MDGC-MS analysis of essential oils from Protium heptaphyllum (Aubl.) and their antifungal activity against Candida specie

Protium heptaphyllum is found in the Amazon region, and in various Brazilian states and South American countries. Also Known as almecega, it produces an oil resin used in traditional medicine as analgesic, anti-inflammatory, cicatrizant and expectorant, it is rich in pentacyclic triterpenes and essential oil. The main objective of this study was to analyze the chemical composition of P. heptaphyllumresin (OEPh) over different extraction times and to evaluate their antifungal activity against Candida species, obtained from gardeners with onychomycosis, using the disk diffusion method. The OEPh was obtained by hydrodistillation and analyzed by Multidimensional Gas Chromatography coupled with Mass Spectrometry (MDGC / MS). Candida species were obtained from lesions on the nails of horticulturist from a community garden in the city of Teresina, Piaui, Brazil. The antifungal activity in concentrations of 1000 µg/L, 500 µg/L and 250 µg/L, PROTOCOL M44-A2 (CLSI 2009) OEPh was tested. The main constituents identified were: l-limonene, α-terpineol, p-cineol, o-cymene and α-phellandrene, however, its composition varies significantly with extraction time. All species, except C. rugosa, were inhibited with halo (≥ 14 mm) at 1000 μg / L. C. krusei is naturally resistant to the drug fluconazole, but when tested with OEPh the clinical species (case 9) demonstrated sensitivity in three dilutions (halo ≤ 10 ≥ 14) and the standard strain was inhibited at concentration of 1000 μg/Lg / L (halo 14mm). A similar situation also occurred with the standard strain of C. parapsilosis (halo ≥ 11mm). OEPh has considerable antifungal activity, which merits further investigation for alternative clinical applications, since this species is widely distributed in our community, and it presents good yields, and also has important therapeutic applications.

[1]  L. Ming,et al.  Efeitos de diferentes tempos de extração no teor e composição química do óleo essencial de folhas de pariparoba [Pothomorphe umbellata (L.) Miq.] , 2015 .

[2]  J. Mello,et al.  Atividade antifúngica do óleo essencial de Origanum vulgare frente a Malassezia pachydermatis , 2014 .

[3]  A. Taher Onychomycosis and Its Treatment , 2013 .

[4]  S. Dinçer,et al.  Research on antifungal and inhibitory effects of DL-limonene on some yeasts , 2012 .

[5]  M. Freire,et al.  Antimicrobial effect of linalool and α-terpineol against periodontopathic and cariogenic bacteria. , 2012, Anaerobe.

[6]  L. Almeida,et al.  ATIVIDADE ANTIFÚNGICA DE EXTRATOS VEGETAIS BRASILEIROS SOBRE CEPAS DE CANDIDA , 2012 .

[7]  L. Almeida,et al.  Atividade Antifúngica de Extratos Vegetais Brasileiros sobre Cepas de Candida Antifungal Activity of Brazilian Plant Extracts Against Candida Strains , 2012 .

[8]  M. Zotti,et al.  Onychomycosis: first case due to Aspergillus nomius. , 2011, Acta dermato-venereologica.

[9]  L. Almeida,et al.  SCREENING DA ATIVIDADE ANTIFÚNGICA DE ÓLEOS ESSENCIAIS SOBRE CANDIDA ALBICANS , 2010 .

[10]  Gregory M. Peterson,et al.  Toenail onychomycosis: an important global disease burden , 2010, Journal of clinical pharmacy and therapeutics.

[11]  Saadia Bashir Hassan,et al.  Alpha terpineol: a potential anticancer agent which acts through suppressing NF-kappaB signalling. , 2010, Anticancer research.

[12]  R. Sartori,et al.  Chemical composition of the essential oils from two subspecies of Protium heptaphyllum , 2010 .

[13]  J. G. M. Costa,et al.  Composição química e toxicidade de óleos essenciais de espécies de Piper frente a larvas de Aedes aegypti L. (Diptera: Culicidae) , 2010 .

[14]  P. M. Imamura,et al.  Preparação do (+)-±-terpineol a partir do (+)-limoneno: monoterpenos de odor agradável em um projeto para química orgânica experimental , 2009 .

[15]  S. H. Alves,et al.  In vitro activity of essential oils extracted from plants used as spices against fluconazole-resistant and fluconazole-susceptible Candida spp. , 2008, Canadian journal of microbiology.

[16]  V. Bolzani,et al.  Comparative study of disk diffusion and microdilution methods for evaluation of antifungal activity of natural compounds against medical yeasts Candida spp and Cryptococcus sp , 2007 .

[17]  P. Schieberle,et al.  Characterization of alpha-terpineol as an anti-inflammatory component of orange juice by in vitro studies using oral buccal cells. , 2007, Journal of agricultural and food chemistry.

[18]  A. Cakir,et al.  Screening of Antibacterial Activities of Twenty-One Oxygenated Monoterpenes , 2007, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[19]  Â. R. Antoniolli,et al.  Atividade antimicrobiana dos óleos essenciais: uma abordagem multifatorial dos métodos , 2007 .

[20]  A. Naglot,et al.  Anticandidial activity of some essential oils of a mega biodiversity hotspot in India , 2007, Mycoses.

[21]  J. F. Packer,et al.  Método para avaliação e pesquisa da atividade antimicrobiana de produtos de origem natural , 2007 .

[22]  J. V. Oliveira,et al.  Chemical composition and acaricidal activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl.) Marchand (Burseraceae) , 2007 .

[23]  V. F. V. Júnior,et al.  The Chemistry and Pharmacology of the South America genus Protium Burm. f. (Burseraceae) , 2007 .

[24]  Tolu Odugbemi,et al.  Evaluation of the antimicrobial properties of different parts of Citrus aurantifolia (lime fruit) as used locally. , 2007, African journal of traditional, complementary, and alternative medicines : AJTCAM.

[25]  Y. Yuasa,et al.  A Practical Synthesis of d-α-Terpineol via Markovnikov Addition of d-Limonene Using Trifluoroacetic Acid , 2006 .

[26]  R. Fenner,et al.  Plantas utilizadas na medicina popular brasileira com potencial atividade antifúngica , 2006 .

[27]  E. Lima,et al.  Atividade antifúngica de óleos essenciais sobre espécies de Candida , 2006 .

[28]  M. Chaves,et al.  Protective effect of α- and β-amyrin, a triterpene mixture from Protium heptaphyllum (Aubl.) March. trunk wood resin, against acetaminophen-induced liver injury in mice , 2005 .

[29]  Adrian C. Williams,et al.  Terpenes and the Lipid–Protein–Partitioning Theory of Skin Penetration Enhancement , 2004, Pharmaceutical Research.

[30]  M. Couladis,et al.  Composition and antifungal activity on soil-borne pathogens of the essential oil of Salvia sclarea from Greece. , 2002, Journal of agricultural and food chemistry.

[31]  T. Riley,et al.  In vitro activity of Melaleuca alternifolia (tea tree) oil against dermatophytes and other filamentous fungi. , 2002, The Journal of antimicrobial chemotherapy.

[32]  O. R. Gautun,et al.  Triterpenes from the resin of Boswellia neglecta , 2002 .

[33]  A. Siani,et al.  Triterpenes from the resin of Protium heptaphyllum. , 2001, Fitoterapia.

[34]  P. Bandeira,et al.  Essential Oil Composition of Leaves, Fruits and Resin of Protium heptaphyllum (Aubl.) March. , 2001 .

[35]  K. Khurshid,et al.  Onychomycosis in Lahore, Pakistan , 1999, International journal of dermatology.

[36]  R. Ribeiro‐dos‐Santos,et al.  Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium. , 1999, Journal of ethnopharmacology.

[37]  M. Zoghbi,et al.  Volatile Constituents from Oleoresin of Protium heptaphyllum (Aubl.) March , 1999 .

[38]  J. Maia,et al.  Volatile Constituents from Leaves and Stems of Protium heptaphyllum (Aubl.) March. , 1995 .

[39]  O. F. Gompertz,et al.  Im vitro antifungal activity of essential oils obtained from officinal plants against dermatophytes , 1993, Mycoses.