Influence of fruit biotypes on the chemical composition and antifungal activity of the essential oils of eugenia uniflora leaves

Abstract

A análise multivariada da composição química dos óleos essenciais das folhas de Eugenia uniflora com diferentes cores de fruto indicou a presença de três grupos de óleos em relação ao biótipo do fruto das amostras. O primeiro grupo incluiu amostras de frutos amarelos, vermelhos escuros e roxos contendo altas percentagens de germacreno B (11,1-30,7%), germacrona (9,8-54%) e atractilona (0-19,9%). No grupo II, com amostras de frutos vermelhos claro, os constituintes majoritários foram o curzereno (42,0-43,2%), germacreno D (8,7-9,0%) e germacreno A (5,9-8,9%), enquanto que o grupo III incluiu amostras com frutos vermelho-alaranjado, caracterizadas por um alto conteúdo de selina-1,3,7(11)-trien-8-ona (40,3-55,4%) e epóxido de selina-1,3,7(11)-trien-8-ona (12,7-24,4%). Os óleos essenciais foram investigados frente ao fungo Paracoccidioides brasiliensis pela técnica de macrodiluição em caldo. O resultado mais significativo foi obtido com o óleo do grupo II, com a forma leveduriforme de P. brasiliensis sendo inibida completamente na concentração de 62,5 mg mL -1 .The multivariate chemical analysis of essential oils of Eugenia uniflora leaves with different fruit colours indicated the presence of three oil clusters regarding sample biotypes. The first cluster included yellowish, dark red and purple fruits with high percentages of germacrene B (11.1-30.7%), germacrone (9.8-54%) and atractylone (0-19.9%). In cluster II, with bright red fruit samples, the major constituents were curzerene (42.0-43.2%), germacrene D (8.7-9.0%) and germacrene A (5.9-8.9%), whereas cluster III included red-orange fruit samples containing high contents of selina-1,3,7(11)-trien-8-one (40.3-55.4%) and selina-1,3,7(11)-trien-8-one epoxide (12.7-24.4%). The clustered oils were investigated against the systemic fungus Paracoccidioides brasiliensis via the broth macrodilution method. The oil from cluster II revealed the most significant result. The yeast form of P. brasiliensis was completely inhibited at a concentration of 62.5 mg mL -1 . Keywords: Eugenia uniflora, essential oil, chemical variability, antifungal activity, Paracoccidioides brasiliensis IntroductionFungal infections are common in tropical countries and may have a major impact on public health. Whereas the dermatophyte fungi group is of common occurrence, 1 the incidence of systemic infections due to Paracoccidioides brasiliensis (Splendore) Almeida has increased in the last two decades. 2 P. brasiliensis is an etiological agent of paracoccidioidomycosis, the most prevalent human systemic mycosis in Latin America, where up to 10 million individuals are estimated to be infected. 3 This thermally dimorphic fungus grows as a filamentous saprobe (mycelium) in the soil at 25 °C and as a multicelular parasitic form (yeast) in the host. The shift from the mycelial to the yeast form (36 °C) is crucial for the infection of the human host. The heat shock response of P. brasiliensis to an abrupt increase in environmental temperature during infection results in the expression of the heat shock...

A new approach for quantifying furanodiene and curzerene: a case study on the essential oils of Eugenia uniflora L., Myrtaceae (pitangueira) leaves

“…The fragments were collected from 40 to 450 u. Identification of oil components was based on the Kovats index, comparison of their mass spectral fragmentation patterns with the Mass Spectra libraries (Wiley 139, 275 and 7 and Nist 127), published data (Weyerstahl et al, 1988;Henriques et al, 1993;Lima et al, 1993;Morais et al, 1996;Maia et al, 1999;Ogunwande et al, 2005;Melo et al, 2007;Costa et al, 2009Costa et al, , 2010Peixoto et al, 2010) and myrrh essential oil injection (Mölleken et al, 1988). The GC-MS quantification was obtained using the total ions chromatogram (TIC) and was expressed as an average of the data obtained for three samples of extracted leaf oil.…”

“…A tea made from the leaves has been used in folk medicine to lower fever and blood pressure and to combat infections (Consolini et al, 1999). There are also reports of strong antibacterial, cytotoxic, molluscicidal, larvicidal and antifungal activities of E. unifl ora L. against pathogenic agents (Lima et al, 1993;Holetz et al, 2002;Souza et al, 2004;Ogunwande et al, 2005;Leite et al, 2009;Costa et al, 2010).…”

“…Excepting this, the minor components present in the sample are well known in essential oils from pitangueira leaves, from South to North Brazil and are also similar to oils from Nigeria. Curzerene is also the principal component in essential oils from pitangueira leaves from Rio de Janeiro (50.2%, Melo et al, 2007), Goiás (42.6%, bright red fruit pitangueira, Costa et al, 2010), Goiás (34.8%, Peixoto et al, 2010) and Nigeria (19.7%, Ogunwande et al, 2005).…”

Influence of seasonality on the yield and composition of the essential oil of Siparuna guianensis Aublet

“…Germacrene D is a hydrocarbon sesquiterpene that has antibacterial activity (Murari et al, 2008) and is studied as a precursor in the biosynthesis of sesquiterpenes (Bulow et al, 2000). The metabolite ɣ-elemene is a sesquiterpene hydrocarbon that has antitumor activity notable for being efficient against several types of cancer (Costa et al, 2010). It has been reported that curzerene (an oxygenated sesquiterpene) has an antiproliferative effect on tumor cells (Costa et al, 2010;Zhong et al, 2011).…”

“…The metabolite ɣ-elemene is a sesquiterpene hydrocarbon that has antitumor activity notable for being efficient against several types of cancer (Costa et al, 2010). It has been reported that curzerene (an oxygenated sesquiterpene) has an antiproliferative effect on tumor cells (Costa et al, 2010;Zhong et al, 2011).…”