Journal articles on the topic 'Y-lactones'

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1

Burger, B. V., and P. J. Pretorius. "Notes: Mammalian Pheromone Studies, VI. Compounds from the Preorbital Gland of the Blue Duiker, Cephalophus monticola." Zeitschrift für Naturforschung C 42, no. 11-12 (December 1, 1987): 1355–57. http://dx.doi.org/10.1515/znc-1987-11-1238.

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Forty five volatile compounds, mostly straight- and branched-chain alcohols and ketones, as well as derivatives of two of these alcohols, two y-lactones, an aromatic thiol ester and other simple aromatic compounds, have been identified in the preorbital secretion of the blue duiker, Cephalophus monticola.
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2

Yates, Edwin A., Bodo Philipp, Catherine Buckley, Steve Atkinson, Siri Ram Chhabra, R. Elizabeth Sockett, Morris Goldner, et al. "N-Acylhomoserine Lactones Undergo Lactonolysis in a pH-, Temperature-, and Acyl Chain Length-Dependent Manner during Growth of Yersinia pseudotuberculosis and Pseudomonas aeruginosa." Infection and Immunity 70, no. 10 (October 2002): 5635–46. http://dx.doi.org/10.1128/iai.70.10.5635-5646.2002.

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ABSTRACT In gram-negative bacterial pathogens, such as Pseudomonas aeruginosa and Yersinia pseudotuberculosis, cell-to-cell communication via the N-acylhomoserine lactone (AHL) signal molecules is involved in the cell population density-dependent control of genes associated with virulence. This phenomenon, termed quorum sensing, relies upon the accumulation of AHLs to a threshold concentration at which target structural genes are activated. By using biosensors capable of detecting a range of AHLs we observed that, in cultures of Y. pseudotuberculosis and P. aeruginosa, AHLs accumulate during the exponential phase but largely disappear during the stationary phase. When added to late-stationary-phase, cell-free culture supernatants of the respective pathogen, the major P. aeruginosa [N-butanoylhomoserine lactone (C4-HSL) and N-(3-oxododecanoyl)homoserine lactone (3-oxo-C12-HSL)] and Y. pseudotuberculosis [N-(3-oxohexanoyl)homoserine lactone (3-oxo-C6-HSL) and N-hexanoylhomoserine lactone (C6-HSL)] AHLs were inactivated. Short-acyl-chain compounds (e.g., C4-HSL) were turned over more extensively than long-chain molecules (e.g., 3-oxo-C12-HSL). Little AHL inactivation occurred with cell extracts, and no evidence for inactivation by specific enzymes was apparent. This AHL turnover was discovered to be due to pH-dependent lactonolysis. By acidifying the growth media to pH 2.0, lactonolysis could be reversed. By using carbon-13 nuclear magnetic resonance spectroscopy, we found that the ring opening of homoserine lactone (HSL), N-propionyl HSL (C3-HSL), and C4-HSL increased as pH increased but diminished as the N-acyl chain was lengthened. At low pH levels, the lactone rings closed but not via a simple reversal of the ring opening reaction mechanism. Ring opening of C4-HSL, C6-HSL, 3-oxo-C6-HSL, and N-octanoylhomoserine lactone (C8-HSL), as determined by the reduction of pH in aqueous solutions with time, was also less rapid for AHLs with more electron-donating longer side chains. Raising the temperature from 22 to 37°C increased the rate of ring opening. Taken together, these data show that (i) to be functional under physiological conditions in mammalian tissue fluids, AHLs require an N-acyl side chain of at least four carbons in length and (ii) that the longer the acyl side chain the more stable the AHL signal molecule.
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3

Loboiko, Yu V., Ye O. Barylo, and B. S. Barylo. "Assessment of macrocyclic lacton group products for ectoparasitosis of carp." Scientific Messenger of LNU of Veterinary Medicine and Biotechnologies 22, no. 98 (August 22, 2020): 16–21. http://dx.doi.org/10.32718/nvlvet9803.

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The material for the study were Lubin carp of one year old spontaneously invaded by the ectoparasites Lernaea cyprinacea and Dactylogyrus vastator. For the experiment we used drugs: "Brovermectin-granulate" (development of “BFP” serial production; 1 g of the preparation contains: active substance (ADR) ivermectin – 3.5 mg; tocopherol acetate (20 mg) and Emamectin benzoate (manufactured by King Quenson Industry Group; 1 g of preparation contains ADR emamectin benzoate (50 mg). Analyzing morphological, biochemical and immunological parameters of blood and organs of fish, it is possible to state that the fact that the anti-parasitic drugs “Brovermectin granulate” and “Emamectin benzoate” has a pronounced antiparasitic effect, normalizing the homeostasis of the body. The results obtained showed significant fluctuations in the number neutrophils, eosinophils and lymphocytes. In ectoparasites infested of fishes used for macrocyclic lactones, y leukocyte formula sharply increases the percentage of rod-shaped neutrophils and at the same time decreases the proportion of lymphocytes. At the same time, there is an increase in the number of eosinophils that perform the function of protecting the body of fish from parasites. Eosinophilia, as in the higher vertebrates, is one of objective indicators of allergy (sensitization) of the body, nature the course of inflammatory processes. The results obtained indicate a decrease in the production of total T-lymphocytes are cells that play a key role in the immune system protection in the body of carp for damage by ectoparasites. In analyzing the above data, attention is drawn to the lower functional the activity of the blood T-lymphocyte system in ectoparasites infested with fish, than those given antiparasitic drugs. From this it follows that the ability of the blood lymphocytes of the fish to which the drugs from the group were given of macrocyclic lactones, before pathogen binding and production of antigens the antibodies that neutralize them are much higher than the fish affected ectoparasites. The immune system in fish provides self-regulation through direct contact of cells (macrophages, neutrophils, cytotoxic T-lymphocytes) as well as due to humoral factors (lysozyme, complement). The use of drugs from the group of macrocyclic lactones promotes the release of infested fish from ectoparasites with the following normalization of their life, increase of immune status and resistance.
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4

Gutenberger, Guido, Siegfried Blechert, and Eberhard Steckhan. "ChemInform Abstract: α-Cyano-y-lactones by Photoinduced Electron Transfer-Catalyzed Oxidation of α-Hydroxyalkylsilanes in the Presence of α-Cyano Acrylates." ChemInform 31, no. 17 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200017109.

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5

Dyszel, Jessica L., Jenee N. Smith, Darren E. Lucas, Jitesh A. Soares, Matthew C. Swearingen, Mathew A. Vross, Glenn M. Young, and Brian M. M. Ahmer. "Salmonella enterica Serovar Typhimurium Can Detect Acyl Homoserine Lactone Production by Yersinia enterocolitica in Mice." Journal of Bacteriology 192, no. 1 (October 9, 2009): 29–37. http://dx.doi.org/10.1128/jb.01139-09.

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ABSTRACT LuxR-type transcription factors detect acyl homoserine lactones (AHLs) and are typically used by bacteria to determine the population density of their own species. Escherichia coli and Salmonella enterica serovar Typhimurium cannot synthesize AHLs but can detect the AHLs produced by other bacterial species using the LuxR homolog, SdiA. Previously we determined that S. Typhimurium did not detect AHLs during transit through the gastrointestinal tract of a guinea pig, a rabbit, a cow, 5 mice, 6 pigs, or 12 chickens. However, SdiA was activated during transit through turtles colonized by Aeromonas hydrophila, leading to the hypothesis that SdiA is used for detecting the AHL production of other pathogens. In this report, we determined that SdiA is activated during the transit of S. Typhimurium through mice infected with the AHL-producing pathogen Yersinia enterocolitica. SdiA is not activated during transit through mice infected with a yenI mutant of Y. enterocolitica that cannot synthesize AHLs. However, activation of SdiA did not confer a fitness advantage in Yersinia-infected mice. We hypothesized that this is due to infrequent or short interactions between S. Typhimurium and Y. enterocolitica or that the SdiA regulon members do not function in mice. To test these hypotheses, we constructed an S. Typhimurium strain that synthesizes AHLs to mimic a constant interaction with Y. enterocolitica. In this background, sdiA + S. Typhimurium rapidly outcompetes the sdiA mutant in mice. All known members of the sdiA regulon are required for this phenotype. Thus, all members of the sdiA regulon are functional in mice.
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da Silva, Cristiane França, Denise da Gama Jaen Batista, Julianna Siciliano De Araújo, Marcos Meuser Batista, Jessica Lionel, Elen Mello de Souza, Erica Ripoll Hammer, et al. "Activities of Psilostachyin A and Cynaropicrin against Trypanosoma cruziIn VitroandIn Vivo." Antimicrobial Agents and Chemotherapy 57, no. 11 (August 12, 2013): 5307–14. http://dx.doi.org/10.1128/aac.00595-13.

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ABSTRACTIn vitroandin vivoactivities againstTrypanosoma cruziwere evaluated for two sesquiterpene lactones: psilostachyin A and cynaropicrin. Cynaropicrin had previously been shown to potently inhibit African trypanosomesin vivo, and psilostachyin A had been reported to showin vivoeffects againstT. cruzi, albeit in another test design.In vitrodata showed that cynaropicrin was more effective than psilostachyin A. Ultrastructural alterations induced by cynaropicrin included shedding events, detachment of large portions of the plasma membrane, and vesicular bodies and large vacuoles containing membranous structures, suggestive of parasite autophagy. Acute toxicity studies showed that one of two mice died at a cynaropicrin dose of 400 mg/kg of body weight given intraperitoneally (i.p.). Although no major plasma biochemical alterations could be detected, histopathology demonstrated that the liver was the most affected organ in cynaropicrin-treated animals. Although cynaropicrin was as effective as benznidazole against trypomastigotesin vitro, the treatment (once or twice a day) ofT. cruzi-infected mice (up to 50 mg/kg/day cynaropicrin) did not suppress parasitemia or protect against mortality induced by the Y and Colombiana strains. Psilostachyin A (0.5 to 50 mg/kg/day given once a day) was not effective in the acute model ofT. cruziinfection (Y strain), reaching 100% animal mortality. Our data demonstrate that although it is very promising against African trypanosomes, cynaropicrin does not show efficacy compared to benznidazole in acute mouse models ofT. cruziinfection.
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7

Habyarimana, Fabien, Matthew C. Swearingen, Glenn M. Young, Stephanie Seveau, and Brian M. M. Ahmer. "Yersinia enterocolitica Inhibits Salmonella enterica Serovar Typhimurium and Listeria monocytogenes Cellular Uptake." Infection and Immunity 82, no. 1 (October 14, 2013): 174–83. http://dx.doi.org/10.1128/iai.00984-13.

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ABSTRACTYersinia enterocoliticabiovar 1B employs two type three secretion systems (T3SS), Ysa and Ysc, which inject effector proteins into macrophages to prevent phagocytosis. Conversely,Salmonella entericaserovar Typhimurium uses a T3SS encoded bySalmonellapathogenicity island 1 (SPI1) to actively invade cells that are normally nonphagocytic and a second T3SS encoded by SPI2 to survive within macrophages. Given the distinctly different outcomes that occur with regard to host cell uptake ofS. Typhimurium andY. enterocolitica, we investigated how each pathogen influences the internalization outcome of the other.Y. enterocoliticareducesS. Typhimurium invasion of HeLa and Caco-2 cells to a level similar to that observed using anS. Typhimurium SPI1 mutant alone. However,Y. enterocoliticahad no effect onS. Typhimurium uptake by J774.1 or RAW264.7 macrophage-like cells.Y. enterocoliticawas also able to inhibit the invasion of epithelial and macrophage-like cells byListeria monocytogenes.Y. enterocoliticamutants lacking either the Ysa or Ysc T3SS were partially defective, while double mutants were completely defective, in blockingS. Typhimurium uptake by epithelial cells.S. Typhimurium encodes a LuxR homolog, SdiA, which detectsN-acylhomoserine lactones (AHLs) produced byY. enterocoliticaand upregulates the expression of an invasin (Rck) and a putative T3SS effector (SrgE). Two different methods of constitutively activating theS. Typhimurium SdiA regulon failed to reverse the uptake blockade imposed byY. enterocolitica.
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8

Rossini, Carmen, and Rodolfo Ungerfeld. "Chemical profile of the cutaneous gland secretions from male pampas deer ( Ozotoceros bezoarticus )." Journal of Mammalogy 97, no. 1 (October 28, 2015): 167–78. http://dx.doi.org/10.1093/jmammal/gyv167.

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Abstract Various cutaneous glands have been identified as sources of chemical signals that mediate many social interactions in deer. The pampas deer, a species considered near threatened, inhabits grasslands of South America. In this work, the chemical compositions from preorbital, tarsal, and digital gland secretions of semi-captive males were characterized by gas chromatography–mass spectrometry. The composition of these secretions showed a great complexity, with 143 compounds detected. Hierarchical cluster and principal component analyses show no relation to age or secretion type. Five compound classes (esters, fatty alcohols, lactones, sterols, and sulphuretted) differed with glands. The chemical complexity of the secretions, the individual differences in the whole compounds composition, and the absence of clustering by age lead to the hypothesis that these secretions may encode at once for individual information and for social status information. Varias glándulas cutáneas han sido identificadas como productoras de señales químicas que median interacciones sociales en losciervos. El venado de las pampas es una especie considerada casi amenazada que habita los pastizales de Sudamérica. En este trabajo se caracterizó la composición química de las secreciones de las glándulas preorbital, tarsal e interdigital de machos por cromatografía de gases-espectrometría de masas. Estas secreciones mostraron una gran complejidad en su composición, con 143 compuestos detectados. No se observó ninguna agrupación de compuestos relacionada con la edad o el tipo de secreción. Cinco clases de compuestos (ésteres, alcoholes grasos, lactonas, esteroles, y compuestos azufrados) difirieron de acuerdo al origen glandular. La complejidad química de las secreciones, las diferencias individuales en dicha composición, y la ausencia de agrupamiento por edad, llevan a postular la hipótesis de que estas secreciones pueden codificar a la vez tanto información individual como del estado social.
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9

Tomova, Teodora, Nina Doncheva, Anita Mihaylova, Ilia Kostadinov, Lyudmil Peychev, and Mariana Argirova. "An experimental study on phytochemical composition and memory enhancing effect of Ginkgo biloba seed extract." Folia Medica 63, no. 2 (April 30, 2021): 203–12. http://dx.doi.org/10.3897/folmed.63.e53060.

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Introduction: The Ginkgo biloba L. tree is considered as one of the oldest species on Earth. It is known as a &ldquo;living fossil&rdquo; dating back approximately 200 million years. Both the leaves and seeds of this tree have been used for millennia in traditional Chinese medicine. Aim: To study the phytochemical profile of Gingko biloba seed extract (GBSE) and its memory enhancing effects. Materials and methods: Liquid chromatography with mass detection (LC-MS) was performed for phytochemical analyses of the extracts. For the in vivo experiments, male Wistar rats were divided randomly into 5 groups (n=8): saline; piracetam; &nbsp;GBSE 50; 100, and 200 mg/kg b.w. Y-maze, T-maze, step-down passive avoidance and novel object recognition test (NORT) were performed. The observed parameters were: percentage of spontaneous alternations (% SA), working memory index, latency of reaction and recognition index, respectively. Statistical analysis was done using SPSS 19. Results: LC-MS analysis showed the presence of the flavonoids quercetin, kaempferol and isorhamnetin (as aglycones), the ginkgolides A, B, C, J, and bilobalide. In Y-maze task, the groups treated with 50 and 100 mg/kg of GBSE significantly increased the % SA during the memory test compared to saline (p<0.05). In T-maze test, the three experimental groups with GBSE significantly increased the working memory index in comparison with that of the control group (p<0.05). In step-down test, the animals receiving 100 mg/kg b.w. GBSE, notably increased the latency during both retention tests (p<0.05 and p<0.01, respectively). In NORT, only the animals with the middle dose of GBSE ameliorated the recognition index when compared to saline (p<0.05). Conclusions: GBSE enhances spatial working memory, recognition memory, and short- and long-term recall in na&iuml;ve rats due to the synergic effects of detected flavonoids and terpene lactones on brain functions. The brain structures involved are probably the hippocampus and prefrontal cortex.
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Echavarria, Ana, Haydelba D'Armas Regnault, Nubia Lisbeth, Lisbeth Matute, Carmita Jaramillo, Luisa Rojas de Astudillo, and Ricardo Benitez. "Evaluación de la capacidad antioxidante y metabolitos secundarios de extractos de dieciséis plantas medicinales / Evaluation of antioxidant capacity and secondary metabolites of sixteen medicinal plants extracts." Ciencia Unemi 9, no. 20 (December 20, 2016): 29. http://dx.doi.org/10.29076/issn.2528-7737vol9iss20.2016pp29-35p.

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El presente estudio evaluó la capacidad antioxidante de los extractos de dieciséis plantas medicinales: escoba amarga (Parthenium hysterophons), ajenjo (Artemisia absinthium), guarumo (t), chaya (Cnidoscolus chayamansa), borraja (Borago officinalis), balsa (Ochroma sp.), linaza (Linum usitatissimum), hierba Luisa (Cymbopogon citratus), toronjil (Melissa officinalis), buganvilla (Bougainvillea spectabilis), alcachofa (Cynara scolymus), guaviduca (Piper carpunya), altamisa (Ambrosia cumanensis), diente de león (Taxacum officinales), buscapina (Parietaria officinalis) y moringa (Moringa oleifera). Para ello, se usó el método DPPH (radical 1,1-difenil-2-picrilhidrazil); además, se realizaron ensayos de reconocimiento de metabolitos secundarios a fin de obtener los primeros indicios de compuestos de interés fitoquímico. La actividad captadora de radicales libres de los extractos se expresó como valor de IC50 (μg/mL) (cantidad necesaria para inhibir la formación de radicales DPPH en un 50%). El valor bajo de IC50 refleja mejor acción eliminadora de radicales libres. Aunque la mayoría de las muestras evaluadas mostraron buena capacidad antioxidante con este método (DPPH), los ensayos de los extractos hidro-alcohólicos demuestran que la alcachofa (IC50 9,89 μg/mL), moringa (IC50 11,4 μg/mL) y borraja (IC50 14,0 μg/mL) presentaron mayor capacidad antioxidante. Mediante las pruebas químicas de caracterización, se detectó la presencia de flavonoides, taninos, triterpenos, alcaloides y saponinas en la mayoría de las especies analizadas (aproximadamente 56-69%); tan sólo un 20% de las mismas mostró la presencia de polifenoles, glucósidos cianogénicos, lactonas, cumarinas, esteroles y antraquinonas. Según los resultados, se podría considerar a estas plantas como fuentes prometedoras de metabolitos secundarios con actividad antioxidante. ABSTRACTThis study evaluated the antioxidant capacity of sixteen medicinal plants: Escoba amarga (Parthenium hysterophons), ajenjo (Artemisia absinthium), guarumo (Cecropia obtusifolia), chaya (Cnidoscolus chayamansa), borraja (Borago officinalis), balsa (Ochroma sp.), linaza (Linum usitatissimum), hierba Luisa (Cymbopogon citratus), toronjil (Melissa officinalis), buganvilla (Bougainvillea spectabilis), alcachofa (Cynara scolymus), guaviduca (Piper carpunya), altamisa (Ambrosia cumanensis), diente de León (Taxacum officinales), buscapina (Parietaria officinalis)and moringa (Moringa oleifera). For this, the DPPH (radical 1, 1-difenil-2-picrilhidrazil) method was used; furthermore, recognition assays of secondary metabolites were performed, in order to obtain the first signs of phytochemical compounds of interest. The free radical scavenging activity of the extracts was expressed as IC50 value (g/mL) (necessary amount to inhibit the formation of 50% of DPPH radical). The low value of IC50 reflects better free radical scavenging action. Although most of the samples tested showed good antioxidant capacity with this method (DPPH), tests of hydroalcoholic extracts show that alcachofa (IC50 9.89 mg/mL), moringa (IC50 11.4 mg/mL) and borraja (IC50 14.0 mg/mL) were those with higher antioxidant capacity. Through chemical characterization tests, the presence of flavonoids, tannins, triterpenes, alkaloids and saponins were detected in most of the analyzed species (approximately 56-69%); only 20% of them showed the presence of polyphenols, cyanogenic glycosides, lactones, coumarins, anthraquinones and sterols. According to the results obtained, these plants might be considered as promising sources of secondary metabolites with antioxidant activity.
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Jacobi, Christoph A., Alexandra Bach, Leo Eberl, Anette Steidle, and Jürgen Heesemann. "Detection of N-(3-Oxohexanoyl)-l-Homoserine Lactone in Mice Infected with Yersinia enterocolitica Serotype O8." Infection and Immunity 71, no. 11 (November 2003): 6624–26. http://dx.doi.org/10.1128/iai.71.11.6624-6626.2003.

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ABSTRACT Yersinia enterocolitica synthesizes N-acyl-l-homoserine lactone (AHL) signal molecules via the LuxR-LuxI homologues YenR-YenI. In this study we checked two prototypes of mouse-virulent Y. enterocolitica serotype O8 strains WA-314 and 8081 for AHL production in vitro and in vivo (mouse infection model). We used thin-layer chromatography in combination with the Escherichia coli AHL biosensor to identify the AHL species produced. We detected only OHHL [N-(3-oxohexanoyl)-l-homoserine lactone] and not HHL (N-hexanoyl-l-homoserine lactone) produced by Y. enterocolitica O8 in culture supernatant or infected mouse tissue. This is the first report demonstrating AHL production by yersiniae during infection.
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Ali, Md Ashraf, Shuji Noguchi, Miteki Watanabe, Yasunori Iwao, and Shigeru Itai. "The antitumour drug 7-ethyl-10-hydroxycamptothecin monohydrate and its solid-state hydrolysis mechanism on heating." Acta Crystallographica Section C Structural Chemistry 72, no. 10 (September 23, 2016): 743–47. http://dx.doi.org/10.1107/s2053229616014492.

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7-Ethyl-10-hydroxycamptothecin [systematic name: (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, SN-38] is an antitumour drug which exerts activity through the inhibition of topoisomerase I. The crystal structure of SN-38 as the monohydrate, C22H20N2O5·H2O, reveals that it is a monoclinic crystal, with one SN-38 molecule and one water molecule in the asymmetric unit. When the crystal is heated to 473 K, approximately 30% of SN-38 is hydrolyzed at its lactone ring, resulting in the formation of the inactive carboxylate form. The molecular arrangement around the water molecule and the lactone ring of SN-38 in the crystal structure suggests that SN-38 is hydrolyzed by the water molecule at (x,y,z) nucleophilically attacking the carbonyl C atom of the lactone ring at (x − 1,y,z − 1). Hydrogen bonding around the water molecules and the lactone ring appears to promote this hydrolysis reaction: two carbonyl O atoms, which are hydrogen bonded as hydrogen-bond acceptors to the water molecule at (x,y,z), might enhance the nucleophilicity of this water molecule, while the water molecule at (−x,y + {1\over 2}, −z), which is hydrogen bonded as a hydrogen-bond donor to the carbonyl O atom at (x − 1,y,z − 1), might enhance the electrophilicity of the carbonyl C atom.
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Xia, Zhengxiang, Jincheng Yao, and Jingyu Liang. "Two new sesquiterpene lactones from Sonchus arvensis." Chemistry of Natural Compounds 48, no. 1 (March 2012): 47–50. http://dx.doi.org/10.1007/s10600-012-0155-y.

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Cardona, M. Luz, Isabel Fernández, José R. Pedro, and Beatriz Pérez. "Sesquiterpene lactones and flavonoids from Centaurea aspera." Phytochemistry 30, no. 7 (January 1991): 2331–33. http://dx.doi.org/10.1016/0031-9422(91)83643-y.

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Atkinson, Steve, Chien-Yi Chang, R. Elizabeth Sockett, Miguel Cámara, and Paul Williams. "Quorum Sensing in Yersinia enterocolitica Controls Swimming and Swarming Motility." Journal of Bacteriology 188, no. 4 (February 15, 2006): 1451–61. http://dx.doi.org/10.1128/jb.188.4.1451-1461.2006.

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ABSTRACT The Yersinia enterocolitica LuxI homologue YenI directs the synthesis of N-3-(oxohexanoyl)homoserine lactone (3-oxo-C6-HSL) and N-hexanoylhomoserine lactone (C6-HSL). In a Y. enterocolitica yenI mutant, swimming motility is temporally delayed while swarming motility is abolished. Since both swimming and swarming are flagellum dependent, we purified the flagellin protein from the parent and yenI mutant. Electrophoresis revealed that in contrast to the parent strain, the yenI mutant grown for 17 h at 26°C lacked the 45-kDa flagellin protein FleB. Reverse transcription-PCR indicated that while mutation of yenI had no effect on yenR, flhDC (the motility master regulator) or fliA (the flagellar sigma factor) expression, fleB (the flagellin structural gene) was down-regulated. Since 3-oxo-C6-HSL and C6-HSL did not restore swimming or swarming in the yenI mutant, we reexamined the N-acylhomoserine lactone (AHL) profile of Y. enterocolitica. Using AHL biosensors and mass spectrometry, we identified three additional AHLs synthesized via YenI: N-(3-oxodecanoyl)homoserine lactone, N-(3-oxododecanoyl)homoserine lactone (3-oxo-C12-HSL), and N-(3-oxotetradecanoyl)homoserine lactone. However, none of the long-chain AHLs either alone or in combination with the short-chain AHLs restored swarming or swimming in the yenI mutant. By investigating the transport of radiolabeled 3-oxo-C12-HSL and by introducing an AHL biosensor into the yenI mutant we demonstrate that the inability of exogenous AHLs to restore motility to the yenI mutant is not related to a lack of AHL uptake. However, both AHL synthesis and motility were restored by complementation of the yenI mutant with a plasmid-borne copy of yenI.
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Adekenov, S. M. "Sesquiterpene lactones from endemic species of the family Asteraceae." Chemistry of Natural Compounds 49, no. 1 (March 2013): 158–62. http://dx.doi.org/10.1007/s10600-013-0543-y.

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Usmanova, Liliia, Olga Bakulina, Dmitry Dar’in, and Mikhail Krasavin. "Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction." Chemistry of Heterocyclic Compounds 53, no. 4 (April 2017): 474–79. http://dx.doi.org/10.1007/s10593-017-2076-y.

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Ma, Guoyi, Li Chong, Zuqiang Li, Andrew H. T. Cheung, and Martin H. N. Tattersall. "Anticancer activities of sesquiterpene lactones from Cyathocline purpurea in vitro." Cancer Chemotherapy and Pharmacology 64, no. 1 (November 9, 2008): 143–52. http://dx.doi.org/10.1007/s00280-008-0863-y.

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Shen, Jianzhong, Suxia Zhang, Congming Wu, Haiyang Jiang, Zhanhui Wang, and Linli Cheng. "Determination of Six Resorcylic Acid Lactones in Feed by GC–MS." Chromatographia 71, no. 1-2 (November 5, 2009): 163–65. http://dx.doi.org/10.1365/s10337-009-1399-y.

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Hummel, G., and R. R. Schmidt. "ChemInform Abstract: Efficient Synthesis of lactoneo Series Antigen Lewis Y (Ley)." ChemInform 30, no. 35 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199935258.

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Cateni, Francesca, Patrizia Nitti, Sara Drioli, Giuseppe Procida, Renzo Menegazzi, and Maurizio Romano. "γ- and δ-lactones as fumarate esters analogues and their neuroprotective effects." Medicinal Chemistry Research 30, no. 4 (January 16, 2021): 913–24. http://dx.doi.org/10.1007/s00044-020-02698-y.

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Belovodskii, A. V., E. E. Shul’ts, M. M. Shakirov, V. E. Romanov, B. Zh Elmuradov, Kh M. Shakhidoyatov, and G. A. Tolstikov. "Synthesis of hybrid molecules containing fragments of sesquiterpene lactones and plant alkaloids." Chemistry of Natural Compounds 46, no. 6 (January 2011): 880–85. http://dx.doi.org/10.1007/s10600-011-9774-y.

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Spring, Otmar, David Vargas, and Nikolaus H. Fischer. "Sesquiterpene lactones and benzofurans in glandular trichomes of three Pappobolus species." Phytochemistry 30, no. 6 (January 1991): 1861–67. http://dx.doi.org/10.1016/0031-9422(91)85029-y.

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Buschmann, H. "Sesquiterpene lactones as a result of interspecific hybridization in Helliathus species." Phytochemistry 39, no. 2 (May 1995): 367–71. http://dx.doi.org/10.1016/0031-9422(94)00870-y.

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Mukhopadhyay, Triptikumar, S. R. Nadkarni, M. V. Patel, R. G. Bhat, K. R. Desikan, B. N. Ganguli, R. H. Rupp, H. W. Fehlhaber, and H. Kogler. "Maclafungin, a new antifungal macrocyclic lactone from Actinomycete sp. Y-8521050." Tetrahedron 54, no. 44 (October 1998): 13621–28. http://dx.doi.org/10.1016/s0040-4020(98)00838-2.

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26

CĂTANĂ, Laura, Raul CĂTANĂ, Roxana CORA, Ştefan RĂILEANU, and Mihai CERNEA. "In Vitro Study of Benzimidazole Derivatives, Tetrahydropyrimidines and Macrocyclic Lactones Therapeutic Efficacy in Dog Hookworms." Bulletin of University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca. Veterinary Medicine 75, no. 2 (December 16, 2018): 199. http://dx.doi.org/10.15835/buasvmcn-vm:2018.0019.

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The study was conducted using faecal samples from 62 dogs. We tested the ovicidal and larvicidal effects of albendazole (ABZ), mebendazole (MBZ), fenbendazole (FBZ) and flubendazole (FLU) by Egg hatch assay (EHA) and larval development assay (LDA). For pyrantel (PYR) and selamectin (SEL) we tested the larvicidal effects by LDA. In all in vitro tests, benzimidazoles efficacy was low, with a high risk of inducing resistance phenomena. In EHA more than 50% of the hookworm eggs hatched, revealing a low efficacy of all tested benzimidazoles. The regression line was positive for all benzimidazoles, FBZ having the smallest value of the Y parameter (62.62), and lower risk of resistance. When testing the larvicidal effects, a superior efficacy of benzimidazoles was observed. The lowest MIC was for MBZ (0.8672μg/ml). ABZ had a very poor effect (8.46750 μg/ml). The Y parameter showed a lower risk of inducing resistance for MBZ (Y= -64.14) and FBZ (Y= -27.89). Pyrantel and Selamectin were very effective, presenting also a very low risk of inducing resistance phenomena. For PYR and SEL, MIC was 0.2131 μg/ml and 2.7921 μg/ml, respectively. The Y parameter was -448.37 for PYR and -62.74 for SEL, with minimal risk of inducing the adaptive phenomena.
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Yang, Nian-Yun, Jin-Ao Duan, Da-Wei Qian, and Li-Juan Tian. "Simultaneous Quantification of Four Sesquiterpene Lactones in Eupatorium lindleyanum DC. by RP-LC." Chromatographia 70, no. 1-2 (April 28, 2009): 205–9. http://dx.doi.org/10.1365/s10337-009-1123-y.

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Bailly, Christian, and Gérard Vergoten. "Japonicone A and related dimeric sesquiterpene lactones: molecular targets and mechanisms of anticancer activity." Inflammation Research 71, no. 3 (January 16, 2022): 267–76. http://dx.doi.org/10.1007/s00011-021-01538-y.

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Zhao, Ran, Hanmin Zhang, Xiang Zou, and Fenglin Yang. "Effects of Inhibiting Acylated Homoserine Lactones (AHLs) on Anammox Activity and Stability of Granules’." Current Microbiology 73, no. 1 (April 9, 2016): 108–14. http://dx.doi.org/10.1007/s00284-016-1031-y.

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Nishide, Kiyoharu, Ryuichi Kurosaki, Kouichi Hosomi, Hitoshi Imazato, Takehisa Inoue, Manabu Node, Toshiumi Ohmori, and Kaoru Fuji. "An Asymmetric Nitroolefination of α-Alkyl-γ-and δ-Lactones with Modified Nitroenamines." Tetrahedron 51, no. 40 (October 1995): 10857–66. http://dx.doi.org/10.1016/0040-4020(95)00683-y.

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Koukoulitsa, Catherine, George D. Geromichalos, and Helen Skaltsa. "VolSurf analysis of pharmacokinetic properties for several antifungal sesquiterpene lactones isolated from Greek Centaurea sp." Journal of Computer-Aided Molecular Design 19, no. 8 (August 2005): 617–23. http://dx.doi.org/10.1007/s10822-005-9018-y.

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32

Daferner, Michael, Sarah Mensch, Timm Anke, and Olov Sterner. "Hypoxysordarin, a New Sordarin Derivative from Hypoxylon croceum." Zeitschrift für Naturforschung C 54, no. 7-8 (August 1, 1999): 474–80. http://dx.doi.org/10.1515/znc-1999-7-803.

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Abstract Hypoxysordarin (1), a new sordarin derivative, was isolated from the fermentation broth of the facultative marine Hypoxylon croceum together with a new y-lactone, hypoxylactone (2) and sordarin (3). The structures were determined by spectroscopic m ethods. Sordarin (3) has previously been isolated from the terrestrial Sordaria araneosa (Sordariaceae). Like the parent com pound hypoxysordarin exhibits high antifungal activities due to a specific inhibition of protein biosynthesis
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MUKHOPADHYAY, T., S. R. NADKARNI, M. V. PATEL, R. G. BHAT, K. R. DESIKAN, B. N. GANGULI, R. H. RUPP, H. W. FEHLHABER, and H. KOGLER. "ChemInform Abstract: Maclafungin, a New Antifungal Macrocyclic Lactone from Actinomycete sp. Y-8521050." ChemInform 30, no. 9 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199909268.

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34

Guan, Hong, Song You, Li Yang, Xu Wang, and Rui Ni. "Newly Detected Specific Hydrogenation of the Conjugated Double Bond of Unsaturated Alkaloid Lactones by Aspergillus sp." Biotechnology Letters 27, no. 16 (August 2005): 1189–93. http://dx.doi.org/10.1007/s10529-005-0015-y.

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35

Windmüller, R. "Efficient synthesis of lactoneo series antigens H, Lewis X (Lex), and Lewis Y (Ley)." Tetrahedron Letters 35, no. 41 (October 10, 1994): 7927–30. http://dx.doi.org/10.1016/s0040-4039(00)78387-0.

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36

Dalla Lana, Daiane F., Ânderson R. Carvalho, William Lopes, Marilene H. Vainstein, Luciano S. P. Guimarães, Mário L. Teixeira, Luis F. S. de Oliveira, et al. "Structure-based design of δ-lactones for new antifungal drug development: susceptibility, mechanism of action, and toxicity." Folia Microbiologica 64, no. 4 (February 7, 2019): 509–19. http://dx.doi.org/10.1007/s12223-018-00675-y.

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37

Priya, Kumutha, Joanita Sulaiman, Kah Yan How, Wai-Fong Yin, and Kok-Gan Chan. "Production of N-acyl homoserine lactones by Chromobacterium haemolyticum KM2 isolated from the river water in Malaysia." Archives of Microbiology 200, no. 7 (May 23, 2018): 1135–42. http://dx.doi.org/10.1007/s00203-018-1526-y.

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38

Windmüller, Rainer, and Richard R. Schmidt. "Efficient synthesis of lactoneo series antigens H, Lewis X (Lex), and Lewis Y (Ley)1." Tetrahedron Letters 35, no. 43 (October 1994): 7927–30. http://dx.doi.org/10.1016/0040-4039(94)80013-8.

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39

Alzérreca, Arnaldo. "New approach to l'C-modified riboside scaffold via stereoselective functionalization of D-(+)-ribonic-y-lactone." Journal of Heterocyclic Chemistry 40, no. 2 (March 2003): 317–20. http://dx.doi.org/10.1002/jhet.5570400218.

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40

SAÚDE-GUIMARÃES, DÊNIA A., DÉLIO S. RASLAN, EGLER CHIARI, and ALAÍDE B. DE OLIVEIRA. "Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives." Anais da Academia Brasileira de Ciências 86, no. 4 (December 2014): 1563–72. http://dx.doi.org/10.1590/0001-3765201420140167.

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Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1′,2′- epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1′,2′-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1′,2′-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, 1H and 13C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain.
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41

Hogardt, Michael, Maximilian Roeder, Anna Maria Schreff, Leo Eberl, and Jürgen Heesemann. "Expression of Pseudomonas aeruginosa exoS is controlled by quorum sensing and RpoS." Microbiology 150, no. 4 (April 1, 2004): 843–51. http://dx.doi.org/10.1099/mic.0.26703-0.

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In Pseudomonas aeruginosa, virulence determinants and biofilm formation are coordinated via a hierarchical quorum sensing cascade, which involves the transcriptional regulators LasR and RhlR and their cognate homoserine lactone activators C12-HSL [N-(3-oxododecanoyl)-l-homoserine lactone] and c4-hsl (n-butanoyl-l-homoserine lactone), which are produced by LasI and RhlI, respectively. The exoenzyme S regulon of P. aeruginosa, comprises genes for a type III secretion system and for four anti-host effector proteins (ExoS, T, U and Y), which are translocated into host cells. It is a reasonable assumption that this ExoS regulon should be downregulated in the biofilm growth state and thus should also be under the regulatory control of the Las/Rhl system. Therefore, an exoS′-gfp reporter construct was used, and the influence of the Las and Rhl quorum sensing systems and the effect of the stationary-phase sigma factor RpoS on regulation of the exoS gene was examined. Evidence is provided for downregulation of exoS during biofilm formation of P. aeruginosa PAO1. The rhlI mutant PDO100 and rhlR mutant PDO111, but not the lasI mutant PDO-JP1, showed approximately twofold upregulation of the exoS′-gfp reporter in comparison to PAO1. Upregulation of exoS′-gfp in the PDO100 mutant could be repressed to normal level by adding C4-HSL autoinducer, indicating a negative regulatory effect of RhlR/C4-HSL on exoS expression. As RhlR/C4-HSL is also involved in regulation of RpoS, the P. aeruginosa rpoS mutant SS24 was examined and the exoS′-gfp reporter was found to be fivefold upregulated in comparison to PAO1. For the first time evidence is reported for a regulatory cascade linking RhlR/RhlI and RpoS with the expression of the anti-host effector ExoS, part of the exoenzyme S regulon. Moreover, these data suggest that the exoenzyme S regulon may be downregulated in P. aeruginosa biofilms.
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42

WINDMUELLER, R., and R. R. SCHMIDT. "ChemInform Abstract: Efficient Synthesis of lactoneo Series Antigens H, Lewis X (Lex), and Lewis Y (Ley)." ChemInform 26, no. 13 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199513267.

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43

Shen, Bingbing, Yupei Yang, Dan Wan, Huanghe Yu, Yuan Cai, Xionglong Wang, Daifeng Tang, Chunyu Tang, and Shuihan Zhang. "Sesquiterpene lactones isolated from Carpesium abrotanoides L. by LC–MS combined with HSCCC inhibit liver cancer through suppression of the JAK2/STAT3 signaling pathway." Medicinal Chemistry Research 31, no. 3 (February 2, 2022): 436–45. http://dx.doi.org/10.1007/s00044-021-02838-y.

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44

Hummel, Gerd, and Richard R. Schmidt. "A versatile synthesis of the lactoneo-series antigens — synthesis of sialyl dimer Lewis X and of dimer Lewis Y." Tetrahedron Letters 38, no. 7 (February 1997): 1173–76. http://dx.doi.org/10.1016/s0040-4039(97)00006-3.

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45

Soulère, Laurent, Nicolas Guiliani, Yves Queneau, Carlos A. Jerez, and Alain Doutheau. "Molecular insights into quorum sensing in Acidithiobacillus ferrooxidans bacteria via molecular modelling of the transcriptional regulator AfeR and of the binding mode of long-chain acyl homoserine lactones." Journal of Molecular Modeling 14, no. 7 (May 14, 2008): 599–606. http://dx.doi.org/10.1007/s00894-008-0315-y.

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46

HUMMEL, G., and R. R. SCHMIDT. "ChemInform Abstract: A Versatile Synthesis of the lactoneo-Series Antigens - Synthesis of Sialyl Dimer Lewis X and of Dimer Lewis Y." ChemInform 28, no. 22 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199722223.

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47

Yap, Mee-Ngan, Ching-Hong Yang, and Amy O. Charkowski. "The Response Regulator HrpY of Dickeya dadantii 3937 Regulates Virulence Genes Not Linked to the hrp Cluster." Molecular Plant-Microbe Interactions® 21, no. 3 (March 2008): 304–14. http://dx.doi.org/10.1094/mpmi-21-3-0304.

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HrpX/Y is a putative two-component system (TCS) encoded within the type III secretion system (T3SS) gene cluster of Dickeya dadantii. A linear regulatory cascade initiated by HrpX/Y that leads to activation of the downstream T3SS genes via HrpS and HrpL was described previously. Therefore, in D. dadantii, HrpX/Y plays an important role in regulation of genes involved in bacteria–plant interactions and bacterial aggregation via the T3SS. HrpX/Y is the only TCS shared among the plant-pathogenic enterobacteria that is not also present in animal-associated enterobacteria. To date, the genes known to be regulated by HrpY are restricted to the hrp and hrc genes and no signal has been identified that triggers HrpY-dependent gene expression. We demonstrated that HrpY interacts with the hrpS promoter in vitro. We then used a transposon-based system to isolate previously unidentified HrpY-dependent genes, including genes previously shown to affect virulence, including kdgM and acsC. HrpY is a dual regulator, positively regulating at least 10 genes in addition to those in the hrp gene cluster and negatively regulating at least 5 genes. The regulatory effect on one gene depended on the culture medium used. Of the 16 HrpY-regulated genes identified in this screen, 14 are not present in Pectobacterium atrosepticum, the nearest relative of D. dadantii with a sequenced genome. None of the newly identified HrpY-regulated genes were required for bacterial aggregation; thus, neither acyl-homoserine lactone-mediated quorum sensing nor the Rcs signal transduction system which regulates colanic acid, a molecule that plays an important role in biofilm formation in other enterobacteria, are required for D. dadantii aggregation.
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48

Weissman, Kira J., Gordon C. Kearney, Peter F. Leadlay, and James Staunton. "Structural elucidation studies of polyketide tetrasubstituted δ-lactones by gas chromatography/tandem mass spectrometry and electrospray mass spectrometry." Rapid Communications in Mass Spectrometry 13, no. 21 (November 15, 1999): 2103–8. http://dx.doi.org/10.1002/(sici)1097-0231(19991115)13:21<2103::aid-rcm760>3.0.co;2-y.

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49

Cárdenas-Laverde, Diego, Sebastián Rincón-Aceldas, and Ericsson Coy-Barrera. "Identification of Antifungal Compounds from Piper Plants Against Fusarium oxysporum: An Untargeted Metabolite Profiling-Based Approach." Natural Product Communications 17, no. 4 (April 2022): 1934578X2210899. http://dx.doi.org/10.1177/1934578x221089995.

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The phytopathogen Fusarium oxysporum produces considerable losses in economically important crops, making alternative control measures urgently required. Piper plants are widely distributed in tropical regions, and they are also known to produce metabolites with biological activity against infectious agents. As part of our continuous search for antifungals, 18 Piper-derived ethanolic extracts were evaluated by their in vitro effect on F oxysporum mycelial growth inhibition. The total content of phenol and flavonoid measurements and liquid chromatography-electrospray ionization-mass spectrometry analysis served as the chemical characterization of the investigated extracts. Piper pulchrum, Piper barcoense, and Piper tuberculatum exhibited the highest mycelial growth inhibition (>74%). The integration of chemical fingerprints and bioactivity datasets led to recognizing 4 bioactive candidates among extracts through single- Y orthogonal partial least squares regression and univariate statistics. These candidates were 2 amides (1,3), an alkyl lactone (2), and a prenylated benzoquinone (4), subsequently isolated and identified by nuclear magnetic resonance spectroscopy. These isolated compounds exhibited reasonable antifungal activity (IC50 < 50 µM). The findings indicated that the correlative association is advantageous for identifying bioactive metabolites within active extracts.
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50

Milagre, Matheus Marques, Renata Tupinambá Branquinho, Maira Fonseca Gonçalves, GMP de Assis, Maykon Tavares de Oliveira, LES Reis, Dênia Antunes Saúde-Guimarães, and Marta de Lana. "Activity of the sesquiterpene lactone goyazensolide against Trypanosoma cruzi in vitro and in vivo." Parasitology 147, no. 1 (September 23, 2019): 108–19. http://dx.doi.org/10.1017/s0031182019001276.

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AbstractBackground:The current drugs for Chagas disease treatment present several limitationsMethods:The sesquiterpene lactone goyazensolide (GZL) was evaluated regarding to cytotoxicity and trypanocidal activity against amastigotes, selectivity index (SI) in vitro, acute toxicity and anti-Trypanosoma cruzi activity in vivo.Results:The in vitro cytotoxicity in H9c2 cells was observed at doses >250 ng mL−1 of GZL and the SI were of 52.82 and 4.85 (24 h) and of 915.00 and 41.00 (48 h) for GZL and BZ, respectively. Nephrotoxicity and hepatotoxicity were not verified. Treatment with GZL of mice infected with CL strain led to a significant decrease of parasitaemia and total survival at doses of 1 and 3 mg kg−1 day−1 by oral and IV, respectively. This last group cured 12.5% of the animals (negativation of HC, PCR, qPCR and ELISA). Animals infected with Y strain showed significant decrease of parasitaemia and higher negativation in all parasitological tests in comparison to BZ and control groups, but were ELISA reactive, as well as the BZ group, but mice treated with 5.0 mg kg−1 day−1 by oral were negative in parasitological tests and survived.Conclusion:GZL was more active against T. cruzi than benznidazole in vitro and presented important therapeutic activity in vivo in both T. cruzi strains.
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