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Article • Quím. Nova 49 • 2026 • https://doi.org/10.21577/0100-4042.20260021 linkcopy

Open-access CHEMICAL PROFILE AND ANTIBACTERIAL ACTIVITY OF THE LEAF ESSENTIAL OIL FROM Oxandra martiana (Schltdl.) R.E.Fr.

AuthorshipSCIMAGO INSTITUTIONS RANKINGS

Abstract

Oxandra martiana is an unexplored Annonaceae species with a geographic distribution restricted to southeastern Brazil. The essential oil obtained from the leaves by hydrodistillation yielded 0.32% and was characterized by epizonarene (41.88-48.24%) as the major component, followed by viridiflorene (6.71-7.98%), (Z)-β-ocimene (4.56-7.05%), and δ-cadinene (4.91 5.43%). The antibacterial activity of the essential oil was evaluated against clinically relevant Gram-positive and Gram-negative strains. The minimum inhibitory concentration (MIC) assays revealed that the oil inhibited the growth of Staphylococcus aureus and Staphylococcus epidermidis at 2 mg mL-1, while no inhibitory effect was observed against Escherichia coli (> 2 mg mL-1). Minimum bactericidal concentration (MBC) analysis indicated a bactericidal effect exclusively against S. aureus (2 mg mL-1). These findings suggest a selective antibacterial potential of O. martiana essential oil, particularly against Gram-positive bacteria, due to differences in cell wall structure and permeability. This study provides the first chemical and antibacterial report of O. martiana leaf essential oil, highlighting its selective activity against Gram-positive bacteria. Further studies are needed to explore the phytochemical diversity of the genus Oxandra and to assess its potential for pharmaceutical and biotechnological applications.

Keywords:
Annonaceae; epizonarene; Staphylococcus; E; coli; cadinene.

INTRODUCTION

The control of pathogenic bacteria is one of the biggest challenges facing the public health sector. Infections caused by sensitive and multi-resistant bacterial strains pose serious threats to human health, especially in hospital environments.1 In 2019, an estimated 4.96 million deaths worldwide were due to bacterial infections.2 The growing resistance to traditional antimicrobials and the limitation of new molecules on the market are driving the search for more effective and safer therapeutic alternatives.3 In this context, natural products such as essential oils and plant extracts have gained attention for their bioactive compounds with antibacterial potential.4

Plants are sources of natural biomolecules derived from secondary metabolism. These substances are widely described in the literature5 due to their biological properties and potential applications. Essential oils are plant-derived products, generally obtained through distillation processes such as hydrodistillation and steam distillation.6 Several essential oils have been reported with promising bacterial inhibition.7-9 The efficacy of these oils is often associated with the presence of volatile compounds such as monoterpenoids, sesquiterpenoids, and phenylpropanoids.6

The genus Oxandra comprises 27 species, mainly found in Latin America.10 Previous studies11 have described the essential oil of Oxandra sessiliflora with the predominance of germacrene D and bicyclogermacrene in the essential oil of leaves, with cytotoxicity in murine and human cell lines, being more effective against leukemia (HL-60). Another study12 with isolated sesquiterpenes 4β,10α-dihydroxy-guai-6-ene and 4β,6β,7β,10α-tetrahydroxy-guaiane from O. sessilifora showed trypanocide effects in trypomastigotes of T. cruzi.

Oxandra martiana (Schltdl.) R.E.Fr. (Annonaceae, synonyms: Guatteria martiana Schltdl., and Oxandra reinhardtiana) is an unexplored native and endemic plant species from the Brazilian Atlantic Forest, with occurrence in the Southeast region (Rio de Janeiro, Minas Gerais, and Espírito Santo states). Popularly known as “Imbiú-preto”, “pindaíba” or “pindaíba-de-poste”, the plant has been described as a tree or shrub (6-30 m height).13 To the best of our knowledge, there are no reports on the chemical or biological potential of the species. Therefore, the aim of this study was to extract, characterize, and evaluate the inhibitory potential of the essential oil from the fresh leaves of O. martiana against Gram-positive and Gram-negative strains of medical interest for the first time in the literature.

EXPERIMENTAL

Plant material

The leaves of Oxandra martiana were collected at Parque da Niteroi Municipal Natural Park (coordinates: 22°56’44.0” S, 43°6’1.0” W), Rio de Janeiro, Brazil. The plant was identified by the botanist Dr. Adriana Quintella Lobão, and a voucher specimen was deposited at the Federal Fluminense University (UFF) herbarium under registration code NIT12697. Access to plant genetic resources was registered in the Brazilian Heritage Registry System (SisGen), under registration code A01BF82 and ICMBio 84009.

Essential oil extraction

The essential oil from the Oxandra martiana was obtained by crushing the fresh leaves (± 250 g) in a blender (model SPL-052, Spolu-benesse, Itajobi, SP, Brazil) with 3 L of distilled water, then transferred to a 5 L round-bottom flask and subjected to hydrodistillation in a Clevenger apparatus for 3 h. After that the essential oil was then treated with anhydrous sodium sulfate (Na2SO4, ≥ 99%, Sigma-Aldrich, St. Louis, MO, USA), filtered, transferred to a 5 mL amber borosilicate screw-top flask with polypropylene plastic caps, and stored at -20 °C. The essential oil extraction was performed in triplicate. The yield (%, w/w) was obtained by the following equation: oil mass/leaf mass × 100.

Essential oil characterization

The gas chromatography (GC) analysis was performed using a GC-MS QP2010 (Shimadzu, Kyoto, Japan) coupled with a mass spectrometer, and relative composition was achieved with a GC-2014 (Shimadzu, Kyoto, Japan) gas chromatograph equipped with a flame ionization detector (FID). The essential oil (1 µL) diluted (1000 ppm) in dichloromethane (≥ 99.9%, Sigma-Aldrich, St. Louis, MO, USA) was injected at 260 °C with a 1:20 split ratio and helium with a 1 mL min-1 flow rate as carrier gas. The column (Restek Corporation, Bellefonte, PA, USA) was RTX-5MS (id. 0.25 mm, 30 m length, 0.25 µm film thickness). The initial oven temperature was 60 °C with a 3 °C min-1 increase until 290 °C. The mass spectrometry (MS) was operated at 70 eV electron ionization with 1 scan s-1 at scan range of 40 to 400 m/z. GC-FID chromatographic conditions were similar to the MS, except for the injection in an RTX 5 column (id. 0.25 mm, 30 m length, 0.25 µm film thickness) and 290 °C FID temperature. The arithmetic index (AI) was calculated by interpolating saturated n-alkanes standard (C7-C40, Sigma-Aldrich, St. Louis, MO, USA) retention times analyzed under the same spectrometric and chromatographic conditions previously described. The constituents were identified by comparing their AI and mass spectra with those reported in the National Institute of Standards and Technology (NIST) and specific literature.14 The relative abundance of the constituents was obtained using the FID peak normalization method.

Bacterial strains

Strains were obtained from the Laboratory of Molecular Epidemiology and Biotechnology (LEMB) from the Federal Fluminense University (UFF), Brazil. The bacterial strains Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228, and Escherichia coli ATCC 25922 were stored in brain heart infusion (BHI) broth with 10% glycerol at -80 °C.

Minimum inhibitory concentration

Strains were cultured in tryptic soy agar (TSA) plates, and colonies were transferred to a 0.9% NaCl solution and adjusted to a 0.5 McFarland standard. Essential oils previously solubilized in 1% DMSO (dimethyl sulfoxide) were applied in 96-well plates with BHI broth and subjected to two-fold serial dilution to obtain concentrations ranging from 2.0 to 0.25 mg mL-1 with the final addition of the inoculum according to a 0.5 McFarland scale. The positive controls were vancomycin for Gram-positive bacteria and ciprofloxacin for Gram-negative bacteria, both diluted in 1% DMSO. Negative controls were 1% of DMSO and BHI to evaluate growth and sterility conditions. Plates were incubated for 24 h at 37 °C. The final volume per well was 200 µL, using a bacterial inoculum adjusted to 0.5 McFarland standard (≈1 × 108 CFU mL-1). After incubation, a 10 µL aliquot was removed from each well for minimum bactericidal concentration (MBC) determination. Subsequently, resazurin was added to the same microplates and incubated for 1 h at 37 °C in the dark. The minimum inhibitory concentration (MIC) was defined as the lowest concentration at which the well remained blue, indicating absence of metabolic activity. All tests were performed in triplicate adapted of the standard broth microdilution method from the CLSI M07-A10.15 Although Mueller-Hinton broth is recommended by CLSI for standard MIC assays, BHI was used due to its higher nutritional content, which ensures consistent bacterial growth and reliable resazurin-based viability assessment.16

Minimum bactericidal concentration

After MIC incubation, aliquots of 10 µL from the wells were plated onto TSA plates divided into fields corresponding to each concentration of the microdilution, including a positive control, followed by incubation for 24 h at 37 °C. The MBC was defined as the lowest concentration showing no visible bacterial growth on the agar surface, corresponding to a ≥ 99.9% reduction in viable cells compared to the initial inoculum. All assays were performed in independent replicates in triplicate to ensure reproducibility.

RESULTS AND DISCUSSION

The hydrodistillation of fresh leaves of O. martiana yielded 0.346% (EO1), 0.313% (EO2), and 0.298% (EO3) of essential oil in each extraction replicate. The mean yield was 0.32 ± 0.024% (Table 1). The yield of essential oil from leaves of other plant species in the Oxandra genus has already been reported.17 The O. sessiliflora oil was reported to have a 0.20-0.28% yield, and is therefore consistent with the yields observed in the present study (0.32%).11 In contrast, the O. lanceolata essential oil showed 0.70%.18 In addition to the intrinsic metabolic differences between plant species, it is important to note the influence of several factors on the yield of essential oils. These include seasonality, collection time, experimental extraction methodologies, and conditions.19 The collective effect of these factors may result in variation in the yield of the essential oils.

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Table 1
Mass weight, essential oil, and respective yields of Oxandra martiana leaves

The chemical characterization of the essential oil from O. martiana allowed the identification of 36 components representing 94-95% of the oils. The chromatogram is presented in Figure 1. The oil was primarily composed of hydrocarbon terpenoids, with non-oxygenated sesquiterpenes as the major fraction in the oil, representing 78.99 to 85.21%, followed by non-oxygenated monoterpenes (8.02 to 12.26%) (Table 2). The major compounds identified were epizonarene (44.44 ± 3.36%), viridiflorene (7.47 ± 0.67%), (Z) β ocimene (6.12 1.36%), δ-cadinene (5.09 ± 0.29%), and β-bisabolene (4.48 ± 0.30%) (Figure 2).

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Table 2
Chemical characterization of the Oxandra martiana essential oil replicates by gas chromatography-mass spectrometry

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Figure 1
Total ion chromatogram of the three replicates of the essential oil (EO) extracted from Oxandra martiana fresh leaves

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Figure 2
Major components of the Oxandra martiana essential oil obtained from fresh leaves: epizonarene (41.88-48.24%), viridiflorene (6.71-7.98%), (Z) β ocimene (4.56-7.05%), δ-cadinene (4.91-5.43%), and β-bisabolene (4.16-4.74%)

Although the chemical profile of the O. martiana essential oil has not been reported in the literature, the essential oil from leaves of Oxandra sessiliflora was described with germacrene D (31.29%), bicyclogermacrene (18.91%), δ-elemene (10.59%), β-phellandrene (10.08%), spathulenol (9.82%), β-caryophyllene (9.81%), and limonene (9.17%) as the major components of the oil at different collection periods.11 Furthermore, the essential oil obtained by hydrodistillation from the leaves of Oxandra lanceolata showed 90 compounds, with the prominence of spathulenol (13.9%), α pinene (7.7%), limonene (6.6%), and β-pinene (5.6%).18 The monoterpenes and sesquiterpenes α-pinene, β-pinene, limonene, β-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, caryophyllene oxide, and β-elemene are listed as the major components of essential oils from plants of the Annonaceae family occurring in Brazil.20 This corroborates the presence of δ-elemene, spathulenol, αand β-pinene, and β-caryophyllene as minor components in the essential oil of the present study (Table 2).

The essential oil from O. martiana leaves demonstrated inhibitory activity at 2 mg mL-1 against the Gram-positive strains S. aureus and S. epidermidis. However, the MBC was only observed against S. aureus (2 mg mL-1). The oil did not inhibit the Gram-negative strain E. coli at the same concentration (> 2 mg mL-1). The positive controls vancomycin and ciprofloxacin showed MIC of 2 µg mL-1 in S. aureus and S. epidermidis, and 0.25 µg mL-1 against E. coli, respectively. The negative controls (1% DMSO and BHI) showed no effect in the bacterial growth. The inhibition and bactericidal effect of the essential oil replicates are shown in Table 3.

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Table 3
Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of Oxandra martiana essential oil (EO) from fresh leaves in Staphylococcus aureus, Staphylococcus epidermidis, and Escherichia coli

According to the literature, the antibacterial activity of essential oils is often discussed in association with their major constituents.8 The essential oil of Oxandra martiana was found to contain a high concentration of cadinane-type sesquiterpenoids. The distinguishing characteristic of these sesquiterpenoids is the presence of a 6/6-bicyclic skeleton. The presence of methyl groups is indicated, with attachment to carbons C-3 and C-9, along with an isopropyl moiety attached to carbon C-6.21

The O. martiana oil exhibited the presence of trans-muurola-3,5-diene, trans-cadina-1(6),4-diene, γ-muurolene, epizonarene, γ-cadinene, δ-cadinene, α-muurolol, β-calacorene, and trans-cadina-1,4-diene, constituting a predominant fraction of the oil EO1, EO2, and EO3 (54.01, 55.28, and 61.06%, respectively). According to the literature,22 the MIC of δ-cadinene against Streptococcus pneumoniae (InDRE 24-CCpn-02 and InDRE 49619) oxacillin-resistant has been reported as 31.25 µg mL-1. In contrast, the cadinane sesquiterpene polygosumic acid obtained from Polygonum viscosum has been reported23 with inhibition of 0.05 0.5 mg mL-1 against several bacteria of medical interest, with the activity being more representative in E. coli penicillin-resistant (NCIMB 4174), and S. aureus (NCTC 10788).

Essential oils rich in aromadendrane-type sesquiterpenes, such as aromadendrene, allo-aromadendrene, viridiflorene, spathulenol, guaiol, globulol, and α-gurjunene, which accounted for 13.83, 14.69, and 13.27% (EO1, EO2, and EO3, respectively) of the essential oils from the present study, have been described in the literature24 with antibacterial properties. The aromadendrane-4α,10α-diol showed inhibition against S. aureus at 300 µg disk-1.25 Whereas the sesquiterpene β-bisabolene has been previously reported26 to exhibit moderate antibacterial properties, with an EC50 (half maximal effective concentration) ranging from 0.089 to 1.03 mM, against S. aureus and Micrococcus luteus. However, the bioactivity was reduced over 36 h. In addition, there was no inhibition in the Gram negative strain E. coli.26 Another study performed by Nascimento et al.27 described inhibition of 8 to 40 µg mL-1 for S. aureus with a synergistic effect with ampicillin.

Only a few studies have reported in the literature the antimicrobial potential of plant derivatives from the Oxandra genus. Contreras Martinez et al.28 described the antifungal effect of the isolated monoterpene isoespintanol obtained from the petroleum benzine extract of Oxandra xylopioides leaves against several bacterial strains, including S. aureus, E. coli, and P. aeruginosa, among others. The MIC for these strains ranges from 649.3 to 916 µg mL-1, with S. epidermidis being the most susceptible strain.

The essential oil from leaves of different Annonaceae species has shown antibacterial properties. Bocageopsis multiflora (spathulenol 20.3%), Ephedranthus amazonicus (spathulenol 16.9%), Guatteria blepharophylla (caryophyllene oxide 55.7%), and Xylopia aromatica (spathulenol 21.5%) showed MIC values of 0.02-2.50 mg mL-1 against the Gram-positive strains S. aureus, Enterococcus faecalis, Streptococcus sanguinis, while it was observed 1.5 to 3.0 mg mL-1 of inhibition against the Gram-negative strains E. coli, Pseudomonas aeruginosa, and Salmonella enterica.29 The essential oil from the aerial parts of Bocageopsis multiflora, Duguetia quitarensis, Fusaea longifolia, and Guatteria punctata has shown MICs of 4.68 to 37.5 µg mL-1, and was therefore partially consistent with the findings of the present study.30

The antibacterial potential of essential oils can vary significantly depending on multiple factors. Key considerations include the intrinsic activity of individual constituents, their relative concentrations within the oil, and the potential for synergistic or antagonistic interactions among the compounds and their specific biological targets. It is evident that structural relationships, including but not limited to water solubility, polarity, dissociation constant, chemical stability, molecular size, and functional groups, can exert influence upon bacterial inhibition.31 Consequently, it is challenging to ascertain the effect of an essential oil or to compare it with data reported in the literature, due to the chemical variability that may be associated with intrinsic or extrinsic factors of the plant metabolism. Altogether, different methodologies, diluents, and growth conditions may contribute to MIC fluctuation.32 However, the evaluation of isolated monoterpenoids, sesquiterpenoids, or phenylpropanoids does allow a glimpse into their potential against specific targets. However, it is important to say that the structure-activity relationship is typically related to the major component of the essential oil.33,34

Gram-positive bacteria are theorized to be more susceptible to essential oils than Gram-negative strains, primarily due to structural differences in their cell membranes.7 The outer membrane of Gram-negative bacteria contains lipopolysaccharides (LPS), which confer increased rigidity and act as a barrier that limits the diffusion of lipophilic compounds, such as monoterpenoids and sesquiterpenoids.31 A phenomenon observed in the present study, as O. martiana essential oil did not inhibit E. coli at the concentrations tested.

A common hypothesis is that the essential oil compounds interact with the Gram-positive membrane surface, leading to perturbations in its structural organization.8 As their concentration increases, these compounds may accumulate within the lipid bilayer, resulting in enhanced membrane permeability and, ultimately, disruption of membrane integrity and cell lysis.7,33 However, the pharmacological effects of essential oils may be mediated by multiple mechanisms, including enzyme inhibition, disruption of the cell wall, leakage of cytoplasmic contents, and cytoplasmic coagulation, among other potential modes of action.33

CONCLUSIONS

This study presents the first report on the chemical composition of O. martiana, and identifies epizonarene as the predominant sesquiterpene hydrocarbon in the essential oil from the leaves. Other constituents included viridiflorene, (Z)-β-ocimene, β-bisabolene, and δ-cadinene. Although the essential oil exhibited only moderate antibacterial activity, the novelty of the species and the lack of previous studies underscore the relevance of these findings. This work lays the groundwork for future studies to explore the chemical and biological potential of the Oxandra genus.

ACKNOWLEDGMENTS

The authors are grateful to the CNPq for the financial support. We would also like to thank the CAPES (financial code 001) and FAPERJ for their support in financing the projects E-26/200.161/2025, E-26/200.162/2025 (304867), E-26/210.740/2024, E-26/204.545/2024 E-26/210.598/2023 (285944), and E-26/200.915/2022 (268191).

DATA AVAILABILITY STATEMENT

All data are available in the text.

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Edited by

  • Executive Editor handled this article:
    Rodrigo O. M. A. de Souza

Publication Dates

  • Publication in this collection
    09 Mar 2026
  • Date of issue
    2026

History

  • Received
    14 Sept 2025
  • Accepted
    08 Jan 2026
  • Published
    23 Jan 2026
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