Abstract Chemical and pharmacological potentials of botanical species found in the Cerrado are well-known and widely studied. Chemical diversity of secondary metabolites produced by plants that belong to this Brazilian biome has triggered several studies in the fields of farming, pharmaceutical and cosmetic industries. Therefore, this study aimed at evaluating the chemical composition of essential oils (EOs) from fresh leaves of three species found in the Brazilian Cerrado: Cardiopetalum calophyllum Schltdl. (EO-CC), Campomanesia adamantium (Cambess.) O. Berg (EO-CA) and Protium ovatum Engl. (EO-PO) and at determining their anti-Malassezia furfur and anti-inflammatory activities. Both GC-FID and GC-MS showed that the most abundant chemical class of the oils was the one of sesquiterpene hydrocarbons. The major constituents identified in EO-CC were germacrene D (34.9%) and bicyclogermacrene (26.8%). EO-CA exhibited mainly germacrene D (21.7%) while EO-PO had high concentrations of germacrene D (25.0%) and γ-muurolene (18.6%). EOs were tested by the broth microdilution method on 96-well microplates and exhibited satisfactory activity against M. furfur, i. e., EO-CA had MIC = 375 µg/mL while EO-CC and EO-PO had MIC = 750 µg/mL. The chemotaxis model, which was used for evaluating their anti-inflammatory activity, showed that EOs exhibited effective results: C. calophyllum (EO-CC; IC50 = 24.4 µg/mL), C. adamantium (EO-CA; IC50 = 15.7 µg/mL) and P. ovatum (EO-PO; IC50 = 32.5 µg/mL). In short, biological activities of EO-CC, EO-CA and EO-PO, such as anti-Malassezia furfur and anti-inflammatory ones, were investigated and described for the first time.

Abstract: Tradescantia pallida (Commelinaceae) has shown promising antibacterial, antioxidant and anticancer activities. This study aimed at extracting hexane from T. pallida (HE-TP) aerial parts to identify and quantify its volatile compounds by GC-MS and GC-FID and at evaluating its antifungal and antiproliferative activities. (E)-4-Methoxycynnamic acid (50.2%), 2,5-di-tert-butyl-1,4-benzoquinone (13.7%) and epijuvabione (10.4%) were the major components identified in HE-TP. HE-TP was incorporated into PDA medium, poured into Petri dishes and transferred to mycelial discs of pathogens. Percentages of inhibition of fungal growth were determined. HE-TP showed remarkable antifungal potential at the dose of 400 µL since it inhibited 100% of Penicillium digitatum and Sclerotinia sclerotiorum growth and 92.6% of Rhizopus stolonifer growth. Besides, HE-TP demonstrated cytotoxic activity against different human tumor cell lines with IC50 values between 231.43 and 428.76 µg/mL. Therefore, results showed that HE-TP has potential against fungi of agronomic interest and tumor cells.

Brazil has the greatest plant diversity in the world. Many species exhibit a wide range of phytochemical compounds which can be exploited in food, agronomic, pharmacological and medicinal plant industries. Therefore, the chemical composition and in vitro bioactivities of volatile oil from Psidium firmum fresh leaves (PfVO) were investigated for the first time. GC-FID and GC-MS analyses revealed 28 compounds in PfVO. The major ones were α-selinene (20.8%), β-caryophyllene (16.5%) and nerolidol (10.4%). Results showed that PfVO affected the growth of Leishmania amazonensis promastigote forms in a dose-dependent manner; its IC50 value was 14.05 µg/mL. PfVO also exhibited antibacterial activity against Salmonella enteritidis, Yersinia enterocolitica, Staphylococcus aureus, Pseudomonas aeruginosa and Listeria monocytogenes; MIC values ranged from 25 μg/mL to 250 μg/mL. Moreover, PfVO promoted normal cell growth inhibition at 61.02 ± 1.97 µg/mL. Antiproliferative activity was observed against human tumor cell lines; IC50 values of MCF-7 cells, HeLa cells and M059J cells were 47.91 µg/mL, 73.78 µg/mL and 41.94 µg/mL, respectively. Results provided strong evidence of the promising potential of PfVO as a nature-based antileishmanial, antibacterial and antiproliferative agent.

Abstract Brazil, the world’s largest citros producer, yields around 19 million tons per year and exports most part of its production as orange juice. Essential oils (EOs) extracted from leaves, fruit and flowers of many species of the genus Citrus have been widely used as the result of their promising bioactivities. The fungus Rhizopus stolonifer (Ehrenb.) Vuill., an agent which causes soft rot in fruit, has been considered one of the main factors that cause postharvest diseases, thus, leading to major economic losses in agribusiness. This research aimed at evaluating the chemical composition and in vitro antifungal effect of EOs from two varieties of fresh Citrus sinensis (lima orange and bahia navel orange) peel on mycelial growth of R. stolonifer. EOs were obtained by hydrodistillation, which was carried out by a Clevenger-type apparatus, while their chemical composition was analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Limonene was the major monoterpene identified in EOs from lima orange (95.2%) and bahia navel orange (93.2%) peel. EOs from lima orange and bahia navel orange inhibited 91.95% and 80.05% mycelial growth of R. stolonifer, respectively, at the highest dose under evaluation (100 µL). This study revealed the biotechnological potential of EOs extracted from fruit peel of two varieties of citros which may applied to biofilm preparation, so as to coat and preserve different types of fruit.

Abstract Propolis is a resinous substance collected and processed by Apis mellifera from parts of plants, buds and exudates. In Minas Gerais (MG) state, Brazil, green propolis is produced from the collection of resinous substance found in shoot apices of Baccharis dracunculifolia. This paper aims to investigate the chemical composition and in vitro antioxidant, anti-Helicobacter pylori, antimycobacterial and antiproliferative activities of essential oil (EO) from Brazilian green propolis (BGP-EO). The oil showed high antibacterial activity against H. pylori (MIC = 6.25 µg/mL), Mycobacterium avium (MIC = 62.5 µg/mL) and M. tuberculosis (MIC = 64 µg/mL). Its antioxidant activity was evaluated in vitro by both DPPH (IC50 = 23.48 µg/mL) and ABTS (IC50 = 32.18 µg/mL) methods. The antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumor cell lines (MCF-7, HeLa and M059J) was analyzed by the XTT assay. BGP-EO showed inhibition of normal cell growth at 68.93 ± 2.56 µg/mL. Antiproliferative activity was observed against human tumor cell lines, whose IC50 values were 56.17, 66.43 and -65.83 µg/mL for MCF-7, HeLa and M059J cells, respectively. Its major constituents, which were determined by GC-FID and GC-MS, were carvacrol (20.7 %), acetophenone (13.5 %), spathulenol (11.0 %), (E)-nerolidol (9.7 %) and β-caryophyllene (6.2 %). These results showed the effectiveness of BGP-EO as a natural product which has promising biological activities.

Abstract Endodontic infections result from oral pathogenic bacteria which reach and infect dental pulp, as well as surrounding tissues, through cracks, unrepaired caries and failed caries restorations. This study aims to determine the chemical composition of essential oil from Psidium cattleianum leaves (PC-EO) and to assess its antibacterial activity against endodontic bacteria. Antibacterial activity of PC-EO was evaluated in terms of its minimum inhibitory concentration (MIC) values by the broth microdilution method on 96-well microplates. Bacteria Porphyromonas gingivalis (MIC = 20 µg/mL), Prevotella nigrescens (MIC = 62.5 µg/mL), Fusobacterium nucleatum (MIC = 12.5 µg/mL), Actinomyces naeslundii (MIC = 50 µg/mL), Bacteroides fragilis (MIC = 12.5 µg/mL), Aggregatibacter actinomycetemcomitans (MIC = 6.25 µg/mL) and Peptostreptococcus anaerobius (MIC = 62.5 µg/mL) were evaluated and compared to chlorhexidine dihydrochloride (CDH), the positive control. PC-EO was obtained by hydrodistillation with the use of a Clevenger-type apparatus whereas its chemical composition was analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Viridiflorol (17.9%), β-caryophyllene (11.8%), 1,8-cineole (10.8%) and β-selinene (8.6%) were the major constituents found in PC-EO, which exhibited high antibacterial activity against all endodontic pathogens under investigation. Therefore, PC-EO, a promising source of bioactive compounds, may provide therapeutic solutions for the field of endodontics.

This study aims to investigate chemical composition of essential oils from Murraya paniculata (L.) Jack (Rutaceae) ripe and unripe fruits and determine their in vitro antibacterial activity. Essential oils were extracted by hydrodistillation from Murraya paniculata (L.) Jack ripe and unripe fruits collected in the Cerrado, in Rio Verde, southwestern Goiás, Brazil. They were analyzed by gas chromatography with flame ionization detector (GC-FID) and by gas chromatography-mass spectrometry (GC-MS). Sesquiterpenes, which represent the most abundant class of compounds in oils, predominated in both ripe and unripe fruits. Major constituents of essential oils extracted from ripe fruits (RF-EO) were (-caryophyllene (21.3%), (-ylangene (13.3%), germacrene-D (10.9%) and (-zingiberene (9.7%) whereas the ones of unripe fruits (UF-EO) were sesquithujene (25.0%), (-zingiberene (18.2%), germacrene-D (13.1%) and (-copaene (12.7%). In vitro antibacterial activity of essential oils was evaluated in terms of its minimum inhibitory concentration (MIC) values by the broth microdilution method in 96-well microplates. Both essential oils under investigation showed moderate anti-streptococcal activity against the following bacteria: Streptococcus mutans, S. mitis, S. sanguinis, S. sobrinus and S. salivarius. MIC values ranged between 100 and 400 µg/mL. Regarding the antimycobacterial activity, essential oils from M. paniculata (L.) Jack unripe and ripe fruits were active against Mycobacterium kansasii (MIC = 250 µg/mL), moderately active against M. tuberculosis (MIC = 500 µg/mL) and inactive against M. avium (MIC = 2000 µg/mL). This study was pioneer in revealing similar chemical profiles of both essential oils extracted from Murraya paniculata (L.) Jack unripe and ripe fruits, besides describing their in vitro anti-streptococcal and antimycobacterial activities.

ABSTRACT Propolis, is a bee product collected from exudates and flower buds of several plants, has strong aroma and several biological applications. This study aimed at evaluating the chemical composition and in vitro antioxidant, antibacterial and cytotoxic properties of volatile oil from Brazilian brown propolis. It was extracted by hydrodistillation and analyzed by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. Volatile oil from brown propolis exhibited strong antibacterial activity against H. pylori (MIC 3.25 µg/ml), Mycobacterium tuberculosis (MIC 50 µg/ml) and M. avium (MIC 62.5 µg/ml). It was evaluated in vitro for antioxidant activity by DPPH (IC50 25.0 µg/ml) and ABTS (IC50 30.1 µg/ml) methods. Its cytotoxic property was evaluated in normal (human fibroblasts, GM07429A) and tumor (MCF-7-human breast adenocarcinoma; HeLa-human cervical adenocarcinoma and M059J-human glioblastoma) cell lines. IC50 values were 81.32 µg/ml for GM07429A and 85.00, 129.40 and 84.12 µg/ml for MCF-7, HeLa and M059J cells, respectively. Three major dereplicated components of volatile oil from brown propolis were acetophenone (15.2%), nerolidol (13.3%), and spathulenol (11.6%). Our results contribute to a better understanding of the chemical and biological properties of Brazilian brown propolis and provide evidence for its potential medicinal use.

ABSTRACT Besides their value as therapeutic resources, medicinal plants may also be used as sources of active ingredients against phytopathogens. Fungi can grow and cause spoilage in food, thus, resusting in decrease in its quality and quantity. This research aimed at evaluating the effect of essential oil from Murraya paniculata (ML-EO) leaves on mycelial growth of Sclerotinia sclerotiorum, a fungus that poses high risk to several cultures, mainly soybean. Essential oil from M. paniculata (Rutaceae) leaves was obtained by hydrodistillation which was carried out by a Clevenger-type apparatus while its chemical composition was analyzed by GC-FID and GC-MS. β-Caryophyllene (23.8%), α-zingiberene (21.0%) and β-cubebene (10.2%) were the main constituents found in ML-EO leaves. In vitro antifungal activity showed that ML-EO, at a 300 µL dose, inhibited 91.2% of mycelial growth of Sclerotinia sclerotiorum . This is the first report of the antifungal activity of ML-EO against S. sclerotiorum and results suggest that the essential oil under evaluation has good potential to control this phytopathogenic fungus.

ABSTRACT Leishmaniasis is a disease that affects millions of people and it is an important public health problem. The drugs currently used for the treatment of leishmaniasis present undesirable side effects and low efficacy. In this study, we evaluated the in vitro activity of Melampodium divaricatum (MD-EO) and Casearia sylvestris (CS-EO) essential oils (EO) against promastigote and amastigote forms of Leishmania amazonensis. Sesquiterpenes E-caryophyllene (56.0%), germacrene D (12.7%) and bicyclogermacrene (9.2%) were identified as the main components of MD-EO, whereas E-caryophyllene (22.2%), germacrene D (19.6%) and bicyclogermacrene (12.2%) were the main constituents of CS-EO. CS-EO and E-caryophyllene were active against promastigote forms of L. amazonensis (IC50 24.2, 29.8 and 49.9 µg/mL, respectively). However, MD-EO, CS-EO and E-caryophyllene were more active against amastigote forms, with IC50 values of 10.7, 14.0, and 10.7 µg/mL, respectively. E-caryophyllene presented lower cytotoxicity against macrophages J774-A1 (CC50 of 62.1 µg/mL) than the EO. The EOs and E-caryophyllene should be further studied for the development of new antileishmanial drugs.

In Brazilian folk medicine, Tetradenia riparia (Hochst.) Codd. (Lamiaceae) is used to treat toothaches and dental abscesses and diseases induced by worms, bacteria, or fungi. This paper aims to investigate the chemical composition and the antibacterial effects of the essential oil obtained from Tetradenia riparia leaves (TR-EO) grown in Southeastern Brazil against a representative panel of oral pathogens. We evaluated the antibacterial activity of TR-EO in terms of the minimal inhibitory concentration (MIC). We identified aromadendrene oxide (14.0%), (E,E)-farnesol (13.6%), dronabinol (12.5%), and fenchone (6.2%) as the major constituents of TR-EO. TR-EO displayed MIC values between 31.2 and 500 μg/mL, with the lowest MIC value being obtained against Streptococcus mitis (31.2 μg/mL), S. mutans (62.5 μg/mL), S. sobrinus (31.2 μg/mL), and Lactobacillus casei (62.5 μg/mL). In time-kill experiments, TR-EO demonstrated bactericidal activity against S. mutans within the first 12 h, resulting in a curve profile similar to that of chlorhexidine. These results revealed that the essential oil of Tetradenia riparia displays promising activity against most of the selected cariogenic bacteria, including Streptococcus mutans.

Abstract This study evaluated the cytotoxicity activity of the essential oils of Tagetes erecta L., Asteraceae (TE-OE), Tetradenia riparia (Hochst.) Codd, Lamiaceae (TR-OE), Bidens sulphurea (Cav.) Sch. Bip., Asteraceae (BS-OE), and Foeniculum vulgare Mill., Apiaceae (FV-OE), traditionally used in folk medicine, against the tumor cell lines murine melanoma (B16F10), human colon carcinoma (HT29), human breast adenocarcinoma (MCF-7), human cervical adenocarcinoma (HeLa), human hepatocellular liver carcinoma (HepG2), and human glioblastoma (MO59J, U343, and U251). Normal hamster lung fibroblasts (V79 cells) were included as control. The cells were treated with essential oil concentrations ranging from 3.12 to 400 µg/ml for 24 h. The cytotoxic activity was evaluated using the XTT assay; results were expressed as IC50, and the selectivity index was calculated. The results were compared with those achieved for classic chemotherapeutic agents. TE-OE was the most promising among the evaluated oils: it afforded the lowest IC50 values for B16F10 cells (7.47 ± 1.08 µg/ml) and HT29 cells (6.93 ± 0.77 µg/ml), as well as selectivity indices of 2.61 and 2.81, respectively. The major BS-EO, FV-EO and TE-EO chemical constituents were identified by gas chromatography mass spectrometry as being (E)-caryophyllene (10.5%), germacrene D (35.0%) and 2,6-di-tert-butyl-4-methylphenol (43.0%) (BS-EO); limonene (21.3%) and (E)-anethole (70.2%) (FV-EO); limonene (10.4%), dihydrotagetone (11.8%), α-terpinolene (18.1%) and (E)-ocimenone (13.0%) (TE-EO); and fenchone (6.1%), dronabinol (11.0%), aromadendrene oxide (14.7%) and (E,E)–farnesol (15.0%) (TR-EO). 2,6-di-tert-butyl-4-methylphenol (43.0%), (E)-anethole (70.2%) and α-terpinolene (18.1%), respectively. These results suggest that TE-OE may be used to treat cancer without affecting normal cells.

Hyptis marrubioides Epling is a native plant from Brazilian Cerrado. In this paper, the response of in vitro microplants of this species to inoculation with bacterial and fungal endophytic isolates is evaluated. HPLC-DAD analysis showed the presence of 3,4-O-(Z)-dicaffeoylquinic acid and quercetin-7-O-glucoside as the main components. GC/MS analysis demonstrated that the sesquiterpenes τ-cadinol and caryophyllene oxide were only produced in microplants inoculated with endophytic bacteria, while methyl hexadecanoate, methyl heptadecanoate and methyl (Z,Z,Z) 9,12,15-octadecatrienoate and the triterpene methyl 3β-hydroxy-urs-12-en-28-oate were overexpressed only when the microplant was treated with endophytic fungi.

This work reviews the current literature about the chemical constituents and the biological activities of the subtribe Lychnophorinae (Vernonieae, Asteraceae). The notable secondary metabolites are sesquiterpene lactones of furanoheliangolide (goyazensolide and eremantholide types) and flavonoids. Some of its most investigated activities include its anti-inflammatory, analgesic, antimicrobial and cytotoxic activities, specially for the Lychnophora and Eremanthus species. The data presented on this paper not only displayed the role played by the Lychnophorinae species as a source of bioactive compounds, but also reinforced the need of further studies involving the species of such subtribe.

An overview of the current literature on the chemical processes involved in the ion formation from low molecular weight organic compounds by electrospray ionization mass spectrometry is given.