2-Undecanone alleviates asthma by inhibiting NF-κB pathway.

Asthma is characterized by airway inflammation and remodeling. 2-Undecanone (methyl nonyl ketone), a volatile organic compound originating from Houttuynia cordata, has the potential to ameliorate inflammatory diseases. This study aimed to explore potential benefits of 2-undecanone in asthma. 2-Undecanone (100, 200, or 400 mg/kg) was administered intragastrically to ovalbumin (OVA)-challenged BALB/c mice. Lung tissues were collected to observe histopathological changes, and bronchoalveolar lavage fluid (BALF) was collected for the detection of inflammatory cells and cytokine production. The results showed that 2-undecanone ameliorated OVA-induced pathologic changes of lungs, including reducing inflammatory cell infiltration, goblet cell hyperplasia, and airway smooth muscle thickness. The number of inflammatory cells and the levels of IL-4, IL-5, IL-13, and IgE in BALF were decreased by 2-undecanone in asthmatic mice. Furthermore, abnormal activation of NF-κB pathway in lung tissues of asthmatic mice was impeded by 2-undecanone. In vitro, 2-undecanone (12.5, 25, or 50 µM) suppressed platelet-derived growth factor-BB-induced proliferation and migration of primary airway smooth muscle cells (ASMCs), and inhibited the switching of ASMCs from contractile phenotype to synthetic phenotype. Consistently, 2-undecanone blocked NF-κB activation in ASMCs. Collectively, 2-undecanone relieves asthma through alleviating airway inflammation and remodeling, and this beneficial effect is achieved by inhibiting NF-κB pathway.

Regioselective Claisen-Schmidt Adduct of 2-Undecanone from Houttuynia cordata Thunb as Insecticide/Repellent against Solenopsis invicta and Repositioning Plant Fungicides against Colletotrichum fragariae.

The U.S. Department of Agriculture (USDA) has established research programs to fight the phytopathogen Colletotrichum fragariae and the invasive red imported fire ant, Solenopsis invicta. C. fragariae is known to cause anthracnose disease in fruits and vegetables, while S. invicta is known for its aggressive behavior and painful stings and for being the cause of significant damage to crops, as well as harm to humans and animals. Many plants have been studied for potential activity against C. fragariae and S. invicta. Among the studied plants, Houttuynia cordata Thunb has been shown to contain 2-undecanone, which h is known for its antifungal activity against Colletotrichum gloesporioides. Based on the mean amount of sand removed, 2-undecanone showed significant repellency at 62.5 µg/g, similar to DEET (N,N-diethyl-meta-toluamide), against S. invicta. The 2-Undecanone with an LC50 of 44.59 µg/g showed toxicity against S. invicta workers. However, neither H. cordata extract nor 2-undecanone had shown activity against C. fragariae despite their known activity against C. gloesporioides, which in turn motivates us in repositioning 2-undecanone as a selected candidate for a Claisen-Schmidt condensation that enables access to several analogs (2a-f). Among the prepared analogs, (E)-1-(3-methylbenzo[b]thiophen-2-yl)dodec-1-en-3-one (2b) and (E)-1-(5-bromothiophen-2-yl)dodec-1-en-3-one (2f) showed promising activity against C. fragariae, revealing a distinctive structural activity relationship (SAR). The generated analogs revealed a clear regioselectivity pattern through forming the C=C alkene bond at position C-1. These data open the window for further lead optimization and product development in the context of managing C. fragariae and S. invicta.

2-undecanone protects against fine particles-induced heart inflammation via modulating Nrf2/HO-1 and NF-κB pathways.

Exposure to air pollution has been closely associated with some cardiovascular disease. One of the mechanisms of PM2.5 -mediated heart injury may be to promote inflammation. We aim to investigate whether the main extract of Houttuynia cordata, 2-undecanone, can prevent the inflammation caused by PM2.5 , and to reveal the underlying mechanisms. The results showed that PM2.5 increased the expression of certain inflammatory cytokines, and caused oxidative damage in BALB/c mice and H9C2 cells. Supplementation with 2-undecanone attenuated this PM2.5 -induced inflammatory injury and oxidative damage. Further, we elucidated that the protective effect of 2-undecanone may be associated with NF-κB and Nrf2/HO-1 pathways. The NF-κB pathway was distinctly activated after treated by PM2.5 , which can be blocked by 2-undecanone, accompanied by increasing Nrf2 and HO-1 levels. To figure out the relationship between NF-κB and Nrf2/HO-1 pathways, we knocked down Nrf2 gene. NF-κB pathway proteins and downstream inflammatory cytokines were significantly increased after treatment with PM2.5 , while 2-undecanone could decrease expression of these proteins. In conclusion, it is possible that 2-undecanone can induce the expression of the antioxidant enzyme HO-1 by activating Nrf2, thereby reducing NF-κB pathway and inflammatory damage of mouse myocardium caused by PM2.5 exposure.

Nematicidal Volatiles from Bacillus atrophaeus GBSC56 Promote Growth and Stimulate Induced Systemic Resistance in Tomato against Meloidogyne incognita.

Bacillus volatiles to control plant nematodes is a topic of great interest among researchers due to its safe and environmentally friendly nature. Bacillus strain GBSC56 isolated from the Tibet region of China showed high nematicidal activity against M. incognita, with 90% mortality as compared with control in a partition plate experiment. Pure volatiles produced by GBSC56 were identified through gas chromatography and mass spectrometry (GC-MS). Among 10 volatile organic compounds (VOCs), 3 volatiles, i.e., dimethyl disulfide (DMDS), methyl isovalerate (MIV), and 2-undecanone (2-UD) showed strong nematicidal activity with a mortality rate of 87%, 83%, and 80%, respectively, against M. incognita. The VOCs induced severe oxidative stress in nematodes, which caused rapid death. Moreover, in the presence of volatiles, the activity of antioxidant enzymes, i.e., SOD, CAT, POD, and APX, was observed to be enhanced in M. incognita-infested roots, which might reduce the adverse effect of oxidative stress-induced after infection. Moreover, genes responsible for plant growth promotion SlCKX1, SlIAA1, and Exp18 showed an upsurge in expression, while AC01 was downregulated in infested plants. Furthermore, the defense-related genes (PR1, PR5, and SlLOX1) in infested tomato plants were upregulated after treatment with MIV and 2-UD. These findings suggest that GBSC56 possesses excellent biocontrol potential against M. incognita. Furthermore, the study provides new insight into the mechanism by which GBSC56 nematicidal volatiles regulate antioxidant enzymes, the key genes involved in plant growth promotion, and the defense mechanism M. incognita-infested tomato plants use to efficiently manage root-knot disease.

Ruta Essential Oils: Composition and Bioactivities.

Ruta L. is a typical genus of the citrus family, Rutaceae Juss. and comprises ca. 40 different species, mainly distributed in the Mediterranean region. Ruta species have long been used in traditional medicines as an abortifacient and emmenagogue and for the treatment of lung diseases and microbial infections. The genus Ruta is rich in essential oils, which predominantly contain aliphatic ketones, e.g., 2-undecanone and 2-nonanone, but lack any significant amounts of terpenes. Three Ruta species, Ruta chalepensis L., Ruta graveolens L., and Ruta montana L., have been extensively studied for the composition of their essential oils and several bioactivities, revealing their potential medicinal and agrochemical applications. This review provides a systematic evaluation and critical appraisal of publications available in the literature on the composition and bioactivities of the essential oils obtained from Ruta species and includes a brief outlook of the potential applications of nanotechnology and chitosan-based products of Ruta essential oils.

Metabolic engineering of ß-oxidation to leverage thioesterases for production of 2-heptanone, 2-nonanone and 2-undecanone.

Medium-chain length methyl ketones are potential blending fuels due to their cetane numbers and low melting temperatures. Biomanufacturing offers the potential to produce these molecules from renewable resources such as lignocellulosic biomass. In this work, we designed and tested metabolic pathways in Escherichia coli to specifically produce 2-heptanone, 2-nonanone and 2-undecanone. We achieved substantial production of each ketone by introducing chain-length specific acyl-ACP thioesterases, blocking the ß-oxidation cycle at an advantageous reaction, and introducing active ß-ketoacyl-CoA thioesterases. Using a bioprospecting approach, we identified fifteen homologs of E. coli ß-ketoacyl-CoA thioesterase (FadM) and evaluated the in vivo activity of each against various chain length substrates. The FadM variant from Providencia sneebia produced the most 2-heptanone, 2-nonanone, and 2-undecanone, suggesting it has the highest activity on the corresponding ß-ketoacyl-CoA substrates. We tested enzyme variants, including acyl-CoA oxidases, thiolases, and bi-functional 3-hydroxyacyl-CoA dehydratases to maximize conversion of fatty acids to ß-keto acyl-CoAs for 2-heptanone, 2-nonanone, and 2-undecanone production. In order to address the issue of product loss during fermentation, we applied a 20% (v/v) dodecane layer in the bioreactor and built an external water cooling condenser connecting to the bioreactor heat-transferring condenser coupling to the condenser. Using these modifications, we were able to generate up to 4.4 g/L total medium-chain length methyl ketones.

Essential Oil Composition of Ruta graveolens L. Fruits and Hyssopus officinalis Subsp. aristatus (Godr.) Nyman Biomass as a Function of Hydrodistillation Time.

The aim of this study was to establish the kinetics regression models for yield and composition of Ruta graveolens fruit and Hyssopus officinalis subsp. aristatus aboveground biomass essential oil (EO), collected at different time intervals during the hydrodistillation process. The hypothesis was that collecting the EO fractions during specific time frames may result in EOs with dissimilar composition that may have differential use by the industry. Furthermore, we calculated the kinetics regression models for the composition of EO, isolated by hydrodistillation in a Clevenger-type apparatus and characterized by GC-MS and GC-FID analyses. The EO yield of R. graveolens fruits was 0.39% (relative area % of GC-FID chromatogram), with major constituents in the Control fraction (0-90 min) being 2-nonanone, 2-undecanone, and 2-undecanol, representing 65% of the total oil. The highest concentration of 2-nonanone (60%) was found in the 30-60 min oil fraction, the concentration of 2-undecanone (35%) was highest in the Control (0-90 min) fraction, and the concentration of eucalyptol (19%) was highest in the 5-10 min fraction. The EO yield of H. officinalis subsp. aristatus dried biomass was 1.12%. The major constituents in the Control fraction (0-90 min) of H. officinalis biomass were eucalyptol, α-pinene, sabinene, ß-pinene, and cis-3-pinanone, representing 86% of the total. Eucalyptol (58%) was the highest in the 0-5 min fraction. The highest ß-pinene (15%) and cis-3-pinanone (20%) contents were found in the 20-40 min fraction. The kinetics regression models that were developed for EO composition of R. graveolens were second-order polynominal, Michaelis-Menten, and Exponential decay, while for EO composition of H. officinalis subsp. aristatus biomass were Exponential decay and Power. The results from this study could benefit the EO industry.

The Male Produced Aggregation Pheromone of a Strawberry Sap Beetle, Lobiopa insularis (Coleoptera: Nitidulidae).

The nitidulid beetle Lobiopa insularis is an important pest of strawberry crops in the United States and Brazil. Both larvae and adults feed on ripe strawberries, causing 20-70% loss in production during serious infestations. Aiming at the development of efficient, clean, and highly specific pest management systems, semiochemicals, especially pheromones, are particularly useful. Analyses of the extracts of both males and females obtained from aeration of live beetles showed the presence of three male specific compounds, 2-nonanone, 2-undecanone, and 2-undecanol (in an enantiomeric ratio of S:R = 3.5:1). This is the first record of ketones and an alcohol as pheromone components in Nitidulidae. These compounds were emitted by males in amounts of 0.3:6:1.5 ng per insect within 24 h (1:30:3), respectively, during the scotophase, indicating nocturnal sexual activity. Field tests with pitfall traps containing different mixtures of compounds and ripe strawberries as a co-attractant summed up to five treatments with 25 replications. As a result, 59% males and 41% females (1:0.7) were caught, indicating the L. insularis pheromone to cause aggregation of both sexes. Results of the field tests showed that the attractivity of the binary mixture of ketones (T3) differed from the control (T5), from traps with 2-undecanone alone (T4), and from the mixture of 2-undecanone and racemic 2-undecanol (T2). Moreover, the activity of the ternary mixture of compounds (T1) was not different from that of T3, indicating that the racemic alcohol did not positively influence trap catches. In future applications, a mixture of synthetic strawberry-derived compounds that are attractive to L. insularis may substitute rapidly decaying fruit in the field, maintaining catches for longer periods. Because of its efficiency and low cost, a mixture of 2-undecanone and 2-nonanone is recommended to catch adult L. insularis in the field.

Monodimensional (GC-FID and GC-MS) and comprehensive two-dimensional gas chromatography for the assessment of volatiles and fatty acids from Ruta chalepensis aerial parts.

INTRODUCTION: Ruta chalepensis L. (Rutaceae) is widespread in the Mediterranean area. This plant has a solid tradition in ethnomedicine because of its various biological activities. Based on previous reports, the main volatile constituents of R. chalepensis are 2-undecanone and 2-nonanone, but most are still unknown, particularly fatty acid composition. OBJECTIVE: To exhaustively characterise the chemical composition of the aerial parts from R. chalepensis plants collected from the wild in Sicily, within a project aiming at the evaluation and characterisation of medicinal plants from the Mediterranean flora. The study was directed toward the determination of volatiles and fatty acids in samples of R. chalepensis obtained from different aerial plant parts and from plants harvested at different times. METHODS: GC with flame ionisation detection, GC-MS and two-dimensional gas chromatography (GC × GC) advanced techniques, with support of dedicated mass spectral databases provided with retention index (RI) information, were applied to determine both volatiles and fatty acids. Samples were extracted by hydrodistillation and underwent methylic transesterification in order to be transformed into the correspondent fatty acid methyl esters (FAMEs). RESULTS: The monodimensional analysis by GC-MS with RI confirmed that 2-nonanone and 2-undecanone are the predominant components in all the plant parts, followed by esters and monoterpenes. A different distribution was observed of the main compounds in the various plant parts depending on the life cycle of the plant (vegetative or reproductive stage). The multidimensional GC × GC analysis allowed for a complete screening of the fatty acids. About 65% of the total were polyunsaturated fatty acids (PUFA), followed by 30% of saturated fatty acids (SFA). CONCLUSION: A detailed GC volatile fingerprint of R. chalepensis flowers, leaves, fruits and stems was established, highlighting the compositional differences depending on plant organs and life cycle. The results indicated R. chalepensis as a good source of fatty acids from the w3 and w6 series. In both essential oil and lipidic extract, many compounds were determined for the first time.

14C-Isotope Use to Quantify Covalent Reactions between Flavor Compounds and ß-Lactoglobulin.

A 14C-based method was developed to study the rate and extent of covalent bond formation between ß-lactoglobulin and three model flavor compounds: a ketone (2-undecanone UDO), an aldehyde (decanal DAL), an isothiocyanate (2-phenylethyl isothiocyanate PEITC), and an unreactive "methods blank" (decane DEC). Aqueous protein solutions with one of the 14C-labeled model flavor compounds were placed in water baths at 25, 45, and 65 °C for 4 weeks measuring the amount of flavor: protein reaction at 1, 3, 7, 14, 21, and 28 days. UDO showed lowest reactivity (max of 0.9% of added compound reacted), DAL (max of 16.4% reacted), and PEITC (max of 71.8% reacted). All compounds showed a rapid initial reaction rate which slowed after ca. 7 days. It appears that only PEITC (at 65 °C) saturated all potential protein-reactive sites over the storage period.

Identification of characteristic flavor compounds of boletus edulis from different regions based on by E-nose, HS-GC-IMS and HS-SPME-GC-MS.

In this study, E-nose, HS-GC-IMS, and HS-SPME-GC-MS technologies were used to evaluate the flavor characteristics of the pileus and stipe of Boletus edulis from eight origins. 23 key Volatile organic compounds (VOCs) with odor activity values (OAVs) > 1 were identified, and 19 aroma types have been identified in Boletus edulis at the same time. Vegetable and earthy were defined as the dominant aroma types for all pileus and stipe samples. Balsamic and musty were the main and characteristic aroma types for the pileus. The highest concentrations of VOCs in the pileus and stipe were originated from Chuxiong Prefecture and Aba Prefecture, respectively. 19 and 16 key VOCs were detected Chuxiong pileus and Aba stipe, respectively, and Methional was the decisive compound that influenced the vegetable aroma type. The results of this study could be helpful for flavor identification and application of pileus and stipe from Boletus edulis.

Effect of different isolation sources of Lactococcus lactis subsp. lactis on volatile metabolites in fermented milk.

Lactococcus lactis subsp. lactis (L. lactis subsp. lactis) is a commonly used starter cultures in fermented dairy products, contributing distinct flavor and texture characteristics with high application value. However, the strains from different isolates have different contributions to milk fermentation. Therefore, this study aimed to investigate the influence of L. lactis subsp. lactis isolated from various sources on the volatile metabolites present in fermented milk. In this study, L. lactis subsp. lactis from different isolation sources (yogurt, koumiss and goat yogurt) was utilized as a starter culture for fermentation. The volatile metabolites of fermented milk were subsequently analyzed by headspace solid phase microextraction gas chromatography-mass spectrography (HS-SPME-GC-MS). The results indicated significant differences in the structure and abundance of volatile metabolites in fermented milk produced with different isolates (R2Y = 0.96, Q2 = 0.88). Notably, the strains isolated from goat yogurt appeared to enhance the accumulation of ketones (goat yogurt vs yogurt milk: 50 %; goat yogur vs koumiss: 27.3 %)and aldehydes (goat yogurt vs yogurt milk: 21.4 %; goat yogurt vs koumiss: 54.5 %) in fermented milk than strains isolated from koumiss and yogurt milk. It significantly promoted the production of 8 flavor substances (1 substance with OAV ≥ 1 and 6 substances with OAV > 0.1) and enhanced the biosynthesis of valine, leucine, and isoleucine. This study provides valuable insights for the application of Lactococcus lactis subsp. lactis isolated from different sources in fermented dairy production and screening of potential starter cultures.

Influence of peeling on volatile and non-volatile compounds responsible for aroma, sensory, and nutrition in ginger (Zingiber officinale).

Industrial use of ginger after peeling results in large amounts of agro-waste. To provide a basic reference for the sustainable processing of ginger products as a spice, we investigated the differences between unpeeled ginger, peeled ginger, and corresponding ginger peel, in terms of aroma, sensory profiles, and nutrition relevant physicochemical properties. The results showed that the total concentrations of identified odor-active compounds in unpeeled ginger, peeled ginger, and ginger peel were 876.56, 672.73, and 105.39 mg/kg, respectively. Unpeeled ginger exhibited more intense citrus-like and fresh impressions compared to peeled ginger, revealed by descriptive sensory analyses. This is relevant to the high odor activity values of odorants such as ß-myrcene (pungent, citrus-like), geranial (citrus-like), citronellal (citrus-like, sourish), and linalool (floral, fresh). In parallel, unpeeled ginger contained higher total polyphenol (84.49 mg/100 g) and total sugar content (33.4 g/kg) in comparison with peeled ginger (76.53 mg/100 g and 28.6 g/kg).

Essential Oils: Useful Tools in Storage-Pest Management.

This study aimed to verify the level of repellent and mortality effect of two chemical substances (DEET and 2-undecanone) and seven essential oils (EOs), Allium sativum, Artemisia annua, Ocimum basilicum, Lavandula angustifolia, Eucalyptus globulus, Pinus sylvestris, and Curcuma longa. The storage pests Tribolium confusum, Tenebrio molitor, and Acanthoscelides obtectus were exposed to various concentrations in an olfactometer-and-mortality test. The effects were recorded 24-48-72 h after the treatments were applied. A. sativum, E. globulus, and L. augustifolia were found to have significant repellence effects. A substantial lethal effect was observed for A. sativum, E. globulus, and O. basilicum. We also found that even if the most efficient EOs were diluted to low concentrations, they still produced repellent and mortality effects. The presented results indicate that A. sativum and O. basilicum were the most effective against T. confusum and T. molitor; simultaneously, L. angustifolia and C. longa showed high activity against A. obtectus. All of these efficient EOs could be applied as effective bio-control agents in various stored conditions.

2-Undecanone Protects against Fine Particle-Induced Kidney Inflammation via Inducing Mitophagy.

Exposure to particulate matter has been associated with diseases of the respiratory and cardiovascular systems. Owing to the dense vasculature of the kidney, it has also been identified as a PM2.5 target organ. A potential contributor to PM2.5-mediated damage may be the promotion of inflammation. The essential oil 2-undecanone (2-methyl nonyl ketone) is an H. cordata isolate, and it has been shown to possess diverse pharmacologic effects, including anti-inflammatory properties. In this study we explored the ability of 2-undecanone to protect against PM2.5-induced kidney inflammation and the exact mechanisms in this process. We found that PM2.5 elevated the levels of certain inflammatory cytokines in BALB/c mice and in HEK 293 cells. Supplementation with 2-undecanone attenuated this PM2.5-induced inflammatory injury. Interestingly, in HEK 293 cells, the PM2.5-associated inflammation was aggravated by the mitophagy inhibitor Medivi-1, while it was attenuated by rapamycin, indicating that the mechanism of 2-undecanone-mediated inhibition of inflammation may relate to mitophagy. Meanwhile, 2-undecanone induces mitophagy in HEK 293 cells by suppressing Akt1-mTOR signaling. These results indicate that PM2.5 can induce kidney inflammation, and mitophagy induced by 2-undecanone may play a protective role against this renal inflammation.

Vapor phase repellency and insecticidal activity of pyridinyl amides against anopheline mosquitoes.

It is important to identify repellents that can provide reliable protection from arthropod biting and prevent arthropod-borne diseases, such as malaria. In the present study, the spatial repellent activity and toxicity of two novel pyridinyl amides (1 and 2) were evaluated against Anopheles albimanus, Anopheles quadrimaculatus, and Anopheles gambiae. In vapor repellency bioassays, compound 2 was generally more effective than DEET and 2-undecanone, while compound 1 was about as active as these standards. Overall, transfluthrin was the most active compound for inducing anopheline mosquito repellency, knockdown, and lethality. Although they were not the most active repellents, the two experimental amides produced the largest electroantennographic responses in female antennae. They also displayed modest toxicity to anopheline mosquitoes. Significant synergism of repellency was observed for the mixture of a pyrethroid-derived acid and the repellent 2-undecanone against anopheline mosquitoes, similar to that observed previously in Aedes aegypti. Overall, this study provides insight for further synthesis of alternative amide compounds for use as spatial treatments.

Reduced effectiveness of repellents in a pyrethroid-resistant strain of Aedes aegypti (Diptera: culicidae) and its correlation with olfactory sensitivity.

BACKGROUND: The mosquito, Aedes aegypti (Diptera: Culicidae), is a vector of dengue fever, zika, chikungunya, and yellow fever viruses, and in many areas possesses significant levels of resistance to pyrethroids. Behavioral performance was assessed in 15, 30, and 60 min exposures in a high throughput vapor phase spatial repellency assay to three contact repellent standards: N,N-diethyl-3-methylbenzamide (DEET), ethyl 3-[acetyl(butyl)amino] propanoate (IR3535), and 2-undecanone, as well as pyrethrum extract, transfluthrin, and metofluthrin in susceptible (Orlando) and a pyrethroid-resistant Puerto Rico strain of Aedes aegypti. Additionally, electroantennographic studies were used to investigate the antennal sensitivities to these compounds in both strains. RESULTS: Resistance was found to all tested insect repellents in the Puerto Rico strain of Ae. aegypti. Resistance ratios at the different time points were about 2 for DEET, 3 for 2-undecanone, and 12 for IR3535. Resistance was also observed to pyrethrum extract (∼9-fold), transfluthrin (∼5-fold), and metofluthrin (∼48-fold) in repellent behavioral response. Electrophysiological analysis found decreased antennal sensitivity to all repellents tested, consistent with their behavioral effects. CONCLUSION: The reduced sensitivity to these repellents may represent a fitness cost arising from the kdr mutation present in Puerto Rico Aedes aegypti. This work highlights the need for understanding collateral effects from the evolution of pesticide resistance in mosquitoes, and the importance of finding alternative strategies to control resistance development. © 2019 Society of Chemical Industry.

Control of Filth Flies, Cochliomyia macellaria (Diptera: Calliphoridae), Musca domestica (Diptera: Muscidae), and Sarcophaga bullata (Diptera: Sarcophagidae), Using Novel Plant-Derived Methyl Ketones.

Filth flies live in close proximity to humans and livestock and transmit pathogens. Current control relies on chemical insecticides, and flies can develop resistance to these insecticides. The public is also interested in natural and safer insecticides. Therefore, alternative pesticides compatible with the synanthropic nature of flies are needed. Four plant aliphatic methyl ketones were evaluated for control of adult house flies, Musca domestica L., blow flies, Cochliomyia macellaria (F.), and gray flesh flies, Sarcophaga bullata (Parker). In sealed petri dish assays, 2-heptanone, 2-octanone, 2-nonanone, and 2-undecanone exhibited fumigant activity against house flies with 24-h LC50s of 6.9, 7.5, 8.0, and 9.2 µg/cm3, respectively. Further research focused on undecanone (a U.S. EPA-registered biopesticide). When tested in larger enclosures at 1.7, 2.3, and 2.8 µg/cm3, undecanone provided 60.4, 82.2, and 94.4% house fly mortality; 56.9, 75.6, and 92.5% flesh fly mortality; and 62.1, 84.5, and 97.9% blow fly mortality, respectively, after a 2-h exposure. In a two-choice behavioral assay with 194.6 µg/cm2 of the test compound on the treatment versus an untreated surface of the same area, the overall mean repellencies for blow flies were 84.7% for undecanone versus 87.6% for N,N-diethyl-meta-toluamide (DEET). For house flies, mean repellencies were 80.7% for undecanone and 84.9% for DEET. The house fly topical LD50 for undecanone was 58.1 µg per fly. Undecanone was far less expensive for filth fly control than the gold standard for insect fumigation, methyl bromide.

Houttuynia cordata Thunb. and its bioactive compound 2-undecanone significantly suppress benzo(a)pyrene-induced lung tumorigenesis by activating the Nrf2-HO-1/NQO-1 signaling pathway.

BACKGROUND: Lung cancer remains the most common cause of cancer-related deaths, with a high incidence and mortality in both sexes worldwide. Chemoprevention has been the most effective strategy for lung cancer prevention. Thus, exploring novel and effective candidate agents with low toxicity for chemoprevention is essential and urgent. Houttuynia cordata Thunb. (Saururaceae) (H. cordata), which is a widely used herbal medicine and is also popularly consumed as a healthy vegetable, exhibits anti-inflammatory, antioxidant and antitumor activity. However, the chemopreventive effect of H. cordata against benzo(a)pyrene (B[a]P)-initiated lung tumorigenesis and the underlying mechanism remain unclear. METHODS: A B[a]P-stimulated lung adenocarcinoma animal model in A/J mice in vivo and a normal lung cell model (BEAS.2B) in vitro were established to investigate the chemopreventive effects of H. cordata and its bioactive compound 2-undecanone against lung tumorigenesis and to clarify the underlying mechanisms. RESULTS: H. cordata and 2-undecanone significantly suppressed B[a]P-induced lung tumorigenesis without causing obvious systemic toxicity in mice in vivo. Moreover, H. cordata and 2-undecanone effectively decreased B[a]P-induced intracellular reactive oxygen species (ROS) overproduction and further notably protected BEAS.2B cells from B[a]P-induced DNA damage and inflammation by significantly inhibiting phosphorylated H2A.X overexpression and interleukin-1ß secretion. In addition, H. cordata and 2-undecanone markedly activated the Nrf2 pathway to induce the expression of the antioxidative enzymes heme oxygenase-1 (HO-1) and NAD(P)H: quinone oxidoreductase 1 (NQO-1). Nrf2 silencing by transfection with Nrf2 siRNA markedly decreased the expression of HO-1 and NQO-1 to diminish the reductions in B[a]P-induced ROS overproduction, DNA damage and inflammation mediated by H. cordata and 2-undecanone. CONCLUSIONS: H. cordata and 2-undecanone could effectively activate the Nrf2-HO-1/NQO-1 signaling pathway to counteract intracellular ROS generation, thereby attenuating DNA damage and inflammation induced by B[a]P stimulation and playing a role in the chemoprevention of B[a]P-induced lung tumorigenesis. These findings provide new insight into the pharmacological action of H. cordata and indicate that H. cordata is a novel candidate agent for the chemoprevention of lung cancer.

Novel use of aliphatic n-methyl ketones as a fumigant and alternative to methyl bromide for insect control.

BACKGROUND: Fumigants like phosphine, methyl bromide and sulfuryl fluoride are highly effective for the control of structural, storage and agricultural arthropod pests. Unfortunately, many of these synthetic compounds are highly toxic to people, many pests have developed resistance to these compounds and methyl bromide, the 'gold standard' for fumigants, was de-registered because of its contribution to depletion of the stratospheric ozone layer. Alternative fumigant chemistry is needed. RESULTS: Several plant species produce n-aliphatic methyl ketones to prevent plant herbivory. To examine the use of methyl ketones as a fumigant, structure-mortality studies were conducted using the red imported fire ant, Solenopsis invicta Buren, as a model. A new easy-to-use, inexpensive and disposable bioassay system was developed for this study. The LC50 values for heptanone, octanone, nonanone and undecanone were 4.27, 5.11, 5.26 and 8.21 µg/cm3 of ambient air, respectively. Although heptanone, octanone and nonanone were more effective than undecanone, subsequent research was conducted with 2-undecanone because this compound already has US Environmental Protection Agency (EPA) registration as a biopesticide. In dose-response field studies, 12.4 mL of undecanone injected into mounds was the lowest application rate that produced no ant activity in the mound with no re-establishment of ants. Reagent grade undecanone was more cost-effective than methyl bromide for fire ants, adult German cockroaches and tobacco budworm eggs, but slightly more expensive for adult flour beetles. CONCLUSION: The naturally occurring methyl ketone undecanone has the potential to be an alternative to current fumigants for a variety of pest applications. © 2017 Society of Chemical Industry.