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BACKGROUND: Bradysia procera, a ginseng stem fungus gnat, is one of the most serious insect pests of Korean ginseng (Panax ginseng), causing significant damage to plant growth. The goal of this study was to determine the toxicity and mechanism of action of phenylpropanoids (trans-anethole and estragole) isolated from the methanol extract and hydrodistillate of Illicium verum fruit against third-instar larvae and eggs of Bradysia procera. RESULTS: The filter-paper mortality bioassay revealed that estragole [median lethal concentration (LC50 ) = 4.68 g/cm2 ] has a significant fumigant effect, followed by trans-anethole (LC50 = 43.92 g/cm2 ). However, estragole had the lowest toxic effect when compared to commercially available insecticides. After 7 days, estragole and trans-anethole at 75 g/cm2 inhibited egg hatchability up to 97% and 93%, respectively. At 0.09 g/cm2 , insecticides had an inhibitory effect on egg-hatching ability ranging from 88% to 94%. Furthermore, in both closed and open containers, these active constituents were able to consistently induce vapor-phased toxicity. Both estragole and trans-anethole have the ability to inhibit acetylcholinesterase (AChE), which is involved in neurotransmitter function. However, the active constituent estragole from I. verum fruit acted as a potent AChE inhibitor and had a slightly lower effect on cyclic adenosine monophosphate (AMP) than octopamine alone. CONCLUSION: This finding suggests that estragole may influence Bradysia procera neurotransmitter function via both the AChE and octopaminergic receptors. More research is needed to demonstrate the potential applications of I. verum fruit-derived products as potential larvicides and ovicides for Bradysia procera population control. © 2022 Society of Chemical Industry.
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Illicium , Insecticidas , Animales , Insecticidas/química , Illicium/química , Frutas/química , Acetilcolinesterasa , Extractos Vegetales/farmacología , NematoceraRESUMEN
As various populations are rapidly becoming an aging society worldwide and interest in health issues has increased, demand for functional foods including herbal products has increased markedly to maintain a healthy state which has led to safety issues about their intake as an inevitable result. The objective of this study was to identify the safety profile of a Korean red ginseng and Salvia plebeia R. Br. extract mixture (KGC-03-PS) which is a valuable ingredient that can be used as a functional food. In the present study, the subacute oral toxicity and bacterial reverse mutagenicity of KGC-03-PS were evaluated. Sprague Dawley rats were administered KGC-03-PS orally for 28 days by gavage. Daily KGC-03-PS dose concentrations were 0, 500, 1,000, or 2,000 mg/kg body weight (bw) per day. Bacterial reverse mutation test with KGC-03-PS dose levels ranging from 312.5 to 5,000 µg/plate was carried out by OECD test guideline No. 471. Five bacterial strains (Salmonella typhimurium TA98, TA100, TA1535, TA1537, and Escherichia coli WP2) were tested in the presence or absence of metabolic activation by plate incorporation method. There were no toxicological effects related with test substance in the clinical evaluation of subacute oral toxicity test including clinical signs, body weight, and food consumption. Moreover, no toxicological changes related to KGC-03-PS were observed in the hematological and serum biochemical characteristics as well as in the pathological examinations, which included organ weight measurements and in the gross- or histopathological findings. KGC-03-PS did not induce an increase in the number of revertant colonies in all bacterial strains of the bacterial reverse mutation test. The no-observed-adverse-effect level of KGC-03-PS is greater than 2,000 mg/kg bw/day, and KGC-03-PS did not induce genotoxicity related to bacterial reverse mutations under the conditions used in this study.
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This study was designed to determine the nutritional profile and functional components of the NZT (New Zealand deer's tail, Cervus elaphus var. scoticus Lönnberg). Twenty-nine fatty acids, eighteen amino acids, twenty-five minerals, chondroitin, and phospholipids were detected by the auto-fatty acid analyzer, auto-amino acid analyzer, inductively coupled plasma optical emission spectrophotometer, absorbance measurements, and by weighing after separating, respectively. 7-Ketocholesterol was isolated from alcohol extract by silica gel column chromatography analysis. Four steroid hormones (androstene-3,17-dione, ß-estradiol, testosterone, and dehydroepiandrosterone), one base and seven nucleosides, and N-acetylneuraminic acid were detected by a HPLC-photodiode array and HPLC-fluorescence detector. As a result, NZT was composed of many nutritional and functional ingredients found in New Zealand deer's antler (NZA) which was one of deer co-products, and it was considered that NZT could be a novel health food resource such as NZA.
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BACKGROUND: Ginsenosides of Korean Red Ginseng extracts (RGE) and its saponin components suppress secretion of inflammasome-mediating cytokines, whereas the nonsaponin fraction (NS) of RGE oppositely stimulates cytokine secretion. Although direct exposure of NS to macrophages in mice induces cytokine production, oral administration of NS has not been studied in inflammasome-related disease in animal models. METHODS: Mice were fed RGE or NS for 7 days and then developed peritonitis. Peritoneal cytokines were measured, and peritoneal exudate cells (PECs) were collected to assay expression levels of a set of toll-like receptors (TLRs) and cytokines in response to NS ingestion. In addition, the role of intestinal bacteria in NS-fed mice was assessed. The effect of preexposure to NS in bone marrow-derived macrophages (BMDMs) on cytokine production was further confirmed. RESULTS: NS ingestion attenuated secretion of peritoneal cytokines resulting from peritonitis. In addition, the isolated PECs from NS-fed mice presented lower TLR transcription levels than PECs from control diet-fed mice. BMDMs treated with NS showed downregulation of TLR4 mRNA and protein expression, which was mediated by the TLR4-MyD88-NFκB signal pathway. BMDMs pretreated with NS produced less cytokines in response to TLR4 ligands. CONCLUSION: NS administration directly inhibits TLR4 expression in inflammatory cells such as macrophages, thereby reducing secretion of cytokines during peritonitis.
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Acne is a chronic inflammatory disease of the skin that occurs when bacteria abnormally grow in hair follicles. The most common treatment is antibiotics, but they are limited due to antibiotic resistance. The purpose of this study was to identify the active ingredients of the antimicrobial effects of red ginseng (Panax ginseng C.A. Meyer), compare it to existing antibacterial substances, and determine its potential efficacy as a natural drug product. The hydrophobic fraction in red ginseng ethanol extract (RGEF) showed the same or better antimicrobial activity against Propionibacterium acnes than benzoyl peroxide or azelaic acid. In addition, the antimicrobial component derived from red ginseng selectively showed a high antimicrobial effect on P. acnes. Nuclear magnetic resonance spectroscopic analysis showed that the active antimicrobial substance in this fraction was panaxynol and panaxydol. Twenty subjects who had acne symptoms were treated with cream containing 3 mg/g of RGEF for 4 weeks. It was found that oxidized sebum contents and redness of the skin were reduced, and symptoms of the early to middle stage of acne were effectively improved. This study showed that red ginseng extract containing panaxynol and panaxydol can effectively control the symptoms of acne.
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Acné Vulgar/tratamiento farmacológico , Antibacterianos/farmacología , Panax/química , Extractos Vegetales/farmacología , Adulto , Antibacterianos/aislamiento & purificación , Fraccionamiento Químico , Cromatografía Líquida de Alta Presión , Cosméticos , Diinos/aislamiento & purificación , Diinos/farmacología , Alcoholes Grasos/aislamiento & purificación , Alcoholes Grasos/farmacología , Femenino , Humanos , Interacciones Hidrofóbicas e Hidrofílicas , Masculino , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Piel/efectos de los fármacos , Crema para la Piel/química , Adulto JovenRESUMEN
The microbial metabolites known as the macrolides are some of the most successful natural products used to treat infectious and immune diseases. Describing the structures of these complex metabolites, however, is often extremely difficult due to the presence of multiple stereogenic centers inherent in this class of polyketide-derived metabolites. With the availability of genome sequence data and a better understanding of the molecular genetics of natural product biosynthesis, it is now possible to use bioinformatic approaches in tandem with spectroscopic tools to assign the full stereostructures of these complex metabolites. In our quest to discover and develop new agents for the treatment of cancer, we observed the production of a highly cytotoxic macrolide, neaumycin B, by a marine-derived actinomycete bacterium of the genus Micromonospora. Neaumycin B is a complex polycyclic macrolide possessing 19 asymmetric centers, usually requiring selective degradation, crystallization, derivatization, X-ray diffraction analysis, synthesis, or other time-consuming approaches to assign the complete stereostructure. As an alternative approach, we sequenced the genome of the producing strain and identified the neaumycin gene cluster ( neu). By integrating the known stereospecificities of biosynthetic enzymes with comprehensive NMR analysis, the full stereostructure of neaumycin B was confidently assigned. This approach exemplifies how mining gene cluster information while integrating NMR-based structure data can achieve rapid, efficient, and accurate stereostructural assignments for complex macrolides.
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Antineoplásicos/química , Genómica/métodos , Macrólidos/química , Secuencia de Aminoácidos , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Línea Celular Tumoral , Biología Computacional , Humanos , Macrólidos/aislamiento & purificación , Macrólidos/farmacología , Micromonospora/química , Micromonospora/genética , Familia de Multigenes , Alineación de Secuencia , EstereoisomerismoRESUMEN
Bradysia procera is a serious insect pest of Panax ginseng plants. This study was conducted to determine the toxicity and mechanism of action of three phenylpropanoids, three terpenoids, and a ketone from Syzygium aromaticum bud methanol extract and hydrodistillate against third-instar larvae and eggs of B. procera. In a filter-paper mortality bioassay, methyl salicylate (LC50, 5.26µg/cm2) was the most toxic compound, followed by 2-nonanone, eugenol, and eugenyl acetate (8.77-15.40µg/cm2). These compounds were significantly less toxic than either thiamethoxam, clothianidin, or cypermethrin. Egg hatching was inhibited by 97, 85, and 40% at 11.7µg/cm2 of methyl salicylate, 2-nonanone, and eugenol, respectively. The egg-hatching inhibition of these insecticides was between 90 and 94% at 0.09µg/cm2. These constituents were consistently more toxic in closed versus open containers, indicating that toxicity was achieved mainly through the action of vapor. The mechanism of larvicidal action of methyl salicylate, eugenol, and eugenyl acetate might be primarily due to interference with the octopaminergic system. 2-Heptyl acetate and 2-nonanone might act on both acetylcholinesterase and the octopaminergic receptor. 2-Heptanone might act primarily on acetylcholinesterase. Further studies will warrant possible applications of S. aromaticum bud-derived products as potential larvicides and ovicides for the control of B. procera.
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Dípteros/efectos de los fármacos , Insecticidas/farmacología , Cetonas/aislamiento & purificación , Larva/efectos de los fármacos , Óvulo/efectos de los fármacos , Fenilpropionatos/aislamiento & purificación , Extractos Vegetales/farmacología , Syzygium/metabolismo , Acetilcolinesterasa/efectos de los fármacos , Animales , Dípteros/crecimiento & desarrollo , Cromatografía de Gases y Espectrometría de Masas , Cetonas/farmacología , Aceites Volátiles/farmacología , Fenilpropionatos/farmacología , Receptores de Amina Biogénica/efectos de los fármacos , Terpenos/aislamiento & purificación , Terpenos/farmacologíaRESUMEN
BACKGROUND: Korean Red Ginseng extracts (RGE) have been suggested as effective immune modulators, and we reported that ginsenosides possess anti-inflammasome properties. However, the properties of nonsaponin components of RGE have not been well studied. METHODS: To assess the roles of nonsaponin fractions (NS) in NLRP3 inflammasome activation, we treated murine macrophages with or without first or second inflammasome activation signals with RGE, NS, or saponin fractions (SF). The first signal was nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB)-mediated transcription of pro-interleukin (IL)-1ß and NLRP3 while the second signal triggered assembly of inflammasome components, leading to IL-1ß maturation. In addition, we examined the role of NS in IL-6 production and IL-1ß maturation in mice. RESULTS: NS induced IL-1ß and NLRP3 transcription via toll-like receptor 4 signaling, whereas SF blocked expression. During the second signal, SF attenuated NLRP3 inflammasome activation while NS did not. Further, NS-injected mice presented increased IL-1ß maturation and IL-6 production. CONCLUSION: SF and NS of RGE play differential roles in the NLRP3 inflammasome activation. Hence, RGE can be suggested as an NLRP3 inflammasome modulator.
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BACKGROUND: The chemical constituents of Panax ginseng are changed by processing methods such as steaming or sun drying. In the present study, the chemical change of Panax ginseng induced by steaming was monitored in situ. METHODS: Samples were separated from the same ginseng root by incision during the steaming process, for in situ monitoring. Sampling was sequentially performed in three stages; FG (fresh ginseng) â SG (steamed ginseng) â RG (red ginseng) and 60 samples were prepared and freeze dried. The samples were then analyzed to determine 43 constituents among three stages of P. ginseng. RESULTS: The results showed that six malonyl-ginsenoside (Rg1, Rb1, Rb3, Rc, Rd, Rb2) and 15 amino acids were decreased in concentration during the steaming process. In contrast, ginsenoside-Rh1, 20(S)-Rg2, 20(S, R)-Rg3 and Maillard reaction product such as AF (arginine-fructose), AFG (arginine-fructose-glucose), and maltol were newly generated or their concentrations were increased. CONCLUSION: This study elucidates the dynamic changes in the chemical components of P. ginseng when the steaming process was induced. These results are thought to be helpful for quality control and standardization of herbal drugs using P. ginseng and they also provide a scientific basis for pharmacological research of processed ginseng (Red ginseng).
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Ginsenosides are used as existing markers of red ginseng (RG) quality, and ginsenoside ratios are also indicative of the different components of red ginseng. For the analysis and classification of ginsenoside content, red ginseng was separated into three parts, namely, main roots, lateral roots, and fine roots, and each extract was subjected to ultra-performance liquid chromatography quadruple time-of-flight mass spectrometry (UPLC-QToF-MS) with multivariate statistical analysis. Principal component analysis (PCA) showed a clear discrimination between the extracts of main roots and fine roots and suggested discrimination markers (four for the main roots and five for the fine roots). The fine root markers were identified as ginsenoside. We identified two markers for the main roots of red ginseng in this study. Moreover, the contents of 22 ginsenosides were analyzed in all three components of red ginseng. Fine roots have the highest protopanaxadiol (PPD)/protopanaxatriol (PPT) ratio. The PPD group of ginsenosides, which is quantitatively dominant in fine roots, clearly distinguishes the main roots from the other parts.
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Ginsenósidos/análisis , Metabolómica/métodos , Panax/química , Raíces de Plantas/química , Cromatografía Líquida de Alta Presión/métodos , Análisis de Componente Principal , Sapogeninas/análisis , Espectrometría de Masas en Tándem/métodosRESUMEN
Panax ginseng C.A. MEYER is one of the most popular medicinal herbs in Asia and the chemical constituents are changed by processing methods such as steaming or sun drying. Metabolomic analysis was performed to distinguish age discrimination of four- and six-year-old red ginseng using ultra-performance liquid chromatography quadruple time of flight mass spectrometry (UPLC-QToF-MS) with multivariate statistical analysis. Principal component analysis (PCA) showed clear discrimination between extracts of red ginseng of different ages and suggest totally six discrimination markers (two for four-year-old and four for six-year-old red ginseng). Among these, one marker was isolated and the structure determined by NMR spectroscopic analysis was 13-cis-docosenamide (marker 6-1) from six-year-old red ginseng. This is the first report of a metabolomic study regarding the age differentiation of red ginseng using UPLC-QToF-MS and determination of the structure of the marker. These results will contribute to the quality control and standardization as well as provide a scientific basis for pharmacological research on red ginseng.
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Metabolómica , Panax/química , Panax/metabolismo , Cromatografía Líquida de Alta Presión , Espectrometría de Masas , República de Corea , Factores de TiempoAsunto(s)
Antibacterianos/aislamiento & purificación , ARN Polimerasas Dirigidas por ADN/antagonistas & inhibidores , Depsipéptidos/aislamiento & purificación , Streptomyces/metabolismo , Microbiología del Agua , Antibacterianos/química , Antibacterianos/farmacología , Depsipéptidos/química , Depsipéptidos/farmacologíaRESUMEN
Anthracimycin is a recently discovered novel marine-derived compound with activity against Bacillus anthracis. We tested anthracimycin against an expanded panel of Staphylococcus aureus strains in vitro and in vivo. All strains of S. aureus tested, including methicillin-susceptible, methicillin-resistant (MRSA) and vancomycin-resistant strains of S. aureus, were susceptible to anthracimycin at MIC values of ⩽0.25 mg l(-1). Although its postantibiotic effects were minimal, anthracimycin exhibited potent and rapid bactericidal activity, with a >4-log kill of USA300 MRSA within 3 h at five times its MIC. At concentrations significantly below the MIC, anthracimycin slowed MRSA growth and potentiated the bactericidal activity of the human cathelicidin, LL-37. The bactericidal activity of anthracimycin was somewhat mitigated in the presence of 20% human serum, and the compound was minimally toxic to human cells, with an IC50 (inhibitory concentration 50)=70 mg l(-1) against human carcinoma cells. At concentrations near the MIC, anthracimycin inhibited S. aureus nucleic acid synthesis as determined by optimized macromolecular synthesis methodology, with inhibition of DNA and RNA synthesis occurring in the absence of DNA intercalation. Anthracimycin at a single dose of 1 or 10 mg kg(-1) was able to protect mice from MRSA-induced mortality in a murine peritonitis model of infection. Anthracimycin provides an interesting new scaffold for future development of a novel MRSA antibiotic.
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Antibacterianos/farmacología , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Peritonitis/microbiología , Policétidos/farmacología , Infecciones Estafilocócicas/tratamiento farmacológico , Animales , Antibacterianos/efectos adversos , Células HeLa , Humanos , Meticilina/farmacología , Resistencia a la Meticilina , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Peritonitis/tratamiento farmacológico , Policétidos/efectos adversos , Infecciones Estafilocócicas/microbiología , Vancomicina/farmacología , Resistencia a la VancomicinaRESUMEN
Licensed to kill: A new antibiotic, anthracimycin (see scheme), produced by a marine-derived actinomycete in saline culture, shows significant activity toward Bacillus anthracis, the bacterial pathogen responsible for anthrax infections. Chlorination of anthracimycin gives a dichloro derivative that retains activity against Gram-positive bacteria, such as anthrax, but also shows activity against selected Gram-negative bacteria.
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Actinobacteria , Carbunco/tratamiento farmacológico , Antibacterianos/farmacología , Bacillus anthracis/efectos de los fármacos , Sedimentos Geológicos/microbiología , Bacterias Grampositivas/efectos de los fármacos , Policétidos/farmacología , Contaminantes Químicos del Agua/química , Carbunco/microbiología , Antibacterianos/química , Sedimentos Geológicos/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Policétidos/química , Estereoisomerismo , Relación Estructura-ActividadRESUMEN
Endothelin-1 (ET-1) is reported to be a potent mitogenic and pro-angiogenic factor that plays a vital role in both physiological and pathological processes. ET-1 is implicated in dermal cell proliferation and skin disorders, such as psoriasis and atopic dermatitis. ET-1, endothelin ET(A) receptor, and endothelin ET(B) receptor could be potential targets for developing specific therapeutics to treat such disorders. Here, we provide the first report that an isonahocol [2,-5-hihydroxy-3-(13-hydroxy-3,-7,-11,-15-tetramethyl-12-oxo-hexadeca-2,-6,-14-trienyl)-phenyl]-acetic acid methyl ester (isonahocol E(3)) from the brown algae Sargassum siliquastrum has functional antagonistic activities against ET-1 induced inflammatory and proangiogenic effects. Isonahocol E(3) significantly inhibited ET-1-induced cell proliferation, as well as inflammatory mediators, such as interleukin-6 (IL-6) and interleukin-8 (IL-8) and tumor necrosis factor-α (TNF-α), and pro-angiogenic factors including metalloproteinases in immortalized human keratinocytes. We also found that isonahocol E(3) reduced expression level of endothelin ET(A) receptor, and endothelin ET(B) receptor as well as suppressed ET-1 induced extracellular signal-regulated kinase (ERK) phosporylation. Taken together, our results suggest that isonahocol E(3) can exert anti-inflammatory and anti-angiogenic activities at least by regulating the expression of ET-1 receptors and ERK signaling pathway.
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Inhibidores de la Angiogénesis/farmacología , Antiinflamatorios/farmacología , Endotelina-1/metabolismo , Queratinocitos/efectos de los fármacos , Fenilacetatos/farmacología , Línea Celular , Movimiento Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Citocinas/metabolismo , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Humanos , Queratinocitos/metabolismo , Metaloproteinasas de la Matriz/metabolismo , Cicatrización de Heridas/efectos de los fármacosRESUMEN
Eight novel cyclic bis-1,3-dialkylpyridiniums, as well as two known compounds from the cyclostellettamine class, were isolated from the sponge Haliclona sp. from Korea. Structures of these novel compounds were determined using combined NMR and FAB-MS/MS analyses. Several of these compounds exhibited moderate cytotoxic and antibacterial activities against A549 cell-line and Gram-positive strains, respectively. The structure-activity relationships of cyclostellettamines are discussed based on their bioactivities.
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Antibacterianos/química , Antibacterianos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Haliclona/química , Poríferos/química , Animales , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales/métodos , Bacterias Grampositivas/efectos de los fármacos , Humanos , Corea (Geográfico) , Espectroscopía de Resonancia Magnética/métodos , Espectrometría de Masas/métodos , Relación Estructura-ActividadRESUMEN
The measurement of nitric oxide in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells is used as a model for evaluating the anti-inflammatory or chemopreventive potential of substances. Thienodolin, isolated from a Streptomyces sp. derived from Chilean marine sediment, inhibited nitric oxide production in LPS-stimulated RAW 264.7 cells (IC50 = 17.2 +/- 1.2 microM). At both the mRNA and protein levels, inducible nitric oxide synthase (iNOS) was suppressed in a dose-dependent manner. Mitogen-activated protein kinases (MAPKs), one major upstream signaling pathway involved in the transcription of iNOS, were not affected by treatment of thienodolin. However, the compound blocked the degradation of IkappaBa resulting in inhibition of NF-kappaB p65 nuclear translocation, and inhibited the phosphorylation of signal transducers and activators of transcription 1 (STAT1) at Tyr701. This study supports further exploration of thienodolin as a potential therapeutic agent with a unique mechanistic activity.
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Antiinflamatorios/farmacología , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Óxido Nítrico Sintasa/antagonistas & inhibidores , Animales , Antiinflamatorios/química , Ratones , Proteínas Quinasas Activadas por Mitógenos/metabolismo , Fosforilación/efectos de los fármacos , Transducción de Señal/efectos de los fármacosRESUMEN
Ten sesquiterpenes, together with 12 known compounds were isolated from leaves of Laurus nobilis L. Based on spectroscopic analyses, the 10 compounds were determined to be eudesmane lactones and their corresponding methyl esters. Most of these compounds exhibited moderate-to-significant cytotoxicity towards K562 leukemia cells. One compound had a higher cytotoxicity than doxorubicin, while other compounds had moderate to no activity.
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Antineoplásicos/química , Antineoplásicos/farmacología , Laurus/química , Hojas de la Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Antineoplásicos/aislamiento & purificación , Humanos , Células K562 , Espectroscopía de Resonancia Magnética , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na(+)/K(+)-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates.