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21 pages, 4404 KB  
Article
Exploring the Antidiabetic Properties of Polyalthia longifolia Leaf and Stem Extracts: In Vitro α-Glucosidase and Glycation Inhibition
by Guglielmina Froldi, Marguerite Kamdem Simo, Laura Tomasi, Giulia Tadiotto, Francine Medjiofack Djeujo, Xavier Gabriel Fopokam, Emmanuel Souana, Modeste Lambert Sameza, Pierre Michel Jazet and Fabrice Fekam Boyom
Molecules 2025, 30(21), 4264; https://doi.org/10.3390/molecules30214264 - 31 Oct 2025
Viewed by 1068
Abstract
Polyalthia longifolia, a member of the Annonaceae family, is traditionally used for its medicinal properties, including as an antidiabetic remedy, primarily in Asia and sub-Saharan Africa. This study investigated the potential of six P. longifolia extracts in counteracting hyperglycemia and diabetes-related complications. [...] Read more.
Polyalthia longifolia, a member of the Annonaceae family, is traditionally used for its medicinal properties, including as an antidiabetic remedy, primarily in Asia and sub-Saharan Africa. This study investigated the potential of six P. longifolia extracts in counteracting hyperglycemia and diabetes-related complications. Aqueous, ethanol, and methanol extracts from leaves and stems were evaluated for their antihyperglycemic, antiglycation, and antiradical properties using α-glucosidase, BSA, and ORAC assays, respectively. Phytochemical characterization was conducted using TPC and TFC assays, and HPLC analysis identified specific bioactive compounds, including various phenolic compounds (gallic acid, (+)-catechin, epicatechin, caffeic acid, ellagic acid and rosmarinic acid) and flavonoids (luteolin, kaempferol and baicalein). The MTT assay on the human cell line HT-29 assessed the activity of extracts on cell viability, showing slight cytotoxicity. Results demonstrated significant antidiabetic activity of the ethanol and methanol extracts from P. longifolia leaves. This study provides new insights into the potential use of P. longifolia in diabetes mellitus and supports the valorization of traditional medicinal plants. Full article
(This article belongs to the Special Issue Bioactivity of Natural Compounds: From Plants to Humans, 2nd Edition)
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15 pages, 1564 KB  
Article
Pawpaw (Asimina triloba) Seed Extract Suppresses High-Fat Diet-Induced Obesity in Mice
by Shiori Takano, Sakura Kaneko, Ryo Midorikawa, Honoka Nara, Yurie Sato, Minori Uchiyama, Haruka Iobe, Yuki Saito-Matsuzawa, Hideyuki Sone and Shin Kamiyama
Int. J. Mol. Sci. 2025, 26(16), 7719; https://doi.org/10.3390/ijms26167719 - 9 Aug 2025
Viewed by 2383
Abstract
Asimina triloba (pawpaw), a member of the Annonaceae family, contains various bioactive phytochemicals, including alkaloids, polyphenols, and acetogenins. In this study, the effects of pawpaw seed extract (PSE) on obesity and plasma lipid concentrations were investigated in mice with high-fat diet (HFD)-induced obesity. [...] Read more.
Asimina triloba (pawpaw), a member of the Annonaceae family, contains various bioactive phytochemicals, including alkaloids, polyphenols, and acetogenins. In this study, the effects of pawpaw seed extract (PSE) on obesity and plasma lipid concentrations were investigated in mice with high-fat diet (HFD)-induced obesity. Male C57BL/6J mice were fed a normal diet (ND) or an HFD for two weeks. The mice in the latter group were then divided into three groups: HFD, L-PSE, and H-PSE. Following a two-week adaptive period, the L-PSE and H-PSE groups were fed an experimental diet containing 250 mg and 500 mg PSE/kg of HFD, respectively, for two weeks. Mice in the HFD group exhibited significantly higher body weights than that of mice in the ND group. A significant decrease in body weight was observed in the H-PSE group compared with that in the HFD group. The perirenal, testicular, and total visceral fat masses of the mice in the H-PSE group were consistently lower than those of the mice in the HFD group. Administration of high-dose PSE decreased the expression of Fasn (encoding fatty acid synthase) and Dgat2 (encoding diglyceride acyltransferase 2) in testicular fat tissues. However, PSE administration did not decrease blood glucose and plasma cholesterol levels compared with that in the HFD group. These findings suggest that the administration of PSE suppresses HFD-induced obesity in mice, while its hypoglycemic or cholesterol-lowering actions are less pronounced. Full article
(This article belongs to the Special Issue Natural-Derived Bioactive Compounds in Disease Treatment)
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15 pages, 2791 KB  
Article
In Vitro and In Vivo Efficacy of the Essential Oil from the Leaves of Annona amazonica R.E. Fries (Annonaceae) Against Liver Cancer
by Maria V. L. de Castro, Milena C. F. de Lima, Gabriela A. da C. Barbosa, Sabrine G. Carvalho, Amanda M. R. M. Coelho, Luciano de S. Santos, Valdenizia R. Silva, Rosane B. Dias, Milena B. P. Soares, Emmanoel V. Costa and Daniel P. Bezerra
Molecules 2025, 30(15), 3248; https://doi.org/10.3390/molecules30153248 - 2 Aug 2025
Viewed by 1276
Abstract
Annona amazonica R.E. Fries (synonyms Annona amazonica var. lancifolia R.E. Fries), popularly known in Brazil as “envireira”, is a tropical tree belonging to the Annonaceae family and is traditionally used as a food source. In this work, the in vitro and in vivo [...] Read more.
Annona amazonica R.E. Fries (synonyms Annona amazonica var. lancifolia R.E. Fries), popularly known in Brazil as “envireira”, is a tropical tree belonging to the Annonaceae family and is traditionally used as a food source. In this work, the in vitro and in vivo anti-liver cancer effects of essential oil (EO) from A. amazonica leaves were investigated for the first time. The chemical composition of the EO was evaluated via GC–MS and GC–FID. The alamar blue assay was used to evaluate the cytotoxicity of EOs against different cancerous and noncancerous cell lines. Cell cycle analyses, YO-PRO-1/PI staining, and rhodamine 123 staining were performed via flow cytometry in HepG2 cells treated with EO. The in vivo antitumor activity of EO was evaluated in NSG mice that were xenografted with HepG2 cells and treated with EO at a dose of 60 mg/kg. The major constituents (>5%) of the EO were (E)-caryophyllene (32.01%), 1,8-cineole (13.93%), α-copaene (7.77%), α-humulene (7.15%), and α-pinene (5.13%). EO increased apoptosis and proportionally decreased the number of viable HepG2 cells. The induction of DNA fragmentation and cell shrinkage together with a significant reduction in the ΔΨm in EO-treated HepG2 cells confirmed that EO can induce apoptosis. A significant 39.2% inhibition of tumor growth in vivo was detected in EO-treated animals. These data indicate the anti-liver cancer potential of EO from A. amazonica leaves. Full article
(This article belongs to the Special Issue Advances and Opportunities of Natural Products in Drug Discovery)
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15 pages, 3067 KB  
Article
Essential Oil from the Leaves of Annona neoinsignis H. Rainer (Annonaceae) Against Liver Cancer: In Vitro and In Vivo Studies
by Melissa P. Souza, Maria V. L. de Castro, Gabriela A. da C. Barbosa, Sabrine G. Carvalho, Amanda M. R. M. Coelho, Rosane B. Dias, Milena B. P. Soares, Emmanoel V. Costa and Daniel P. Bezerra
Molecules 2025, 30(14), 2971; https://doi.org/10.3390/molecules30142971 - 15 Jul 2025
Cited by 2 | Viewed by 1290
Abstract
Annona neoinsignis H. Rainer (Annonaceae) is a tree native to the Amazon rainforest. Its fruits are also suitable for human consumption in their natural state or are processed to make desserts. In this work, we characterized the chemical composition of the essential oil [...] Read more.
Annona neoinsignis H. Rainer (Annonaceae) is a tree native to the Amazon rainforest. Its fruits are also suitable for human consumption in their natural state or are processed to make desserts. In this work, we characterized the chemical composition of the essential oil (EO) from the leaves of A. neoinsignis and evaluated its anti-liver-cancer potential via in vitro and in vivo approaches. Chemical composition analysis revealed β-elemene, (E)-caryophyllene, germacrene D, and germacrene B as the main constituents. The EO had IC50 values ranging from 12.28 to 37.50 μg/mL for B16-F10 cells and MCF-7 cells, whereas an IC50 value of >50 μg/mL was found for noncancerous MRC-5 cells. DNA fragmentation, YO-PRO-1 staining, and loss of mitochondrial transmembrane potential were detected in EO-treated HepG2 cells, indicating the induction of apoptosis. Significant in vivo growth inhibition of 53.7% was observed in mice bearing HepG2 cell xenografts treated with EO at a dosage of 40 mg/kg. These data suggest that EO from A. neoinsignis leaves is a drug source for liver cancer. Full article
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18 pages, 4943 KB  
Article
The Coexistence of Bicellular and Tricellular Pollen Might Be the Third Type of Pollen Cell Number: Evidence from Annonaceae
by Yangying Gan, Qi Zhang, Chunfen Xiao and Jingyao Ping
Biology 2025, 14(5), 562; https://doi.org/10.3390/biology14050562 - 17 May 2025
Cited by 1 | Viewed by 1078
Abstract
Anther is thought to release either bicellular or tricellular pollen when mature. Though a few species had been found to shed both bicellular and tricellular pollen, due to their low frequency, they had been overlooked as special cases of bicellular or tricellular pollen [...] Read more.
Anther is thought to release either bicellular or tricellular pollen when mature. Though a few species had been found to shed both bicellular and tricellular pollen, due to their low frequency, they had been overlooked as special cases of bicellular or tricellular pollen in previous phylogenetic studies. In the present work, the pollen cytologies of 89 species from 26 genera of Annonaceae were observed using the overall transparency method and paraffin sectioning method. The results show that 73 species from 25 genera distribute bicellular pollen, while 16 species from 10 genera shed both bicellular and tricellular pollen. This is the first time that so many species with both types of pollen has been observed in the same family. Combined with reports from other families, the plants that were known to shed both types of pollen included 15 families, 40 genera, and 52 species. Our results indicate that the coexistence of bicellular and tricellular pollen might be the third type of pollen cell number. And the systematic relationship among them is needed to be reanalyzed. Full article
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18 pages, 2356 KB  
Article
Effect of Auxins on the Accumulation of Alkaloids in Ungrafted Annona emarginata (Schltdl.) H. Rainer and Annona emarginata (Schltdl.) H. Rainer Grafted with Annona atemoya Mabb.
by Carolina Ovile Mimi, Iván De-la-Cruz-Chacón, Felipe Moura Araujo da Silva, Victor Cauan Rocha Roberto and Gisela Ferreira
Molecules 2025, 30(9), 2070; https://doi.org/10.3390/molecules30092070 - 7 May 2025
Cited by 1 | Viewed by 1213
Abstract
Plant regulators, such as auxins, modulate the synthesis of specialized metabolites and aid in the bioprospection of molecules. Annona emarginata is known to produce antifungal alkaloids and serves as a rootstock for Annona atemoya. This study evaluated the effects of indoleacetic acid [...] Read more.
Plant regulators, such as auxins, modulate the synthesis of specialized metabolites and aid in the bioprospection of molecules. Annona emarginata is known to produce antifungal alkaloids and serves as a rootstock for Annona atemoya. This study evaluated the effects of indoleacetic acid (IAA), indolebutyric acid (IBA), and naphthaleneacetic acid (NAA) applications on the accumulation of alkaloids in ungrafted A. emarginata and grafted with A. atemoya. Total alkaloids were analyzed by spectrophotometry, and alkaloid profiles were analyzed by DI-MS at 8, 14, and 20 days after treatments (DAT). The results indicated that IAA and NAA had the strongest effects on increasing the synthesis of alkaloids in the roots of ungrafted seedlings. In grafted plants, IBA had a more pronounced effect on roots; however, at final evaluation, all three auxins had an impact on both roots and leaves. Chemometric analysis revealed that auxins also altered the alkaloid composition in both seedling types. Nineteen alkaloids were identified regardless of treatment and harvest time. Eight alkaloids were identified for the first time in A. emarginata and nine were identified in A. atemoya. The main alkaloids found in ungrafted seedlings treated with IAA, IBA, and NAA were liriodenine and lanuginosine. In grafted seedlings, liriodenine and reticuline were the primary alkaloids found in roots, whereas liriodenine, lanuginosine, and reticuline were significantly present in leaves. The use of auxins to enhance alkaloid biosynthesis demonstrates their potential for bioprospection and the development of crops tolerant to biotic stress. Full article
(This article belongs to the Special Issue Synthesis, Characterization, and Biological Evaluation of Alkaloids)
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15 pages, 2857 KB  
Article
Isoespintanol Isolated from Oxandra cf. xylopioides (Annonaceae) Leaves Ameliorates Pancreatic Dysfunction and Improves Insulin Sensitivity in Murine Model of Fructose-Induced Prediabetes
by Sherley Catherine Farromeque Vásquez, Luisa González Arbeláez, Benjamín Rojano, Guillermo Schinella, Bárbara Maiztegui and Flavio Francini
Plants 2025, 14(5), 745; https://doi.org/10.3390/plants14050745 - 1 Mar 2025
Cited by 2 | Viewed by 1218
Abstract
In rats, a fructose-rich diet triggers endocrine-metabolic disturbances similar to those present in human prediabetes. We evaluated the protective effect of isoespintanol, a monoterpene isolated from Oxandra cf. xylopioides (Annonaceae), on pancreatic islet. Rats were kept for three weeks with a standard commercial [...] Read more.
In rats, a fructose-rich diet triggers endocrine-metabolic disturbances similar to those present in human prediabetes. We evaluated the protective effect of isoespintanol, a monoterpene isolated from Oxandra cf. xylopioides (Annonaceae), on pancreatic islet. Rats were kept for three weeks with a standard commercial diet and tap water (C), plus 10% fructose (F), or F plus isoespintanol (I; 10 mg/kg, i.p.). Glycemia, triglyceridemia, total cholesterol, HDL-cholesterol, insulin resistance index (IRX), and glucose tolerance tests were determined. Glucose-stimulated insulin secretion (GSIS) and gene expression of insulin signalling mediators (insulin receptor -IR-, IRS1/2, PI3K), oxidative stress (SOD-2, GPx, GSR, 3’-nitrotyrosine), inflammation (TNF-α, IL-1β, PAI-1), mitochondrial function (Bcl-2, mtTFA, PGC-1α), and apoptosis markers were evaluated in pancreatic islets. The F group increased triglyceridemia, non-HDL-cholesterol, and IRX, and decreased HDL-cholesterol and impaired glucose tolerance, with alterations reversed by isoespintanol administration (p < 0.05). Isoespintanol normalized higher GSIS recorded in the F group. F decreased mRNA levels of insulin signalling mediators and mitochondrial function markers, and increased the expression of inflammatory, apoptotic, and oxidative stress markers, alterations that were significantly reversed by isoespintanol. Current results suggest that isoespintanol improved insular oxidative stress and inflammation by affecting the IR-PI3K pathway, which plays a pivotal role in insulin resistance development, underlying its therapeutic potential for the prevention of type 2 diabetes before its onset (prediabetes). Full article
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13 pages, 2187 KB  
Article
Defense Mechanisms of Xylopia aromatica (Lam.) Mart. in the Dry Season in the Brazilian Savanna
by Felipe Campos, Maria Vieira, Marília Sousa, Letícia Jorge, Gisela Ferreira, Marcia Marques and Carmen Boaro
Life 2024, 14(11), 1416; https://doi.org/10.3390/life14111416 - 2 Nov 2024
Cited by 1 | Viewed by 1560
Abstract
Water availability and light during the dry and rainy seasons in the Cerrado may influence plants’ stomatal movement and the entry of CO2 for organic synthesis, which is the main electron drain. A lower stomatal conductance may contribute to the energy accumulated [...] Read more.
Water availability and light during the dry and rainy seasons in the Cerrado may influence plants’ stomatal movement and the entry of CO2 for organic synthesis, which is the main electron drain. A lower stomatal conductance may contribute to the energy accumulated in the chloroplasts being directed towards the synthesis of compounds, which contributes to the activity of antioxidant enzymes to neutralize reactive oxygen species. Xylopia aromatica is a characteristic Cerrado species, and it is often recommended for recovering degraded areas. This study aimed to investigate the influence of the dry and rainy seasons on the metabolic adjustments of Xylopia aromatica in a portion of the Brazilian savanna in the state of São Paulo. In the rainy season, better photosynthetic performance led to greater investment in essential oil production. In the dry season, the plants may direct part of their reducing sugars to the syntheses of carotenoids and anthocyanins, which may help the antioxidant enzymes to neutralize reactive oxygen species. Carotenoids assist in the dissipation of photosystem energy, which has the potential to cause oxidative stress. During this season, lower stomatal conductance prevented excessive water loss. These results suggest the acclimatization of this species to the conditions of the Brazilian savanna. Full article
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21 pages, 8382 KB  
Article
Laherradurin Inhibits Colorectal Cancer Cell Growth by Induction of Mitochondrial Dysfunction and Autophagy Induction
by Izamary Delgado-Waldo, Svetlana Dokudovskaya, Yahir A. Loissell-Baltazar, Eduardo Pérez-Arteaga, Jossimar Coronel-Hernández, Mariano Martínez-Vázquez, Eloy Andrés Pérez-Yépez, Alejandro Lopez-Saavedra, Nadia Jacobo-Herrera and Carlos Pérez Plasencia
Cells 2024, 13(19), 1649; https://doi.org/10.3390/cells13191649 - 3 Oct 2024
Cited by 2 | Viewed by 3258
Abstract
LAH, an acetogenin from the Annonaceae family, has demonstrated antitumor activity in several cancer cell lines and in vivo models, where it reduced the tumor size and induced programmed cell death. We focused on the effects of LAH on mitochondrial dynamics, mTOR signaling, [...] Read more.
LAH, an acetogenin from the Annonaceae family, has demonstrated antitumor activity in several cancer cell lines and in vivo models, where it reduced the tumor size and induced programmed cell death. We focused on the effects of LAH on mitochondrial dynamics, mTOR signaling, autophagy, and apoptosis in colorectal cancer (CRC) cells to explore its anticancer potential. Methods: CRC cells were treated with LAH, and its effects on mitochondrial respiration and glycolysis were measured using Seahorse XF technology. The changes in mitochondrial dynamics were observed through fluorescent imaging, while Western blot analysis was used to examine key autophagy and apoptosis markers. Results: LAH significantly inhibited mitochondrial complex I activity, inducing ATP depletion and a compensatory increase in glycolysis. This disruption caused mitochondrial fragmentation, a trigger for autophagy, as shown by increased LC3-II expression and mTOR suppression. Apoptosis was also confirmed through the cleavage of caspase-3, contributing to reduced cancer cell viability. Conclusions: LAH’s anticancer effects in CRC cells are driven by its disruption of mitochondrial function, triggering both autophagy and apoptosis. These findings highlight its potential as a therapeutic compound for further exploration in cancer treatment. Full article
(This article belongs to the Special Issue Targeting Hallmarks of Cancer)
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17 pages, 2756 KB  
Article
Biopolymer from Annona muricata Residues as a Potential Sustainable Raw Material for Industrial Applications
by Igor F. S. Ramos, Samuel C. Dias, Talissa B. C. Lopes, Francisco T. dos S. Silva Júnior, Ricardo de Araújo, Stanley J. C. Gutierrez, Claudia Pessoa, Josy A. Osajima, Marcia S. Rizzo, Edson C. Silva-Filho, Manuela Amorim, Óscar Ramos, Alessandra B. Ribeiro and Marcilia P. Costa
Polysaccharides 2024, 5(4), 523-539; https://doi.org/10.3390/polysaccharides5040033 - 26 Sep 2024
Cited by 1 | Viewed by 3056
Abstract
Annona muricata is a fruit species belonging to the Annonaceae family, which is native to the warmer tropical areas of North and South America. A large amount of discarded residue from A. muricata is of interest for obtaining new industrial inputs. To propose [...] Read more.
Annona muricata is a fruit species belonging to the Annonaceae family, which is native to the warmer tropical areas of North and South America. A large amount of discarded residue from A. muricata is of interest for obtaining new industrial inputs. To propose the applications of the biopolymer from A. muricata residues (Biop_AmRs), this study aimed to characterize this input chemically and functionally, as well as to evaluate its potential for hemocompatibility and cytotoxicity activity in vitro. Biop_AmRs is an anionic heteropolysaccharide composed of glucose, arabinose, xylose, galactose, mannose, uronic acid, and proteins. This biopolymer exhibited a semicrystalline structure and good thermal stability. Biop_AmRs exhibited excellent water holding capacity, emulsifying properties, and mucoadhesiviness and demonstrated hemocompatibility and cytocompatibility on the L929 cell line. These results indicate possible applications for this biopolymer as a potential environmentally friendly raw material in the food, pharmaceutical, biomedical, and cosmetic industries. Full article
(This article belongs to the Topic Polymers from Renewable Resources, 2nd Volume)
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18 pages, 594 KB  
Article
Impact of External Sources of Indole Acetic Acid and 2,3,5-Triiodobenzoic Acid on Alkaloid Production and Their Relationships with Primary Metabolism and Antioxidant Activity in Annona emarginata (Schltdl.) H. Rainer
by Bruna Cavinatti Martin, Ivan De-la-Cruz-Chacón, Carolina Ovile Mimi, Carmen Silvia Fernandes Boaro, Felipe Girotto Campos, Inara Regiane Moreira-Coneglian and Gisela Ferreira
Plants 2024, 13(18), 2637; https://doi.org/10.3390/plants13182637 - 21 Sep 2024
Cited by 2 | Viewed by 1510
Abstract
Annona emarginata is a native Brazilian species capable of producing at least ten alkaloids of ecological, agronomic, and pharmacological importance. Some studies have explored the effect of external phytoregulators on the production of alkaloids, including the effect of auxins, which, like alkaloids, derive [...] Read more.
Annona emarginata is a native Brazilian species capable of producing at least ten alkaloids of ecological, agronomic, and pharmacological importance. Some studies have explored the effect of external phytoregulators on the production of alkaloids, including the effect of auxins, which, like alkaloids, derive from the shikimic acid pathway. Thus, this study aimed to evaluate how indole acetic acid (IAA) and its inhibitor 2,3,5-triiodobenzoic acid (TIBA) impact the production of alkaloids and the primary metabolism of A. emarginata, which brings advances in the understanding of the mechanisms of alkaloid synthesis and can aid in the bioprospection of molecules of interest in Annonaceae. The design was completely randomized, with three treatments (control, IAA [10−6 M] and TIBA [10−6 M]) and five collection times (12, 36, 84, 156, and 324 h). The following variables were analyzed: total alkaloids, alkaloid profile, nitrate reductase activity, gas exchange in photosynthesis, chlorophyll a fluorescence, sugars, starch, and antioxidant activity. Of the twelve alkaloids analyzed, discretine and xylopine were not detected in the control plants; however, both were detected when IAA was applied (in roots and leaves) and xylopine (in roots) when the inhibitor was applied. The alkaloid asimilobine was not detected with the use of TIBA. Variations in alkaloid concentrations occurred in a punctual manner, without significant variations in photosynthesis and nitrate reductase activity, but with variations in the antioxidant system and sugar concentrations, mainly at 156 h, when the highest alkaloid concentrations were observed with the use of TIBA. It could be concluded that IAA is capable of selectively modulating the production of alkaloids in A. emarginata, either due to an external source or by the application of its inhibitor (TIBA). Full article
(This article belongs to the Special Issue Advances in Plant Auxin Biology)
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19 pages, 4998 KB  
Article
The Development and Pre-Clinical Anti-Inflammatory Efficacy of a New Transdermal Ureasil–Polyether Hybrid Matrix Loaded with Flavonoid-Rich Annona muricata Leaf Extract
by Camila Beatriz Barros Araújo, José de Oliveira Alves Júnior, Mariana Rillo Sato, Kammila Martins Nicolau Costa, Jéssica Roberta Lima, Bolívar Ponciano Goulart de Lima Damasceno, Francisco José Batista de Lima Junior, Bruna Galdorfini Chiari Andréo, Vanda Lucia dos Santos and João Augusto Oshiro-Junior
Pharmaceutics 2024, 16(8), 1097; https://doi.org/10.3390/pharmaceutics16081097 - 21 Aug 2024
Cited by 2 | Viewed by 1986
Abstract
This study aimed to develop a novel ureasil–polyether transdermal hybrid matrix (U-PEO) loaded with Annona muricata concentrated extract (AMCE), which exhibits potent anti-inflammatory activity. The extract was obtained by maceration, a method that allowed for the extraction of a high concentration of flavonoids [...] Read more.
This study aimed to develop a novel ureasil–polyether transdermal hybrid matrix (U-PEO) loaded with Annona muricata concentrated extract (AMCE), which exhibits potent anti-inflammatory activity. The extract was obtained by maceration, a method that allowed for the extraction of a high concentration of flavonoids (39.27 mg/g of extract). In vivo tests demonstrated that 10 mg/kg of AMCE inhibited inflammation for 6 h. The physicochemical characterization of U-PEO with AMCE was conducted via a thermogravimetric analysis (TGA), while its surface was recorded using atomic force microscopy (AFM). The in vitro macroscopic swelling and release tests demonstrated the hydrophilic profile of the material and the percentage of AMCE released. The TGA results demonstrated that the system exhibited physical compatibility due to the thermal stability of U-PEO. Additionally, the AFM analysis revealed a rough and porous surface, with a particular emphasis on the system with AMCE. The release resulted in the liberation of 23.72% of AMCE within 24 h. Finally, the preclinical tests demonstrated that U-PEO with AMCE was also capable of effectively inhibiting inflammation for 6 h, a duration comparable to that of a commercial formulation. The results permit the advancement of the study towards the development of a transdermal system, thereby rendering its application in clinical studies feasible. Full article
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16 pages, 1206 KB  
Article
Gouregine, an α-Gem-Dimethyltetradehydrocularine Alkaloid, and Other Aporphinoid Alkaloids from the Bark of Guatteria olivacea (Annonaceae) and Their In Vitro Cytotoxic Activities
by Emmanoel V. Costa, José Guilherme C. Freitas, Steve Pereira Manickchand, Morgana de S. Araújo, Valdenizia R. Silva, Luciano de S. Santos, Hector Henrique Ferreira Koolen, Felipe M. A. da Silva, Milena Botelho Pereira Soares and Daniel P. Bezerra
Molecules 2024, 29(16), 3834; https://doi.org/10.3390/molecules29163834 - 13 Aug 2024
Cited by 2 | Viewed by 1886
Abstract
Guatteria olivacea R.E. Fries is an Amazonian species known as ‘envira-bobó’ and ‘envira-fofa’ and is common in the states of Amazonas, Acre, and Pará. Recently, the essential oil from the leaves of this species has shown promising antitumor activity both in vitro and [...] Read more.
Guatteria olivacea R.E. Fries is an Amazonian species known as ‘envira-bobó’ and ‘envira-fofa’ and is common in the states of Amazonas, Acre, and Pará. Recently, the essential oil from the leaves of this species has shown promising antitumor activity both in vitro and in vivo. The presence of isoquinoline-derived alkaloids, including aporphinoids and tetrahydroprotoberberine alkaloids, has also been previously reported. In our ongoing search for bioactive compounds from Annonaceae Amazonian plants, the bark of G. olivacea was investigated via classical chromatography techniques, which revealed nine compounds, eight isoquinoline-derived alkaloids, a rare alkaloid with a α-gem-dimethyltetradehydrocularine structure known as gouregine, seven known aporphinoid alkaloids: isopiline, O-methylisopiline, melosmine, 9-hydroxyiguattescine, dihydromelosmine, lysicamine, and guattouregidine, and one known pimaradiene diterpene: acanthoic acid. All the isolated compounds were described for the first time in the bark of G. olivacea, and their structures were elucidated by extensive analyses of their 1D and 2D NMR spectra in combination with MS data. The NMR data of the alkaloids isopiline, O-methylisopiline, melosmine, dihydromelosmine, and guattouregidine were revised due to incomplete data in the literature and some ambiguities. The in vitro cytotoxic activities of the isolated compounds were evaluated against human cancer (HepG2, KG-1a, and HCT116) and noncancerous (MRC-5) cell lines via the Alamar blue assay after 72 h of incubation. Among the compounds evaluated against human cancer cell lines, the most active was the oxoaporphine alkaloid lysicamine, which has strong activity against HCT116 cells, with an IC50 value of 6.64 µg/mL (22.79 µmol/L). Melosmine had a moderate effect on HCT116 cells, with an IC50 value of 16.77 µg/mL (49.70 µmol/L), whereas acanthoic acid had moderate effects on HepG2 and HCT116 cells, with IC50 values of 14.63 µg/mL (48.37 µmol/L) and 21.25 µg/mL (70.25 µmol/L), respectively. Full article
(This article belongs to the Special Issue Antiproliferative Activities of Natural and Synthetic Compounds)
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13 pages, 738 KB  
Article
Liriodenine and Its Probable Role as an Osmolyte during Water Stress in Annona lutescens (Annonaceae)
by Alfredo Cisneros-Andrés, Rocío Cruz-Ortega, Marisol Castro-Moreno and Alma Rosa González-Esquinca
Int. J. Plant Biol. 2024, 15(2), 429-441; https://doi.org/10.3390/ijpb15020033 - 22 May 2024
Cited by 3 | Viewed by 2324
Abstract
In tropical deciduous forests (TDFs), plants have developed various strategies to tolerate desiccation during the dry season. One strategy is osmotic adjustment, which includes the accumulation of secondary metabolites. Annona lutescens, a species that inhabits TDFs, increases and accumulates liriodenine alkaloid in [...] Read more.
In tropical deciduous forests (TDFs), plants have developed various strategies to tolerate desiccation during the dry season. One strategy is osmotic adjustment, which includes the accumulation of secondary metabolites. Annona lutescens, a species that inhabits TDFs, increases and accumulates liriodenine alkaloid in its roots during the dry season. In this study, we evaluate the possible role of this molecule as an osmolyte and in pH homeostasis. We performed growth analyses and determined liriodenine concentrations during water stress in Annona lutescens seedlings grown under controlled temperature, water, and light conditions. We also calculated their osmotic adjustment based on pressure–volume curves and performed solubility tests along a pH gradient. Osmotic adjustment was compared between control plants (irrigated) and plants subjected to 15, 25, and 35 days of water stress. Osmotic adjustment was dramatically higher in plants subjected to 35 days of water stress compared to the control. The solubility of liriodenine was 54% at pH 4.5, and when liriodenine was in contact with malic acid solutions, the pH increased slightly. The highest concentration of liriodenine was in the roots, with a significant increase from 540.855 μg g−1 after 15 days of water stress to 1239.897 μg g−1 after 35 days. Our results suggest that liriodenine plays an important role in the response to water stress as an osmolyte and in pH homeostasis. Full article
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14 pages, 1757 KB  
Article
Antibacterial and Antibiofilm Potential of Ethanolic Extracts of Duguetia vallicola (Annonaceae) against in-Hospital Isolates of Pseudomonas aeruginosa
by Orfa Inés Contreras-Martínez, Daniela Sierra-Quiroz and Alberto Angulo-Ortíz
Plants 2024, 13(10), 1412; https://doi.org/10.3390/plants13101412 - 18 May 2024
Cited by 3 | Viewed by 3030
Abstract
Pseudomonas aeruginosa is an opportunistic pathogen that is especially dominant in people with cystic fibrosis; the drug resistance expressed by this pathogen and its capacity for adaptation poses a significant challenge to its treatment and control, thereby increasing morbidity and mortality rates globally. [...] Read more.
Pseudomonas aeruginosa is an opportunistic pathogen that is especially dominant in people with cystic fibrosis; the drug resistance expressed by this pathogen and its capacity for adaptation poses a significant challenge to its treatment and control, thereby increasing morbidity and mortality rates globally. In this sense, the search for new treatment alternatives is imminent today, with products of plant origin being an excellent alternative for use. The objective of this research was to evaluate the antibacterial and antibiofilm potential and to explore the possible effect of ethanolic extracts from the wood and bark of Duguetia vallicola on the cell membrane. Microdilution assays showed the inhibition of bacterial growth by more than 50%, with the lowest concentration (62.5 μg/mL) of both extracts evaluated. Furthermore, we report the ability of both extracts to inhibit mature biofilms, with inhibition percentages between 48.4% and 93.7%. Intracellular material leakage experiments (260/280 nm), extracellular pH measurements, and fluorescence microscopy with acridine orange (AO) and ethidium bromide (EB) showed cell membrane damage. This indicates that the antibacterial action of ethanolic extracts of D. vallicola is associated with damage to the integrity of the cell membrane and consequent death of these pathogens. These results serve as a reference for future studies in establishing the mechanisms of action of these extracts. Full article
(This article belongs to the Special Issue Biological Activities of Plant Extracts 2023)
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