Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and α-glycosidase inhibitors

2020 ◽  
Vol 75 (5-6) ◽  
pp. 153-159
Author(s):  
Tuba Aydin
Keyword(s):  
Secondary Metabolites ◽  
Carbonic Anhydrase ◽  
Folk Medicine ◽  
Inhibitory Effect ◽  
Glycosidase Inhibitors ◽  
Meoh Extract ◽  
Chemical Structures ◽  
Liquid Chromatography Tandem Mass ◽  
First Time

AbstractHelichrysum plicatum species are used in Turkish folk medicine as lithagogue, diuretic, and nephritic. Research on the methanol (MeOH) extract of flowers of H. plicatum DC. subsp. plicatum resulted in the isolation of eight known compounds (1–8). The chemical structures of the compounds were determined as β-sitosterol (1), apigenin (2), nonacosanoic acid (3), astragalin (4), β-sitosterol-3-O-β-D-glucopyranoside (5), helichrysin A (6), helichrysin B (7), and isosalipurposide (8) by spectroscopic and chromatographic/spectrometric methods, including 1D and 2D nuclear magnetic resonance and liquid chromatography-tandem mass spectrometry. Nonacosanoic acid (3) was isolated for the first time from H. plicatum DC. subsp. plicatum. The MeOH extract and isolated compounds were evaluated for their in vitro human carbonic anhydrase I (hCAI) and II (hCAII), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase inhibitory activities. The IC50 values of H. plicatum DC. subsp. plicatum MeOH extract for hCAI, hCAII, AChE, BChE, and α-glycosidase were found to be 77.87, 52.90, 115.50, 117.46, and 81.53 mg/mL, respectively. The compounds showed IC50 values of 1.43–4.47, 1.40–4.32, 1.69–2.90, 1.09–3.89, and 1.61–3.80 μM against hCAI, hCAII, AChE, BChE, and α-glycosidase, respectively. In summary, H. plicatum DC. subsp. plicatum secondary metabolites demonstrated strong inhibitory effects especially against hCAI and hCAII, whereas the MeOH extract showed a weak inhibitory effect on all enzymes.

scholarly journals Isolation and Identification of the Five Novel Flavonoids from Genipa americana Leaves

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2521 ◽  
Author(s):  
Larissa Silva ◽  
Jovelina Alves ◽  
Emerson da Silva Siqueira ◽  
Manoel de Souza Neto ◽  
Lucas Abreu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Medicinal Plant ◽  
Ethyl Acetate ◽  
Folk Medicine ◽  
Ethyl Acetate Fraction ◽  
Spectroscopic Methods ◽  
Isolation And Identification ◽  
1H And 13C Nmr ◽  
Chemical Structures ◽  
First Time

Genipa americana is a medicinal plant popularly known as “jenipapo”, which occurs in Brazil and belongs to the Rubiaceae family. It is a species widely distributed in the tropical Central and South America, especially in the Cerrado biome. Their leaves and fruits are used as food and popularly in folk medicine to treat anemias, as an antidiarrheal, and anti-syphilitic. Iridoids are the main secondary metabolites described from G. americana, but few studies have been conducted with their leaves. In this study, the aim was to chemical approach for identify the main compounds present at the extract of G. americana leaves. The powdered leaves were extracted by maceration with EtOH: water (70:30, v/v), following liquid-liquid partition with petroleum ether, chloroform, ethyl acetate and n-butanol. A total of 13 compounds were identified. In addition three flavonoids were isolated from the ethyl acetate fraction: quercetin-3-O-robinoside (GAF 1), kaempferol-3-O-robinoside (GAF 2) and isorhamnetin-3-O-robinoside (GAF 3) and, from n-butanol fraction more two flavonoids were isolated, kaempferol-3-O-robinoside-7-O-rhamnoside (robinin) (GAF 4) and isorhamnetin-3-O-robinoside-7-rhamnoside (GAF 5). Chemical structures of these five flavonoids were elucidated using spectroscopic methods (MS, 1H and 13C-NMR 1D and 2D). These flavonoids glycosides were described for the first time in G. americana.

Synergistic Antitumor Effect of 5-Fluorouracil Combined with Constituents from Pleurospermum lindleyanum in Hepatocellular carcinoma SMMC-7721 Cells

2020 ◽  
Vol 20 ◽  
Author(s):  
Xiao-Feng Zhu ◽  
Xiao-Jin Li ◽  
Zhong-Lian Cao ◽  
Xiu-Jie Liu ◽  
Ping Yang ◽  
...  
Keyword(s):  
Hepatocellular Carcinoma ◽  
Treatment Effectiveness ◽  
Synergistic Effects ◽  
Folk Medicine ◽  
Inhibitory Effect ◽  
Caspase 9 ◽  
Whole Plant ◽  
Anti Cancer ◽  
Induced Apoptosis

Background: A Chinese folk medicine plant Pleurospermum lindleyanum possesses pharmacological activities of heat-clearing, detoxifying and preventing from hepatopathy, coronary heart disease, hypertension, and high altitude sickness. We isolated and characterized its constituents to investigate its synergistic effects against human hepatoma SMMC-7721 cells. Objective: The aim of this study was to explore the synergistic anti-cancer activities of isolates from P. lindleyanum with 5-FU on hepatoma SMMC-7721 cells in vitro and their primary mechanisms. Methods: Sequential chromatographic techniques were conducted for the isolation studies. The isolates structures were established by spectroscopic analysis as well as X-ray crystallographic diffraction. Growth inhibition was detected by MTT assay. The isobologram method was used to assess the effect of drug combinations. Flow cytometry and western blot were used to examine apoptosis and protein expression. Results: A new coumarin (16), along with sixteen known compounds, were isolated from the whole plant of P. lindleyanum and their structures were elucidated by spectroscopic methods. Four coumarins (2, 3, 5, and 16), two flavonoids (8 and 9) and three phytosterols and triterpenes (12-14) were found to synergistically enhance the inhibitory effect of 5-FU against SMMC-7721 cells. Among them, compounds 3 and 16 exhibited the best synergistic effects with IC50 of 5-FU reduced by 16-fold and 22-fold possessing the minimum Combination Index (CI) 0.34 and 0.27. The mechanism of action of combinations might be through synergistic arresting for the cell cycle at G1 phases and the induction of apoptosis. Moreover, western blotting and molecular docking revealed that compounds 3 or 5 might promote 5-FU-induced apoptosis by regulating the expression of Caspase 9 and PARP. Conclusion: Constituents from P. lindleyanum may improve the treatment effectiveness of 5-FU against hepatocellular carcinoma cells.

scholarly journals CONSTITUENTS AND INHIBITORY EFFECT ON HUMAN PATHOGENIC BACTERIA OF THE ROOTS OF SCUTELLARIA BAICALENSIS

2019 ◽  
Vol 57 (1) ◽  
pp. 7
Author(s):  
Duc Long Le ◽  
Huu Tung Nguyen ◽  
Thi Thom Nguyen ◽  
Gyung Ja Choi ◽  
Dinh Hoang Vu ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Pathogenic Bacteria ◽  
Inhibitory Effect ◽  
Scutellaria Baicalensis ◽  
Plant Materials ◽  
Chemical Structures ◽  
Human Pathogenic Bacteria ◽  
Antibiotic Effect ◽  
Study Results

Abstract-HCTN_16Methanol extract of the roots of Scutellaria baicalensis effectively inhibited the bacterial growth of human pathogenic bacteria Staphylococcus aureus ATCC 6538, Bacillus cereus ATCC 21768 and Bacillus subtilis ATCC 6633 at MICs of 2,000 µg/mL. n-Hexane, ethyl acetate and aqueous residues were prepared by successively partitioning the methanol extract with n-hexane and ethyl acetate. Among them, only ethyl acetate layer showed antibiotic effect; whereas n-hexane and aqueous layers were inactive against tested bacteria. The ethyl acetate residue was fractionated by silica gel column chromatography to afford three flavonoids and an oligosaccharide. Their chemical structures were elucidated as wogonin (SB1), baicalein (SB4), baicalin (SB5) and tetrasaccharide (SB10) on the basis of the analysis of NMR and MS spectroscopic data. The isolates were evaluated for in vitro inhibitory effect against human pathogenic bacteria using micro dilution bioassay method. Baicalein (SB4) showed a broad-spectrum inhibition against various human pathogenic bacteria. In particular, it was found to potently inhibit S. aureus ATCC 6538 and B. cereus ATCC 21768 with MICs of 9.5 and 38 µg/mL, respectively. The study results demonstrated antibiotic effect of the extracts from the roots of S. baicalensis and characterization of compounds isolated from the plant materials.

scholarly journals Isolation of furanocoumarins from Pastinaca sativa L. callus culture

2014 ◽  
Vol 69 (3) ◽  
pp. 193-195 ◽  
Author(s):  
Halina Ekiert ◽  
Wanda Kisiel
Keyword(s):  
Secondary Metabolites ◽  
Callus Culture ◽  
Spectral Methods ◽  
Solid Medium ◽  
Intact Plant ◽  
Pastinaca Sativa ◽  
First Report ◽  
Callus Tissues ◽  
First Time

Four furanocoumarins: bergapten, xanthotoxin, isopimpinellin (linear furanocoumarins) and sphondin (angular furanocoumarin) were isolated for the first time from callus tissues of <em>Pastinaca sativa</em> L.(<em>Apiaceae</em>) cultured in vitro on solid medium. The compounds were identified using spectral methods. They are well-known secondary metabolites of the intact plant. This is the first report on the isolation of sphondin from in vitro plant cultures.

scholarly journals In Vitro Schistosomicidal Activity of the Alkaloid-Rich Fraction from Ruta graveolens L. (Rutaceae) and Its Characterization by UPLC-QTOF-MS

2019 ◽  
Vol 2019 ◽  
pp. 1-8 ◽  
Author(s):  
Lara Soares Aleixo de Carvalho ◽  
Lucas Sales Queiroz ◽  
Ismael José Alves Junior ◽  
Ayla das Chagas Almeida ◽  
Elaine Soares Coimbra ◽  
...  
Keyword(s):  
Folk Medicine ◽  
Peritoneal Macrophages ◽  
Antileishmanial Activity ◽  
Parasitic Infections ◽  
Leishmania Braziliensis ◽  
Ruta Graveolens ◽  
Active Fraction ◽  
Ms Analysis ◽  
First Time

Schistosomiasis is a neglected tropical disease that affects million people worldwide, mostly in developing countries. Ruta graveolens (Rutaceae) is a plant used in folk medicine to treat several diseases, including parasitic infections. In this study, we reported the in vitro schistosomicidal activity of the R. graveolens extract (Rg) and its active fraction (Rg-FAE). Also, the characterization of Rg-FAE by UPLC-ESI-QTOF-MS analysis and its in vitro antileishmanial activity against Leishmania braziliensis were also performed. In vitro schistosomicidal assays were assessed against adult worms of S. mansoni, while cell viability against peritoneal macrophages was measured by MTT assay. Rg (100 μg/mL) exhibited noticeable schistosomicidal activity, causing 100% mortality and decreasing motor activity of all adult male and female schistosomes, but with low activity against L. braziliensis. After chromatographic fractionation of Rg, fraction Rg-FAE was obtained, showing high activity against adult schistosomes. UPLC-ESI-QTOF-MS analysis of Rg-FAE revealed the presence of eleven alkaloids and one furanocoumarin. No significant antileishmanial activity was found for Rg, while Rg-FAE exhibited activity against L. braziliensis promastigotes. We demonstrated, for the first time, that the R. graveolens extract (Rg) and its alkaloid-rich fraction (Rg-FAE) are active against adult worms of S. mansoni, with no significant cytotoxicity on macrophages. Our findings open the route to further antiparasitic studies with the active fraction of R. graveolens and its identified compounds, especially alkaloids.

In Vitro Human Dihydroorotate Dehydrogenase Inhibitory, Anti-inflammatory and Cytotoxic Activities of Alkaloids from the Seeds of Nigella glandulifera

Planta Medica ◽  
2018 ◽  
Vol 84 (14) ◽  
pp. 1013-1021 ◽  
Author(s):  
Jun-Bo Gao ◽  
Xing-Jie Zhang ◽  
Rui-Han Zhang ◽  
Li-Li Zhu ◽  
De-Bing Pu ◽  
...  
Keyword(s):  
Folk Medicine ◽  
Positive Control ◽  
Cytotoxic Activities ◽  
Dihydroorotate Dehydrogenase ◽  
X Ray Diffraction ◽  
Ic50 Values ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

AbstractFour new dolabellane-type diterpene alkaloids, glandulamines A – D (1 – 4), together with twelve known compounds (5 – 16), were isolated from the seeds of Nigella glandulifera using repeated column chromatography and semipreparative HPLC. The structures of 1 – 16 were elucidated based on NMR data analysis, HRMS experiments and other spectroscopic interpretations. The absolute configuration of 5 was determined by single-crystal X-ray diffraction data for the first time. Compounds 10 and 12 showed human dihydroorotate dehydrogenase inhibitory activity with IC50 values of 61.1 ± 5.3 and 45.9 ± 3.0 µM, respectively. Molecular docking of the active compound 12 and positive control teriflunomide on the inhibitor-binding site of human dihydroorotate dehydrogenase was subsequently performed to visualize the interaction pattern. In addition, compounds 8 and 10 exhibited inhibitory effects against lipopolysaccharide-induced nitric oxide production with inhibition rates of 61 and 41%, respectively, at the concentration of 10 µM. Compounds 9 and 12 showed cytotoxic activities with cell viability varying from 29 ~ 57% at 100 µM against T98G, U87, U251, and GL261 glioma cancer cell lines. These data provide new insights on the pharmacologically active compounds of this plant widely used in folk medicine.

scholarly journals Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

Molecules ◽  
2019 ◽  
Vol 25 (1) ◽  
pp. 129
Author(s):  
Dario Matulja ◽  
Maria Kolympadi Markovic ◽  
Gabriela Ambrožić ◽  
Sylvain Laclef ◽  
Sandra Kraljević Pavelić ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Biological Activities ◽  
Structural Characteristics ◽  
Antimicrobial Activities ◽  
Chemical Structures ◽  
Gorgonian Corals ◽  
Synthetic Approaches ◽  
Further Development

Gorgonian corals, which belong to the genus Eunicella, are known as natural sources of diverse compounds with unique structural characteristics and interesting bioactivities both in vitro and in vivo. This review is focused primarily on the secondary metabolites isolated from various Eunicella species. The chemical structures of 64 compounds were divided into three main groups and comprehensively presented: a) terpenoids, b) sterols, and c) alkaloids and nucleosides. The observed biological activities of depicted metabolites with an impact on cytotoxic, anti-inflammatory, and antimicrobial activities were reviewed. The most promising biological activities of certain metabolites point to potential candidates for further development in pharmaceutical, cosmetic, and other industries, and are highlighted. Total synthesis or the synthetic approaches towards the desired skeletons or natural products are also summarized.

Synthesis, in vitro inhibition effect of novel phthalocyanine complexes as carbonic anhydrase and paraoxonase enzyme inhibitors

2020 ◽  
Vol 24 (08) ◽  
pp. 1047-1053
Author(s):  
Emre Güzel ◽  
Barış Seçkin Arslan ◽  
Kübra Çıkrıkçı ◽  
Adem Ergün ◽  
Nahit Gençer ◽  
...  
Keyword(s):  
Carbonic Anhydrase ◽  
Enzyme Inhibitors ◽  
Inhibition Effect ◽  
H Nmr ◽  
Vis Spectroscopy ◽  
Ft Ir ◽  
First Time ◽  
Ft Ir Spectroscopy ◽  
C Nmr

The preparation and assessment of carbonic anhydrase and paraoxonase enzyme inhibition properties of 3-(2-(5-amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its nitrogen-containing non-peripheral phthalocyanine derivatives (3 and 4) are reported for the first time. The new phthalonitrile and its phthalocyanine derivatives have been elucidated by FT-IR spectroscopy, 1H-NMR, [Formula: see text]C-NMR, mass and UV-vis spectroscopy. The results demonstrated that all synthesized compounds moderately inhibited carbonic anhydrase and paraoxonase enzymes. Among the compounds, the most active ones were found to be compound 4 for PON (Ki : 0.14 [Formula: see text]M), compound 3 for hCA I (Ki : 22.52 [Formula: see text]M) and compound 1 for hCA II (Ki : 13.62 [Formula: see text]M).

scholarly journals Dual inhibitors of urease and carbonic anhydrase-II from Iris species

2019 ◽  
Vol 91 (10) ◽  
pp. 1695-1707 ◽  
Author(s):  
Muhammad Saleem ◽  
Sumaira Hareem ◽  
Ajmal Khan ◽  
Suad Naheed ◽  
Muslim Raza ◽  
...  
Keyword(s):  
Carbonic Anhydrase ◽  
Significant Inhibition ◽  
Carbonic Anhydrase Ii ◽  
Natural Organic Compounds ◽  
Mass Spectrogram ◽  
Urease Enzyme ◽  
Dual Inhibitors ◽  
Inhibition Studies ◽  
First Time

Abstract Twenty seven (1–27) known natural organic compounds were isolated for first time from two species of Iris, i.e. loczyi and Iris unguicularis. The structures of these compounds were deduced from the spectral data of NMR, IR, and mass spectrogram. These were evaluated against urease and carbonic anhydrase inhibition studies. For carbonic anhydrase-II inhibition studies, these compounds were evaluated by biochemical mechanism based in vitro bio-assay. Some compounds showed significant inhibition against CA-II enzyme. Compartively, compound (12) showed IC50 value of 17.60 ± 0.08 μM against urease enzyme, while compound (3) was found to be most active against carbonic anhydrase-II, having an IC50 value of 66.27 ± 0.89 μM. Izalpinin (3), 5,7-dihydroxy-2′,6-dimethoxyisoflavone (9), 4′,5,7-trihydroxy-6-methoxyflavanone (16), 4′,5,7-trihydroxy-3′,8-dimethoxyflavanone (20), 8-methoxyeriodictyol (21), and mangiferin (26) were found to be dual inhibitors of both the enyzmes. The most active compounds were docked using Autodock Vina and i-GEMDOCK softwares. The docking and in-vitro results are in agreement which showed secondary interactions with the enzymes. The compounds can serve as therapeutic agents to treat urease and carbonic anhydrase associated disorders.

scholarly journals Aspergillus flavus as a Model System to Test the Biological Activity of Botanicals: An Example on Citrullus colocynthis L. Schrad. Organic Extracts

Toxins ◽  
2019 ◽  
Vol 11 (5) ◽  
pp. 286 ◽  
Author(s):  
Francesca Degola ◽  
Belsem Marzouk ◽  
Antonella Gori ◽  
Cecilia Brunetti ◽  
Lucia Dramis ◽  
...  
Keyword(s):  
Biological Activity ◽  
Aspergillus Flavus ◽  
Folk Medicine ◽  
Inhibitory Effect ◽  
Phytopathogenic Fungus ◽  
Citrullus Colocynthis ◽  
Desert Areas ◽  
Derivatives Of ◽  
Stem Leaf

Citrullus colocynthis L. Schrader is an annual plant belonging to the Cucurbitaceae family, widely distributed in the desert areas of the Mediterranean basin. Many pharmacological properties (anti-inflammatory, anti-diabetic, analgesic, anti-epileptic) are ascribed to different organs of this plant; extracts and derivatives of C. colocynthis are used in folk Berber medicine for the treatment of numerous diseases—such as rheumatism arthritis, hypertension bronchitis, mastitis, and even cancer. Clinical studies aimed at confirming the chemical and biological bases of pharmacological activity assigned to many plant/herb extracts used in folk medicine often rely on results obtained from laboratory preliminary tests. We investigated the biological activity of some C. colocynthis stem, leaf, and root extracts on the mycotoxigenic and phytopathogenic fungus Aspergillus flavus, testing a possible correlation between the inhibitory effect on aflatoxin biosynthesis, the phytochemical composition of extracts, and their in vitro antioxidant capacities.

Sign in / Sign up

Export Citation Format

Share Document