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1.
Sci Total Environ ; 918: 170562, 2024 Mar 25.
Artículo en Inglés | MEDLINE | ID: mdl-38307293

RESUMEN

The often-overlooked importance of foliar absorption on the plant uptake of organic pollutants was investigated by an exposure chamber test. Rice seedlings were exposed to organophosphate esters (OPEs) through 8 scenarios arranged from 3 major uptake pathways: root uptake via solution, foliar uptake via gas, and foliar uptake via particles, to identify the contributions of these 3 uptake pathways and their influences on the translocation and metabolism of OPEs in rice. The concentration of OPEs in rice tissues showed an "additive effect" with the increase of exposure pathways. OPEs in rice shoots mainly originated from foliar uptake through particle (29.6 %-63.5 %) and gaseous (28.5 %-49.4 %) absorptions rather than root uptake (7.86 %-24.2 %) under the exposure condition. In comparison with stomal absorption, wax layer penetration was the main pathway for most OPEs to enter into leaves, especially for those compounds with high octanol-air partition coefficients. Although the subcellular distributions of OPEs in the rice tissues of the foliar exposure were slightly different from those of the root exposure, hydrophobic OPEs were mainly stored in the cell wall with hydrophilic OPEs mainly in the cytosol. The translocation of OPEs from the exposed tissue to the unexposed tissue were significantly negatively correlated with their octanol-water partition coefficients, but their basipetal translocation were limited. The result suggested that the translocation of OPEs within rice is prioritized over their degradation. This study deepens our understanding of the processes behind OPE uptake by rice and highlights the importance of foliar uptake, especially for those via particle absorption.


Asunto(s)
Contaminantes Ambientales , Retardadores de Llama , Oryza , Oryza/metabolismo , Transporte Biológico , Contaminantes Ambientales/metabolismo , Organofosfatos/metabolismo , Octanoles/metabolismo , Ésteres/metabolismo , Retardadores de Llama/análisis , Monitoreo del Ambiente , China
2.
Environ Toxicol Chem ; 43(1): 42-51, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37818875

RESUMEN

The bioaccumulation behavior, including the uptake, internal distribution, depuration, and biotransformation rates, of three widely used linear methyl-siloxanes was investigated in rainbow trout. Dietary uptake efficiencies of octamethyltrisiloxane (L3), decamethyltetrasiloxane (L4), and dodecamethylpentasiloxane (L5) were 15% (3.3% standard error [SE]), 8.6% (1.4% SE), and 15% (1.8% SE), respectively, and for L3 and L4 were well below those of nonmetabolizable reference chemicals with similar octanol-water partition coefficients, suggesting significant intestinal biotransformation of L3 and L4. Somatic biotransformation rate constants were 0.024 (0.003 SE) day-1 for L3 and 0.0045 (0.0053 SE) day-1 for L4 and could not be determined for L5. Lipid-normalized biomagnification factors for L3, L4, and L5 were 0.24 (0.02 SE), 0.24 (0.01 SE), and 0.62 (0.05 SE) kg-lipid kg-lipid-1 , respectively. Bioconcentration factors standardized to a 5% lipid content fish for water in Canadian oligotrophic lakes with a dissolved organic carbon content of 7.1 mg L-1 were 2787 (354 SE) for L3, 2689 (312 SE) for L4, and 1705 (418 SE) L kg-wet weight-1 , respectively, and 3085 (392 SE) for L3, 4227 (490 SE) for L4, and 3831 (938 SE) L kg-wet weight-1 in water with a dissolved organic carbon content of 2.0 mg L-1 . A comparison of 238 bioaccumulation profiles for 166 different chemicals shows that the bioaccumulation profiles for L3, L4, and L5 are vastly different from those of other very hydrophobic compounds found in the environment. Environ Toxicol Chem 2024;43:42-51. © 2023 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.


Asunto(s)
Oncorhynchus mykiss , Contaminantes Químicos del Agua , Animales , Bioacumulación , Siloxanos/análisis , Siloxanos/metabolismo , Materia Orgánica Disuelta , Canadá , Oncorhynchus mykiss/metabolismo , Contaminantes Químicos del Agua/análisis , Agua/metabolismo , Octanoles/metabolismo
3.
Fungal Biol ; 127(7-8): 1231-1240, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-37495313

RESUMEN

All fungi emit mixtures of volatile organic compounds (VOCs) during growth. The qualitative and quantitative composition of these volatile mixtures vary with the species of fungus, the age of the fungus, and the environmental parameters attending growth. In nature, fungal VOCs are found as combinations of alcohols, aldehydes, acids, ethers, esters, ketones, terpenes, thiols and their derivatives, and are responsible for the characteristic odors associated with molds, mushrooms and yeasts. One of the single most common fungal volatiles is 1-octen-3-ol also known as "mushroom alcohol" or "matsutake alcohol." Many volatiles, including 1-octen-3-ol, serve as communication agents and display biological activity as germination inhibitors, plant growth retardants or promoters, and as semiochemicals ("infochemicals") in interactions with arthropods. Volatiles are understudied and underappreciated elements of the chemical lives of fungi. This review gives a brief introduction to fungal volatiles in hopes of raising awareness of the physiological importance of these gas phase fungal metabolites to encourage mycologists and other biologists to stop "throwing away the head space."


Asunto(s)
Compuestos Orgánicos Volátiles , Octanoles/metabolismo , Cetonas
4.
J Biol Chem ; 298(11): 102507, 2022 11.
Artículo en Inglés | MEDLINE | ID: mdl-36122804

RESUMEN

1-Octen-3-ol is a volatile oxylipin found ubiquitously in Basidiomycota and Ascomycota. The biosynthetic pathway forming 1-octen-3-ol from linoleic acid via the linoleic acid 10(S)-hydroperoxide was characterized 40 years ago in mushrooms, yet the enzymes involved are not identified. The dioxygenase 1 and 2 genes (Ccdox1 and Ccdox2) in the mushroom Coprinopsis cinerea contain an N-terminal cyclooxygenase-like heme peroxidase domain and a C-terminal cytochrome P450-related domain. Herein, we show that recombinant CcDOX1 is responsible for dioxygenation of linoleic acid to form the 10(S)-hydroperoxide, the first step in 1-octen-3-ol synthesis, whereas CcDOX2 conceivably forms linoleic acid 8-hydroperoxide. We demonstrate that KO of the Ccdox1 gene suppressed 1-octen-3-ol synthesis, although added linoleic acid 10(S)-hydroperoxide was still efficiently converted. The P450-related domain of CcDOX1 lacks the characteristic Cys heme ligand and the evidence indicates that a second uncharacterized enzyme converts the 10(S)-hydroperoxide to 1-octen-3-ol. Additionally, we determined the gene KO strain (ΔCcdox1) was less attractive to fruit fly larvae, while the feeding behavior of fungus gnats on ΔCcdox1 mycelia showed little difference from that on the mycelia of the WT strain. The proliferation of fungivorous nematodes on ΔCcdox1 mycelia was similar to or slightly worse than that on WT mycelia. Thus, 1-octen-3-ol seems to be an attractive compound involved in emitter-receiver ecological communication in mushrooms.


Asunto(s)
Agaricales , Dioxigenasas , Oxigenasas/metabolismo , Ácido Linoleico , Peróxido de Hidrógeno , Dioxigenasas/genética , Octanoles/metabolismo , Agaricales/genética , Agaricales/metabolismo , Etanol , Hemo
5.
Environ Microbiol Rep ; 14(6): 934-946, 2022 12.
Artículo en Inglés | MEDLINE | ID: mdl-35651318

RESUMEN

The extensive use of petrochemicals has produced serious environmental pollution problems; fortunately, bioremediation is considered an efficient way to fight against pollution. In line with Synthetic Biology is that robust microbial chassis with an expanded ability to remove environmental pollutants are desirable. Pseudomonas putida KT2440 is a robust lab microbe that has preserved the ability to survive in the environment and is the natural host for the self-transmissible TOL plasmid, which allows metabolism of toluene and xylenes to central metabolism. We show that the P. putida KT2440 (pWW0) acquired the ability to use octane as the sole C-source after acquisition of an almost 62-kb ICE from a microbial community that harbours an incomplete set of octane metabolism genes. The ICE bears genes for an alkane monooxygenase, a PQQ-dependent alcohol dehydrogenase and aldehyde dehydrogenase but lacks the electron donor enzymes required for the monooxygenase to operate. Host rubredoxin and rubredoxin reductase allow metabolism of octane to octanol. Proteomic assays and mutants unable to grow on octane or octanoic acid revealed that metabolism of octane is mediated by redundant host and ICE enzymes. Octane is oxidized to octanol, octanal and octanoic acid, the latter is subsequently acylated and oxidized to yield acetyl-CoA that is assimilated via the glyoxylate shunt; in fact, a knockout mutant in the aceA gene, encoding isocitrate lyase was unable to grow on octane or octanoic acid.


Asunto(s)
Pseudomonas putida , Pseudomonas putida/metabolismo , Proteómica , Octanos/metabolismo , Oxigenasas de Función Mixta/metabolismo , Octanoles/metabolismo
6.
Biomolecules ; 11(4)2021 04 08.
Artículo en Inglés | MEDLINE | ID: mdl-33917773

RESUMEN

Olfaction is orchestrated at different stages and involves various proteins at each step. For example, odorant-binding proteins (OBPs) are soluble proteins found in sensillum lymph that might encounter odorants before reaching the odorant receptors. In tsetse flies, the function of OBPs in olfaction is less understood. Here, we investigated the role of OBPs in Glossina fuscipes fuscipes olfaction, the main vector of sleeping sickness, using multidisciplinary approaches. Our tissue expression study demonstrated that GffLush was conserved in legs and antenna in both sexes, whereas GffObp44 and GffObp69 were expressed in the legs but absent in the antenna. GffObp99 was absent in the female antenna but expressed in the male antenna. Short odorant exposure induced a fast alteration in the transcription of OBP genes. Furthermore, we successfully silenced a specific OBP expressed in the antenna via dsRNAi feeding to decipher its function. We found that silencing OBPs that interact with 1-octen-3-ol significantly abolished flies' attraction to 1-octen-3-ol, a known attractant for tsetse fly. However, OBPs that demonstrated a weak interaction with 1-octen-3-ol did not affect the behavioral response, even though it was successfully silenced. Thus, OBPs' selective interaction with ligands, their expression in the antenna and their significant impact on behavior when silenced demonstrated their direct involvement in olfaction.


Asunto(s)
Comunicación Animal , Proteínas de Insectos/metabolismo , Receptores Odorantes/metabolismo , Moscas Tse-Tse/fisiología , Secuencia de Aminoácidos , Animales , Antenas de Artrópodos/metabolismo , Sitios de Unión , Femenino , Proteínas de Insectos/antagonistas & inhibidores , Proteínas de Insectos/genética , Masculino , Simulación del Acoplamiento Molecular , Simulación de Dinámica Molecular , Octanoles/química , Octanoles/metabolismo , Interferencia de ARN , ARN Interferente Pequeño/metabolismo , Receptores Odorantes/antagonistas & inhibidores , Receptores Odorantes/genética , Alineación de Secuencia
7.
J Chem Ecol ; 47(4-5): 351-393, 2021 May.
Artículo en Inglés | MEDLINE | ID: mdl-33725235

RESUMEN

Vector control and personal protection against anthropophilic mosquitoes mainly rely on the use of insecticides and repellents. The search for mosquito-attractive semiochemicals has been the subject of intense studies for decades, and new compounds or odor blends are regularly proposed as lures for odor-baited traps. We present a comprehensive and up-to-date review of all the studies that have evaluated the attractiveness of volatiles to mosquitoes, including individual chemical compounds, synthetic blends of compounds, or natural host or plant odors. A total of 388 studies were analysed, and our survey highlights the existence of 105 attractants (77 volatile compounds, 17 organism odors, and 11 synthetic blends) that have been proved effective in attracting one or several mosquito species. The exhaustive list of these attractants is presented in various tables, while the most common mosquito attractants - for which effective attractiveness has been demonstrated in numerous studies - are discussed throughout the text. The increasing knowledge on compounds attractive to mosquitoes may now serve as the basis for complementary vector control strategies, such as those involving lure-and-kill traps, or the development of mass trapping. This review also points out the necessity of further improving the search for new volatile attractants, such as new compound blends in specific ratios, considering that mosquito attraction to odors may vary over the life of the mosquito or among species. Finally, the use of mosquito attractants will undoubtedly have an increasingly important role to play in future integrated vector management programs.


Asunto(s)
Culicidae/química , Feromonas/química , Compuestos Orgánicos Volátiles/química , Amoníaco/química , Amoníaco/metabolismo , Animales , Dióxido de Carbono/química , Dióxido de Carbono/metabolismo , Culicidae/metabolismo , Femenino , Interacciones Huésped-Parásitos , Humanos , Ácido Láctico/química , Ácido Láctico/metabolismo , Masculino , Control de Mosquitos , Octanoles/química , Octanoles/metabolismo , Odorantes , Feromonas/metabolismo , Extractos Vegetales/química , Plantas/química , Compuestos Orgánicos Volátiles/metabolismo
8.
Annu Rev Microbiol ; 74: 101-116, 2020 09 08.
Artículo en Inglés | MEDLINE | ID: mdl-32905756

RESUMEN

Many volatile organic compounds (VOCs) associated with industry cause adverse health effects, but less is known about the physiological effects of biologically produced volatiles. This review focuses on the VOCs emitted by fungi, which often have characteristic moldy or "mushroomy" odors. One of the most common fungal VOCs, 1-octen-3-ol, is a semiochemical for many arthropod species and also serves as a developmental hormone for several fungal groups. Other fungal VOCs are flavor components of foods and spirits or are assayed in indirect methods for detecting the presence of mold in stored agricultural produce and water-damaged buildings. Fungal VOCs function as antibiotics as well as defense and plant-growth-promoting agents and have been implicated in a controversial medical condition known as sick building syndrome. In this review, we draw attention to the ubiquity, diversity, and toxicological significance of fungal VOCs as well as some of their ecological roles.


Asunto(s)
Hongos/fisiología , Odorantes , Olfato , Compuestos Orgánicos Volátiles/metabolismo , Octanoles/metabolismo , Plantas/microbiología , Compuestos Orgánicos Volátiles/análisis
9.
J Biosci Bioeng ; 130(5): 489-495, 2020 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-32753307

RESUMEN

1-Octen-3-ol is a major aroma component of awamori, a traditional distilled liquor produced in Okinawa Prefecture, Japan. As 1-octen-3-ol is thought to affect the sensory properties of awamori, it is important to fully characterize the compound's biosynthetic pathway and control mechanism. We previously reported that the fatty acid oxygenase ppoC (ppo: psi-produced oxygenase) of Aspergillus luchuensis is directly involved in the production of 1-octen-3-ol in rice koji (Kataoka et al., J. Biosci. Bioeng., 129, 192-198, 2020). In the present study, we constructed A. luchuensis ppoD disruptants to characterize the role of ppo genes in 1-octen-3-ol biosynthesis. A small-scale awamori fermentation test was performed using ppoA, ppoC, and ppoD single disruptants (ΔppoA, ΔppoC, and ΔppoD, respectively), along with the parent strain, ΔligD. 1-Octen-3-ol was not detected in the distillate prepared using the ΔppoC strain. We conclude that A. luchuensis ppoC is the only 1-octen-3-ol-producing factor in the awamori brewing process. Because ΔppoA and ΔppoD slightly enhanced 1-octen-3-ol productivity, these two genes may play a role in negatively controlling 1-octen-3-ol biosynthesis.


Asunto(s)
Bebidas Alcohólicas/microbiología , Aspergillus/metabolismo , Ácidos Grasos/metabolismo , Fermentación , Octanoles/metabolismo , Oxigenasas/genética , Oxigenasas/metabolismo , Aspergillus/genética , Biotecnología , Odorantes , Oryza/genética , Oryza/metabolismo , Oxidación-Reducción
10.
Food Microbiol ; 91: 103502, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32539966

RESUMEN

Myxobacteria have excellent biocontrol activity against various phytopathogens due to their rich spectrum of secondary metabolites and active predatory characteristics. In this study, the mycelial growth of Fusarium oxysporum f. sp. cucumerinum (FOC) was found to be significantly inhibited by volatile compounds (VOCs) produced by Corallococcus sp. EGB. A total of 32 compounds were identified among the VOCs produced by strain EGB, of which isooctanol exhibited the highest antifungal activity, with dosages of 3.75 and 4.0 µL/plate being sufficient to suppress FOC and Penicillum digitatum, respectively. Isooctanol was found to damage the cell wall and cell membranes of FOC and P. digitatum. Apoptosis-like cell death of FOC and P. digitatum induced by isooctanol was observed subsequently due to the accumulation of reactive oxygen species (ROS). The transcription level of genes related to cell wall integrity (CWI) pathway and redox reactions were significantly upregulated by 15- to 40-fold, indicating the stress caused by isooctanol. Postharvest storage experiments showed that the disease severity of post-harvest oranges infected with P. digitatum could be significantly reduced by isooctanol at 114.2 µL/L.


Asunto(s)
Antifúngicos/farmacología , Myxococcales/metabolismo , Compuestos Orgánicos Volátiles/farmacología , Antifúngicos/metabolismo , Pared Celular/efectos de los fármacos , Pared Celular/metabolismo , Citrus sinensis/microbiología , Almacenamiento de Alimentos , Fusarium/efectos de los fármacos , Fusarium/crecimiento & desarrollo , Fusarium/metabolismo , Viabilidad Microbiana/efectos de los fármacos , Micelio/efectos de los fármacos , Micelio/crecimiento & desarrollo , Micelio/metabolismo , Octanoles/metabolismo , Octanoles/farmacología , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Especies Reactivas de Oxígeno/metabolismo , Compuestos Orgánicos Volátiles/metabolismo
11.
J Microbiol Biotechnol ; 30(2): 296-305, 2020 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-32120462

RESUMEN

Tricholoma matsutake is an ectomycorrhizal fungus, related with the host of Pinus densiflora. Most of studies on T. matsutake have focused on mycelial growth, genes and genomics, phylogenetics, symbiosis, and immune activity of this strain. T. matsutake is known for its unique fragrance in Eastern Asia. The most major component of its scent is (R)-(-)-1-octen-3-ol and is biosynthesized from the substrate linoleic acid by the sequential reaction of lipoxygenase and peroxide lyase. Here, we report for the first time the biosynthesis of (R)-(-)- 1-octen-3-ol of T. matsutake using the yeast Saccharomyces cerevisiae as a host. In this study, cDNA genes correlated with these reactions were cloned from T. matsutake, and expression studies of theses genes were carried out in the yeast Saccharomyces cerevisiae. The product of these genes expression study was carried out with Western blotting. The biosynthesis of (R)-(-)- 1-octen-3-ol of T. matsutake in recombinant Saccharomyces cerevisiae was subsequently identified with GC-MS chromatography analysis. The biosynthesis of (R)-(-)-1-octen-3-ol with S. cerevisiae represents a significant step forward.


Asunto(s)
Aldehído-Liasas/genética , Sistema Enzimático del Citocromo P-450/genética , Expresión Génica , Lipooxigenasa/genética , Octanoles/metabolismo , Saccharomyces cerevisiae/metabolismo , Tricholoma/enzimología , Tricholoma/genética , Clonación Molecular , Fermentación , Isoenzimas , Proteínas Recombinantes , Temperatura , Transformación Genética
12.
J Biosci Bioeng ; 129(2): 192-198, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31585859

RESUMEN

Awamori is a distilled spirit produced in Okinawa Prefecture, in southern Japan. Awamori contains the volatile organic compound 1-octen-3-ol, an important flavor component. Here, using solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GCMS), we demonstrate that the black koji mold Aspergillus luchuensis produces 1-octen-3-ol in rice koji. To examine the role of the fatty acid oxygenase genes ppoA and ppoC in 1-octen-3-ol biosynthesis by A. luchuensis, we constructed ppoA and ppoC disruptants, ΔppoA and ΔppoC, respectively, via protoplast-PEG transformation. No clear differences in growth and conidiation were observed between the transformants and the parent strain. Volatile compounds in rice koji prepared using these gene disruptants were analyzed by SPME-GCMS. The amount of 1-octen-3-ol contained in koji produced by the ΔppoA strain was the same as that produced by the parental strain. In contrast, although the ΔppoC strain grew on the rice koji, 1-octen-3-ol was not detected. These results indicate that ppoC is involved in 1-octen-3-ol biosynthesis in A. luchuensis.


Asunto(s)
Aspergillus/metabolismo , Octanoles/metabolismo , Oxigenasas/metabolismo , Aspergillus/genética , Ácidos Grasos/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Oryza/microbiología , Oxigenasas/genética , Microextracción en Fase Sólida
13.
Proc Natl Acad Sci U S A ; 116(28): 14300-14308, 2019 07 09.
Artículo en Inglés | MEDLINE | ID: mdl-31221757

RESUMEN

Tsetse flies transmit trypanosomiasis to humans and livestock across much of sub-Saharan Africa. Tsetse are attracted by olfactory cues emanating from their hosts. However, remarkably little is known about the cellular basis of olfaction in tsetse. We have carried out a systematic physiological analysis of the Glossina morsitans antenna. We identify 7 functional classes of olfactory sensilla that respond to human or animal odorants, CO2, sex and alarm pheromones, or other odorants known to attract or repel tsetse. Sensilla differ in their response spectra, show both excitatory and inhibitory responses, and exhibit different response dynamics to different odor stimuli. We find striking differences between the functional organization of the tsetse fly antenna and that of the fruit fly Drosophila melanogaster One morphological type of sensilla has a different function in the 2 species: Trichoid sensilla respond to pheromones in Drosophila but respond to a wide diversity of compounds in G. morsitans. In contrast to Drosophila, all tested G. morsitans sensilla that show excitatory responses are excited by one odorant, 1-octen-3-ol, which is contained in host emanations. The response profiles of some classes of sensilla are distinct but strongly correlated, unlike the organization described in the Drosophila antenna. Taken together, this study defines elements that likely mediate the attraction of tsetse to its hosts and that might be manipulated as a means of controlling the fly and the diseases it transmits.


Asunto(s)
Octanoles/metabolismo , Odorantes/análisis , Atractivos Sexuales/genética , Olfato/genética , Moscas Tse-Tse/fisiología , Animales , Antenas de Artrópodos/metabolismo , Antenas de Artrópodos/fisiología , Dióxido de Carbono/química , Dióxido de Carbono/metabolismo , Drosophila melanogaster/genética , Drosophila melanogaster/fisiología , Humanos , Octanoles/química , Sensilos/química , Sensilos/metabolismo , Atractivos Sexuales/metabolismo , Olfato/fisiología , Tripanosomiasis/genética , Tripanosomiasis/transmisión , Moscas Tse-Tse/genética
14.
J Ind Microbiol Biotechnol ; 46(7): 977-991, 2019 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-30923972

RESUMEN

Inhibition of spore germination offers an attractive and effective target for controlling fungal species involved in food spoilage. Mushroom alcohol (1-octen-3-ol) functions as a natural self-inhibitor of spore germination for many fungi and, therefore, provides a useful tool for probing the molecular events controlling the early stages of fungal growth. In Penicillium spp., the R and S enantiomers of 1-octen-3-ol delayed spore germination and sporulation in four species of Penicillium involved in soils of fruit and grains, but to different degrees. Because of its well-annotated genome, we used Penicillium chrysogenum to perform a comprehensive comparative transcriptomic analysis of cultures treated with the two enantiomers. Altogether, about 80% of the high-quality reads could be mapped to 11,396 genes in the reference genome. The top three active pathways were metabolic (978 transcripts), biosynthesis of secondary metabolites (420 transcripts), and microbial metabolism in diverse environments (318 transcripts). When compared to the control, treatment with (R)-(-)-1-octen-3-ol affected the transcription levels of 91 genes, while (S)-(+)-1-octen-3-ol affected only 41 genes. Most of the affected transcripts were annotated and predicted to be involved in transport, establishment of localization, and transmembrane transport. Alternative splicing and SNPs' analyses indicated that, compared to the control, the R enantiomer had greater effects on the gene expression pattern of Penicillium chrysogenum than the S enantiomer. A qRT-PCR analysis of 28 randomly selected differentially expressed genes confirmed the transcriptome data. The transcriptomic data have been deposited in NCBI SRA under the accession number SRX1065226.


Asunto(s)
Octanoles/metabolismo , Penicillium chrysogenum/metabolismo , Expresión Génica , Octanoles/química , Penicillium/efectos de los fármacos , Penicillium chrysogenum/genética , Estereoisomerismo , Transcriptoma
15.
BMC Plant Biol ; 19(1): 37, 2019 Jan 22.
Artículo en Inglés | MEDLINE | ID: mdl-30669983

RESUMEN

BACKGROUND: Short chain oxylipins in plants as the main volatile organic carbon have been speculated to playing an important role for plant innate immunity, however, not yet intensively studied and far away established as the fully recognized algae defense signals. RESULTS: The production of 1-octen-3-ol is self-amplified via the fatty acid-oxylipin metabolic cycle through positive feedback loop. Production of 1-octen-3-ol may act as a messenger that induces P. haitanensis to be in a "primed" state and ready for defense by upregulating the synthesis of methyl jasmonic acid, indole-3-acetic acid, and gibberellin A3. Production of these oxylipins also adjust the redox state in cells, resulting in host defense activation. CONCLUSIONS: We provide the first demonstration that 1-octen-3-ol from P. haitanensis, can act as a self-stimulating community messenger. The multiple effects of 1-octen-3-ol may explain why P. haitanensis, a very ancient lineage within plant kingdom, thrives in the niche of intertidal zones.


Asunto(s)
Octanoles/metabolismo , Oxilipinas/metabolismo , Rhodophyta/metabolismo , Transducción de Señal , Bacterias/metabolismo , Ácidos Grasos no Esterificados/metabolismo , Expresión Génica , Metabolismo de los Lípidos , Lipooxigenasa/genética , Lipooxigenasa/metabolismo , Oxidación-Reducción , Fosfolipasas/metabolismo , Rhodophyta/genética , Rhodophyta/inmunología , Rhodophyta/microbiología
16.
J Insect Physiol ; 107: 144-151, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29559304

RESUMEN

Action potentials from individual cells were recorded from antennae (funiculi) of living tsetse flies, Glossina p. palpalis and Glossina f. fuscipes using a "surface-contact" recording technique. Stimuli were vapours of 1-octen-3-ol, acetone and 3-methylphenol. Of the 101 and 128 olfactory cells tested for their sensitivity to odour stimuli in G. p. palpalis and G. f. fuscipes, respectively, the majority (83 and 77%) were activated by more than one chemical. The numbers of these "generalist" cells were 20 and 15% higher in females than in males. Response intensity increased with increasing odour dose. Temporal patterns of excitation were phasic-tonic and showed cells with relatively rapid cessation of spike activity after the end of stimulation and cells which continued firing for several seconds or even minutes after stimulation. Inhibition by odours only occurred in a minority of cells and was dose-dependent. For each of the three substances the excitatory response was significantly higher in G. f. fuscipes than in G. p. palpalis, whereas no significant differences between inhibitory responses were found. In G. f. fuscipes each stimulus evoked equal excitatory responses. In G. p. palpalis, however, acetone induced significantly higher responses than 1-octen-3-ol and 3-methylphenol. Response intensities to each of the three chemicals did not differ between male and female G. p. palpalis, whereas in G. f. fuscipes 1-octen-3-ol evoked significantly higher responses in males. Possible mechanisms of receptor cell odour coding and behavioural effects of the various cell type activities are discussed.


Asunto(s)
Acetona/metabolismo , Quimiotaxis , Cresoles/metabolismo , Octanoles/metabolismo , Odorantes/análisis , Moscas Tse-Tse/fisiología , Potenciales de Acción/fisiología , Animales , Antenas de Artrópodos/fisiología , Femenino , Masculino , Receptores Odorantes/fisiología , Especificidad de la Especie
17.
Nat Protoc ; 13(5): 856-874, 2018 05.
Artículo en Inglés | MEDLINE | ID: mdl-29599442

RESUMEN

In this protocol, we describe a recently developed on-chip microfluidic method to form monodisperse, cell-sized, unilamellar, and biocompatible liposomes with excellent encapsulation efficiency. Termed octanol-assisted liposome assembly (OLA), it resembles bubble-blowing on a microscopic scale. Hydrodynamic flow focusing of two immiscible fluid streams (an aqueous phase and a lipid-containing 1-octanol phase) by orthogonal outer aqueous streams gives rise to double-emulsion droplets. As the lipid bilayer assembles along the interface, each emulsion droplet quickly evolves into a liposome and a 1-octanol droplet. OLA has several advantages as compared with other on-chip techniques, such as a very fast liposome maturation time (a few minutes), a relatively straightforward and completely on-chip setup, and a biologically relevant liposome size range (5-20 µm). Owing to the entire approach being on-chip, OLA enables high-throughput liposome production (typical rate of tens of Hz) using low sample volumes (∼10 µl). For prolonged on-chip experimentation, liposomes are subsequently purified by removing the 1-octanol droplets. For device fabrication, a reusable silicon template is produced in a clean room facility using electron-beam lithography followed by dry reactive ion etching, which takes ∼3 h. The patterned silicon template is used to prepare polydimethylsiloxane (PDMS)-based microfluidic devices in the wet lab, followed by a crucial surface treatment; the whole process takes ∼2 d. Liposomes can be produced in ∼1 h and further manipulated, depending on the experimental setup. OLA offers an ideal microfluidic platform for diverse bottom-up biotechnology studies by enabling creation of synthetic cells, microreactors and bioactive cargo delivery systems, and also has potential as an analytical tool.


Asunto(s)
Dispositivos Laboratorio en un Chip , Liposomas/síntesis química , Microfluídica/métodos , Microfluídica/instrumentación , Octanoles/metabolismo , Agua/metabolismo
18.
J Biosci Bioeng ; 125(2): 218-223, 2018 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-28916301

RESUMEN

Monoterpene alcohols (MTAs) are characteristic flavour-imparting compounds in sweet potato shochu (Japanese distilled spirit) that are liberated following hydrolysis by specific enzymes during fermentation. In the present study, we evaluated the effect of an exogenously added diglycoside-specific ß-glycosidase (ß-primeverosidase) on aroma formation during shochu brewing using various sweet potato species to address whether MTAs are predominantly present as diglycosidic precursors in raw materials. The results showed that the amount of MTAs produced from enzyme-treated mash was dramatically increased by 2- to 9-fold compared with untreated controls, and the increase varied with sweet potato species. In addition, levels of methyl salicylate, 1-octene-3-ol and ethyl benzoate were also elevated by enzyme treatment. These results indicate that a large amount of MTAs and other volatile aroma compounds are stored in the form of disaccharide ß-glycosides such as ß-primeverosides in sweet potato. This enzyme may therefore be useful for controlling aroma formation during shochu manufacturing, and may ultimately contribute to diversifying shochu quality.


Asunto(s)
Bebidas Alcohólicas/análisis , Alcoholes/metabolismo , Fermentación , Glicósido Hidrolasas/metabolismo , Glicósidos/metabolismo , Ipomoea batatas/metabolismo , Monoterpenos/metabolismo , Benzoatos/metabolismo , Disacáridos/metabolismo , Aromatizantes/metabolismo , Hidrólisis , Ipomoea batatas/enzimología , Octanoles/metabolismo , Odorantes/análisis , Salicilatos/metabolismo
19.
J Pharm Sci ; 107(2): 727-738, 2018 02.
Artículo en Inglés | MEDLINE | ID: mdl-28818392

RESUMEN

Partition coefficients between human stratum corneum lipids and water (Ksclip/w) are collected or deduced from a variety of sources in a manner that approximately doubles the available data compared to the current state-of-the-art model (Hansen et al., Adv Drug Deliv Rev. 2013;65(2):251-264). An additional datum for water itself in porcine SC that considerably extends the molecular size and lipophilicity range of the data set is considered. The data are analyzed in terms of an extended linear free energy relationship involving octanol/water partition coefficients, Abraham solvation parameters, and a secondary, power law molecular weight dependence. The optimum fit to log Ksclip/w for the full data set reduces the standard error of prediction from 0.50 for a Hansen-like model to 0.39; corresponding multiplicative errors in Ksclip/w are reduced from a factor of 3.1 to one of 2.5. The difference in performance is driven by the water datum, which requires a more complex dependence on molecular size than that afforded by Abraham parameters. In the absence of the water value, the Hansen-like model, which does not include a dependence on molecular size, is essentially optimum. A comparison is presented to fluid-phase phospholipid-water systems, which have a demonstrably different structure-property relationship.


Asunto(s)
Fosfolípidos/metabolismo , Absorción Cutánea/fisiología , Piel/metabolismo , Agua/metabolismo , Humanos , Octanoles/metabolismo , Tamaño de la Partícula
20.
J Chem Ecol ; 43(7): 662-669, 2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28674827

RESUMEN

Culicoides biting midges (Diptera: Ceratopognidae) cause pain and distress through blood feeding, and transmit viruses that threaten both animal and human health worldwide. There are few effective tools for monitoring and control of biting midges, with semiochemical-based strategies offering the advantage of targeting host-seeking populations. In previous studies, we identified the host preference of multiple Culicoides species, including Culicoides impunctatus, as well as cattle-derived compounds that modulate the behavioral responses of C. nubeculosus under laboratory conditions. Here, we test the efficacy of these compounds, when released at different rates, in attracting C. impunctatus under field conditions in Southern Sweden. Traps releasing 1-octen-3-ol, decanal, phenol, 4-methylphenol or 3-propylphenol, when combined with carbon dioxide (CO2), captured significantly higher numbers of C. impunctatus compared to control traps baited with CO2 alone, with low release rates (0.1 mg h-1, 1 mg h-1) being generally more attractive. In contrast, traps releasing octanal or (E)-2-nonenal at 1 mg h-1 and 10 mg h-1 collected significantly lower numbers of C. impunctatus than control traps baited with CO2 only. Nonanal and 2-ethylhexanol did not affect the attraction of C. impunctatus when compared to CO2 alone at any of the release rates tested. The potential use of these semiochemicals as attractants and repellents for biting midge control is discussed.


Asunto(s)
Ceratopogonidae/efectos de los fármacos , Control de Insectos/métodos , Aldehídos/metabolismo , Animales , Dióxido de Carbono/metabolismo , Bovinos , Ceratopogonidae/fisiología , Cresoles/metabolismo , Diseño de Equipo , Humanos , Control de Insectos/instrumentación , Octanoles/metabolismo , Fenol/metabolismo , Fenoles/metabolismo , Feromonas/metabolismo
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