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1.
An Acad Bras Cienc ; 96(2): e20231075, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38747797

RESUMEN

Mangroves buffer metals transfer to coastal areas though strong accumulation in sediments making necessary to investigate metals' bioavailability to plants at the rhizosphere. This work evaluates the effect of mangrove root activity, through iron plaque formation, on the mobility of iron and copper its influence on metals' uptake, and translocation through simultaneous histochemical analysis. The Fe2+ and Fe3+ contents in porewaters ranged from 0.02 to 0.11 µM and 1.0 to 18.3 µg.l-1, respectively, whereas Cu concentrations were below the method's detection limit (<0.1 µM). In sediments, metal concentrations ranged from 12,800 to 39,500 µg.g-1 for total Fe and from 10 to 24 µg.g-1 for Cu. In iron plaques, Cu concentrations ranged from 1.0 to 160 µg.g-1, and from 19.4 to 316 µg.g-1 in roots. Fe concentrations were between 605 to 36,000 µg.g-1 in the iron plaques and from 2,100 to 62,400 µg.g-1 in roots. Histochemical characterization showed Fe3+ predominance at the tip of roots and Fe2+ in more internal tissues. A. schaueriana showed significant amounts of Fe in pneumatophores and evident translocation of this metal to leaves and excretion through salt glands. Iron plaques formation was essential to the Fe and Cu regulation and translocation in tissues of mangrove plants.


Asunto(s)
Avicennia , Cobre , Hierro , Raíces de Plantas , Rhizophoraceae , Rhizophoraceae/química , Hierro/análisis , Hierro/metabolismo , Brasil , Cobre/análisis , Avicennia/química , Raíces de Plantas/química , Sedimentos Geológicos/química , Sedimentos Geológicos/análisis , Disponibilidad Biológica , Contaminantes Químicos del Agua/análisis , Monitoreo del Ambiente/métodos
2.
Chem Biodivers ; 21(7): e202400687, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38702295

RESUMEN

Rhizophora extracts have several potential biological activities, and their metabolites can be used in the pharmaceutical industry. Extracts of Rhizophora species obtained from mangroves have shown prospective activity against Staphylococcus aureus. This study aimed to investigate the chemical profile of Rhizophora mangle leaves from fringe, basin, and transition mangrove zones and their bactericidal/bacteriostatic potential against S. aureus. R. mangle leaves were collected monthly in 2018 from litterfall in three different zones of the mangrove of Guaratiba State Reserve: fringe, basin, and transition. Extracts were prepared from the material collected in October and December for LC-HRMS/MS analysis, and dereplication was performed using a molecular library search and the classical molecular networking GNPS platform. The minimum inhibitory concentrations (MICs) of the aqueous extract of R. mangle against S. aureus were determined. No S. aureus growth was observed compared to the control for extracts collected from September to December. Different compounds were annotated in each region, yet a marked presence of phenolic compounds was noted, among them glycosylated flavonoid derivatives of quercetin and kaempferol. The results suggest bactericidal/bacteriostatic activity for extracts of R. mangle leaves collected in 2018 from three mangrove forest zones.


Asunto(s)
Antibacterianos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales , Hojas de la Planta , Rhizophoraceae , Staphylococcus aureus , Rhizophoraceae/química , Rhizophoraceae/microbiología , Staphylococcus aureus/efectos de los fármacos , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química
3.
Chem Biodivers ; 20(9): e202201144, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37471640

RESUMEN

Mangroves are abundant in bioactive natural substances that fight off pathogenic diseases. Different parts of R. apiculata, an abundant mangrove found in Bhitarkanika National Park, India were extracted with methanol and a mixture of solvents methanol/ethanol/chloroform (60 : 20 : 20) to evaluate their antimicrobial properties. The combination solvent extract of bark had the highest zone of inhibition (ZOI) of 18.62 mm against Pseudomonas aeruginosa and a ZOI of 17.41 mm against Streptococcus mitis. Bark extracts had the highest DPPH (43 %) and FRAP (96 %) activities. The combination solvent bark extract of R. apiculata had the highest ZOI of 20.42 mm (lowest MIC of 2.12 µg/ml) against Candida albicans and ZOI of 15.33 mm (MIC of 3.02 µg/mL) against Penicillium chrysogenum. Combination bark extracts of R. apiculata contained flavanols than methanolic extracts. The crude extract of R. apiculata bark made with a mixture of solvents containing more active ingredients could be used in novel drug formulation.


Asunto(s)
Antiinfecciosos , Rhizophoraceae , Antioxidantes/farmacología , Antioxidantes/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Rhizophoraceae/química , Metanol , Antiinfecciosos/farmacología , Solventes , Pruebas de Sensibilidad Microbiana
4.
Mar Pollut Bull ; 189: 114827, 2023 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-36931158

RESUMEN

In this study, we used Kandelia obovata to explore the toxicities of three typical MPs in mangroves: polyethylene, polypropylene, and polyvinylchloride. MPs were mixed into soils at 5 % (w/w) for cultivation in mangrove tide-tank system. Plant growth and soil characteristics were determined after 12 months. The results showed that MPs multiply restricted root growth, leaf ionome, chlorophyll concentration, and photosynthetic efficiency, changed leaf photochemical efficiency and excited energy distribution. Polyethylene and polypropylene MPs with 150 µm sizes significantly reduced leaf and root biomass. As for soil properties, all MPs mainly reduced bulk density but improved porosity, with 600 µm polyethylene resulting in 1.4 g cm-3 bulk density and 55.1 % porosity. This study represent the first paper highlighting that MPs negatively affect mangrove plants by affecting plant growth, leaf ionome, and photosynthesis, which may be related with the changed soil properties, especially reduced bulk density and improved porosity.


Asunto(s)
Rhizophoraceae , Rizosfera , Microplásticos , Plásticos , Rhizophoraceae/química , Suelo/química , Polipropilenos , Fotosíntesis , Polietileno
5.
J Biomol Struct Dyn ; 41(4): 1424-1436, 2023 03.
Artículo en Inglés | MEDLINE | ID: mdl-34963406

RESUMEN

The main objective of the present study is to isolate and characterise the novel bioactive molecule, 2-methoxy mucic acid (4) from Rhizophora apiculate Blume under the Rhizophoraceae family. In this study, the 2-methoxy mucic acid (4) was isolated for the first time from the methanolic extract of the leaves of R. apiculata. Anticancer activity of 2-methoxy mucic acid (4) was evaluated against HeLa and MDA-MB-231 cancer cell lines and they displayed promising activity with IC50 values of 22.88283 ± 0.72 µg/ml in HeLa and 2.91925 ± 0.52 µg/ml in the case of MDA-MB-231, respectively. Furthermore, the antioxidant property of 2-methoxy mucic acid (4) was found to be (IC50) 21.361 ± 0.41 µg/ml. Apart from in vitro studies, we also performed extensive in silico studies (molecular docking and molecular dynamics simulation) on four critical antiapoptotic Bcl-2 family members (Bcl-2, Bcl-w, Bcl-xL and Bcl-B) towards 2-methoxy mucic acid (4). The results revealed that this molecule showed higher binding affinity towards Bcl-B protein (ΔG = -5.8 kcal/mol) and the structural stability of this protein was significantly improved upon binding of this molecule. The present study affords vital insights into the importance of 2-methoxy mucic acid (4) from R. apiculata. Furthermore, it opens the therapeutic route for the discovery of anticancer drugs. Research HighlightsThis is a first report on a bioactive compound identified and characterised; a novel 2-methoxy mucic acid derived from methanolic crude extract from the leaves of R. apiculata from ANI.Estimated binding free energy of 2-methoxy mucic acid is found to be -5.8 kcal/mol to the anti-apoptotic Bcl-B protein.2-methoxy mucic acid showed both significant anti-cancer and anti-oxidant activity.Communicated by Ramaswamy H. Sarma.


Asunto(s)
Antioxidantes , Rhizophoraceae , Antioxidantes/farmacología , Rhizophoraceae/química , Rhizophoraceae/metabolismo , Extractos Vegetales/farmacología , Extractos Vegetales/química , Simulación del Acoplamiento Molecular , Proteínas Proto-Oncogénicas c-bcl-2/metabolismo , Proteínas Reguladoras de la Apoptosis/metabolismo , Metanol
6.
Infect Disord Drug Targets ; 23(3): e031122210623, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-36330619

RESUMEN

OBJECTIVE: Nonsteroidal anti-inflammatory drugs (NSAIDs) are a group of drugs widely used around the world for their analgesic, antipyretic and anti-inflammatory effect, but still have many limitations due to their side effects. So, these lead to the development of a new approach to search for a new product from natural plants that have similar therapeutic effects without common side effects like gastrointestinal ulcers. METHODS: The anti-inflammatory effect of ß-amyrin palmitate (1) as triterpene and 1,7-bis (4- hydroxyphenyl) hept-4-en-3-one (2) as diarylheptanoid, isolated from Pellacalyx axillaris was studied by molecular docking to find the probability of binding position and binding strength of new compounds with particular Prostaglandin G/H synthase 2 (PDB ID: 1CX2). In vivo acute anti-inflammatory activity of the isolated compounds (1 and 2) was evaluated in rats using the egg-white induced edema model of inflammation in a dose correspondent to 3 mg/Kg of Diclofenac Sodium. RESULTS: The tested isolated compounds showed a high activity to inhibit the swelling in paw edema and their anti-inflammatory effect began shortly after the injection of the egg white and continued to the end of the experiment in comparison to the reference and control. CONCLUSION: The isolated compounds show a rapid onset of action and a very potent effect, this may be related to their suitable acidity and may have perfect hydrophilic -lipophilic balance. This is the first study of anti-inflammatory effect using Paw edema model and molecular docking.


Asunto(s)
Diarilheptanoides , Preparaciones de Plantas , Rhizophoraceae , Triterpenos , Animales , Ratas , Antiinflamatorios/farmacología , Antiinflamatorios/uso terapéutico , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/uso terapéutico , Carragenina/efectos adversos , Diarilheptanoides/efectos adversos , Edema/inducido químicamente , Edema/tratamiento farmacológico , Simulación del Acoplamiento Molecular , Triterpenos/efectos adversos , Rhizophoraceae/química , Preparaciones de Plantas/uso terapéutico
7.
Plant Genome ; 15(3): e20217, 2022 09.
Artículo en Inglés | MEDLINE | ID: mdl-35608212

RESUMEN

Mangrove ecosystems are unique, highly diverse, provide benefits to humans, and aid in coastal protection. The Indian mangrove, or spurred mangrove, [Ceriops tagal (Perr.) C. B. Rob.] is a member of the Rhizophoraceae family and is commonly found along the intertidal zones in tropical regions in Southeast Asia, southern Asia, and Africa. Here, we present the first high-quality reference genome assembly of the Ceriops species. A preliminary draft assembly, generated from the 10× Genomics linked-read library, was scaffolded using the proximity ligation chromatin contact mapping technique (Hi-C) to obtain a chromosome-scale assembly of 231,919,005 bases with an N50 length of 11,408,429 bases. The benchmarking universal single-copy orthologs (BUSCO) analysis revealed that C. tagal gene predictions recovered 95.8% of the highly conserved orthologs. Phylogenetic analyses suggested that C. tagal diverged from the last common ancestor of flat-leaf spurred mangrove [C. decandra (Griff.) Ding Hou] and C. zippeliana Blume ∼10.4 million yr ago (MYA), and the last common ancestor of genera Ceriops, Kandelia, and Rhizophora diverged from that of genus Bruguiera ∼49.4 MYA. In addition, our analysis of the transversion rate at fourfold-degenerate sites from orthologous gene pairs provided evidence supporting a recent whole-genome duplication in C. tagal. The STRUCTURE and principal component analyses illustrated that C. tagal individuals investigated in this study were the admixture of two subpopulations, the genetic background of which was influenced primarily by location. The availability of genomic and transcriptomic resources and biodiversity data reported in this work will be useful for future studies that may shed light on adaptive evolutions of mangrove species.


Asunto(s)
Rhizophoraceae , Cromatina , Cromosomas , Ecosistema , Humanos , Filogenia , Rhizophoraceae/química , Rhizophoraceae/genética
8.
Injury ; 53(7): 2462-2469, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35341596

RESUMEN

INTRODUCTION: Necrosis in ischemic cutaneous flaps (ISF) is a type of surgical failure more feared among surgical complications. Currently, synthetic drugs are applied during the treatment of necrosis in ISF and although several substances show improvement in viability, some require application at high systemic doses, which can produce important side effects. Therefore, the search for natural substances with fewer side effects is constant. The use of medicinal plants that stimulate angiogenesis is commonly mentioned in previous studies and in this case Rhizophora mangle L. (R. mangle) highlights that among its main compounds have tannins and flavonoids that are very chemically reactive in various biological activities. This study aimed to associate a natural hydrogel to the 5% extract of R. mangle and to evaluate its potential in the prevention of tissue necrosis in distal portions of ISF in rats, using the model proposed by Macfarlane, et al. (1965). METHODS: Ischemic skin flaps were made in the thin dorsal skin area of 28 Wistar rats and divided into 4 groups, group A: received only saline, group B where the aqueous extract of R. mangle was applied, group C received the 1.5% hydrogel of xanthan gum (XG) + placebo and group D was applied the hydrogel associated with 5% R. mangle extract. Morphometric analyses of the areas of tissue necrosis were performed from photographic records using the software Photoshop® and ImageJ®. In addition, 5 photomicrographs were taken from each histological sample of each animal for histomorphometric analysis that obtained the count of fibroblasts and blood vessels. RESULTS: The mean percentage of necrotic areas was: group (A) - 50,66%, group (B) - 40,49%, group (C) - 37,44% and group (D) - 34,25%. The statistical analysis, using the Kruskal-Wallis test, showed a significant difference (p < 0.001).


Asunto(s)
Rhizophoraceae , Animales , Humanos , Hidrogeles/farmacología , Isquemia , Necrosis/prevención & control , Ratas , Ratas Wistar , Rhizophoraceae/química , Trasplante de Piel
9.
Mar Drugs ; 20(2)2022 Feb 05.
Artículo en Inglés | MEDLINE | ID: mdl-35200654

RESUMEN

Demethylincisterol A3 (Sdy-1), a highly degraded sterol that we previously isolated from Chinese mangrove Rhizophora mucronata endophytic Pestalotiopsis sp. HQD-6, exhibits potent antitumor activity towards a variety of cancer cells. In this study, we further verified that Sdy-1 effectively inhibited the proliferation and migration of human liver (HepG2) and cervical cancer (HeLa) cells in vitro and it can induce cell apoptosis and arrest the cell cycle in the G1-phase. Mechanistically, we demonstrated that Sdy-1 executes its function via inhibition of the Wnt/ß-catenin signaling pathway. Sdy-1 may not inhibit the Wnt signaling pathway through the cascade reaction from upstream to downstream, but directly acts on ß-catenin to reduce its transcription level, thereby reducing the level of ß-catenin protein and further reducing the expression of downstream related proteins. The possible interaction between Sdy-1 and ß-catenin protein was further confirmed by molecular docking studies. In the nude mouse xenograft model, Sdy-1 can also significantly inhibit tumor growth. These results indicated that Sdy-1 is an efficient inhibitor of the Wnt signaling pathway and is a promising antitumor candidate for therapeutic applications.


Asunto(s)
Carcinoma Hepatocelular/tratamiento farmacológico , Neoplasias Hepáticas/tratamiento farmacológico , Esteroles/farmacología , Neoplasias del Cuello Uterino/tratamiento farmacológico , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Apoptosis/efectos de los fármacos , Puntos de Control del Ciclo Celular/efectos de los fármacos , Movimiento Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Femenino , Células HeLa , Células Hep G2 , Humanos , Ratones , Ratones Desnudos , Simulación del Acoplamiento Molecular , Rhizophoraceae/química , Esteroles/aislamiento & purificación , Vía de Señalización Wnt/efectos de los fármacos , Ensayos Antitumor por Modelo de Xenoinjerto
10.
J Biomol Struct Dyn ; 40(4): 1490-1502, 2022 03.
Artículo en Inglés | MEDLINE | ID: mdl-32996435

RESUMEN

Gallic acid (PubChem CID: 370) and quercetin (PubChem CID: 5280343) are major phenolic compounds in many mangrove plants that have been related to health cure. In the present study, the active fractions namely gallic acid (1) and quercetin (2) were isolated from the methanolic extract of leaves of Ceriops tagal in a Tropical mangrove ecosystem of Andaman and Nicobar Island (ANI), India. The chemical structures were determined by spectroscopic analysis: Fourier-Transform Infrared spectroscopy (FT-IR), 1H, 13C Nuclear Magnetic Resonance (NMR) spectroscopy, and High-resolution mass spectrometry (HRMS). The anticancer activity of isolated compounds (1) and (2) were evaluated by in vitro assays against two human cancer cell lines namely, HeLa (Cervical) and MDA-MB231 (Breast) cancer cells revealed that IC50 values of gallic acid (HeLa: 4.179197 ± 0.45 µg/ml; MDA-MB231: 80.0427 ± 0.19 µg/ml at 24 h) and quercetin (HeLa: 99.914 ± 0.18 µg/ml; MDA-MB231: 18.288382 ± 0.12 µg/ml at 24 h), respectively. Antioxidant properties of gallic acid (1) and quercetin (2) are found to be IC50 value of 0.77 ± 0.41 µg/ml and 1.897 ± 0.81 µg/ml, respectively. Molecular docking results explained that gallic acid (1) and quercetin (2) showed estimated binding free energy (ΔG) of -5.4 and -6.9 kcal/mol towards drug target Bcl-B protein, respectively. The estimated inhibition constant (Ki) for these two molecules are 110 and 8.75 µM, respectively. The MD simulation additionally supported that quercetin molecule is significantly improved the structural stability of Bcl-B protein. The present study provides key insights about the importance of polyphenols, and thus leads to open the therapeutic route for anti-cancer drug discovery process.Communicated by Ramaswamy H. Sarma.


Asunto(s)
Quercetina , Rhizophoraceae , Antioxidantes/farmacología , Ecosistema , Ácido Gálico/farmacología , Humanos , Simulación del Acoplamiento Molecular , Extractos Vegetales/química , Quercetina/farmacología , Rhizophoraceae/química , Espectroscopía Infrarroja por Transformada de Fourier
11.
Molecules ; 26(19)2021 Sep 23.
Artículo en Inglés | MEDLINE | ID: mdl-34641314

RESUMEN

The recent emergence of Zika virus (ZIKV) in Brazil and the increasing resistance developed by pathogenic bacteria to nearly all existing antibiotics should be taken as a wakeup call for the international authority as this represents a risk for global public health. The lack of antiviral drugs and effective antibiotics on the market triggers the need to search for safe therapeutics from medicinal plants to fight viral and microbial infections. In the present study, we investigated whether a mangrove plant, Bruguiera gymnorhiza (L.) Lam. (B. gymnorhiza) collected in Mauritius, possesses antimicrobial and antibiotic potentiating abilities and exerts anti-ZIKV activity at non-cytotoxic doses. Microorganisms Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae ATCC 70603, methicillin-resistant Staphylococcus aureus ATCC 43300 (MRSA), Salmonella enteritidis ATCC 13076, Sarcina lutea ATCC 9341, Proteus mirabilis ATCC 25933, Bacillus cereus ATCC 11778 and Candida albicans ATCC 26555 were used to evaluate the antimicrobial properties. Ciprofloxacin, chloramphenicol and streptomycin antibiotics were used for assessing antibiotic potentiating activity. ZIKVMC-MR766NIID (ZIKVGFP) was used for assessing anti-ZIKV activity. In silico docking (Autodock 4) and ADME (SwissADME) analyses were performed on collected data. Antimicrobial results revealed that Bruguiera twig ethyl acetate (BTE) was the most potent extract inhibiting the growth of all nine microbes tested, with minimum inhibitory concentrations ranging from 0.19-0.39 mg/mL. BTE showed partial synergy effects against MRSA and Pseudomonas aeruginosa when applied in combination with streptomycin and ciprofloxacin, respectively. By using a recombinant ZIKV-expressing reporter GFP protein, we identified both Bruguiera root aqueous and Bruguiera fruit aqueous extracts as potent inhibitors of ZIKV infection in human epithelial A549 cells. The mechanisms by which such extracts prevented ZIKV infection are linked to the inability of the virus to bind to the host cell surface. In silico docking showed that ZIKV E protein, which is involved in cell receptor binding, could be a target for cryptochlorogenic acid, a chemical compound identified in B. gymnorhiza. From ADME results, cryptochlorogenic acid is predicted to be not orally bioavailable because it is too polar. Scientific data collected in this present work can open a new avenue for the development of potential inhibitors from B. gymnorhiza to fight ZIKV and microbial infections in the future.


Asunto(s)
Antibacterianos/farmacología , Antifúngicos/farmacología , Antivirales/farmacología , Extractos Vegetales/farmacología , Rhizophoraceae/química , Virus Zika/crecimiento & desarrollo , Antibacterianos/química , Antifúngicos/química , Antivirales/química , Brasil , Candida albicans/efectos de los fármacos , Candida albicans/crecimiento & desarrollo , Simulación por Computador , Sinergismo Farmacológico , Escherichia coli/efectos de los fármacos , Escherichia coli/crecimiento & desarrollo , Klebsiella pneumoniae/efectos de los fármacos , Klebsiella pneumoniae/crecimiento & desarrollo , Mauricio , Pruebas de Sensibilidad Microbiana , Viabilidad Microbiana/efectos de los fármacos , Extractos Vegetales/química , Proteus mirabilis/efectos de los fármacos , Proteus mirabilis/crecimiento & desarrollo , Pseudomonas aeruginosa/efectos de los fármacos , Pseudomonas aeruginosa/crecimiento & desarrollo , Staphylococcus aureus/efectos de los fármacos , Staphylococcus aureus/crecimiento & desarrollo , Virus Zika/efectos de los fármacos
12.
J Nat Prod ; 84(8): 2272-2281, 2021 08 27.
Artículo en Inglés | MEDLINE | ID: mdl-34342431

RESUMEN

Seven new tropane alkaloids, including five monomeric (1-5), one dimeric (6), and one trimeric (7) 3α-nortropane ester, along with two known monomeric nortropane alkaloids (8 and 9), were isolated from the leaves and bark of Pellacalyx saccardianus. Their structures, including the absolute configuration of the enantiomeric pair of (±)-6, were elucidated by comprehensive spectroscopic analyses. Alkaloids 6 and 7 showed cytotoxicity toward human pancreatic cancer cell lines (AsPC-1, BxPC3, PANC-1, and SW1990). Alkaloids 1, 4, and 9 induced a smooth muscle relaxation effect comparable to that of atropine (Emax 106.1 ± 7.5%, 97.0 ± 5.2%, 100.9 ± 1.4%, 111.7 ± 1.7%, respectively) on isolated rat tracheal rings.


Asunto(s)
Alcaloides/farmacología , Antineoplásicos Fitogénicos/farmacología , Músculo Liso/efectos de los fármacos , Rhizophoraceae/química , Tropanos/farmacología , Alcaloides/aislamiento & purificación , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Técnicas In Vitro , Malasia , Masculino , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Corteza de la Planta/química , Hojas de la Planta/química , Ratas , Ratas Sprague-Dawley , Tráquea/efectos de los fármacos , Tropanos/aislamiento & purificación
13.
Molecules ; 26(16)2021 Aug 11.
Artículo en Inglés | MEDLINE | ID: mdl-34443439

RESUMEN

Ten polyketide derivatives (1-10), including a new natural product named (E)-2,4-dihydroxy-3-methyl-6-(2-oxopent-3-en-1-yl) benzaldehyde (1), and five known diketopiperazines (11-15), were isolated from the mangrove-sediment-derived fungus Aspergillus sp. SCSIO41407. The structures of 1-15 were determined via NMR and MS spectroscopic analysis. In a variety of bioactivity screening, 3 showed weak cytotoxicity against the A549 cell line, and 2 exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Compounds 3, 5, and 6 showed inhibition against acetylcholinesterase (AChE) with IC50 values of 23.9, 39.9, and 18.6 µM. Compounds 11, 12, and 14 exhibited obvious inhibitory activities of lipopolysaccharide (LPS)-induced nuclear factor-κB (NF-κB) with IC50 values of 19.2, 20.9, and 8.7 µM, and they also suppressed RANKL-induced osteoclast differentiation in bone marrow macrophages cells (BMMCs), with the concentration of 5 µM. In silico molecular docking with AChE and NF-κB p65 protein were also performed to understand the inhibitory activities, and 1, 11-14 showed obvious protein/ligand-binding effects to the NF-κB p65 protein.


Asunto(s)
Aspergillus/efectos de los fármacos , Dicetopiperazinas/farmacología , Sedimentos Geológicos/microbiología , Policétidos/farmacología , Rhizophoraceae/química , Células A549 , Acetilcolinesterasa/metabolismo , Muerte Celular/efectos de los fármacos , Diferenciación Celular/efectos de los fármacos , Inhibidores de la Colinesterasa/farmacología , Dicetopiperazinas/química , Humanos , Lipopolisacáridos/farmacología , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , FN-kappa B/metabolismo , Osteoclastos/citología , Osteoclastos/efectos de los fármacos , Policétidos/química , Espectroscopía de Protones por Resonancia Magnética , Ligando RANK/farmacología
14.
Bioorg Med Chem Lett ; 48: 128235, 2021 09 15.
Artículo en Inglés | MEDLINE | ID: mdl-34216746

RESUMEN

Vomifoliol, a natural sesquiterpene compound, is a secondary metabolite isolated from the mangrove plant Ceriops tagal. The present study aimed to determine the immunosuppressive effects and underlying mechanisms of vomifoliol on Jurkat cells in vitro. The results show that vomifoliol significantly inhibited calcineurin (CN) at concentrations resulting in relatively low cytotoxicity. Moreover, vomifoliol was found to exert an inhibitory effect on phorbol 12-myristate 13-acetate (PMA)/ ionomycin (Io) -induced Jurkat cells and the dephosphorylation of NFAT1. In addition, it reduced the expression of IL-2. Based on these results, we concluded that vomifoliol may inhibit the immune response of Jurkat cells, and vomifoliol may use CN as the target enzyme to inhibit NFAT signaling pathway. Therefore, vomifoliol may be promising as a low-toxic natural immunosuppressant.


Asunto(s)
Butanoles/farmacología , Ciclohexanonas/farmacología , Factores de Transcripción NFATC/antagonistas & inhibidores , Rhizophoraceae/química , Butanoles/química , Butanoles/aislamiento & purificación , Ciclohexanonas/química , Ciclohexanonas/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Humanos , Células Jurkat , Estructura Molecular , Factores de Transcripción NFATC/metabolismo , Transducción de Señal/efectos de los fármacos , Relación Estructura-Actividad
15.
Steroids ; 172: 108860, 2021 08.
Artículo en Inglés | MEDLINE | ID: mdl-33971207

RESUMEN

Four biogenic ß-sitosterol analogues were identified from methanolic extract of the leaves of loop-root mangrove Rhizophora mucronata. These were characterized as 4, 14, 23-trimethyl-3ß-sitosterol (1), 7-ethyl-3ß-sitosterol (2), sitosteryl-3ß-(33E)-pent-33-enoate (3) and 12α-hydroxy-3ß-sitosterol (4) based on comprehensive spectroscopic techniques. Anti-inflammatory activities of ß-sitosterol 4 against pro-inflammatory enzymes 5-lipoxygenase and cyclooxygenase-2 were found to be significantly higher (IC50 1.85 and 1.92 mM, respectively) compared to those demonstrated by compounds of 1-3 (p < 0.05). These ß-sitosterol analogues disclosed superior selectivity indices (1.43-2.07) with regard to inducible cyclooxygenase-2 than its constitutive isoform cyclooxygenase-1, when compared to the standard, ibuprofen (0.44). Antioxidant properties of 12α-hydroxy-ß-sitosterol (4) were found to be significantly greater (IC50 1.43-1.67 mM) than those of other sitosterol analogues. Structure-activity correlation analyses put forward that the bioactive potencies of the titled ß-sitosterols were positively correlated to their electronic parameters. Molecular docking simulations were carried out in the active sites of 5-lipoxygenase/cyclooxygenase-2, and the docking scores and binding energies of the studied ß-sitosterol analogues were positively correlated with their attenuation properties against 5-lipoxygenase and cyclooxygenase-2.


Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Inhibidores de la Ciclooxigenasa 2/farmacología , Inhibidores de la Lipooxigenasa/farmacología , Extractos Vegetales/farmacología , Rhizophoraceae/química , Sitoesteroles/farmacología , Araquidonato 5-Lipooxigenasa/química , Ciclooxigenasa 2/química , Raíces de Plantas/química
16.
Molecules ; 26(5)2021 Mar 04.
Artículo en Inglés | MEDLINE | ID: mdl-33806398

RESUMEN

Bruguiera gymnorhiza (L.) Lam is a mangrove plant that spread in many parts of the world. Though mangrove plant polyphenols have been reported to exhibit many biological activities, little is known about mangrove plant tannins. To explore the application value of tannins from B. gymnorhiza, analyses on the structure and biological activity of condensed tannins (CTs) from Bruguiera gymnorhiza (L.) Lam were carried out. The results from 13C nuclear magnetic resonance (13C-NMR) and reversed-phase, high-performance liquid chromatography (RP-HPLC) showed that the CTs were dominated by procyanidins, with a small quantity of prodelphinidins and propelargonidins; and that the monomeric constituents of B. gymnorhiza tannins were catechin/epicatechin, gallocatechin/epigallocatechin and afzelechin/epiafzelechin. The CTs were reversible and mixed competitive inhibitors of tyrosinase and the 50% inhibiting concentration (IC50) was estimated to be 123.90 ± 0.140 µg/mL. The antioxidant activities of CTs from B. gymnorhiza leaves were evaluated, the IC50 for 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid diammonium salt) (ABTS) scavenging activities were 88.81 ± 0.135 and 105.03 ± 0.130 µg/mL, respectively, and the ferric ion reducing antioxidant power (FRAP) value was 1052.27 ± 4.17 mgAAE/g. In addition, the results from fresh-keeping assays on fresh-cut lotus root reveal that CTs from B. gymnorhiza had excellent effects on inhibiting the activities of polyphenol oxidase (PPO) and peroxidase (POD), protecting fresh-cut lotus root from the oxidation of total phenolics and malondialdehyde (MDA) content and slowing the increase in total phenol content (TPC) at 4 °C during the whole storage period. Therefore, CTs showed good effects against the browning of fresh-cut lotus root. Together, these results suggested that B. gymnorhiza CTs are promising antibrowning agents for fresh-cut fruits.


Asunto(s)
Antioxidantes/farmacología , Lotus/efectos de los fármacos , Monofenol Monooxigenasa/antagonistas & inhibidores , Extractos Vegetales/farmacología , Raíces de Plantas/efectos de los fármacos , Rhizophoraceae/química , Taninos/farmacología , Agaricales/enzimología , Oxidación-Reducción , Proantocianidinas/análisis , Taninos/aislamiento & purificación
17.
Appl Radiat Isot ; 170: 109601, 2021 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-33515930

RESUMEN

Experimental particleboards are made from Rhizophora spp. wood trunk with three different percentages of lignin and soy flour (0%, 6% and 12%) as adhesives. The objective was to investigate the equivalence of Rhizophora spp. particleboard as phantom material with human soft tissue using Computed Tomography (CT) number. The linear and mass attenuation coefficient of Rhizophora spp. particleboard at low energy range was also explored using X-ray Fluorescence (XRF) configuration technique. Further characterization of the particleboard was performed to determine the effective atomic number, Zeff using Energy Dispersive X-Ray (EDX) method. Adhesive-bonded Rhizophora spp. particleboard showed close similarities with water, based on the average CT numbers, electron density calibration curve and the analysis of CT density profile, compared to the binderless particleboard. The effective atomic number obtained from the study indicated that the attenuation properties of all the particleboards at different percentages of adhesives were almost similar to water. The mass attenuation coefficient calculated from XRF configuration technique showed good agreement with water from XCOM database, suggesting its potential as phantom material for radiation study.


Asunto(s)
Glycine max/química , Lignina/química , Radiometría/métodos , Rhizophoraceae/química , Tomografía Computarizada por Rayos X/métodos , Bases de Datos Factuales , Espectrometría por Rayos X/métodos
19.
Molecules ; 25(17)2020 Aug 24.
Artículo en Inglés | MEDLINE | ID: mdl-32847069

RESUMEN

The larvicidal potential of crude leaf extracts of Rhizophora mucronata, the red mangrove, using diverse solvent extracts of the plant against the early fourth instar larvae of Anopheles stephensi, Culex quinquefasciatus and Aedes aegypti mosquito vectors was analyzed. The acetone extract of R. mucronata showed the greatest efficacy: for Cx. quinquefasciatus (LC50 = 0.13 mg/mL; LC90 = 2.84 mg/mL), An. stephensi (LC50 = 0.34 mg/mL; LC90 = 6.03 mg/mL), and Ae. aegypti (LC50 = 0.11 mg/mL; LC90 = 1.35 mg/mL). The acetone extract was further fractionated into four fractions and tested for its larvicidal activity. Fraction 3 showed stronger larvicidal activity against all the three mosquito larvae. Chemical characterization of the acetone extract displayed the existence of several identifiable compounds like phytol, 3,7,11,15-tetramethyl-2-hexadecen-1-ol, 1-hexyl-2-nitrocyclohexane, eicosanoic acid etc. Enzyme assay displayed that R. mucronata active F3-fractions exert divergent effects on all three mosquitos' biochemical defensive mechanisms. The plant fractions displayed significant repellent activity against all the three mosquito vectors up to the maximum repellent time of 210 min. Thus, the bioactive molecules in the acetone extract of R. murconata leaves showed significant larvicidal and enzyme inhibitory activity and displayed novel eco-friendly tool for mosquito control.


Asunto(s)
Culicidae/enzimología , Repelentes de Insectos , Insecticidas , Extractos Vegetales , Hojas de la Planta/química , Rhizophoraceae/química , Animales , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Insecticidas/química , Insecticidas/farmacología , Larva/enzimología , Control de Mosquitos , Extractos Vegetales/química , Extractos Vegetales/farmacología
20.
J Nat Prod ; 83(7): 2207-2211, 2020 07 24.
Artículo en Inglés | MEDLINE | ID: mdl-32558565

RESUMEN

Geosmin (1) is a microbial terpene metabolite that is responsible for the typical smell of soil and causes an off-odor of food and water. Eudesmane sesquiterpenes are commonly found in plant essential oils. Here we describe the discovery of four geosmin-type metabolites, 7R-hydroxygeosmin (2), 3-oxogeosmin (3), 2R-hydroxy-7-oxogeosmin (4), 5-deoxy-7ß,9ß-dihydroxygeosmin (5), the plant-like eudesmanes 4ß,10α-eudesmane-5ß,11-diol (6) and (1S,5S,6S,7S,10S)-10α-eudesm-4(15)-ene-1α,6α-diol (7), and the known 1(10)E,5E-germacradiene-2,11-diol (8) from a bacterial endophyte (Streptomyces sp. JMRC:ST027706) of the mangrove plant Bruguiera gymnorrhiza. By means of NMR, MS, and ECD spectroscopy, all chemical structures as well as the absolute configurations for the new compounds were elucidated. Compounds 2-5 represent the first geosmin-related metabolites directly as bacterial natural products. The plant-derived eudesmane-5ß,11-diol (6) and (1S,5S,6S,7S,10S)-10α-eudesm-4(15)-ene-1α,6α-diol (7) are also now reported as bacterial products. The broad antimicrobial activities of 6 against a suite of fungal and bacterial pathogens including methicillin-resistant Staphylococcus aureus suggest that this terpene could be an important active principle of the medicinal plant Cymbopogon distans. The discovery of geosmin metabolites from one actinomycete indicated that these bacteria could possess enzymes for modifying geosmin and offer a possibility for bioremediation.


Asunto(s)
Antibacterianos/aislamiento & purificación , Endófitos/química , Naftoles/aislamiento & purificación , Oxígeno/química , Rhizophoraceae/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Antibacterianos/química , Antibacterianos/farmacología , Pruebas de Sensibilidad Microbiana , Naftoles/química , Naftoles/farmacología , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Análisis Espectral/métodos
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