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Chemical characterization and biological evaluation of the essential oils from leaves of Eugenia
tapacumensis (O Berg) and E. diplocampta (Diels)
Sidney gomes azevedo
1,1
, Marcos B. Machado
1
, Raimundo Carlos Pereira Junior
1,2
, Elenn S. P. Aranha
1
, Ingrid Reis da
Silva
2
, Marne C. Vasconcellos
1
, Emerson S. Lima
1
, Rudi E. L. Procpio
2
1
UFAM - Universidade Federal do Amazonas (69077-000, Manaus/AM, Brazil),
2
CBA - Centro de Biotecnologia da
Amaznia (69075-351, Manaus/AM, Brazil)
sidneyazevedo1@gmail.com
Abstract
Eugenia has over 500 species distributed mainly in the neotropical region. In Brazil, Eugenia spp. mostly occur in the Mata
Atlntica, Floresta de Restinga, and Amaznia. In the Reserva Florestal Adolpho Ducke (RFAD) in Manaus/AM, were
identified 28 species of Eugenia. Chemical studies with Eugenia have shown a composition rich in flavonoids/glycosides,
hydrolysable tannins, coumarins, anthocyanins, monoterpenes/sesquiterpenes, and triterpenes/steroids. Biological studies
involving essential oils of Eugenia spp. have been confirmed several biological activities (antibacterial, antifungal, antitumor,
and antioxidant). However, chemical and biological studies of Eugenia spp. from the Amazon biome are still rare. In this
context, the goals of the present study were to investigate the chemical composition of the essential oils from the leaves of
Eugenia tapacumensis (O Berg.) (ET) and ,E. diplocampta (Diels) (ED), and to evaluate the bacterial and cytotoxic activities
of these species. Branches of an individual of ET and two individuals of ED were collected in the RFAD in 2012/2013, were
identified and dried at room temperature. The essential oils of leaves were obtained by hydrodistillation, dried, weighed, and
analyzed by GC-FID/GC-MS. The chemical composition was obtained comparing the chromatographic retention indices and
the mass spectra obtained with those described in the literature. The yield of the derived essential oils ranged from 0.36% up
to 0.93% (% w/w). The analysis by GC-FID and GC-MS have lead to the identification of 55 constituents. The major
components identified in the essential oil of ET, ED1-1, ED2-1, and ED2-2 were, respectively, caryophyllene oxide
(34.2/25.8/22.3/23.0%), E-caryophyllene (0.0/9.1/11.2/8.6 %), -copaene (8.9/8.5/10.7/10.3%), spathulenol
(0.0/5.6/2.7/2.5%), -bisabolene (8.7/0.0/0.0/0.0%), epoxide humulene II (2.61 / 2.1/2.2/2.6%), E-verbenol (2.3/0.0/0.0/0.0%),
-elemene (0.0/3.2/0.0/0.0%), -cubebene (0.0/3.1/8.5/7.6%), E-calamenene (0.0/0.0/5.6/6.2%), -humulene
(0.0/0.0/2.3/0.0%), and ledol (0.0/0.0/0.0/2,1%). The PCA of the relative intensities of the mass spectra from the 55
constituents identified in species/specimens selected have showed segregation by species (PC1, 80%) and specimen (PC2,
15%). A detailed analyze of the loadings map (PC1vsPC2) have demonstrated E-vebenol and -bisabolene as chemical
characteristic for ET, and E-caryophyllene, spathulenol, and -cubenene for ED. The HCA have showed a distinct separation
in two groups (species) and two sub-groups (individuals and collection period). ED1-1 and ED2-1/2 have -elemene and E-
calamenene as characteristic in the chemical composition, and have been distinguished by the presence of -humulene and
ledol, respectively. The essential oils were tested to evaluate their bioactivities by the diffusion method in agar disk
containing microorganisms Gram-positive and Gram-negative resistant to methicillin. Essentials oils have showed moderate
to high antimicrobial activity for both Gram-positive (Staphylococcus aureus, Streptococcus pneumonia, and Enterococcus
faecalis) and Gram-negative (Escherichia coli, Klebsiella pneumoniae, and Burkholderia cepacia). The essential oil of ET
(source of E-verbenol and -bisabolene) have significant bacterial activity against microorganisms S. aureus, S.
peneumoniae, E. faecalis, B. cepacia, K. pneumoniae, and E. coli. The essential oil of ED-1 (source of -elemene) has
shown moderate activity only against E. faecalis. The essential oils of ED2-1 (wet season) and ED2-2 (dry season) (absent
of -elemene and source to E-calamenene) has shown high activity in almost all organisms, except to E. faecalis, which has
exposed moderate activity. In addition, this work have been evaluated the susceptibility of three tumor cell lines [MCF-7
(human breast), HCT-116 (human colon), and SKMEL-19 (human melanoma)] and a normal cell line [MRC-5 (human
fibroblast)] against the essential oils of ET and ED using the test Alamar-blue. The essential oils of ET e ED2-1/2 have
demonstrated a cytotoxic activity against normal cells (MRC-5) with IC50 values ranged from 33.21 up to 38.38 g.mL-1. All
samples have exhibited cytotoxic activity against tumor cell lines MCF-7 (IC50: from 20.81 up to 35.90) and HCT-116 (IC50:
from 23.63 up to 32.63 g.mL-1). All samples have shown IC50 above to 50 g.mL-1 to SKMEL-19 cell line. Finally,
essential oils of ET and ED have common constituent (caryophyllene oxide, -copaene, and epoxide humulene II) and
distinct (-bisabolene, -elemene, -humulene, and ledol) in its composition, as well as have a significant microbial and
cytotoxic activities.
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Keywords: Eugenia, essential oil, GC-MS