Chemical composition, anti-Trypanosoma cruzi and cytotoxic activities of the essential oil from green fruits of Protium ovatum (BURSERACEAE)

Abstract

-Chagas disease is a major neglected tropical disease caused by Trypanosoma cruzi. It has been treated with the antiparasitic drugs nifurtimox and benzonidazole, which cause several side effects. The market for natural products has considerably grown lately and the use of plants has become an alternative to the development of novel drugs to cure the disease. Therefore, this study aimed at describing the chemical analysis of the essential oil from green fruits of Protium ovatum and evaluating their trypanocidal and cytotoxic potential. The essential oil was obtained by Clevenger hydrodistillation whereas its chemical composition was determined by gas chromatography coupled to mass spectrometry (GC-MS). The major compounds found in the essential oil from green fruits of P. ovatum were β-myrcene (62.0 %), α-pinene (11.3 %) and limonene (7.3 %). To the best of our knowledge, this was the first time that the chemical composition of the essential oil from green fruits of P. ovatum was described. Results showed that the essential oil had strong trypanocidal activity against trypomastigote forms of theY strain of Trypanosoma cruzi (IC 50 = 1.2 µg/mL). In addition, the essential oil from green fruits of P. ovatum did not display cytotoxicity against LLCMK 2 adherent epithelial cell at the concentration range under analysis (CC 50 = 550.3 μg/mL). As a result, it is an excellent option for the development of novel antiparasitic drugs. Index terms: Protium ovatum, β-myrcene, fruits, essential oil, Trypanosoma cruzi, cytotoxic analysis. Composição química, atividades anti-Trypanosoma cruzi e citotóxica do óleo essencial dos frutos verdes de Protium ovatum (BURSERACEAE)Resumo -A doença de Chagas é uma das principais doenças tropicais negligenciadas causadas pelo Trypanosoma cruzi, e em seu tratamento utilizam-se medicamentos como o nifurtimox e o benzonidazol, que causam vários efeitos colaterais. O mercado de produtos naturais tem aumentado consideravelmente nos últimos anos, e o uso das plantas continua sendo uma alternativa para o desenvolvimento de novos medicamentos para cura de doenças. Portanto, este estudo aborda a composição química do óleo essencial dos frutos verdes de Protium ovatum e a avaliação de seus potenciais tripanocida e citotóxico. O óleo essencial foi obtido por hidrodestilação, utilizando o aparato do tipo Clevenger. A composição química foi determinada por cromatografia gasosa acoplada à espectrometria de massas (CG-EM). Os principais compostos encontrados no óleo essencial dos frutos verdes de P. ovatum foram: β-mirceno (62,0 %), α-pineno (11,3 %) e limoneno (7,3 %).

Essential Oils from Different Myrtaceae Species from Brazilian Atlantic Forest Biome – Chemical Dereplication and Evaluation of Antitrypanosomal Activity

“…( E )‐caryophyllene was one of the major compounds in the species considered promising active, corroborating with previous anti‐ T. cruzi activitites studies involving ( E )‐caryophyllene rich EOs such as Cordia verbenaceae (18.77 %), Eugenia brejoensis (9.77 %), Hyptis pectinata (30.91 %), Annona pickelii (27.8 %), Protium ovatum (14 %), and Vernonia brasiliana (10.4 %) [21–25] …”

“…It is interesting to observe that among the identified compounds in E. florida EOs, a significant trypanocidal activity can be attributed to the presence of α‐pinene and ( E )‐caryophyllene, since both compounds displayed anti‐ T. cruzi activity in previous studies [17,21–25] . There are also reports of improved anti‐ T. cruzi activity achieved by the combination of limonene and caryophyllene oxide [26,27] …”

Chemical constituents of essential oil from Murraya paniculata leaves and its application to in vitro biological control of the fungus Sclerotinia sclerotiorum

“…Studies carried out by this research group have aimed at analysing the chemical composition and biological activities of essential oils (Estevam et al, 2017;Estevam et al, 2018), and this one, specifically, addresses the chemical composition and the in vitro antifungal activity of M. paniculata (Figure 1) against S. sclerotiorum.…”

Antiproliferative activity of essential oils from three plants of the Brazilian Cerrado: Campomanesia adamantium (Myrtaceae), Protium ovatum (Burseraceae) and Cardiopetalum calophyllum (Annonaceae)

“…Previous studies carried out by the members of this research group reported the content and the chemical composition of essential oils extracted from C. adamantium and C. calophyllum leaves and from P. ovatum leaves and green fruits. Mean contents of essential oils found after hydrodistillation of C. adamantium and C. calophyllum leaves and of P. ovatum leaves and green fruits were 0.32%, 0.06%, 0.30% and 0.50%, respectively (Oliveira et al, 2017;Xavier et al, 2016b;Estevam et al, 2017;Estevam et al, 2018).…”

“…Major constituents identified in essential oils from C. adamantium leaves were spathulenol (19.27%), germacrene-B (18.27%) and β-caryophyllene oxide (12.37%) (Oliveira et al, 2017), whereas, in the ones from P. ovatum leaves, they were spathulenol (17.60%), β-caryophyllene (14.00%) and β-myrcene (8.40%) (Estevam et al, 2017). Major constituents of essential oils from P. ovatum green fruits were and β-myrcene (62.0%), α-pinene (11.3%) and limonene (7.3%) (Estevam et al, 2018), while C. calophyllum leaves displayed spathulenol (28.78%), viridiflorol (9.99%) and (Z,E)-pharnesol (6.51%) (Xavier et al, 2016b).…”