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1.
Nat Prod Res ; 36(23): 5991-5998, 2022 Dec.
Article in English | MEDLINE | ID: mdl-35369818

ABSTRACT

Chemical investigation of the MeOH extract of the leaves of Scyphocephalium mannii (Benth. & Hook.f.) Warb. (Myristicaceae) led to the isolation and characterization of one new metabolite (+)-(7'S, 8S, 8'S)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-2,7'-cyclolignan (1) along with five known compounds. Their structures were elucidated by spectroscopic means, including 1 D and 2 D NMR, HRESI-MS and by comparison with published data. The absolute configuration of compound 1 was determined by single-crystal X-RAY diffraction. Compound 1 showed moderate antifungal activity against Cryptococcus neoformans with respective MIC and MMC values of 64 and 256 µg/mL.


Subject(s)
Anti-Infective Agents , Myristicaceae , Molecular Structure , Magnetic Resonance Spectroscopy , Plant Leaves , Anti-Infective Agents/pharmacology
2.
Nat Prod Res ; 36(11): 2783-2790, 2022 Jun.
Article in English | MEDLINE | ID: mdl-33993799

ABSTRACT

The phytochemical study of the CH2Cl2- MeOH (1:1, v/v) extract of the stem bark of Carapa procera DC (Meliaceae) led to the isolation and characterisation of a new natural limonoid 7ß-obacunol (6), along with seven known compounds. Their structures were elucidated by spectroscopic means, including 1 D and 2 D NMR, HRESI-MS and by comparison with published data. The cytotoxicity of compounds 1-6 was assessed in vitro by the WST-1 assay on human lung adenocarcinoma A549 and Raw 264.7 mouse macrophage cell lines. Results suggested that obacunone (3) exhibited the most potent cytotoxic effect against A549 and Raw 264.7 cells with respective IC50 values of 25.24 µM and 29.14 µM, while the new natural limonoid 7ß-obacunol (6) exhibited 32.75 µM and 39.19 µM, respectively on both cell lines. Therefore, limonoid derivatives might be promising sources of natural bioactive metabolites against cancer.


Subject(s)
Antineoplastic Agents , Limonins , Meliaceae , Animals , Antineoplastic Agents/analysis , Benzoxepins , Dental Porcelain , Limonins/chemistry , Limonins/pharmacology , Meliaceae/chemistry , Metal Ceramic Alloys , Mice , Molecular Structure , Plant Bark/chemistry , Titanium
3.
J Ethnopharmacol ; 268: 113637, 2021 Mar 25.
Article in English | MEDLINE | ID: mdl-33264661

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Ocimum gratissimum is a plant spice widely used in African traditional medicine to treat pain-related conditions. However, the anti-inflammatory mechanisms underlying this activity and the main active ingredients in O. gratissimum have not yet been fully characterized. AIM OF THE STUDY: To isolate and identify the main anti-inflammatory active constituents of Ocimum gratissimum extract and their underlying mechanisms in murine macrophages. MATERIAL AND METHODS: Chromatographic techniques and spectroscopic data were used for compounds isolation and identification. Inflammatory conditions were produced in cultured RAW 264.7 macrophage cells by the application of lipopolysaccharide (LPS). The WST-1 assay was used to evaluate the cell viability, and the nitric oxide production was quantified by the Griess reagent method. The fluorometric cyclooxygenase (COX) activity assay kit was used to assess the activity of COX-1 and COX-2 enzymes. The levels of IFN-γ, TNF-α, IL-2, IL-4, IL-6, and IL-10 cytokines and the apoptosis-inducing effect were measured by flow cytometer using the cytometric Bead Array (CBA) Human Th1/Th2 Cytokine Kit II and FITC Annexin V Apoptosis Detection kit, respectively. RESULTS: The results showed that the extract and fractions of Ocimum gratissimum inhibit nitric oxide production and the proliferation of Raw 264.7 macrophage cells. The bioguided fractionation led to the identification of pentacyclic triterpenes as anti-inflammatory bioactive compounds. Pomolic and tormentic acids being the most active, inhibiting the secretion of IFN-γ cytokine, COX enzyme, and inducing apoptosis in activated Raw 264.7 macrophage cells. CONCLUSIONS: This study revealed that pomolic and tormentic acids are the main active principles responsible at least in part for the anti-inflammatory effect of the extract of Ocimum gratissimum. Besides of providing more evidence for the traditional use of Ocimum gratissimum against inflammatory disorders, this study reveals the multitarget potential of pomolic and tormentic acids as promising future drugs against inflammatory diseases.


Subject(s)
Anti-Inflammatory Agents/isolation & purification , Inflammation Mediators/antagonists & inhibitors , Ocimum , Pentacyclic Triterpenes/isolation & purification , Phytochemicals/isolation & purification , Plant Extracts/isolation & purification , Animals , Anti-Inflammatory Agents/pharmacology , Cell Survival/drug effects , Cell Survival/physiology , Dose-Response Relationship, Drug , Humans , Inflammation Mediators/metabolism , Mice , Pentacyclic Triterpenes/pharmacology , Phytochemicals/pharmacology , Plant Extracts/pharmacology , RAW 264.7 Cells
4.
Nat Prod Res ; 33(2): 196-203, 2019 Jan.
Article in English | MEDLINE | ID: mdl-29502449

ABSTRACT

Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), ß-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.


Subject(s)
Limonins/chemistry , Meliaceae/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Plant Bark/chemistry , Plant Extracts/chemistry , Scopoletin/chemistry , Scopoletin/isolation & purification , Stigmasterol/chemistry , Stigmasterol/isolation & purification
5.
Nat Prod Res ; 32(1): 85-90, 2018 Jan.
Article in English | MEDLINE | ID: mdl-28587572

ABSTRACT

One new degraded diterpenoid 3,6-dihydroxy-1,7-dimethyl-9,10-phenantroquinone (neomacrodione) (1) together seven known compounds were isolated from the roots of Neoboutonia macrocalyx (Euphorbiaceae). The structures of the compounds were established based on their NMR and mass spectrometric data in conjunction with those previously reported in the literature. Compound (1) displayed moderate antibacterial activities.


Subject(s)
Anti-Bacterial Agents/chemistry , Diterpenes/chemistry , Euphorbiaceae/chemistry , Phenanthrenes/chemistry , Anti-Bacterial Agents/pharmacology , Diterpenes/pharmacology , Drug Evaluation, Preclinical/methods , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Phenanthrenes/pharmacology , Plant Roots/chemistry
6.
Rev. bras. farmacogn ; 27(2): 251-253, Mar.-Apr. 2017. tab, graf
Article in English | LILACS | ID: biblio-1042249

ABSTRACT

ABSTRACT Four compounds including beauvericin, parahydroxybenzaldehyde, indole-3-carboxylic acid and quinizarin were isolated from endophytic fungus Epicoccum nigrum and their cytotoxicity, antibacterial and antioxidant activity were evaluated. Beauvericin had remarkable activity against two Gram-negative strains (Bacillus cereus and Salmonella typhimurium) with respective MIC values of 3.12 and 6.25 µg/ml. All the compounds had weak cytotoxic effect on both normal and tumor cells. LC50 values ranged from 40.42 to 86.56 µg/ml, 31.87 to 86.57 µg/ml and 21.59 to 67.27 µg/ml on Vero cells, THP-1 and RAW 264.7 respectively. The present study showed that these compounds could be developed for the formulation of antioxidant-rich therapeutic diets and as a therapeutic agent against bacterial infections.

7.
BMC Res Notes ; 10(1): 118, 2017 Mar 06.
Article in English | MEDLINE | ID: mdl-28264698

ABSTRACT

BACKGROUND: Entada abyssinica is a plant traditionally used against gastrointestinal bacterial infections. Eight compounds including three flavonoids, three terpenoids, a monoglyceride and a phenolic compound isolated from E. abyssinica were investigated for their cytotoxicity, antibacterial and antioxidant activity. RESULTS: Compounds 7 and 2 had remarkable activity against Salmonella typhimurium with the lowest respective minimum inhibitory concentration (MIC) values of 1.56 and 3.12 µg/mL. The antioxidant assay gave IC50 values varied from 0.48 to 2.87 µg/mL in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, from 2.53 to 17.04 µg/mL in the 2,2'-Azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS) assay and from 1.43 to 103.98 µg/mL in the FRAP assay. Compounds had relatively low cytotoxicity (LC50 values ranging from 22.42 to 80.55 µg/mL) towards Vero cells. Ursolic acid had the most potent cytotoxicity against THP-1 and RAW 264.7 cells with LC50 values of 9.62 and 4.56 µg/mL respectively, and selectivity index values of 7.32 and 15.44 respectively. CONCLUSION: Our findings suggest that among the terpenoid and flavonoid compounds studied, entadanin (compound 7) possess tremendous antibacterial activity against S. typhimurium and could be developed for the treatment of bacterial diseases.


Subject(s)
Anti-Infective Agents/pharmacology , Antioxidants/pharmacology , Cytotoxins/pharmacology , Fabaceae , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Plant Extracts/pharmacology , Plants, Medicinal , Africa , Anti-Infective Agents/isolation & purification , Antioxidants/isolation & purification , Bacillus cereus/drug effects , Cytotoxins/isolation & purification , Enterococcus faecalis/drug effects , Escherichia coli/drug effects , Microbial Sensitivity Tests , Plant Bark , Plant Extracts/isolation & purification , Plant Leaves , Plant Stems , Pseudomonas aeruginosa/drug effects , Salmonella typhimurium/drug effects , Staphylococcus aureus/drug effects
8.
Biol Res ; 48: 57, 2015 Oct 13.
Article in English | MEDLINE | ID: mdl-26463660

ABSTRACT

BACKGROUND: Limonoids are highly oxygenated compounds with a prototypical structure. Their occurrence in the plant kingdom is mainly confined to plant families of Meliaceae and Rutaceae. Owing to their wide range of pharmacological and therapeutic properties, this study was aimed at investigating the potential nitric oxide (NO) and acetylcholinesterase (AChE) inhibitory activity and the cytotoxicity of three limonoids: trichilia lactone D5 (1), rohituka 3 (2) and dregeanin DM4 (3), isolated from Trichilia welwitschii C.DC. RESULTS: Results indicated that the three limonoids had low cytotoxicity towards Vero cells with LC50 values ranging from 89.17 to 75.82 µg/mL. Compounds (2) and (3) had lower cytotoxicity compared to puromycin and doxorubicin used as reference cytotoxic compounds. Compound (1) (LC50 of 23.55 µg/mL) had good antiproliferative activity against RAW 264.7 cancer cells. At the lowest concentration tested (0.5 µg/mL), compound (2) and (3) released the lowest amount of nitric oxide (2.97 and 2.93 µM, respectively). The three limonoids had anti-AChE activity with IC50 values ranged of 19.13 µg/mL for (1), 34.15 µg/mL for (2) and 45.66 µg/mL for (3), compared to galantamine (IC50 of 8.22 µg/mL) used as positive control. CONCLUSION: The limonoid compounds studied in this work inhibited nitric oxide production in LPS-stimulated macrophages and had anti-AChE activity. Trichilia lactone D5 had potential antiproliferative activity against RAW 264.7 cancer cells. The limonoids had low cytotoxicity towards Vero cells lines. This study provided further examples of the importance of limonoids compounds as potential AChE inhibitors and anti-inflammatory agents targeting the inhibition of NO production.


Subject(s)
Cholinesterase Inhibitors/pharmacology , Limonins/pharmacology , Meliaceae/chemistry , Nitric Oxide/antagonists & inhibitors , Animals , Anti-Inflammatory Agents/pharmacology , Cell Proliferation/drug effects , Chlorocebus aethiops , Inhibitory Concentration 50 , Lactones/analysis , Lactones/pharmacology , Lethal Dose 50 , Limonins/analysis , Limonins/isolation & purification , Lipopolysaccharides , Macrophages/drug effects , Mice , Nitric Oxide/analysis , RAW 264.7 Cells , Vero Cells
9.
Biol. Res ; 48: 1-6, 2015. ilus, graf, tab
Article in English | LILACS | ID: biblio-950821

ABSTRACT

BACKGROUND: Limonoids are highly oxygenated compounds with a prototypical structure. Their occurrence in the plant kingdom is mainly confined to plant families of Meliaceae and Rutaceae. Owing to their wide range of pharmacological and therapeutic properties, this study was aimed at investigating the potential nitric oxide (NO) and acetylcholinesterase (AChE) inhibitory activity and the cytotoxicity of three limonoids: trichilia lactone D5 (1), rohituka 3 (2) and dregeanin DM4 (3), isolated from Trichilia welwitschii C.DC. RESULTS: Results indicated that the three limonoids had low cytotoxicity towards Vero cells with LC50 values ranging from 89.17 to 75.82 µg/mL. Compounds (2) and (3) had lower cytotoxicity compared to puromycin and doxorubicin used as reference cytotoxic compounds. Compound (1) (LC50 of 23.55 µg/mL) had good antiproliferative activity against RAW 264.7 cancer cells. At the lowest concentration tested (0.5 µg/mL), compound (2) and (3) released the lowest amount of nitric oxide (2.97 and 2.93 µM, respectively). The three limonoids had anti-AChE activity with IC50 values ranged of 19.13 µg/mL for (1), 34.15 µg/mL for (2) and 45.66 µg/mL for (3), compared to galantamine (IC50 of 8.22 µg/mL) used as positive control. CONCLUSION: The limonoid compounds studied in this work inhibited nitric oxide production in LPS-stimulated macrophages and had anti-AChE activity. Trichilia lactone D5 had potential antiproliferative activity against RAW 264.7 cancer cells. The limonoids had low cytotoxicity towards Vero cells lines. This study provided further examples of the importance of limonoids compounds as potential AChE inhibitors and anti-inflammatory agents targeting the inhibition of NO production.


Subject(s)
Animals , Mice , Cholinesterase Inhibitors/pharmacology , Meliaceae/chemistry , Limonins/pharmacology , Nitric Oxide/antagonists & inhibitors , Vero Cells , Chlorocebus aethiops , Lipopolysaccharides , Inhibitory Concentration 50 , Limonins/isolation & purification , Limonins/analysis , Cell Proliferation/drug effects , RAW 264.7 Cells , Lactones/analysis , Lactones/pharmacology , Lethal Dose 50 , Macrophages/drug effects , Anti-Inflammatory Agents/pharmacology , Nitric Oxide/analysis
10.
Nat Prod Commun ; 9(10): 1499-502, 2014 Oct.
Article in English | MEDLINE | ID: mdl-25522546

ABSTRACT

A new monoglyceride, l',26'-bis-[(S)-2,3-dihydroxypropyl] hexacosanedioate (1a) and the new peltogynoid, entadanin (3), along with eight known compounds, were isolated from the stem bark of Entada abyssinica (Fabaceae). The structures of the new compounds were determined by detailed analyses of 1D and 2D NMR spectra, in combination with high-resolution mass spectrometry data, and by comparison with related data from the literature. The stereochemistry of la was derived by comparison of the optical rotation with reference data. Peltogynoids have been reported previously from other Fabaceae, however this is the first report ofa peltogynoid from the genus Entada.


Subject(s)
Fabaceae/chemistry , Glycerides/chemistry , Plant Bark/chemistry , Plant Extracts/chemistry , Plants, Medicinal/chemistry
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