Isolation and identification of two new compounds from the seeds of Moringa oleifera and their antiviral and anti-inflammatory activities

Extensive phytochemical and chromatographic analysis of different root fractions of Jatropha pelargoniifolia Courb. (Euphorbiaceae) resulted in the isolation and identification of 22 distinct secondary metabolite compounds. Two new compounds, 6-hydroxy-8-methoxycoumarin-7-O-β-D-glycopyranoside and (3-(2-(methylamino) ethyl)-1H-indol-2-yl) methanol, were isolated and identified for the first time from a natural source. In addition, other known compounds, such as hovetricoside C and N-methyltryptamine were isolated from Euphorbiaceae, and hordenine, N-methyltyramine, their salts, cynaroside and linarin were identified in Jatropha spp. for the first time. Some isolated metabolites, such as β-sitosterol, β-sitosterol glucoside, curcusons D and C, naringenin, apigenin, cleomiscosins B and A, spruceanol, propacin, jatrophadiketone, and uracil were previously identified in various Jatropha species. The structures of the isolated compounds were determined using different spectroscopic techniques. The anti-inflammatory, antinociceptive, antipyretic, and antioxidant activities were evaluated for some adequately available isolated compounds. Compounds showed significant antinociceptive activity compared with the standard analgesic drug indomethacin. The edema size was significantly reduced (p< 0.05–0.001) in the animals treated with low doses (5 and 10 mg/kg) of the isolated compounds compared with those treated with a high dose (100 mg/kg) of standard anti-inflammatory drug (phenylbutazone). Furthermore, all tested compounds showed a significant (p< 0.05–0.001) reduction in the rectal temperature of hyper-thermic mice.

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Analyzing the Carotenoid Composition of Melilot (Melilotus officinalis (L.) Pall.) Extracts and the Effects of Isolated (All-E)-lutein-5,6-epoxide on Primary Sensory Neurons and Macrophages

Molecules ◽

10.3390/molecules26020503 ◽

2021 ◽

Vol 26 (2) ◽

pp. 503

Author(s):

Györgyi Horváth ◽

Eszter Csikós ◽

Eichertné Violetta Andres ◽

Tímea Bencsik ◽

Anikó Takátsy ◽

...

Keyword(s):

Liquid Chromatography ◽

Sensory Neurons ◽

Biological Activities ◽

Water Soluble ◽

Soluble Form ◽

Primary Sensory Neurons ◽

Isolation And Identification ◽

Melilotus Officinalis ◽

Carotenoid Composition ◽

Anti Inflammatory

Melilotus officinalis is known to contain several types of secondary metabolites. In contrast, the carotenoid composition of this medicinal plant has not been investigated, although it may also contribute to the biological activities of the drug, such as anti-inflammatory effects. Therefore, this study focuses on the isolation and identification of carotenoids from Meliloti herba and on the effect of isolated (all-E)-lutein 5,6-epoxide on primary sensory neurons and macrophages involved in nociception, as well as neurogenic and non-neurogenic inflammatory processes. The composition of the plant extracts was analyzed by high performance liquid chromatography (HPLC). The main carotenoid was isolated by column liquid chromatography (CLC) and identified by MS and NMR. The effect of water-soluble lutein 5,6-epoxide-RAMEB (randomly methylated-β-cyclodextrin) was investigated on Ca2+-influx in rat primary sensory neurons induced by the activation of the transient receptor potential ankyrin 1 receptor agonist to mustard-oil and on endotoxin-induced IL-1β release from isolated mouse peritoneal macrophages. (all-E)-Lutein 5,6-epoxide significantly decreased the percent of responsive primary sensory neurons compared to the vehicle-treated stimulated control. Furthermore, endotoxin-evoked IL-1β release from macrophages was significantly decreased by 100 µM lutein 5,6-epoxide compared to the vehicle-treated control. The water-soluble form of lutein 5,6-epoxide-RAMEB decreases the activation of primary sensory neurons and macrophages, which opens perspectives for its analgesic and anti-inflammatory applications.

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An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea

Marine Drugs ◽

10.3390/md19010038 ◽

2021 ◽

Vol 19 (1) ◽

pp. 38

Author(s):

Chi-Jen Tai ◽

Chiung-Yao Huang ◽

Atallah F. Ahmed ◽

Raha S. Orfali ◽

Walied M. Alarif ◽

...

Keyword(s):

Red Sea ◽

Superoxide Anion ◽

Dermal Fibroblast ◽

Fibroblast Cell ◽

Inhibitory Effect ◽

Human Dermal Fibroblast ◽

Superoxide Anion Generation ◽

Potent Inhibitory Effect ◽

Anti Inflammatory ◽

New Compounds

Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed. Compound 1 was found to significantly reduce the superoxide anion generation and elastase release at a concentration of 10 μM, and compound 5 was also found to display strong inhibitory activity against superoxide anion generation at the same concentration. Due to the noncytotoxic activity and the potent inhibitory effect toward the superoxide anion generation and elastase release, 1 and 5 can be considered to be promising anti-inflammatory agents.

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A Pilot Study on Antimalarial Effects of Moringa oleifera Leaf Extract in Plasmodium berghei Infection in Mice

Walailak Journal of Science and Technology (WJST) ◽

10.48048/wjst.2018.4593 ◽

2017 ◽

Vol 15 (2) ◽

pp. 151-156

Author(s):

Somrudee NAKINCHAT ◽

Voravuth SOMSAK

Keyword(s):

Plasma Glucose ◽

Crude Extract ◽

Plasmodium Berghei ◽

Leaf Extract ◽

Moringa Oleifera ◽

Dependent Manner ◽

Glucose Levels ◽

New Compounds ◽

Dose Dependent

The emergence and spread of antimalarial drug resistance of Plasmodium parasites, as well as hypoglycemia, during malaria infection, and subsequent death, are critical problems in malaria-endemic areas. Hence, finding new compounds, especially plant extracts having antimalarial and anti-hypoglycemic activities, are urgently needed. The present study aimed to investigate the antimalarial and anti-hypoglycemic effects of Moringa oleifera leaf extract in Plasmodium berghei infection in mice. Aqueous crude extract of M. oleifera leaves was freshly prepared and used for an efficacy test in vivo. Groups of ICR mice (5 mice in each) were infected with 1´107 infected red blood cells of P. berghei ANKA by intraperitoneal injection and given the extract orally with doses of 100, 500, and 1000 mg/kg for 4 consecutive days. Parasitemia and plasma glucose levels were subsequently measured. The results showed that M. oleifera leaf extract presented significant (p < 0.001) inhibition of parasitemia in a dose-dependent manner. Moreover, this extract exerted anti-hypoglycemia effects in infected mice in a dose-dependent manner. The highest degrees of activity were found at a dose of 1000 mg/kg of the extract. Additionally, no effect on plasma glucose was found in normal mice treated with this extract. It can be concluded that aqueous crude extract of M. oleifera leaves exerted antimalarial and anti-hypoglycemic effects in P. berghei infection in mice.

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C5-curcuminoid-dithiocarbamate based molecular hybrids: synthesis and anti-inflammatory and anti-cancer activity evaluation

RSC Advances ◽

10.1039/c4ra03655g ◽

2014 ◽

Vol 4 (54) ◽

pp. 28756-28764 ◽

Cited By ~ 9

Author(s):

Amit Anthwal ◽

Kundan Singh ◽

M. S. M. Rawat ◽

Amit K. Tyagi ◽

Bharat B. Aggarwal ◽

...

Keyword(s):

Cancer Cells ◽

Cell Lines ◽

Cancer Cell ◽

Activity Evaluation ◽

Anti Cancer ◽

Molecular Hybrids ◽

Anti Inflammatory ◽

New Compounds ◽

Cancer Activity ◽

Proliferation Potential

The C5-curcumin-dithiocarbamate analogues were synthesized in search of new molecules with anti-proliferation potential against cancer cells. These new compounds demonstrated higher anti-proliferation and anti-inflammatory activity against cancer cell lines in comparison to curcumin.

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Antioxidant, Anti-Inflammatory and Cytotoxic Activities of Jasminum multiflorum (Burm. F.) Andrews Leaves towards MCF-7 Breast Cancer and HCT 116 Colorectal Cell Lines and Identification of Bioactive Metabolites

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520621666210901103440 ◽

2021 ◽

Vol 21 ◽

Author(s):

Seham Salah El-Hawary ◽

Hala M. EL-Hefnawy ◽

Samir Mohamed Osman ◽

Mohamed A. El-Raey ◽

Fatma Alzahraa Mokhtar ◽

...

Keyword(s):

Breast Cancer ◽

Cell Lines ◽

Mass Spectroscopy ◽

Cytotoxic Activities ◽

Isolation And Identification ◽

Antioxidant Power ◽

Hct 116 ◽

Anti Inflammatory ◽

Β Carotene ◽

Mcf 7

Background: The plants of high phenolic contents are perfect antioxidant and anti-inflammatory candidates and participate in biological studies as effective agents towards different cancer cell lines. Objective: To investigate the antioxidant, anti-inflammatory, and cytotoxic activities of the hydromethanolic leaf extract of Jasminum multiflorum (Burm. f.) Andrews. (J. multiflorum), and phenolic profiling of the extract. Methods: The antioxidant activity for the extract was estimated using β-Carotene-linoleic and ferric reducing antioxidant power (FRAP) assays. The anti-inflammatory activity was evaluated by histamine release assay. Cytotoxicity of J. multiflorum was performed using a neutral red uptake assay towards breast cancer (MCF-7) and colorectal cancer (HCT 116) cell lines. Phenolic profiling of the leaves was characterized using high performance liquid chromatography coupled to photodiode array detector-mass spectroscopy-mass spectroscopy (HPLC-PDA-MS/MS), and chromatographic isolation and identification of the isolated compounds were performed using spectroscopic and NMR data, and virtual docking was performed to the isolated compounds against HSP90 (HEAT SHOCK PROTEIN 90). Results : At a concentration of 75 µg mL-1, J. multiflorum extract showed high antioxidant power; 68.23±0.35 % inhibition and 60.30±0.60 a TEAC (µmol Trolox g-1) for β-Carotene-linoleic assay and FRAP assay; respectively, and possessed anti-inflammatory activity with IC50 67.2 µg/ml. J. multiflorum showed high cytotoxic activity with IC50 of 24.81 µg/ml and 11.38 µg/ml for MCF-7 and HCT 116 cell lines, respectively. HPLC-PDA-MS/MS analysis tentatively identified 39 compounds; major compounds are secoiridoid glycosides, kaempferol, and quercetin glycosides, in addition to simple phenylethanoid compounds. Isolation of active metabolites was performed and led to the isolation and identification of four compounds. On the basis of docking study using HSP90 legend, kaempferol neohesperidoside showed a high cytotoxic potential supported by a high affinity score towards HSP90 legend protein. Conclusion: Jasminum multiflorum is a good candidate to isolate cytotoxic agents.

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A Study on Green Synthesis of Nano Cu Compounds (Malachite and Rouaite), Using Moringa oleifera Leaf Extract and their Photocatalytic, Antifungal, Anti-Inflammatory, and Antioxidant Properties

10.9734/bpi/nicb/v2/3768f ◽

2021 ◽

pp. 79-89

Author(s):

S. Darani ◽

N. Nivedha Devi ◽

R. Rajakumari

Keyword(s):

Green Synthesis ◽

Leaf Extract ◽

Moringa Oleifera ◽

Antioxidant Properties ◽

Anti Inflammatory

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Pyrrolizine-5-carboxamides: Exploring the impact of various substituents on anti-inflammatory and anticancer activities

Acta Pharmaceutica ◽

10.2478/acph-2018-0026 ◽

2018 ◽

Vol 68 (3) ◽

pp. 251-273 ◽

Cited By ~ 9

Author(s):

Ahmed M. Gouda ◽

Ahmed H. Abdelazeem ◽

Ashraf N. Abdalla ◽

Muhammad Ahmed

Keyword(s):

Anticancer Activity ◽

Cell Lines ◽

Inflammatory Activity ◽

Electronic Effects ◽

Anticancer Activities ◽

Phenyl Rings ◽

Anti Inflammatory ◽

New Compounds ◽

The Impact ◽

Mcf 7

Abstract Towards optimization of the pyrrolizine-5-carboxamide scaffold, a novel series of six derivatives (4a-c and 5a-c) was prepared and evaluated for their anti-inflammatory, analgesic and anticancer activities. The (EZ)-7-cyano-6-((4-hydroxybenzylidene)amino)-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4b) and (EZ)-6-((4-chlorobenzylidene)-amino)-7-cyano-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5b) bearing the electron donating methyl group showed the highest anti-inflammatory activity while (EZ)-6-((4-chlorobenzylidene)amino)-7-cyano-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5a) was the most active analgesic agent. Cytotoxicity of the new compounds was evaluated against the MCF-7, A2780 and HT29 cancer cell lines using the MTT assay. Compounds 4b and 5b displayed high anticancer activity with IC50 in the range of 0.30–0.92 μmol L−1 against the three cell lines, while compound (EZ)-N-(4-chlorophenyl)-7-cyano-6-((4-hydroxybenzylidene)-amino)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4c) was the most active against MCF-7 cells (IC50 = 0.08 μmol L−1). Both the anti-inflammatory and anticancer activities of the new compounds were dependent on the type of substituent on the phenyl rings. Substituents with opposite electronic effects on the two phenyl rings are preferable for high cytotoxicity against the MCF-7 and A2780 cells. COX inhibition was suggested as the molecular mechanism of the anti-inflammatory activity of the new compounds while no clear relationship could be observed between COX inhibition and anticancer activity. Compound 5b, the most active against the three cell lines, induced dose-dependent early apoptosis with 0.1–0.2 % necrosis in MCF-7 cells. New compounds showed promising drug-likeness scores while the docking study revealed high binding affinity to COX-2. Taken together, this study highlighted the significant impact of the substituents on the anti-inflammatory and anticancer activity of pyrrolizine-5-carboxamides, which could help in further optimization to discover good leads for the treatment of cancer and inflammation.

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