAD) was optimized and validated for determination of p-synephrine. The results indicate that all of analyzed samples present p-synephrine in amounts that range from 0.012% to 0.099% in the unripe fruits and 0.029 to 0.438% inthe leaves. Acute oral administration of C. aurantium extracts (2.5% p-synephrine, 300– 5000 mg/kg) in mice produced reduction of locomotor activity, p-synephrine (150–2000 mg/kg) produced piloerection, gasping, salivation, exophtalmia and reduction in locomotor activity, which was confirmed in spontaneous locomotor activity test. All the effects were reversible and persisted for 3– 4 h. The toxiceffects observed seem to be related with adrenergic stimulation and should alert for possible side effects of p-synephrine and C. aurantium. Ó 2008 Elsevier Ltd. All rights reserved.

Article history: Received 26 November 2007 Accepted 29 April 2008

Keywords: Synephrine Citrus Rutaceae Acute toxicity

1. Introduction p-Synephrine (Fig. 1) is an amine also referred as oxedrine and worldwideused in the treatment of hypotensive states and as an ocular descongestant (Reynolds, 1993). It is the most abundant active component of extracts from Citrus aurantium L. unripe fruits (bitter orange or zhi shi in Traditional Chinese Medicine, Rutaceae). Structurally is related to endogenous neurotransmitters (epinephrine and norepinephrine) and has gained significant popularity for the treatmentof obesity (Fugh-Bergman and Myers, 2004) as an alternative to ephedra alkaloids, which have been banned from dietary supplements by the United States Food and Drug Administration (FDA) in April 2004 because of an association with serious adverse health effects (Bouchard et al., 2005; Avula et al., 2005). The new dietary supplements produced have been marketed as ‘‘ephedra free” weight loss andusually contain C. aurantium extracts standardized from 3% to 6% of p-synephrine (De Smet, 2004). Among past year supplement users, almost 75% used a
* Corresponding author. Tel.: +55 51 3308 5297; fax: +55 51 3308 5437. E-mail address: (R.P. Limberger). 0278-6915/$ - see front matter Ó 2008 Elsevier Ltd. All rights reserved. doi:10.1016/j.fct.2008.04.037