Triterpenes of leaves from Piranhea trifoliata (Picrodendraceae)

Abstract

* Autor correspondente: cecilia@inpa.gov.br RESUMO A floresta Amazônica é rica em diversas espécies vegetais, dentre elas, destaca-se Piranhea trifoliata, a qual é conhecida popularmente como piranheira, por seus frutos servirem de alimentos para peixes. Suas cascas são utilizadas como curativo para inflamação no útero em banhos de assento e para chás no tratamento de malária. O objetivo deste trabalho foi o fracionamento cromatográfico do extrato diclorometânico e da fase diclorometânica do extrato metanólico das folhas de Piranhea trifoliata. As folhas foram secas, moídas e extraídas com diclorometano, metanol e água. O extrato metanólico foi submetido à partição com diclorometano e acetato de etila. O fracionamento cromatográfico conduziu ao isolamento de seis triterpenoides pentacíclicos: friedelan-3-ona, 28-hidroxi-friedelan-3-ona, 30-hidroxi-friedelan-3-ona, lupeol, mistura de α-e β-amirina, além da mistura dos esteroides β-sitosterol e estigmasterol. As estruturas das substâncias foram identificadas pela análise dos espectros de Ressonância Magnética Nuclear (RMN) de 1 H e de 13 C e comparações com dados da literatura. Este é o primeiro relato descrevendo o estudo químico das folhas de P. trifoliata. PALAVRAS-CHAVE: Floresta amazônica, análise de RMN, esteroides, terpenos. Triterpenes of leaves from Piranhea trifoliata (Picrodendraceae) ABSTRACTThe Amazon forest is rich in plant species diversity, among them, Piranhea trifoliata stands out, which is popularly known as piranheira, because their fruits are eaten by fish. Their barks are used as bath composition on uterus inflammation and as tea in malaria treatment. This study aimed to fractionate the dichloromethane and dichloromethane phase from methanolic extract of leaves of Piranhea trifoliata. The leaves were dried, grounded and extracted with dichloromethane, methanol and water. The methanol extract was partitioned with dichloromethane and ethyl acetate. The chromatographic fractionation yielded six pentacyclic triterpenoids: friedelan-3-one, 28-hydroxy-friedelan-3-one, 30-hydroxy-friedelan-3-one, lupeol, α-and β-amyrin mixture, besides the mixture of the steroids: β-sitosterol and stigmasterol. The substances structures were identified by 1 H-and 13 C-Nuclear Magnetic Resonance (NMR) analysis and literature data comparison. This is the first report describing the chemical study of P. trifoliata leaves.

Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil

“…The signal at δ C 71.8 ppm was assigned to the carbinolic carbon (C‐3) of compounds 3 and 4 . The other signals were attributed to the carbon atoms of the aliphatic structures of these steroids [22,24] . The 1 H‐NMR spectrum ( Figure 12) allowed the identification of an apparent doublet at δ H 5.35 ppm, which according to the literature refers to the hydrogen H‐6 of the sterol system, corresponding to compounds 3 and 4 .…”

“…[17] The 13 C-NMR spectrum (Figure 11) the aliphatic structures of these steroids. [22,24] The 1 H-NMR spectrum (Figure 12) allowed the identification of an apparent doublet at δ H 5. hydrogen atoms of aliphatic groups typical of steroids. [22,24,25,26] The infrared spectrum of compounds 3 and 4 (Figure 13) showed an absorption band at 3432 cm À 1 assigned to the OÀ H stretching vibration.…”

Phytochemical Survey and Antifungal Activity of Plant Extracts in Angico Seeds (Anadenanthera Colubrina Vell. Brenan)

“…Lupeol is a triterpene with antimicrobial action, and its reactions are catalyzed by lupeol synthase (JEFFREYS et al, 2016). Gallic acid is an important phenol for plant defense, with proven antimicrobial activity, and is the reference standard for quantifying phenol (MORAIS et al, 2016).…”

Piranhea trifoliata an Amazonian Plant with Therapeutic Action: A Review

“…In bark and leaf extracts, the 28-hydroxyfriedelin-3-one triterpene and its isolated methanolic extracts showed antimalarial, antioxidant, and antibacterial activities [14,34]. Also, studies have demonstrated the isolation of friedelan-3-one, 28-hydroxy-friedelan-3-one, 30-hydroxy-friedelan-3-one, lupeol, the mixture of α-and β-amirine, in addition steroids as βsitosterol, stigmasterol, 7,4dimethylamentofavone and 3'-O-methylloniflavone from P. trifoliata, which contributed to the first report of triterpenes (28-hydroxyfriedelan-3-one and 30-hydroxy-friedelan-3-one) and bioflavonoids (7,4-dimethylamentofavone and 3'-O-methyl-loniflavone) in the Picrodendraceae family [41]. There are few phytochemical studies with P. trifoliata; however, actual results demonstrated significant biological activities Table 1.…”

“…There are few phytochemical studies with P. trifoliata; however, actual results demonstrated significant biological activities Table 1. [41], B [42] DCM and MeOH [41,42] Anti malarialin vitro [42] IC 50 5.8 μg/mL [42] Red DCM and MeOH [41,42] Antimalarial -in vitro [42] IC 50 5.8 μg/mL [42] Red blood cells infected by P. falciparum, clone W2, resistant to chloroquine [42] Stigmasterol L [41], B [42] DCM and MeOH [41,42] Antimalarial -in vitro [42] IC 50 5.8 μg/mL [42] Red…”