Detection of anthraquinones and identification of 1,4-naphthohydroquinone in cell suspension cultures of Rudgea jasminoides (Cham.) Müll. Arg. (Rubiaceae)

In Rubiaceae, anthraquinones and naphthoquinones are secondary metabolites characteristic of the subfamily Rubioideae, in which Rudgea jasminoides is included. Thin-layer chromatography using specific solvent systems and spray reagents indicated the presence of anthraquinones constitutively produced by cell suspension cultures of R. jasminoides. GC/MS analysis detected 1,4-naphthohydroquinone as a product of biosynthesis only after elicitation of the cells with yeast extract (Saccharomyces cerevisiae). The latter compound is probably a phytoalexin produced by suspension cultures of R. jasminoides.

Antimicrobial activity of the essential oil from Lippia sidoides, carvacrol and thymol against oral pathogens

Dental caries and periodontal disease are associated with oral pathogens. Several plant derivatives have been evaluated with respect to their antimicrobial effects against such pathogenic microorganisms. Lippia sidoides Cham (Verbenaceae), popularly known as "Alecrim-pimenta" is a typical shrub commonly found in the Northeast of Brazil. Many plant species belonging to the genus Lippia yield very fragrant essential oils of potential economic value which are used by the industry for the commercial production of perfumes, creams, lotions, and deodorants. Since the leaves of L. sidoides are also extensively used in popular medicine for the treatment of skin wounds and cuts, the objective of the present study was to evaluate the composition and antimicrobial activity of L. sidoides essential oil. The essential oil was obtained by hydro-distillation and analyzed by GC-MS. Twelve compounds were characterized, having as major constituents thymol (56.7%) and carvacrol (16.7%). The antimicrobial activity of the oil and the major components was tested against cariogenic bacterial species of the genus Streptococcus as well as Candida albicans using the broth dilution and disk diffusion assays. The essential oil and its major components thymol and carvacrol exhibited potent antimicrobial activity against the organisms tested with minimum inhibitory concentrations ranging from 0.625 to 10.0 mg/mL. The most sensitive microorganisms were C. albicans and Streptococcus mutans. The essential oil of L. sidoides and its major components exert promising antimicrobial effects against oral pathogens and suggest its likely usefulness to combat oral microbial growth.

Serum metabolic profiling of human gastric cancer based on gas chromatography/mass spectrometry

Research on molecular mechanisms of carcinogenesis plays an important role in diagnosing and treating gastric cancer. Metabolic profiling may offer the opportunity to understand the molecular mechanism of carcinogenesis and help to non-invasively identify the potential biomarkers for the early diagnosis of human gastric cancer. The aims of this study were to explore the underlying metabolic mechanisms of gastric cancer and to identify biomarkers associated with morbidity. Gas chromatography/mass spectrometry (GC/MS) was used to analyze the serum metabolites of 30 Chinese gastric cancer patients and 30 healthy controls. Diagnostic models for gastric cancer were constructed using orthogonal partial least squares discriminant analysis (OPLS-DA). Acquired metabolomic data were analyzed by the nonparametric Wilcoxon test to find serum metabolic biomarkers for gastric cancer. The OPLS-DA model showed adequate discrimination between cancer and non-cancer cohorts while the model failed to discriminate different pathological stages (I-IV) of gastric cancer patients. A total of 44 endogenous metabolites such as amino acids, organic acids, carbohydrates, fatty acids, and steroids were detected, of which 18 differential metabolites were identified with significant differences. A total of 13 variables were obtained for their greatest contribution in the discriminating OPLS-DA model [variable importance in the projection (VIP) value >1.0], among which 11 metabolites were identified using both VIP values (VIP >1) and the Wilcoxon test. These metabolites potentially revealed perturbations of glycolysis and of amino acid, fatty acid, cholesterol, and nucleotide metabolism of gastric cancer patients. These results suggest that gastric cancer serum metabolic profiling has great potential in detecting this disease and helping to understand its metabolic mechanisms.

Volatile profile of the headspace fraction of "assa-peixe" (Vernonia sp.) honeys

The volatile compounds were isolated from the headspace fraction of "assa-peixe" honeys by adsorptive column chromatography, eluted with acetone and analysed by GC-FID and GC-MS. Volatile compounds were separated using a polar phase column. Low- and medium-boiling point volatile compounds predominated in the headspace. A large proportion of 3-penten-2-one (80.5 ± 13.9 µg.kg-1) and benzaldehyde (25.9 ± 4.2 µg.kg-1) was found in the headspace fraction, while 2-penten-1-ol, 3-hexenyl butanoate, octadecane and hexanoic acid (<0.01 µg.kg-1) were by far the less abundant volatile compounds. A total of 12 volatile compounds were identified and, among them, 5 compounds were reported as "assa-peixe" honey constituents for the first time. Of the 5 new volatile compounds reported, 3-penten-2-one, dodecane, tridecane and benzaldehyde were definitively identified in the headspace fraction of Brazilian "assa-peixe" honeys.

Comparison of volatile and polyphenolic compounds in Brazilian green propolis and its botanical origin Baccharis dracunculifolia

Ethanolic extracts and essential oils from Green Propolis from southeastern Brazil and leaf buds from its botanical origin Baccharis dracunculifolia were analyzed by Reversed Phase High Performance Liquid Chromatography (RP-HPLC), Reversed Phase High Performance Thin Layer Chromatography (RP-HPTLC) and Gas Chromatography - Mass Spectrometry (GC-MS). The essential oils were obtained by hydro-distillation. Both ethanolic extracts and essential oils showed similar chromatographic profiles. Thirteen flavonoids were identified by RP-HPLC and RP-HPTLC analyses in both samples. Twenty-three volatile compounds were identified by GC-MS analyses. Seventeen were present in both essential oils. The major flavonoid compound in both extracts was artepillin C. The major volatile compound in both essential oils was nerolidol. The major compounds identified in this work could be used as chemical markers in order to classify and identify botanical origins of propolis.

Interference of heating on the antimicrobial activity and chemical composition of Origanum vulgare L. (Lamiaceae) essential oil

Origanum vulgare L. (oregano), Lamiaceae, essential oil has a variety of biological properties and its antimicrobial activity has received a renewed interest for use in food conservation. The aim of this study was to evaluate the interference of heating on the antimicrobial activity and chemical composition of O. vulgare essential oil. The antimicrobial activity of the essential oil kept at room temperature and exposed to different heating temperatures (60, 80, 100 and 120 °C during 1 hour) was evaluated by observing antimicrobial effectiveness at absolute concentration and determining MIC values by the solid medium diffusion procedure. The essential oil chemical composition analysis was performed by GC-MS. O. vulgare essential oil showed interesting antimicrobial activity on all assayed microbial strains (Candida albicans, C.krusei, C. tropicalis, Bacillus cereus, Escherichia coli, Staphylococcus aureus, Yersinia enterocolitica, Salmonella enterica, Serratia marcencens), noted by large growth inhibition zones (30-42 mm). Heating treatment showed no significant interference (p < 0.05) on the essential oil antimicrobial activity, noted by the development of microbial growth inhibition zones with similar or close diameters when evaluating the essential oil kept at room temperature and after exposure to different thermal treatments. MIC values oscillated between 10and 40 µL.mL-1 (20µL.mL-1 for most strains). However, no significant difference (p < 0.05) was noted among the MIC values found for the essential oil aliquots exposed to different temperatures. Moreover, heating did not significantly (p < 0.05) affect the chemical composition of O. vulgare essential oil. Monoterpenes, terpenic compounds and sesquiterpenes were found in the essential oil, with carvacrol (68.06-70.27%) and p-cymene (12.85-15.81%) being the compounds found in the highest amounts. These results showed the thermal stability and intense antimicrobial properties of O. vulgare essential oil and support its possible concomitant use with heating temperatures in order to reach microbial safety in foods.

Rosemary (Rosmarinus officinalis): a study of the composition, antioxidant and antimicrobial activities of extracts obtained with supercritical carbon dioxide

Rosemary leaf extracts were obtained by supercritical fluid extraction (SFE) and Soxhlet extraction. Their chemical compositions were evaluated by GC-MS. The extracts were analyzed for compounds reported in the literature as showing antimicrobial and antioxidant activities. The rosemary extracts were tested with regard to antioxidant (DPPH radical scavenging and total phenolic content - Folin-Denis reagent), antibacterial (Gram-positive bacteria - Staphylococcus aureus ATCC 25923 and Bacillus cereus ATCC 11778 - and Gram-negative bacteria - Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and antifungal (Candida albicans) activities. Antioxidant, antibacterial and antifungal activities of the SFE extracts were confirmed.

Volatile profile of heated soybean oil treated with quercetin and chlorogenic acid

Changes in the profile of volatile compounds after the heating of refined soybean oil without adding antioxidants, and treated with quercetin and chlorogenic acid (5-CQA) were investigated by GC/FID, GC/MS, and GC/SNIFFING. The heating temperature of the oil sample was 20 °C for the first minute, and then it was increased up to 160 °C at the rate of 10 °C min-1. The final temperature was kept for 10 minutes. 19 volatiles were identified in the heated samples without antioxidants. Medium-chain carbonyls predominated in the volatile fraction, mainly 2-heptenal, 2,4-heptadienal and 2,4-decadienal. Around 11 to 15 volatile compounds were detected in the heated samples treated with 5-CQA and quercetin, respectively. 5-CQA was not very efficient in delaying the formation of oxidative volatile compounds. The samples quercetin presented lower proportion of carbonyls with C6-C9.. The GC peak area data were used as an approach to estimate the relative content of each volatile compound and indicate that the samples treated with quercetin (p < 0.05) had significantly lower values for, 1-pentanol, 2,4-heptadienal, and 2,4-decadienal compared with those without antioxidants and treated with 5-CQA. GC/SNIFFING analysis revealed a smaller odor perception in the samples treated with 5-CQA compared to those without antioxidants. No odor was perceived in the heated samples treated with quercetin. These results indicate greater effectiveness of quercetin in delaying the formation of oxidative volatile compounds in soybean oils subjected to mild heating conditions. Apparently, biopolyphenols used in the present work showed good oxidative stability since no new volatile compound was detected in the heated samples treated with them.

Volatile compounds profile of fresh-cut peki fruit stored under different temperatures

The objective of this work was to identify and verify the influence of time and temperature on the volatile compounds profile of fresh cut peki. Peki fruits were washed, sanitized, their kernels were extracted, and they were packaged and stored for 15 days at 0, 5, and 10 °C and 6 days at 22 °C. The volatiles compounds were analyzed by GC - MS. Ethyl hexanoate and ethyl octanoate were found in higher percentages, 63 and 16.3%, respectively. The determined volatiles were not influenced by the storage period. Hexanoic acid, ethyl 2-octenoate and ethyl decanoate were not influenced by the different temperatures. The temperatures 0, 5, and 10 °C did not influence ethyl hexanoate, ethyl 2-hexenoate and ethyl octanoate either. In addition, the temperatures 5, 10, and 22 °C did not influence ethyl hexanoate, cis-β-ocimene and ethyl octanoate. The temperature of 22 °C determined higher percentages of ethyl hexanoate and lower percentages of ethyl octanoate, in comparison to the temperature of 0 °C, and higher percentages of ethyl 2-hexenoate in comparison to the temperatures of 0, 5, and 10 °C. The temperature of 5 °C determined higher percentage of cis-β-ocimene when compared with the temperature of 0 °C. The storage temperatures of 0 and 5 °C were the most appropriate for the conservation.

Volatile compounds in noni (Morinda citrifolia L.) at two ripening stages

The volatile components of noni at two ripening stages were isolated by headspace solid-phase microextraction using 65 µm Polydimethylsiloxane-Divinylbenzene (PDMS/DVB) fibers and analyzed using GC/MS. Both maturation stages had several compounds in common. Ninety-six compounds were identified, from which octanoic acid ( 70% of total extract) and hexanoic acid ( 8% of total extract) were found to be the major constituents. Due to noni maturation, octanoic acid, decanoic acid and 2E-nonenal decreased their concentrations, while some esters (methyl hexanoate, methyl octanoate, ethyl octanoate and methyl 4E-decenoate), which their fruity odor notes, increased their contents. Two unsaturated esters, reported for the first time in this fruit, 3-methyl-3-buten-1-yl hexanoate and 3-methyl-3-buten-1-yl octanoate, significantly decreased their concentration in the ripe to over-ripe fruits.

Evaluation of noni (Morinda citrifolia) volatile profile by dynamic headspace and gas chromatography-mass spectrometry

Noni is a fruit that has interested the scientific community due to its medicinal and functional activities. Different products that contain noni are already in the market, but their consumption could be impaired by their distinctive unpleasant aroma and flavor. The aim of this work was to evaluate the noni pulp volatile profile by dynamic headspace and gas chromatography-mass spectrometry. Thirty seven volatile compounds were detected, mainly alcohols (63.3%), esters (26.9%), cetones (7.4%), and acids (1.2%).

Inhibitory effect of the essential oil from Cinnamomum zeylanicum Blume leaves on some food-related bacteria

Cinnamomum zeylanicum Blume, Lauraceae, has long been known for having many biological properties. This study aimed to identify the constituents of the essential oil from C. zeylanicum leaves using GC-MS and to assess its inhibitory effect on Salmonella enterica, Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa based on MIC and MBC determination and kill-time study. Eugenol (73.27%) was the most prevalent compound in the essential oil followed by trans-β-cariophyllene (5.38%), linalool (3.31%), and alcohol cinamic acetate (2.53%). The results showed an interesting antibacterial activity of the oil with MIC ranging from 1.25 to 10 µL.mL-1. MBC values were in the range of 20 - 80 µL.mL-1. A concentration of 10 and 40 µL.mL-1 of the essential oil caused a fast and steady decrease in viable cell count (2 to 5 log cycles) of all assayed strains along 24 hours. A concentration of 40 µL.mL-1 of the oil provided a total elimination of the initial inocula of S. aureus after 2 hours. These results show the possibility of regarding the essential oil from C. zeylanicum leaves as alternative sources of antimicrobial compounds to be applied in food conservation systems.

Changes in guava (Psidium guajava L. var. Paluma) nectar volatile compounds concentration due to thermal processing and storage

Guava nectars were formulated for approximately 10, 12, or 14 ºBrix, with 40% guava pulp. Sodium benzoate, 500 mg.kg-1 was used as preservative. The Brix value was adjusted with saturated sucrose syrup. The guava nectar was pasteurized (85 ºC/42 seconds) in tubular heat exchanger and then hot filled in 500 mL white glass bottles. The products were stored either at room temperature (25 ± 5 ºC) or refrigerated (5 ± 2 ºC) under fluorescent light exposure and analyzed on the day after processing (time zero) and also 40, 80, and 120 days of storage. Eight compounds were identified and quantified by Gas Chromatography (GC) -Mass Spectrometry (MS): hexanal, (E)-hex-2-enal, 1-hexenol, (Z)-hex-3-enol, (Z)-hex-3-enyl acetate, phenyl-3-propyl acetate, cinnamyl acetate, and acetic acid. There was no significant effect of thermal treatment on the volatile compound concentrations, except for a significant decrease (p = 0.0001) in hexanal and (Z)-hex-3-enyl acetate (p = 0.0029). As for the storage time, there was a much greater decrease in the esters contents, such as (Z)-hex-3-enyl and phenyl-3-propyl acetates. Cinnamyl acetate had the greatest decrease over storage time. Refrigeration was better than room temperature for guava nectar volatile compounds stability over storage time, mainly for esters compounds, which are important for the product aroma and flavor

Stability of volatile profile and sensory properties of passion fruit juice during storage in glass bottles

This study aimed at assessing the stability of passion fruit juice in glass bottles during a 120-day storage period, regarding its volatile compounds profile and sensory properties (aroma and flavor). Samples were obtained from a Brazilian tropical juice industry (Fortaleza, Brazil) and submitted to sensory and chromatographic analyses. The characteristic aroma and flavor of passion fruit were evaluated by a trained panel with a non-structured scale of 9 cm. The headspace volatile compounds were isolated from the product by suction and trapped in Porapak Q, analyzed through high-resolution gas chromatography and identified through gas chromatography-mass spectrometry (GC-MS). Twelve odoriferous compounds were monitored: ethyl butanoate, ethyl propanoate, 3-methyl-1-butanol, 3-methyl-2-butenol, (E)-3-hexenol, (Z)-3-hexenol, 3-methylbutyl acetate, benzaldehyde, ethyl hexanoate, hexyl acetate, limonene and furfural. The slight variations observed in the volatile profile were not enough to provoke significant changes in the characteristic aroma and flavor of the passion fruit juice.

Identification of volatile compounds in thinning discards from plum trees (Prunus salicina Lindl.) cultivar Harry Pickstone

Plum (Prunus salicina Lindl. cv. Harry Pickstone), a China indigenous fruit, is widely produced and consumed in countries such as Japan and Brazil. The practice of thinning is common in horticulture and the fruits removed are discarded as waste. Like the great majority of vegetables, these thinning discards also contain essential oils which have not been investigated until the present time. The extraction of the plum thinning discards volatile oil, through the hydrodistillation method, produced a yield of 0.06% (m/m) and a total of 21 components were identified, with 11 of them being responsible for 72,9% of the total oil composition. The major compounds determined through GC and GC-MS were Z-α-bisabolene (13.7%), n-hexadecanoic acid (12.7%), phytol (12.7%), and β-caryophyllene (10.4%).