Copaifera duckei Oleoresin and Its Main Nonvolatile Terpenes: In Vitro Schistosomicidal Properties

Abstract

In this article, the in vitro schistosomicidal effects of three Brazilian Copaifera oleoresins (C. duckei, C. langsdorffii, and C. reticulata) are reported. From these botanical sources, the oleoresin of C. duckei (OCd) demonstrated to be the most promising, displaying LC values of 75.8, 50.6, and 47.2 μg/ml at 24, 48, and 72 h of incubation, respectively, against adult worms of Schistosoma mansoni, with a selectivity index of 10.26. Therefore, the major compounds from OCd were isolated, and the diterpene, (-)-polyalthic acid (PA), showed to be active (LC values of 41.7, 36.2, and 33.4 μg/ml, respectively, at 24, 48, and 72 h of incubation). Moreover, OCd and PA affected the production and development of eggs, and OCd modified the functionality of the tegument of S. mansoni. Possible synergistic and/or additive effects of this balsam were also verified when a mixture of the two of its main compounds (PA and ent-labd-8(17)-en-15,18-dioic acid) in the specific proportion of 3:1 (w/w) was tested. The obtained results indicate that PA should be considered for further investigations against S. mansoni, such as, synergistic (combination with praziquantel (PZQ)) and in vivo studies. It also shows that diterpenes are an important class of natural compounds for the investigation of agents capable of fighting the parasite responsible for human schistosomiasis.

Antibacterial Effect of Copaifera duckei Dwyer Oleoresin and Its Main Diterpenes against Oral Pathogens and Their Cytotoxic Effect

“…C. duckei was identified by Silvana Tavares Rodrigues from Embrapa, Belém, Pará, and the voucher specimen was deposited at the Embrapa Herbarium under number NID:96/2012. Pure (–)-polyalthic acid (1 - PA) and eperu-8(20)-15,18-dioic acid ( 2 ) were obtained according to the methodology reported by our research group (Borges et al, 2016 ).…”

“…The Copaifera duckei Dwyer oleoresin exhibits biological activities such as antiproliferative, antimutagenic, embryotoxic, anti-inflammatory, and analgesic actions (Castro-e-Silva et al, 2004 ; Carvalho et al, 2005 ; Maistro et al, 2005 ; Lima et al, 2011 ; Leandro et al, 2012 ). Recently, Borges et al ( 2016 ) evaluated the in vitro schistosomicidal effects of the C. duckei oleoresin and its major secondary metabolite, (–)-polyalthic acid, to demonstrate that these substances are active against Schistosoma mansoni and may be employed for further investigations into compounds that can combat this parasite. Santos et al ( 2013 ) assessed the antibacterial activity of the C. duckei oleoresin against bacteria of clinical and food interest, to verify that the oleoresin showed good activity against Gram-positive bacteria and acted on the bacterial cell wall of Bacillus cereus , affecting the cell-division process.…”

Antimicrobial and cytotoxic effects of the Copaifera reticulata oleoresin and its main diterpene acids

“…Ent-copalic acid was also active against amastigote forms of Trypanosoma cruzi together with 3β-hydroxycopalic acid and methyl copalate (Izumi et al, 2012). Entpolyalthic acid (3) was investigated against Schistosoma mansoni and found schistosomicidal with LD50 values from 33.4 to 41.7 µg/mL and to affect the production and the development of eggs (Borges et al, 2016).…”

Biotransformações dos ácidos ent-poliáltico e ent-diidroagático por culturas microbianas e microssomas hepáticos

“…Através da análise fitoquímica da fração não volátil deste bálsamo, os metabólitos secundários ácido ent-poliáltico (AP) e ácido ent-diidroagático (ADA) foram identificados entre os constituintes químicos majoritários (CASCON & GILBERT, 2000;BORGES et al, 2016, CARNEIRO et al, 2018 (REYES-TREJO et al;.…”

“…O AP já foi reportado como antimicrobiano (TINCUSI et al, 2002;ABRÃO et al, 2018), gastroprotetor (REYES-TREJO et al, 2008), tripanocida (IZUMI et al, 2012, leishmanicida (DOS SANTOS et al, 2013;MIZUNO et al, 2015) e esquistossomicida (BORGES et al, 2016). O AP da série normal apresentou atividade anti-mutagênica (MIYAZAWA et al, 1995) e induziu a glicação de proteínas do plasma (ATOLANI & OLATUNJI, 2014), indicando a necessidade de maior conhecimento sobre as possíveis propriedades tóxicas dos diterpenos.…”