Limonoides isolados dos frutos de Carapa guianensis Aublet (Meliaceae)

Abstract

LIMONOIDS ISOLATED FROM FRUITS OF Carapa guianensis Aublet (Meliaceae). Six limonoids were isolated in hexane extract obtained from the seeds and pericarps of Carapa guianensis. The structures of the limonoids were determined based on the analysis of High Resolution Mass Spectroscopy and Nuclear Magnetic Resonance (uni-and bi-dimensional experiments) data. This is the first report of isolation of the limonoid 6α-acetoxy-7-deacetilgedunin from the seeds of the C. guianensis species. The limonoid 6-hydroxy-methyl angolensate was also described for the first time in this species.

In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production

“…Isolated and semi-synthetic limonoids 1 - 5 were fully characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) one and two-dimensional spectrometric techniques. Comparison of the NMR spectral data with literature data and analysis of the 1D and 2D NMR data allowed for the positive identification and spectral assignment of isolated limonoids 1 [ 32 ], 2 [ 33 ], 3 [ 34 ] and 4 [ 35 ] (Figure 1 ). Di-deacetylation of 3 led to the formation of a product that exhibited HRMS, 1 H and 13 C NMR data consistent with 6α-hydroxydeacetylgedunin ( 5 ).…”

“…However, gedunin ( 6 ) was not isolated in the present work from RPSM. Interestingly, a recent study on the fruit from the same tree specimens from which fruit for the present study was collected described the isolation of 7-deacetyl gedunin ( 9 ), but not gedunin ( 6 ) [ 35 ]. Gedunin was considered to be an optimal structure for its high in vitro activity against different strains of P. falciparum and because structural modification of gedunin through semi-synthetic reactions yielded derivatives exhibiting decreased in vitro anti-plasmodial activity compared to gedunin [ 21 , 22 ].…”

Phytochemical profile and antioxidant potential of Carapa guianensis Aubl. (Meliaceae) Leaves

“…Quimicamente, a familia Meliaceae (particularmente nas espécies Carapa guianensis Aubl. e Carapa procera D. C. é caracterizada pela síntese de triterpenos modificados conhecidos como limonóides (Paritala et al, 2015;Pereida da Silva et al, 2023), substâncias de característica apolar responsáveis pela sua atividade cicatrizante e anti-inflamatória (Nayak et al, 2011;Silva et al, 2012). Como o intuito do trabalho era investigação de atividade antioxidante e antifúngica de compostos fenólicos, a partição com hexano permitiu a retirada de substâncias mais apolares, que poderiam perturbar a obtenção do perfil fitoquímico das frações.…”

Chemical composition and acaricidal activity of seed oils of the palms Mauritia flexuosa and Mauritiella armata in Rhipicephalus microplus (Ixodidae)

“…According to Ambrozin et al (2006) and Silva and Nunomura (2012), oils that are rich in fatty acids, such as oleic, palmitic, stearic and linoleic acids, have biological activity against arthropods. Research has identified the presence of limonoids in oils extracted from andiroba seeds, which have proven insecticidal and repellent abilities (Ambrozin et al, 2006).…”