HPLC-UV and LC-MS analysis of quinonemethides triterpenes in hydroalcoholic extracts of "espinheira santa" (Maytenus aquifolium Martius, Celastraceae) leaves

Abstract

Alguns triterpenos quinonametídicos são conhecidos pela sua citotoxicidade, havendo relatos destas substâncias em várias espécies do gênero Maytenus (Celastraceae), inclusive em Maytenus aquifolium Martius, uma das espécies conhecidas no Brasil como "espinheira santa". Com o objetivo de dispor de um método analítico útil na avaliação da qualidade de medicamentos fitoterápicos de "espinheira santa", foi desenvolvido um procedimento de análise por cromatografia líquida de alta eficiência com detector ultravioleta (CLAE-UV). Foi realizada a quantificação dos triterpenos quinonametídicos maitenina e pristimerina, nos extratos hidroalcoólico e aquoso ("chá") das folhas e das cascas das raízes de M. aquifolium. As análises por cromatografia líquida acoplada à espectrometria de massas (LC-MS) usando a interface de ionização química à pressão atmosférica (APCI), confirmaram a presença de maitenina e pristimerina nos extratos hidroalcoólicos de M. aquifolium, enquanto que nos extratos aquosos estes triterpenos estão abaixo do limite de detecção.Some quinonemethide triterpenes are known for their cytotoxicity, and the presence of these compounds has been reported in several Maytenus (Celastraceae) species, including Maytenus aquifolium Martius, one of the species known in Brazil as "espinheira santa". A quantitative HPLC-UV procedure was therefore developed with the purpose of devising a useful analytical method for evaluating the quality of "espinheira santa"-based phytomedicines. Quinonemethide triterpenes pristimerin and maitenin were quantified in hydroalcoholic and aqueous extracts ("teas") prepared from the leaves and root bark of M. aquifolium. Analyses by liquid chromatography coupled to mass spectrometry (LC-MS), using the atmospheric pressure chemical ionization (APCI) interface, provided unequivocal confirmation of the presence of maitenin and pristimerin in M. aquifolium hydroalcoholic extracts, although these compounds were below detection limits in aqueous extracts. Keywords: Maytenus aquifolium Martius, Celastraceae, quinonemethide triterpenes, HPLC-UV, LC-MS IntroductionMaytenus aquifolium Martius and M. ilicifolia Martius (Celastraceae) are both known in Brazil as "espinheira santa", and systematic studies are focusing on their use as phytomedicines for the treatment of gastric ulcers and gastritis.1-3 Reports on studies of Maytenus aquifolium include pharmacology, 4 phytochemistry of flavonoids 5 and sesquiterpene 6 pyridine alkaloids biosynthesis studies 7 and authentication of phytomedicines (leaf samples) by chromatographic analysis (GC, 8 HPTLC 9 ). Use of any medicinal plant as a phytomedicine requires the prior evaluation of its efficacy and safety. Toxicological essays of Maytenus aquifolium leaf extracts spray-dried with 70% ethanol have indicated no significant toxicity in mice. 2 However, reports in the literature on quinonemethide triterpenes (displaying cytotoxic activity and therefore containing potentially toxic compounds) in Maytenus samples suggest that "espinheira santa"-based phyt...

Comparative fingerprint analyses of extracts from the root bark of wildHippocratea excelsaand “Cancerina” by high-performance liquid chromatography

“…Similar results have been reported when using a partition of more polar solvents, such as ethanol, with n ‐hexane or resuspension in n ‐hexane . Some authors have reported the extraction of these compounds with a mixture of n ‐hexane (e.g., ethyl ether (1:1, v/v) or only n ‐hexane) ; however, such extractions are performed through exhaustive maceration or with a Soxhlet apparatus.…”

“…However, the system exhibits poor selectivity and low chromatographic resolution for pristimerin. Different isocratic systems have been reported in the literature for the elution of QMTs in RP chromatography ; however, the same chromatographic problems, including low selectivity and poor resolution, are observed.…”

Cytotoxic Triterpenes from Salacia crassifolia and Metabolite Profiling of Celastraceae Species

“…However, we detected pristimerin ( 2 ) and 6-oxopristimerol ( 3 ) in all plant parts of all species studied ( Figure 5 ), including leaves, albeit at a lower concentration than in the roots. Detection of pristimerin ( 2 ) in the hydroalcoholic leaf extract of Maytenus aquifolium has previously been reported [ 19 ]. Salaquinone A and 11 β -hydroxypristimerin were detected in C. cognatum , S. crassifolia and S. elliptica extracts, while vitideasin ( 4 ) was only detected in Salacia extracts ( Figure 5 ).…”

Potencial Nutricional De Frutos De Romã

“…Os triterpenos das folhas são o friedelan-3-ol e a friedelina. A raiz possui maitenina, pristimerina e os triterpenos quininametídeos (MOSSI et al, 2004;YARIWAKE et al, 2005;NOSSAK et al, 2004). SIQUEIRA et al, 2007;DDINE et al, 2012).…”