RESUMEN
In this study, we report a facile transformation starting from 5α-hydroxyergosta-7,22-dien-3,6-dione (1) to afford two novel compounds: 6-methoxyergosta-4,6,8(14),22-tetraen-3-one (2) and 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one (3) using alcoholic acid catalysis. Their structures were elucidated using NMR experiments, FT-IR, MS and X-ray analysis. These compounds were evaluated for antibacterial activity using the disk and broth diffusion test. In those tests, compound 3 was found to be the most significant antibacterial agent. In general, compounds 1-3 showed inhibition zone in the range of 7.00-12.3 mm for S. aureus and S. mutans, meanwhile for Gram-negative bacteria E. coli and Pseudomonas sp. was found to be in the range of 7.00-8.00 mm. For the most active, compound 3, MIC was significantly lower than that reported for ergosterol, in a value of 160 µg/mL. Overall, these compounds were more active than their natural precursor.
Asunto(s)
Escherichia coli , Trientina , Espectroscopía Infrarroja por Transformada de Fourier , Staphylococcus aureus , Antibacterianos/farmacologíaRESUMEN
The greater wax moth, Galleria mellonella, is a global pest for beehives, doing damage in the larval stage. Although a significant number of studies have reported on larvae and adults, to date no effective pest control has been implemented. In this study, we tested larval resistance to alkaloids from Berberis microphylla, and the objective was to identify enzymes that participate in alkaloid detoxification through enzymatic assays, bioinformatics analysis and qRT-PCR. Findings suggest glutathione-S-transferases (GSTs), from an increased metabolic mechanism, are responsible for alkaloid detoxification rather than cytochrome P450 (CYP), carboxylesterases (CarE). A bioinformatics analysis from transcriptome data revealed 22 GSTs present in both G. mellonella larvae and adults. The qRT-PCR experiments corroborated the presence of the 22 GSTs in larvae, where GST8 and GST20 stood out with the highest expression after berberine treatment. Structural information around GST8 and GST20 suggests that GST8 could bind berberine stronger than GST20. These findings represent an important advance in the study of detoxification enzymes in G. mellonella, expanding the role of delta-class GSTs towards alkaloids. Likewise, GST inhibition by alkaloid analogs is proposed in the framework of integrated pest management strategies.
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We present the first study that compares phenological variation in parasite load and inflammatory response in a lizard with asynchronous male and female gonadal cycles. Other studies have used many species with seasonal and synchronous reproductive cycles, in which it is difficult to decouple the effects of internal and external factors that can affect parasite abundance in each sex. Species with asynchronous reproductive cycles provide the opportunity to study the effects of seasonality and reproductive condition separately, but few studies have documented variation in parasite abundance in these species. We made an extensive comparison of parasite load and inflammatory response of the lizard Sceloporus torquatus, a species with asynchronous reproductive cycles, throughout its active period. We hypothesized that the parasite load would be higher in the period of maximum gonadal activity for each sex, negatively related to body condition and inflammatory response. Our results partially support the hypothesis; males had more parasites in summer than in spring and autumn, while females had more parasites in spring and summer than in autumn; however, we do not find a relationship between parasite load, body condition and inflammatory response. Our results indicated that host-parasite interactions are complex and depend upon both environmental and internal factors. Therefore, longer-term studies may provide a more comprehensive picture of host-parasite dynamics in populations of wild lizards.
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Lagartos , Parásitos , Animales , Femenino , Interacciones Huésped-Parásitos , Lagartos/fisiología , Masculino , Carga de Parásitos , Reproducción , Estaciones del AñoRESUMEN
Heloderma horridum is one of the few known venomous lizards in the world. Their populations are in decline due to habitat destruction and capture for the pet trade. In México, many zoos have decided to take care of this species, most of them at altitudes greater than the natural altitudinal distribution. However, we know little about the capacity of the reptiles to face high-altitude environments. The objective of this study was to compare hematological traits of H. horridum in captivity in high and low altitude environments. Our findings show that H. horridum does not respond to hypoxic environments, at least in blood traits, and that the organisms appear to be in homeostasis. Although we cannot know if individual H. horridum housed in high-altitude environments are completely comfortable, it appears hypoxia can be avoid without modifications of blood parameters. We suggest that future work should address changes in metabolic rates and in behavioral aspects to understand how to maintain the health and comfort of the reptiles native to low altitude when they are housed in high-altitude environments.
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Altitud , Bienestar del Animal , Hipoxia/sangre , Lagartos/fisiología , Animales , Animales de Zoológico/fisiología , Recuento de Eritrocitos , Hematócrito , Hemoglobinas/fisiología , MéxicoRESUMEN
From a bioactive methanolic extract of Senecio fistulosus, the antifeedant effects of the alkaloidal and non-alkaloidal fractions were tested against the insects Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi, with the non-alkaloidal fraction being antifeedant. The phytochemical study of the non-alkaloidal fraction of S. fistulosus, resulted in the isolation of four compounds, two 9-oxo-furanoeremophilanes (1, 2), an eremophilanolide, 1ß,10ß-epoxy-6-acetoxy-8α-hydroxy-eremofil-7(11)-en-8ß,12-olide (3) and a maaliol derivative (4). The alkaloidal fraction yielded two known pyrrolizidine alkaloids (5, 6). Compounds 1, 3 and 4 are new natural products. Furanoeremophilane 2 was a strong antifeedant against S. littoralis and maaliane 4 inhibited the settling of M. persicae.
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BACKGROUND: Geographic variation in body size and condition can reveal differential local adaptation to resource availability or climatic factors. Body size and condition are related to fitness in garter snakes (Thamnophis), thus good body condition may increase survival, fecundity in females, and mating success in males. Phylogenetically related species in sympatry are predicted to exhibit similar body condition when they experience similar environmental conditions. We focused on interspecific and geographical variation in body size and condition in three sympatric Mexican garter snakes from the highlands of Central Mexico. METHODS: We assessed SVL, mass, and body condition (obtained from Major axis linear regression of ln-transformed body mass on ln-transformed SVL) in adults and juveniles of both sexes of Thamnophis eques, T. melanogaster, and T. scalaris sampled at different locations and ranges from 3-11 years over a 20-year period. RESULTS: We provide a heterogeneous pattern of sexual and ontogenic reproductive status variations of body size and condition among local populations. Each garter snake species shows locations with good and poor body condition; juvenile snakes show similar body condition between populations, adults show varying body condition between populations, and adults also show sex differences in body condition. We discuss variations in body condition as possibly related to the snakes' life cycle differences.
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Ptilonines A-F, pyranosylmagellanicus D-E and magellenediol are previously undescribed acetogenins isolated from the red alga Ptilonia magellanica. Their structures were determined from spectroscopic evidence. The absolute configuration of the known pyranosylmagellanicus A, was established by derivatization with (R)- and (S)-α-methoxy -α-phenylacetic acids (MPA). Ptilonines exhibit an unusual halogenation pattern, that may confer evolutionary advantages to Ptilonia magellanica, for which a biogenetic origin is proposed. The antimicrobial effect of some of these compounds was evaluated.
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Acetogeninas/farmacología , Antibacterianos/farmacología , Antifúngicos/farmacología , Rhodophyta/química , Acetogeninas/química , Acetogeninas/aislamiento & purificación , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Bacillus cereus/efectos de los fármacos , Candida albicans/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Enterococcus faecalis/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Klebsiella pneumoniae/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Proteus mirabilis/efectos de los fármacos , Salmonella/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
SUMMARY: Vertebrates exhibit structural changes in their cardiovascular and gas exchange systems in response to hypoxic conditions in high altitude environments. In highland neotenic mole salamanders, as other amphibians, the majority of gases exchange is carried out for skin and gills. But, in high altitude environments, the available oxygen is lower than it is in the air thus, the scarcity of oxygen limits the survival of organisms. Many studies on this subject have focused on understanding the hematological mechanisms that amphibians exhibit in response to hypoxia. However, little is known about possible morphological changes in respiratory structures that may permit increased gas exchange during respiration in high altitude amphibians like Ambystoma leorae and A. rivulare, two threatened Mexican salamander species. The aim of the present study was to describe and compare the histological characteristics of the gills and dorsal skin of A. leorae and A. rivulare from populations at low and high altitudes. We found that, in comparison to lowland organisms, highland ones exhibited more pronounced skin folds, greater numbers of secondary branches in the gills, thinner dorsal and gill epidermises, and greater quantity of melanin surrounding the gill blood vessels. These differences permit a greater capacity for gas exchange and also increase thermoregulatory capacity in high altitude environments.
RESUMEN: Los anfibios que viven en ambientes de altitud se enfrentan a factores abióticos que limitan la vida, tales como la disminución de la presión barométrica con la consecuente disminución de la presión parcial de oxígeno (O2). Conocer los mecanismos que optimizan la obtención del O2 en estos animales es de gran importancia para entender las diferencias en la sensibilidad a la hipoxia de las diferentes especies. Ambystoma rivulare y A. leorae son anfibios endémicos del Estado de México que viven en ambientes de alta altitud por lo que se cree presentan estrategias fenotípicas para asimilar eficazmente el O2 y poder subsistir en los ambientes de altitud. El objetivo de este trabajo fue analizar las características histológicas de branquias y piel cefálica (que son las principales estructuras que se encargan del intercambio gaseoso) provenientes de tres poblaciones con diferente altitud. Nuestros resultados muestran que los organismos que habitan a mayor altitud tienden a aumentar la superficie de intercambio gaseoso, como es el caso de pliegues epidérmicos y ramas branquiales secundarias. Las diferencias histológicas de branquias y piel cefálica tanto interespecíficas como intraespecíficas respecto a la altitud parecen apoyar la idea de que los organismos modifican sus estructuras para contrarrestar las limitantes de la vida en ambientes de altitud.
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Animales , Piel/anatomía & histología , Altitud , Ambystoma/anatomía & histología , Branquias/anatomía & histología , DorsoRESUMEN
The abdominal aorta of the rabbit has been in the focus of research to develop new platforms of training diagnostic and therapeutic protocols; and for testing endovascular devices and materials, however, few descriptions of the anatomy of the abdominal aorta and its emerging visceral branches has been reported on the scientific literature for this specie. Anatomical variations are common and should have in mind during research and clinical trials. The aim of this study was to describe the different patterns that can occur in the visceral branches arising from the abdominal aorta in the rabbit.
La aorta abdominal del conejo ha sido objeto de estudio e investigación para desarrollar nuevas plataformas de entrenamiento para protocolos diagnósticos y terapéuticos así como para probar las virtudes de materiales y equipos endovasculares, sin embargo, existen muy pocas descripciones en la literatura de las ramas viscerales que emergen de la aorta abdominal en esta especie. Las variaciones anatómicas son eventos de ocurrencia común y por lo tanto deben ser considerados para realizar investigación y ensayos clínicos. El objetivo del presente estudio ha sido describir los diferentes patrones que pueden presentar las ramas viscerales que emergen de la aorta abdominal en el conejo.
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Animales , Variación Anatómica , Aorta Abdominal/anatomía & histología , Conejos/anatomía & histología , Vísceras/irrigación sanguíneaRESUMEN
Berberis microphylla is a native plant that grows in Patagonia and is commonly used by aboriginal ethnic groups in traditional medicine as an antiseptic for different diseases. The present study evaluated the antibacterial and synergistic activity of alkaloid extracts of B. microphylla leaves, stems and roots used either individually or in combination with antibiotics against Gram-positive and Gram-negative bacteria. The in vitro antibacterial activities of leaf, stem and root alkaloid extracts had significant activity only against Gram-positive bacteria. Disc diffusion tests demonstrated that the root extract showed similar activity against B. cereus and S. epidermidis compared to commercial antibiotics, namely ampicillin and cephalothin, and pure berberine, the principal component of the alkaloid extracts, was found to be active only against S. aureus and S. epidermidis with similar activity to that of the root extract. The minimum inhibitory concentrations (MICs) of the alkaloid extracts ranged from 333 to 83 µg/mL, whereas minimum bactericidal concentrations (MBCs) varied from 717 to 167 µg/mL. In addition, synergistic or indifferent effects between the alkaloid extracts and antibiotics against bacterial strains were confirmed.
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Ampicilina/farmacología , Antibacterianos/farmacología , Alcaloides de Berberina/farmacología , Berberis/química , Cefalotina/farmacología , Antibacterianos/aislamiento & purificación , Alcaloides de Berberina/aislamiento & purificación , Sinergismo Farmacológico , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Gramnegativas/crecimiento & desarrollo , Bacterias Grampositivas/efectos de los fármacos , Bacterias Grampositivas/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Hojas de la Planta/química , Raíces de Plantas/química , Tallos de la Planta/químicaRESUMEN
Type 2 diabetes mellitus (T2DM) is a common chronic disease whose prevalence is currently increasing worldwide. Nowadays, the main antidiabetic agent used is metformin. However, between 10 and 30 percent of patients undergoing metformin therapy have nonspecific gastric alterations as an undesired secondary effect. Therefore, the search for new therapeutic alternatives is especially useful, where plant- derived products emerge as an excellent phytochemical resource. The objective of this review is to present and discuss the state of the art of current research conducted on the Berberis gender with hypoglycemic activity, which is normally used in alternative medicine therapy for the treatment of T2DM, and its possible mechanisms of action described in literature.
La diabetes mellitus tipo 2 (DM2) es una enfermedad crónica común, cuya prevalencia está actualmente aumentando en todo el mundo. Al presente, el principal fármaco antidiabético utilizado es la metformina. Sin embargo, entre un 10 y 30 por ciento de los pacientes tratados presentan como efecto no deseado de alteraciones gástricas inespecíficas. Por lo tanto, la búsqueda de nuevas alternativas terapéuticas es de gran utilidad, en donde los productos derivados de plantas emergen como un excelente recurso fitoquímico. El objetivo de esta revisión es presentar y discutir sobre el estado del arte de investigaciones realizadas en las especies del género Berberis con actividad hipoglicemiante, las cuales son normalmente utilizadas en medicina alternativa como terapia para el tratamiento de DM, y sus posibles mecanismos de acción descritos en la literatura.
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Berberis/química , /tratamiento farmacológico , Hipoglucemiantes/uso terapéutico , Extractos Vegetales/uso terapéutico , Terapias ComplementariasRESUMEN
Twenty-four compounds including eleven eremophilanolides (1-11), one eremophilane (13), five shikimic acid derivatives (14-18), six flavonoids (19-24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were isolated from Senecio kingii, an endemic species from the Magallanes Region (Chile). Compounds 3, 5, 6, 8-11 and 13-18 have not been previously reported as natural products. Their molecular structures were determined by NMR spectroscopic analysis and comparison with published NMR data. An X-ray-analysis of compound 3 has been performed. Their insecticidal and antifungal activities were tested, being compound 3 the strongest insect antifeedant. Compounds 6, 9 and 18 were moderate antifungals.
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Antifúngicos/farmacología , Flavonoides/química , Insecticidas/farmacología , Alcaloides de Pirrolicidina/química , Senecio/química , Sesquiterpenos/química , Animales , Antifúngicos/química , Áfidos/efectos de los fármacos , Chile , Cristalografía por Rayos X , Evaluación Preclínica de Medicamentos/métodos , Flavonoides/farmacología , Fusarium/efectos de los fármacos , Insecticidas/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Alcaloides de Pirrolicidina/farmacología , Sesquiterpenos/farmacología , Ácido Shikímico/química , Spodoptera/efectos de los fármacosRESUMEN
Berberis microphylla (G. Forst) is a native plant growing in Patagonia. In recent years Patagonia Berberis are becoming important due to their interesting biological properties related to their alkaloids content. The aim of this study was determine the distribution and proportion of isoquinoline alkaloids in leaves, stems and roots of B. microphylla collected in two different climatic zones from Chilean Patagonia. Using by HPLC ESI-MS/MS isocorydine, jatrorrhizine, palmatine, reticuline, scoulerine, tetrahydroberberine and thalifendine were detected for the first time in this specie, and the presence of allocryptopine, berberine, calafatine and protopine, previously isolated in B. microphylla was corroborated. The alkaloids profile showed differences of compounds in samples collected in two climatic zones, where more compounds were detected in plants from Lago Deseado than Cerro Sombrero. Furthermore, a greater number of alkaloids were found in stem and root extracts and berberine and thalifendine were detected in higher proportion in these structures.
Berberis microphylla (G. Forst) es un arbusto nativo que crece en la Patagonia. Actualmente, esta planta ha sido foco de estudio dada las propiedades biológicas que presenta, atribuidas principalmente al contenido de alcaloides. El objetivo de este estudio fue determinar la distribución y proporción de alcaloides isoquinolínicos en hojas, tallos y raíces de B. microphylla colectadas en dos zonas climáticas de la Patagonia chilena. Mediante CLAE IES-MS/MS se informa por primera vez la presencia de isocoridina jatrorrizina, palmatina, reticulina, escoulerina, tetrahidroberberina y talifendina en esta especie y se confirma la presencia de allocriptopina, berberina, calafatina y protopina, identificados previamente en B. microphylla. El perfil de alcaloides mostró diferencias en la presencia de compuestos en las muestras colectas en las dos zonas climáticas, observándose un mayor número de compuestos en plantas provenientes de Lago Deseado. Además, un mayor número de compuestos se identificó en extractos de tallos y raíces donde berberina y talifendina fueron detectados en mayor proporción.
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Alcaloides/análisis , Berberis/química , Hojas de la Planta/química , Cromatografía Líquida de Alta Presión , Raíces de Plantas/química , Espectrometría de Masa por Ionización de Electrospray , Tallos de la Planta/químicaRESUMEN
Different analyses were carried out on the following plant species: Adesmia boronioides Hook.F., Senecio patagonicus Hook. & Arn. and Lepidophyllum cupressiforme (Lam.) Cass. in order to compare the photosynthetic pigment, carotenoid and phenylpropanoid contents. Total phenolic content and antioxidant capacity were measured by using common established reagents: Folin-Ciocalteau and ABTS respectively. Plant samples were collected from specimens growing inside the National Park Pali Aike and the Botanic Garden Carl Skottsberg in Punta Arenas city. The results showed no marked tendencies between photosynthetic pigments. Nevertheless, a good correlation was found among the antioxidant capacity and phenolic compounds. Furthermore, species growing in the Pali Aike National Park seem to be more adapted to the environmental conditions.
Se realizaron diferentes análisis al contenido de pigmentos fotosintéticos, carotenoides y fenilpropanoides. El contenido de fenoles totales y la capacidad antioxidante se midieron usando reactivos ampliamente conocidos: Folin-Ciocalteau y ABTS respectivamente en las siguientes especies: Adesmia boronioides, Senecio patagonicus y Lepidophyllum cupressiforme. Estas plantas se encuentran en el Parque Nacional Pali Aike y en el Jardín Botánico Carl Skottsberg en la ciudad de Punta Arenas. Los resultados no muestran una tendencia clara entre las muestras de pigmentos fotosintéticos. Sin embargo, se pudo observar una buena correlación entre la capacidad antioxidante y el contenido de compuestos fenólicos. Además, aparentemente las especies que crecen en el Parque Nacional Pali Aike están más adaptadas a esas condiciones ambientales.
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Antioxidantes/química , Asteraceae/química , Fabaceae/química , Senecio/química , Adaptación Fisiológica , Asteraceae/crecimiento & desarrollo , Chile , Fabaceae/crecimiento & desarrollo , Fenoles/análisis , Estrés Fisiológico , Senecio/crecimiento & desarrolloRESUMEN
Six guaiane sesquiterpenes recurvatiane A-F, including the previously known recurvatiane E and xanthomicrol, were isolated from the Andean Perezia recurvata and their structures determined by spectroscopic evidence. The absolute stereochemistry of recurvatiane A was established by derivatization with (R)- and (S)-α-methoxy-α-phenylacetic acids (MPA). The suite of guaiane-based metabolites here reported, which we have named recurvatianes A-F, provide an example of a pathway by which molecular diversity is generated by the occurrence of specific oxidation reactions in the late biosynthetic steps of the frame structure.
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Asteraceae/química , Fenilacetatos/química , Sesquiterpenos de Guayano/aislamiento & purificación , Chile , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Oxidación-Reducción , Sesquiterpenos de Guayano/química , EstereoisomerismoRESUMEN
Genetic analyses of Gnaphalium's DNA showed a high degree of polymorphism in UV-B irradiated plants when compared to controls. Among the five tested primers the four ISSR primers selected for this analysis generated a total of 189 fragments. A high proportion of polymorphic bands ranging from 70% to 28% were found using these ISSR markers. Nei and Li similarity indexes [1] were used to evaluate genetic divergence among plants. The dendrograms obtained using these markers efficiently separate plants from different treatments. A linear relationship was observed between UV-B dose and percentage of dissimilarity which may be related to DNA damage caused by the different UV-B treatments.
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Gnaphalium/genética , Proteínas de Plantas/genética , Polimorfismo Genético , Rayos Ultravioleta , Daño del ADN , ADN de Plantas/análisis , Gnaphalium/clasificación , Hojas de la Planta/genéticaRESUMEN
Pronuciferine N-oxide (1), a proaporphine N-methyl-N-oxide alkaloid, along with the parent alkaloid pronuciferine (2) were isolated from Berberis coletioides. The structure of the new compound was determined by spectroscopic evidence. Compound 1 is the first naturally occurring proaporphinoid alkaloid with an N-oxide functionality.
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Berberis/química , Compuestos de Espiro/aislamiento & purificación , Alcaloides/química , Chile , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Compuestos de Espiro/químicaRESUMEN
In women, birth trauma can result in altered anatomy of supporting structures of the pelvic floor and in the development of urinary incontinence. The goal of this study was to investigate the association between parturition and the morphology and function of perineal and pelvic muscles in the female rabbit. In ten nulliparous and ten multiparous same-age females, we investigated morphological, histological (n = 5 females/group), and contractile characteristics (n = 5 females/group) of the perineal bulbospongiosus (Bsm) and the pelvic pubococcygeus (Pcm) muscles. Bsm and Pcm muscles of multiparous females were significantly lighter, they had a smaller cross-sectional fiber area, and developed significantly lower twitch and tetanic tension force in response to electrical stimulation than muscles of nulliparous females. In female rabbits, multiparity is associated with potentially pathological changes in the morphological and functional characteristics of these perineal and pelvic muscles, possibly as a result of stretching during parturition.
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Contracción Muscular/fisiología , Diafragma Pélvico/anatomía & histología , Diafragma Pélvico/fisiología , Perineo/anatomía & histología , Perineo/fisiología , Animales , Electromiografía , Femenino , Músculo Esquelético/anatomía & histología , Músculo Esquelético/fisiología , Paridad , Embarazo , ConejosRESUMEN
Citotoxicity (inhibition of cell division in fertilized eggs of Loxechinus albus) and general toxicity (using embryos of Artemia salina) of plants belonging to the genera Senecio, Deschampsia, Alstroemeria, Anarthrophyllum, Chloraea and Geranium were investigated.
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Artemia/efectos de los fármacos , División Celular/efectos de los fármacos , Extractos Vegetales/toxicidad , Animales , Chile , Larva/efectos de los fármacos , Óvulo/efectos de los fármacos , Poaceae , Erizos de Mar/efectos de los fármacosRESUMEN
Treatment of Jaborosa magellanica with artificial UV-B radiation caused changes in plant growth, plant chemistry and increase DNA polymorphisms. Spectrophotometric analysis showed that UV-B radiation decreases the chlorophylls content, and increases the amount of UV-B absorbing compounds (e.g., phenylpropanoids). Other UV-induced alterations include reduction in leaf area, alterations in plant architecture, and DNA damage. Using random primers and PCR amplification procedure, a high degree of polymorphism was detected when treated plants were compared to non-irradiated plants. These biochemical changes may be interpreted as plant response to UV-B radiation stress and as an indicator of DNA damage.