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Keywords = Calceolaria

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11 pages, 1767 KB  
Article
Calceolarioside A, a Phenylpropanoid Glycoside from Calceolaria spp., Displays Antinociceptive and Anti-Inflammatory Properties
by Stefano Pieretti, Anella Saviano, Adriano Mollica, Azzurra Stefanucci, Anna Maria Aloisi and Marcello Nicoletti
Molecules 2022, 27(7), 2183; https://doi.org/10.3390/molecules27072183 - 28 Mar 2022
Cited by 16 | Viewed by 3138
Abstract
Phenylpropanoid glycosides are a class of natural substances of plant origin with interesting biological activities and pharmacological properties. This study reports the antinociceptive and anti-inflammatory effects of calceolarioside A, a phenylpropanoid glycoside previously isolated from various Calceolaria species. In models of acute nociception [...] Read more.
Phenylpropanoid glycosides are a class of natural substances of plant origin with interesting biological activities and pharmacological properties. This study reports the antinociceptive and anti-inflammatory effects of calceolarioside A, a phenylpropanoid glycoside previously isolated from various Calceolaria species. In models of acute nociception induced by thermal stimuli, such as the hot plate and tail flick test, calceolarioside administered at doses of 1, 5, and 10 μg in the left cerebral ventricles did not modify the behavioral response of mice. In an inflammatory based persistent pain model as the formalin test, calceolarioside A at the high dose tested (100 μg/paw) reduced the licking activity induced by formalin by 35% in the first phase and by 75% in the second phase of the test. In carrageenan-induced thermal hyperalgesia, calceolarioside A (50 and 100 μg/paw) was able to significantly reverse thermal hyperalgesia induced by carrageenan. The anti-inflammatory activity of calceolarioside A was then assessed using the zymosan-induced paw edema model. Calceolarioside A (50 and 100 μg/paw) induced a significant reduction in the edema from 1 to 4 h after zymosan administration. Measuring IL-6, TNFα, and IL-1β pro-inflammatory cytokines released from LPS-stimulated THP-1 cells, calceolarioside A in a concentration-dependent manner reduced the release of these cytokines from THP-1 cells. Taken together, our results highlight, for the first time, the potential and selective anti-inflammatory properties of this natural-derived compound, prompting its rationale use for further investigations. Full article
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13 pages, 1521 KB  
Article
Mating Disruption of Pseudococcus calceolariae (Maskell) (Hemiptera, Pseudococcidae) in Fruit Crops
by Carolina Ballesteros, Alda Romero, María Colomba Castro, Sofía Miranda, Jan Bergmann and Tania Zaviezo
Insects 2021, 12(4), 343; https://doi.org/10.3390/insects12040343 - 13 Apr 2021
Cited by 8 | Viewed by 4137
Abstract
Pseudococcus calceolariae, the citrophilous mealybug, is a species of economic importance. Mating disruption (MD) is a potential control tool. During 2017–2020, trials were conducted to evaluate the potential of P. calceolariae MD in an apple and a tangerine orchard. Two pheromone doses, [...] Read more.
Pseudococcus calceolariae, the citrophilous mealybug, is a species of economic importance. Mating disruption (MD) is a potential control tool. During 2017–2020, trials were conducted to evaluate the potential of P. calceolariae MD in an apple and a tangerine orchard. Two pheromone doses, 6.32 g/ha (2017–2018) and 9.45 g/ha (2019–2020), were tested. The intermediate season (2018–2019) was evaluated without pheromone renewal to study the persistence of the pheromone effect. Male captures in pheromone traps, mealybug population/plant, percentage of infested fruit at harvest and mating disruption index (MDI) were recorded regularly. In both orchards, in the first season, male captures were significantly lower in MD plots compared to control plots, with an MDI > 94% in the first month after pheromone deployment. During the second season, significantly lower male captures in MD plots were still observed, with an average MDI of 80%. At the third season, male captures were again significant lower in MD than control plots shortly after pheromone applications. In both orchards, population by visual inspection and infested fruits were very low, without differences between MD and control plots. These results show the potential use of mating disruption for the control of P. calceolariae. Full article
(This article belongs to the Special Issue From Insect Pheromones to Mating Disruption: Theory and Practice)
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23 pages, 3986 KB  
Article
Accumulation of As, Ag, Cd, Cu, Pb, and Zn by Native Plants Growing in Soils Contaminated by Mining Environmental Liabilities in the Peruvian Andes
by Edith Cruzado-Tafur, Katarzyna Bierla, Lisard Torró and Joanna Szpunar
Plants 2021, 10(2), 241; https://doi.org/10.3390/plants10020241 - 27 Jan 2021
Cited by 21 | Viewed by 6617
Abstract
The capability of native plant species grown in polluted post-mining soils to accumulate metals was evaluated in view of their possible suitability for phytoremediation. The study areas included two environmental liabilities in the Cajamarca region in the Peruvian Andes. The content of As, [...] Read more.
The capability of native plant species grown in polluted post-mining soils to accumulate metals was evaluated in view of their possible suitability for phytoremediation. The study areas included two environmental liabilities in the Cajamarca region in the Peruvian Andes. The content of As, Ag, Cd, Cu, Pb, and Zn was determined in individual plant organs and correlated with soil characteristics. The degree of the pollution depended on the metal with results ranging from uncontaminated (Cd) to moderately (Zn), strongly (As, Cu), and extremely contaminated (Pb, Ag) soils. The metals were mainly present in the fractions with limited metal mobility. The bioaccumulation of the metals in plants as well the translocation into overground organs was determined. Out of the 21 plants evaluated, Pernettya prostrata and Gaultheria glomerate were suitable for Zn, and Gaultheria glomerata and Festuca sp. for Cd, phytostabilization. The native species applicable for Cd phytoremediation were Ageratina glechonophylla, Bejaria sp., whereas Pernettya prostrata Achyrocline alata,Ageratina fastigiate, Baccharis alnifolia, Calceolaria tetragona, Arenaria digyna, Hypericum laricifolium, Brachyotum radula, and Nicotiana thyrsiflora were suitable for both Cd and Zn. None of the studied plants appeared to be suitable for phytoremediation of Pb, Cu, As and Ag. Full article
(This article belongs to the Special Issue Heavy Metal Pollution and Plants Growth)
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12 pages, 1433 KB  
Article
Self-Compatibility Not Associated with Morphological or Genetic Diversity Reduction in Oil-Rewarding Calceolaria Species
by Maureen Murúa, Anahí Espíndola and Fernanda Pérez
Plants 2020, 9(10), 1377; https://doi.org/10.3390/plants9101377 - 16 Oct 2020
Cited by 4 | Viewed by 2812
Abstract
One of the most common evolutionary transitions in angiosperms is the reproductive change from outcrossing to selfing, commonly associated with changes in floral biology and genetic diversity. Here, we aim to test whether self-compatibility leads to a reduction of floral traits and genetic [...] Read more.
One of the most common evolutionary transitions in angiosperms is the reproductive change from outcrossing to selfing, commonly associated with changes in floral biology and genetic diversity. Here, we aim to test whether self-compatibility leads to a reduction of floral traits and genetic diversity. For this, we experimentally estimate levels of self-compatibility, measure three floral traits and estimate four genetic diversity parameters using nine microsatellites in nine Calceolaria species. Our analysis indicated that four of the study species were self-incompatible. In addition, we found that self-compatible species did not show a reduction in floral traits size, but rather displayed larger corolla and elaiophore areas. Our analyses of genetic diversity identified larger allele number and observed heterozygosity in selfers than in outcrossers, but did not find larger inbreeding in the self-compatible species. Even though our results contradict our expectations, in the case of Calceolaria, their high dependence on only two genera of oil-bees puts the genus in a vulnerable reproductive position, probably facilitating the evolution of reproductive assurance mechanisms in the absence of pollinators. As a result, plants maintain their pollinator attraction traits while evolving the ability to self, possibly in a delayed way. Full article
(This article belongs to the Section Plant Ecology)
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10 pages, 2437 KB  
Brief Report
Different Pollinators’ Functional Traits Can Explain Pollen Load in Two Solitary Oil-Collecting Bees
by Maureen Murúa
Insects 2020, 11(10), 685; https://doi.org/10.3390/insects11100685 - 11 Oct 2020
Cited by 10 | Viewed by 3465
Abstract
Functional traits have been shown to be a good predictor of pollen load for some pollinator bee species, but little is known about solitary bees. In this study, I used two solitary oil-collecting bees to explore the impact of functional traits on the [...] Read more.
Functional traits have been shown to be a good predictor of pollen load for some pollinator bee species, but little is known about solitary bees. In this study, I used two solitary oil-collecting bees to explore the impact of functional traits on the pollen load of two oil-secreting Calceolaria species. I therefore measured the visitation frequency, the time spent manipulating the flower, pollinator body size and pollen load for each bee species. The results reveal that each pollinator visits different Calceolaria species (C. cavanillesii and C. filicaulis) for pollen and/or oil and at least another four herb species for pollen in different proportions. In addition, each bee species presents different functional traits that affect Calceolaria pollen load. For C. chilensis, it was only its body size that affected the Calceolaria pollen load, while in C. subcaeruleus, both body size and handling time together account for its pollen load. Overall, these results highlight the role of pollinators’ functional traits in different stages of the pollination process, and even more in specialized plant-pollination systems. Full article
(This article belongs to the Section Insect Ecology, Diversity and Conservation)
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14 pages, 1448 KB  
Article
Multiple Mating in the Citrophilous Mealybug Pseudococcus calceolariae: Implications for Mating Disruption
by Renato Ricciardi, Andrea Lucchi, Giovanni Benelli and David Maxwell Suckling
Insects 2019, 10(9), 285; https://doi.org/10.3390/insects10090285 - 5 Sep 2019
Cited by 12 | Viewed by 4189
Abstract
The citrophilous mealybug Pseudococcus calceolariae (Maskell) (Hemiptera, Pseudococcidae) is a primary pest of various crops, including grapevines. The use of insecticides against this species is difficult in most cases because its life cycle includes an extended duration of eggs, juveniles, and adults under [...] Read more.
The citrophilous mealybug Pseudococcus calceolariae (Maskell) (Hemiptera, Pseudococcidae) is a primary pest of various crops, including grapevines. The use of insecticides against this species is difficult in most cases because its life cycle includes an extended duration of eggs, juveniles, and adults under the bark and on the roots. Pheromone-based control strategies can present new eco-friendly opportunities to manage this species, as in the case of Planococcus ficus (Signoret) and Planococcus citri (Risso). With this aim it is critical to understand behavioral aspects that may influence pheromone-based control strategies. Herein, the capability of males to fertilize multiple females was investigated, trying to understand whether this behavior could negatively impact the efficacy of mass trapping, mating disruption, or the lure and kill technique. Results showed that a P. calceolariae male can successfully mate and fertilize up to 13 females. The copulation time in subsequent mating events and the time between copulations did not change over time but the number of matings per day significantly decreased. In a further experiment, we investigated the mate location strategy of P. calceolariae males, testing the attractiveness of different loadings of sex pheromone on males in a flight tunnel. Males constantly exposed to 16 rubber septa loaded with the sex pheromone showed a significant decrease in female detection at 1 and 30 μg loadings (0.18 and 0.74 visits per female for each visit per septum, respectively), whereas in the control about 9.2-fold more of the released males successfully detected the female in the center of the array of 16 septa without pheromone. Male location of females in the control (45%) was significantly higher than in the arrays with surrounding pheromone (5% and 20% at 1 and 30 μg loadings, respectively). Mating only occurred in the control arrays (45%). This study represents a useful first step to developing pheromone-based strategies for the control of citrophilous mealybugs. Full article
(This article belongs to the Special Issue From Insect Pheromones to Mating Disruption: Theory and Practice)
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16 pages, 2935 KB  
Article
In Silico Studies on Compounds Derived from Calceolaria: Phenylethanoid Glycosides as Potential Multitarget Inhibitors for the Development of Pesticides
by Marco A. Loza-Mejía, Juan Rodrigo Salazar and Juan Francisco Sánchez-Tejeda
Biomolecules 2018, 8(4), 121; https://doi.org/10.3390/biom8040121 - 23 Oct 2018
Cited by 50 | Viewed by 7127
Abstract
An increasing occurrence of resistance in insect pests and high mammal toxicity exhibited by common pesticides increase the need for new alternative molecules. Among these alternatives, bioinsecticides are considered to be environmentally friendly and safer than synthetic insecticides. Particularly, plant extracts have shown [...] Read more.
An increasing occurrence of resistance in insect pests and high mammal toxicity exhibited by common pesticides increase the need for new alternative molecules. Among these alternatives, bioinsecticides are considered to be environmentally friendly and safer than synthetic insecticides. Particularly, plant extracts have shown great potential in laboratory conditions. However, the lack of studies that confirm their mechanisms of action diminishes their potential applications on a large scale. Previously, we have reported the insect growth regulator and insecticidal activities of secondary metabolites isolated from plants of the Calceolaria genus. Herein, we report an in silico study of compounds isolated from Calceolaria against acetylcholinesterase, prophenoloxidase, and ecdysone receptor. The molecular docking results are consistent with the previously reported experimental results, which were obtained during the bioevaluation of Calceolaria extracts. Among the compounds, phenylethanoid glycosides, such as verbascoside, exhibited good theoretical affinity to all the analyzed targets. In light of these results, we developed an index to evaluate potential multitarget insecticides based on docking scores. Full article
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20 pages, 5451 KB  
Review
(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †
by Angela La Bella, Francesca Leonelli, Luisa Maria Migneco and Rinaldo Marini Bettolo
Molecules 2016, 21(9), 1197; https://doi.org/10.3390/molecules21091197 - 8 Sep 2016
Cited by 11 | Viewed by 7669
Abstract
In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the [...] Read more.
In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned. Full article
(This article belongs to the Special Issue Synthesis of Bioactive Compounds from the Chiral Pool)
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12 pages, 571 KB  
Article
Diterpenylhydroquinones from Natural ent-Labdanes Induce Apoptosis through Decreased Mitochondrial Membrane Potential
by Joan Villena, Alejandro Madrid, Iván Montenegro, Enrique Werner, Mauricio Cuellar and Luis Espinoza
Molecules 2013, 18(5), 5348-5359; https://doi.org/10.3390/molecules18055348 - 10 May 2013
Cited by 14 | Viewed by 4980
Abstract
In this study, we examined the cytotoxic effects of seven ent-labdane derivatives 17 (0–100 μM) in different human cancer cell lines. Our results showed that compounds 13 exhibited significant dose-dependent inhibition on the growth of the three different [...] Read more.
In this study, we examined the cytotoxic effects of seven ent-labdane derivatives 17 (0–100 μM) in different human cancer cell lines. Our results showed that compounds 13 exhibited significant dose-dependent inhibition on the growth of the three different human cell lines, according to the sulphorhodamine B assay and produced morphological changes consistent with apoptosis, as confirmed by Hoestch 3342 staining analysis. They induced apoptosis in various cancer cell lines, as shown by nuclear condensation and fragmentation and caspase 3 activation. Such induction was associated with the depletion of mitochondrial membrane potential. These activities led to the cleavage of caspases and the trigger of cell death process. Overall, the compounds showed potent proapoptotic effects on the two different cancer cell lines, suggesting that the compounds deserve more extensive investigation of their potential medicinal applications. Full article
(This article belongs to the Section Medicinal Chemistry)
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2 pages, 15 KB  
Abstract
Chemistry of the Calceolaria Genus. Structural and Biological Aspects
by Juan A. Garbarino, María C. Chamy and Marisa Piovano
Molecules 2000, 5(3), 302-303; https://doi.org/10.3390/50300302 - 22 Mar 2000
Cited by 17 | Viewed by 6915
Abstract
Autochthonous species of the Calceolaria (Scrophulariaceae) genus are studied. From their apolar extracts 55 new diterpenes of six skeleton types, naphtoquinones and flavonoids have been isolated. Among the different diterpenes malonic substitutions and bis-diterpenes in which both units are joined by a malonic [...] Read more.
Autochthonous species of the Calceolaria (Scrophulariaceae) genus are studied. From their apolar extracts 55 new diterpenes of six skeleton types, naphtoquinones and flavonoids have been isolated. Among the different diterpenes malonic substitutions and bis-diterpenes in which both units are joined by a malonic acid unit stand out. Pimaranes present C-9 epimerisation and, consequently, H-9 has the same orientation as Me-20. From C.sessilis naphthoquinones with antichagasic activity have been isolated; and the biotransformation of 2α,19-dihydroxy-9-epi-entpimara-7,15-diene with Giberella fujikuroi produced 7 new diterpenes. Full article
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