3-Octanone

Albizia lebbeck and Albizia zygia volatile oils exhibit anti-nociceptive and anti-inflammatory properties in pain models.[Pubmed:33301915]

J Ethnopharmacol. 2020 Dec 7:113676.

ETHNOPHARMACOLOGICAL RELEVANCE: Albizia lebbeck and Albizia zygia are used in Nigeria, South Africa and other countries for the treatment of flu, fever, pain, epilepsy, and inflammation. AIM OF THE STUDY: Application of plant essence for treating ailments is common among local communities. This research was designed to characterize the volatile compounds and evaluate the toxicity, anti-inflammatory and anti-nociceptive properties of this plant species. MATERIALS AND METHODS: The volatile oils were analysed comprehensively utilizing gas chromatography-flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS) using the HP-5 column. The toxicity was evaluated using the toxicity assay. The anti-nociceptive and anti-inflammatory assays were analysed by a hot plate, Formalin, and carrageenan-induced edema assays, respectively. RESULTS: The essential oils were obtained in a yield of 0.1% (v/w) calculated on a dry weight basis for both oils. The main compounds of A. lebbeck were 2-pentylfuran (16.4%), (E)-geranyl acetone (15.46%), (E)-alpha-ionone (15.45%) and 3-Octanone (11.61%), while the oil of A. zygia is mainly hexahydrofarnesyl acetone (33.14%), (E)-methyl isoeugenol (11.7%) and 2-methyl tetradecane (6.64%). The volatile oils are non-toxic to about 5,000 mg/kg dose. Albizia zygia significantly (P<0.001) suppressed the nociceptive afferent fibres in a non-dose dependent manner in comparison to A. lebbeck in the hot plate model. Both oils inhibited nociceptive mediators at both phases of the formalin-induced assay, with a maximum inhibition (100%) at the inflammatory stage. The volatile oils inhibited the Carrageenan-induced inflammation at all phases ranging from P<0.05 to P<0.001. The probable pro-inflammatory inhibitory mechanism might be the suppression of some pain biomarkers such as histamine, serotonin, bradykinin, and the Interleukins(ILs) induced by the edema. Volatile constituents such as ionones, eugenol derivatives and other compounds cause the anti-nociceptive and anti-inflammatory activities reported. CONCLUSION: This is the first report of the volatile oils and bioassays of Albizia zygia, while the study also confirms previous studies of A. lebbeck. Generally, the findings further prove the use of the plants as pain ameliorating agents.

Quantification of seven microbial volatile organic compounds in human serum by solid-phase microextraction gas chromatography-tandem mass spectrometry.[Pubmed:33228985]

Chemosphere. 2020 Nov 13:128970.

Microbial volatile organic compounds (MVOCs) are primary and secondary metabolites of fungal and bacterial growth. Changes in environmental conditions (e.g., humidity, light, oxygen, and carbon dioxide) influence microbial growth in indoor environments. Prolonged human exposure to MVOCs has been directly associated with sick building syndrome (SBS), respiratory irritation, and asthma-like symptoms. However, no method exists for assessing MVOC exposure by quantifying them in human serum. We developed a novel, high-throughput automated method for quantifying seven MVOCs (3-methylfuran, 2-hexanone, 2-heptanone, 3-Octanone, 1-octen-3-ol, 2-ethyl-1-hexanol, and geosmin) in human serum. The method quantifies the target analytes using solid-phase microextraction gas chromatography-tandem mass spectrometry at low parts-per-billion levels. Limits of detection ranged from 0.076 to 2.77 mug/L. This method provides excellent linearity over the concentration range for the analytes, with coefficients of determination >0.992. Recovery in human serum was between 84.5% and 113%, and analyte precision ranged from 0.38% to 8.78%. The intra-day and inter-day reproducibility showed coefficients of variation

Sixty-One Volatiles Have Phylogenetic Signals Across Bacterial Domain and Fungal Kingdom.[Pubmed:33101231]

Front Microbiol. 2020 Sep 30;11:557253.

Microorganisms are diverse in their genome sequences and subsequently in their encoded metabolic pathways, which enabled them to adapt to numerous environmental conditions. They produce thousands of small molecules, many of which are volatiles in nature and play important roles in signaling in intra- and inter-species to kingdom and domain interactions, survival, or virulence. Many of these compounds have been studied, characterized, and organized in the mVOC 2.0 database. However, such dataset has not been investigated comprehensively in terms of its phylogeny to determine key volatile markers for certain taxa. It was hypothesized that some of the volatiles described in the mVOC 2.0 database could function as a phylogenetic signal since their production is conserved among certain taxa within the microbial evolutionary tree. Our meta-analysis revealed that some volatiles were produced by a large number of bacteria but not in fungal genera such as dimethyl disulfide, acetic acid, 2-nonanone, dimethyl trisulfide, 2-undecanone, isovaleric acid, 2-tridecanone, propanoic acid, and indole (common bacterial compounds). In contrast, 1-octen-3-ol, 3-Octanone, and 2-pentylfuran (common fungal compounds) were produced primarily by fungal genera. Such chemical information was further confirmed by investigating genomic data of publicly available databases revealing that bacteria or fungi harbor gene families involved in these volatiles' biosynthesis. Our phylogenetic signal testing identified 61 volatiles with a significant phylogenetic signal as demonstrated by phylogenetic D statistic P-value < 0.05. Thirty-three volatiles were phylogenetically conserved in the bacterial domain (e.g., cyclocitral) compared to 17 volatiles phylogenetically conserved in the fungal kingdom (e.g., aristolochene), whereas 11 volatiles were phylogenetically conserved in genera from both bacteria and fungi (e.g., geosmin). These volatiles belong to different chemical classes such as heterocyclic compounds, long-chain fatty acids, sesquiterpenoids, and aromatics. The performed approaches serve as a starting point to investigate less explored volatiles with potential roles in signaling, antimicrobial therapy, or diagnostics.

Key aroma compounds of Chinese dry-cured Spanish mackerel (Scomberomorus niphonius) and their potential metabolic mechanisms.[Pubmed:33097327]

Food Chem. 2020 Oct 16:128381.

The key aroma compounds of six commercially available dry-cured Spanish mackerel (Scomberomorus niphonius, DCSM) were identified using electronic nose (E-nose), gas chromatography-olfactometry (GC-O), and two-dimensional gas chromatography-time-of-flight mass spectrometry (GC x GC-TOFMS). A total of 38-55 aroma compounds were identified, and 21-26 of them, which presented high flavor dilution factors based on aroma extract dilution analysis, were quantified. Lastly, 9-14 key aroma compounds with high odor-active value, including 3-methyl-1-butanal, octanal, 1-octen-3-ol, nonanal, cis-4-decenal, ethyl caproate, (E)-2-octenal, (Z)-2-nonenal decanal, 3-methyl-1-butanol, 1-heptanol, 3-Octanone, 2-octanol, and 6-methyl-5-hepten-2-one, were identified as the key aroma contributors in DCSM. Results also indicated that a longer dry-curing time would promote the generation of aroma compounds. The metabolism analysis implied that the auto-oxidation/oxidation of unsaturated fatty acids, such as oleic and linoleic acid, and the enzymatic degradation of l-leucine might be potential metabolic mechanisms.

Fungal Volatiles as Olfactory Cues for Female Fungus Gnat, Lycoriella ingenua in the Avoidance of Mycelia Colonized Compost.[Pubmed:33026596]

J Chem Ecol. 2020 Oct;46(10):917-926.

The chemical signatures emitted by fungal substrates are key components for mycophagous insects in the search for food source or for suitable oviposition sites. These volatiles are usually emitted by the fruiting bodies and mycelia. The volatiles attract fungivorous insects, like flowers attract pollinators; certain flowers mimic the shape of mushroom fruiting bodies and even produce a typical mushroom odor to exploit on fungus-insect mutualism. There are numerous insects which are mycophagous or eat fungi additionally, but only a few are considered a threat in agriculture. Lycoriella ingenua is one of the most serious pests in mushroom cultivation worldwide. Here we attempt to examine the role of environmental volatiles upon behavioral oviposition preference. In two-choice bioassays, fungus gnats preferred uncolonized compost compared to colonized compost but preferred colonized compost against nothing. However, when colonized compost was paired against distilled water, no significant choice was observed. The comparison of fresh casing material and mycelium colonized casing material resulted in no significant preference. From colonized compost headspace, three antennally active volatiles were isolated by gas chromatography coupled with electroantennography and subsequently identified with gas chromatography coupled mass spectrometry as 1-hepten-3-ol, 3-Octanone and 1-octen-3-ol. In behavioral assays the addition of said synthetic volatiles to uncolonized compost separately and in combination to mimic colonized compost resulted in avoidance. We thus partially elucidate the role of fungal volatiles in the habitat seeking behavior of Lycoriella ingenua.

Chemical composition of a volatile fraction from the leaves of Clerodendrum infortunatum L.[Pubmed:32787567]

Nat Prod Res. 2020 Aug 13:1-4.

The volatile composition of plants is of great importance because of its wide applications in aromatherapy, pharmaceuticals, perfumes and chemical ecology. This article describes the volatile fraction of Clerodendrum infortunatum L. leaves extracted by partitioning the hydro-distillate using hexane. A fatty acid derivative, 1-octen-3-ol is found as the main component in the volatile fraction ranging from 48.7 to 63.7%. Other compounds found with significant amounts were trans-3-hexenol, 1-hexanol, (3E)-hexen-1-ol acetate, 3-Octanone, phenylacetaldehyde, linalool and methyl salicylate. Irregular terpenoid compounds like (E)-beta-damascenone, (E)-beta-ionone and isophorone are also present in the volatile part of C. infortunatum. The chemical composition of the volatile fraction was identified by spectroscopic analysis, GC and GC-MS.

Inclusion and release of ant alarm pheromones from metal-organic frameworks.[Pubmed:32691808]

Dalton Trans. 2020 Aug 4;49(30):10334-10338.

Zinc(ii) and zirconium(iv) metal-organic frameworks show uptake and slow release of the ant alarm pheromones 3-Octanone and 4-methyl-3-heptanone. Inclusion of N-propyl groups on the MOFs allows for enhanced uptake and release over several months. In preliminary field trials, leaf cutting ants show normal behavioural responses to the released pheromones.

Volatile Composition and Sensory Attributes of Smoothies Based on Pomegranate Juice and Mediterranean Fruit Purees (Fig, Jujube and Quince).[Pubmed:32674294]

Foods. 2020 Jul 14;9(7). pii: foods9070926.

To increase the intake of fruits and vegetables-especially among young people-the food industry is trying to develop new, easy-to-eat and long-shelf-life products, such as smoothies. Nowadays, consumers are choosing their foods based not only on nutritional/functional properties (content of polyphenols, vitamins, minerals, among others), but also on sensory attributes. The aim of this study was to investigate the volatile composition by HS-SPME and the sensory profile by descriptive sensory analysis of novel smoothies prepared by blending fig, jujube or quince puree with pomegranate juices (cv. Mollar de Elche or Wonderful) at two ratios puree:juice (40:60 or 60:40). Twenty-three volatile compounds were identified by GC-MS and classified as alcohols, aldehydes, esters, furans, ketones, terpenes and terpenoids. Among volatile compounds, the five predominant ones in the studied smoothies were: (i) 5-HMF (30.6%); (ii) 3-hexen-1-ol (9.87%); (iii) hexanal (9.43%); (iv) 1-hexanol (8.54%); and (v) 3-Octanone (7.67%). Fig smoothies were sweet and had flavor and volatiles related to fig, pomegranate, and grape. While jujube products were bitter and had jujube and pear notes. Finally, quince smoothies were consistent, sour and had quince, apple and floral notes. Thus, the type of fruit puree used clearly determined the flavor of the final product. The smoothies prepared with Mollar de Elche pomegranate juice were characterized by having high intensity of pear odor/aroma and consistency, and the Wonderful smoothies were characterized by lower consistency and more intense pomegranate aroma and sourness.

Astatine partitioning between nitric acid and conventional solvents: indication of covalency in ketone complexation of AtO().[Pubmed:32638758]

Chem Commun (Camb). 2020 Aug 14;56(63):9004-9007.

Astatine-211 has been produced at Texas A&M University on the K150 cyclotron, with a yield of 890 +/- 80 MBq through the (209)Bi(alpha,2n)(211)At reaction via an 8 h bombardment with a beam current of 4-8 muA and an alpha-particle beam energy of 28.8 MeV. The target was then dissolved in HNO3 and the extraction of (211)At was investigated into a variety of organic solvents in 1-3 M HNO3. Extraction of (211)At with distribution ratios as high as 11.3 +/- 0.6, 12.3 +/- 0.8, 42.2 +/- 2.2, 69 +/- 4, and 95 +/- 6 were observed for diisopropyl ether, 1-decanol, 1-octanol, 3-Octanone, and methyl isobutyl ketone, respectively, while the distribution ratios for (207)Bi were 3-Octanone showed a strong, linear dependence on the HNO3 initial aqueous concentration and better extraction than other solvents. DFT calculations show stronger binding between the carbonyl oxygen of the ketone and the At metal center.

Generation of flavor compounds by biotransformation of genetically modified hairy roots of Hypericum perforatum (L.) with basidiomycetes.[Pubmed:32566198]

Food Sci Nutr. 2020 Apr 16;8(6):2809-2816.

Altogether, 14 basidiomycetes (12BAD, 95PCH, 9WCOC, 5PSA, 96BCI, 331SHIBD, 4MSC, 74HFA, 220MPS, 115PFLA, 111 ICO C, 16LED, 6TSU, and 61LYP) were grown on solid and in liquid media using hairy roots of genetically modified Hypericum perforatum (L.) as the only source of carbon and nitrogen. After the first screening by GC-MS/MS-O, two fungi (115PFLA and 61LYP) which resulted in the most pleasant complex natural flavor by biotransformation were selected for further analysis. Twenty-four new volatile compounds were produced, from which 21 were identified (ethyl hexanoate, ethyl octanoate, benzaldehyde, 2-undecanone, (E,E)-2,4-decadienal, 1-octen-3-one, (E)-2-nonenal, ethyl nonanoate, 2-heptenal, 1-methoxy-4-methylbenzene, 3-Octanone, 1-decen-3-one, (E)-2-octenal, 1-octen-3-ol, beta-linalool, +/-trans-nerolidol, anisole, methyl benzoate, 2-pentylfuran, 1,3-dichloro-2-methoxybenzene, and 1-dodecanol). Thereof, 15 compounds were perceived at the ODP, from which 13 were identified. Compound identification was performed by comparison of Kovats indices (KI) and mass spectra to those of authentic reference compounds on a polar VF-WAXms column using headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS).

Nanosecond Pulsed Dielectric Barrier Discharge Ionization Mass Spectrometry.[Pubmed:32083845]

Anal Chem. 2020 Mar 17;92(6):4468-4474.

Dielectric barrier discharge ionization (DBDI) is an emerging technique for ionizing volatile molecules directly from complex mixtures for sensitive detection by mass spectrometry (MS). In conventional DBDI, a high frequency and high voltage waveform with pulse widths of approximately 50 mus (and approximately 50 mus between pulses) is applied across a dielectric barrier and a gas to generate "low temperature plasma." Although such a source has the advantages of being compact, economical, robust, and sensitive, background ions from the ambient environment can be formed in high abundances, which limits performance. Here, we demonstrate that high voltage pulse widths as narrow as 100 ns with a pulse-to-pulse delay of approximately 900 mus can significantly reduce background chemical noise and increase ion signal. Compared to microsecond pulses, approximately 800 ns pulses can be used to increase the signal-to-noise and signal-to-background chemical noise ratios in DBDI-MS by up to 172% and 1300% for six analytes, including dimethyl methylphosphonate (DMMP), 3-Octanone, and perfluorooctanoic acid. Using nanosecond pulses, the detection limit for DMMP and PFOA in human blood plasma can be lowered by more than a factor of 2 in comparison to microsecond pulses. In "nanopulsed" plasma ionization, the extent of internal energy deposition is as low as or lower than in electrospray ionization and micropulsed plasma ionization based on thermometer ion measurements. Overall, nanosecond high-voltage pulsing can be used to significantly improve the performance of DBDI-MS and potentially other ion sources involving high voltage waveforms.

Olfactory Receptor Neurons for Plant Volatiles and Pheromone Compounds in the Lucerne Weevil, Sitona discoideus.[Pubmed:32048118]

J Chem Ecol. 2020 Mar;46(3):250-263.

Antennal olfactory receptor neurons (ORNs) for pheromone-related and plant volatile compounds were identified and characterized in the lucerne weevil, Sitona discoideus (Gyllenhal), using the single sensillum recording technique. Our study using five pheromone-related compounds and 42 plant volatile compounds indicates that S. discoideus have highly specialized ORNs for pheromone and plant volatile compounds. Different groups of ORNs present in both males and females of S. discoideus were highly sensitive to 4-methylheptane-3,5-dione (diketone) and four isomers (RR, RS, SR and SS) of 5-hydroxy-4-methylheptan-3-one, respectively. Our results also indicate that male S. discoideus, using the sensory input from antennal ORNs, can distinguish both diketone and the RR-isomer from others, and RS- and SS-isomers from others, although it was unclear if they can distinguish between RS-isomer and SS-isomer, or between diketone and the SR-isomer. It also appeared that female S. discoideus could distinguish between RS-isomer and SS-isomers. The antennae of S. discoideus thus contain sex-specific sets of ORNs for host- and non-host plant volatile compounds. Both sexes of S. discoideus have highly sensitive and selective ORNs for some green-leaf volatiles, such as (Z)-3-hexenol and (E)-2-hexenal. In contrast, male antennae of S. discoideus house three distinct groups of ORNs specialized for myrcene and (E)-beta-ocimene, 2-phenylethanol, and phenylacetaldehyde, respectively, whereas female antennae contain three groups of ORNs specialized for (+/-)-linalool and (+/-)-alpha-terpineol, myrcene and (E)-beta-ocimene, (+/-)-1-octen-3-ol, and 3-Octanone. Our results suggest that S. discoideus use a multi-component pheromone communication system, and a sex-specific set of ORNs with a narrow range of response spectra for host-plant location.