scholarly journals Flavonoid Glycosides from Endemic Bulgarian Astragalus aitosensis (Ivanisch.)

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1419 ◽  
Author(s):  
Hristo Vasilev ◽  
Samir Ross ◽  
Karel Šmejkal ◽  
Petr Maršík ◽  
Dagmar Jankovská ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Structural Analysis ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
2D Nmr ◽  
Biologically Active ◽  
Spectral Studies ◽  
Flavonoid Glycosides ◽  
Phenolic Components ◽  
First Time

Astragalus is a very interesting plant genus, well-known for its content of flavonoids, triterpenes and polysaccharides. Its secondary metabolites are described as biologically active compounds showing several activities, e.g., immunomodulating, antibacterial, antiviral and hepatoprotective. This inspired us to analyze the Bulgarian endemic A. aitosensis (Ivanisch.) to obtain deeper information about its phenolic components. We used extensive chromatographic separation of A. aitosensis extract to obtain seven phenolic compounds (1–7), which were identified using combined LC-MS and NMR spectral studies. The 1D and 2D NMR analyses and HR-MS allowed us to resolve the structures of known compounds 5–7 as isorhamnetin-3-O-robinobioside, isorhamnetin-3-O-(2,6-di-O-α-rhamno-pyranosyl-β-galactopyranoside), and alangiflavoside, respectively, and further comparison of these spectral data with available literature helped us with structural analysis of newly described flavonoid glycosides 1–4. These were described in plant source for the first time.

In vivo Anti-Inflammatory and Antinociceptive Activity Evaluation of Phenolic Compounds from Sideritis stricta

2007 ◽  
Vol 62 (7-8) ◽  
pp. 519-525 ◽  
Author(s):  
Esra Küpeli ◽  
Erdem Yeșilada ◽  
İhsan Caliș ◽  
Nurten Ezer ◽  
Keyword(s):  
Phenolic Compounds ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Acetone Extract ◽  
Antinociceptive Activity ◽  
Flavonoid Glycosides ◽  
Phenolic Fraction ◽  
Phenolic Components ◽  
Anti Inflammatory

An acetone extract obtained from aerial parts of S. stricta Boiss. & Heldr. apud Bentham, its fractions and phenolic compounds were investigated for their in vivo anti-inflammatory and antinociceptive activities. For the anti-inflammatory activity and for the antinociceptive activity assessment, carrageenan-induced hind paw edema and p-benzoquinone-induced abdominal constriction tests were used, respectively. The acetone extract of the plant and its phenolic fraction exhibited potent inhibitory activity against both bioassay models in mice. From the active phenolic fraction a well-known phenylethanoid glycoside, verbascoside (acteoside) (1), and two flavonoid glycosides, isoscutellarein 7-O-[6‴-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (2) and isoscutellarein 7-O-[6‴-O-acetyl-β-D-allopyranosyl-(1→2)]-6‴-O-acetyl-β-d-glucopyranoside (3), were isolated. During phytochemical studies we also isolated a methoxyflavone, xanthomicrol (4), from the non-polar fraction. The structures of the isolated compounds were established by spectroscopic evidence (UV, IR, 1D- and 2D-NMR, MS). Although antinociceptive and anti-inflammatory activities of the phenolic components were found not significant in the statistical analysis, compounds 1 to 3 showed a notable activity without inducing any apparent acute toxicity as well as gastric damage. Furthermore, a mixture of flavonoid glycosides (2 + 3) exhibited a significant inhibitory effect in both models at a higher dose

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

PHENOLIC COMPOUNDS AND ANTIOXIDANT ACTIVITY GLYCYRRHIZA PALLIDIFLORA HERB (GLYCYRRHIZA PALLIDIFLORA MAXIM.)

2021 ◽  
pp. 42-46
Author(s):  
Maltseva E.M. ◽  
Egorova I.N. ◽  
Pinchuk L.G.
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Russian Far East ◽  
Far East ◽  
Biologically Active ◽  
Perennial Herb ◽  
Total Phenolic ◽  
Plant Antioxidants ◽  
Phytochemical Studies ◽  
First Time

Pale-flowered licorice (Glycyrrhiza pallidiflora Maxim.) is the pea family (Fabaceae) perennial herb. It is a Russian Far East endemic. Pale-flowered licorice refers to the false (not sweet) licorice section (Pseudoglycyrrhiza Krug.), which do not accumulate glycyrrhizin derivatives. The G. pallidiflora successful introduction has been carried out over the past 5 years in the “Apothecary garden” territory, FRC UUH SB RAS, Kemerovo. Phytochemical studies screening biologically active compounds main classes of the plant aerial part confirmed the presence of a complex of phenolic compounds. The content of catechin derivatives and condensed-type tannins - proanthocyanidins (PAC) data in G. pallidiflora herb were obtained for the first time. In different years of cultivation, licorice herb accumulates phenolic compounds - up to 2.83 ± 0.22% in terms of gallic acid, flavonoids - up to 2.44 ± 0.03% in terms of rutin and PAC in terms of cyanidine chloride - up to 2.61 ± 0.11%. It was found that the maximum content of the phenolic compounds and PAC sum was observed in the herb for 4 years development. The greatest number of flavonoids accumulates in the herb harvested in the 3rd year of cultivation. A positive significant linear relation was found between antioxidant activity (AOA) and the total phenolic compounds and PAC content (r≥0.98). Considering that BAC with IC values ≤ 50 μg / ml in the DPPH assay refer to active antioxidant’s licorice herb can be classified as a plant with high antioxidant potential. It was found that the iron chelating activity of the G. pallidiflora herb is in direct dependence (r≥0.94) on the content of flavonoids. The obtained results demonstrate the importance of further study of this plant as a source of BAC, including plant antioxidants.

scholarly journals Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2772 ◽  
Author(s):  
You-Min Ying ◽  
Lu Huang ◽  
Ting Tian ◽  
Cui-Yu Li ◽  
Shi-Lei Wang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Natural Occurrence ◽  
Fungal Metabolites ◽  
Isolation And Identification ◽  
Late Step ◽  
Neosartorya Fischeri ◽  
The One ◽  
First Time

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

scholarly journals PHYTOCHEMICAL SCREENING AND BIOLOGICAL EVALUATION OF DYPSIS LEPTOCHEILOS LEAVES EXTRACT AND MOLECULAR DOCKING STUDY OF THE ISOLATED COMPOUNDS

2020 ◽  
pp. 106-113
Author(s):  
HAITHAM ALI IBRAHIM ◽  
FATEHIA SAYED ELSHARAWY ◽  
MAHMMOUD ELHASSAB ◽  
SAMAH SHABANA ◽  
EMAN GABER HAGGAG
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Ethyl Acetate ◽  
Chromatographic Separation ◽  
Ethyl Acetate Fraction ◽  
Docking Study ◽  
Separation Techniques ◽  
Reference Drug ◽  
First Time ◽  
Mcf 7

Objective: phytochemical investigation of the ethyl acetate fraction (EAF) of 80% aqueous methanol extract (AME) of Dypsis leptocheilos leaves, in addition to evaluation of the antioxidant, cytotoxic and antimicrobial activities of the AME and EAF. Docking was used to predict and understand cytotoxicity of the isolated compounds. Methods: The ethyl acetate fraction (EAF) of Dypsis leptocheilos leaves was subjected to different chromatographic separation techniques. Structures of the isolated compounds were established by different spectroscopic techniques (1H/13C NMR). Antioxidant activity was evaluated by DPPH assay, while cytotoxicity was evaluated by MTT cell viability assay. Antimicrobial activity was evaluated by agar diffusion method. The docking study was conducted using Auto Dock Vina; the estrogen receptor (PDB 5t92) was used as a receptor for the docking. Results: Chromatographic separation techniques were led to the isolation of five phenolic compounds; these compounds were identified to be apigenin 8-C-β-D-glucopyranoside (Vitexin) (1), apigenin 6-C-β-D-glucopyranoside (Isovitexin) (2), luteolin 7-O-β-D-glucopyranoside (3), luteolin 8-C-β-D-glucopyranoside (Orientin) (4), luteolin 6-C-β-D-glucopyranoside (Isoorientin) (5). They were isolated and identified for the first time from this plant species. The AME and EAF showed moderate activity against Gram positive and Gram negatvie bacteria, while both of them showed similar and powerful antioxidant activity with SC50 = 12.8±0.56 µg/ml and SC50 = 17±0.77 µg/ml respectively, compared to ascorbic (reference drug) SC50 = 14.2±0.35 µg/ml. The EAF showed higher cytotoxic activity on the MCF-7 cells (human breast cancer cell line), with IC50 = 12.3 ± 1.82 µg/ml, compared to Vinblastine Sulfate (reference drug). All isolated compounds showed good binding affinity to the estrogen receptors existed in the MCF-7 cell. Conclusion: Five phenolic compounds were isolated for the first time from the EAF of Dypsis leptocheilos leaves. The AME and EAF extracts showed variable antioxidant, antimicrobial and cytotoxic activities.

scholarly journals Phenolic Composition Influences the Health-Promoting Potential of Bee-Pollen

Biomolecules ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 783 ◽  
Author(s):  
Mirjana Mosić ◽  
Jelena Trifković ◽  
Irena Vovk ◽  
Uroš Gašić ◽  
Živoslav Tešić ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
High Performance ◽  
Ion Trap ◽  
Therapeutic Potential ◽  
Flavonoid Glycosides ◽  
Phenolic Composition ◽  
Bee Pollen ◽  
Orbitrap Mass Spectrometry ◽  
Health Promoting ◽  
First Time

Information on compositional, nutritional and functional properties of bee-pollen, as a health-promoting food, is essential for defining its quality. Concerning the nutritional importance of phenolic compounds, the aim of this study was to determine the phenolic profile and antioxidant activity of twenty-four bee-pollen samples collected from different regions of Serbia. High-performance thin-layer chromatographic (HPTLC) fingerprinting was used for profiling of bee-pollen samples according to the botanical type. HPTLC hyphenated with image analysis and a pattern recognition technique confirmed the grouping of samples caused by the specific phenolic composition of pollens of different botanical origin. Flavonoid glycosides in bee-pollen samples were identified by applying ultra-high-performance liquid chromatography (UHPLC) coupled with linear ion trap-Orbitrap mass spectrometry (LTQ Orbitrap MS). Eight out of twenty-seven flavonol glycosides were identified in bee-pollen samples for the first time. All analyzed bee-pollen samples showed a high number of phenolic compounds which may have therapeutic potential.

scholarly journals Isolation and Characterization of Crotosparsamide, a New Cyclic Nonapeptide from Croton sparsiflorus

2010 ◽  
Vol 5 (12) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Rashad Mehmood ◽  
Abdul Malik
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Spectral Studies ◽  
Isolation And Characterization ◽  
First Time

Crotosparsamide (1), a new cyclic nonapeptide, has been isolated from the n-butanol soluble sub-fraction of Croton sparsiflorus along with p-hydroxy methylcinnamate and kaempferol, which are reported for the first time from this species. Their structures were determined by chemical and spectral studies including ESIMS, and 1D and 2D NMR spectroscopic data.

scholarly journals Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

Marine Drugs ◽  
2020 ◽  
Vol 18 (12) ◽  
pp. 608
Author(s):  
Elena V. Girich ◽  
Anton N. Yurchenko ◽  
Olga F. Smetanina ◽  
Phan Thi Hoai Trinh ◽  
Ngo Thi Duy Ngoc ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Secondary Metabolites ◽  
Cell Viability ◽  
Chemical Structure ◽  
Aspergillus Terreus ◽  
Marine Fungi ◽  
2D Nmr ◽  
Natural Source ◽  
Low Molecular Weight ◽  
First Time

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity.

scholarly journals Flavonoids and Other Phenolic Compounds in Needles of Pinus peuce and Other Pine Species from the Macedonian Flora

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Marija Karapandzova ◽  
Gjose Stefkov ◽  
Ivana Cvetkovikj ◽  
Jasmina Petreska Stanoeva ◽  
Marina Stefova ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Free Form ◽  
Flavonoid Glycosides ◽  
Total Phenolic ◽  
Total Flavonoids ◽  
Coumaric Acid ◽  
Phenolic Components ◽  
Total Flavonoids Content ◽  
Pinus Peuce ◽  
Pine Species

Flavonoids and other phenolic compounds in young needles of four pine species, Pinus peuce, P. nigra, P. mugo and P. sylvestris from the Macedonian flora were investigated. The amount of total phenols and total flavonoids were determined using Folin-Ciocalteau and aluminum chloride assay, respectively. The obtained results revealed that the total phenolic content (TPC) and total flavonoids content (TFC) varied among different pine species ranging from 9.8 to 14.0 mg GAE/g and from 3.3 to 7.2 mg CE/g of dried plant material, respectively. Qualitative analysis of flavonoids and other phenolic components was made by a LC-DAD/ESI-MSn optimized chromatographic method. A total of 17 phenolic components were identified and classified as: acids (2), procyanidins (2) and flavonoid glycosides (13). The most prevalent components were flavonoid glycosides, especially flavonols and methylated flavonols (9). Additionally, 3 components were found as acylated flavonol glycosides with ferulic and p-coumaric acid. The last one was found not only in esterified form but also in the free form. Only one flavone-apigenin glycoside was detected. Procyanidins were identified as catechin derivatives, both dimers and trimers.

Characterization of phenolic compounds from inner bark of Betula pendula

Holzforschung ◽  
2012 ◽  
Vol 66 (2) ◽  
Author(s):  
Jaana Liimatainen ◽  
Maarit Karonen ◽  
Jari Sinkkonen ◽  
Marjo Helander ◽  
Juha-Pekka Salminen
Keyword(s):  
Phenolic Compounds ◽  
High Performance ◽  
Betula Pendula ◽  
Silver Birch ◽  
Biologically Active ◽  
Array Detector ◽  
Ionization Mass ◽  
Inner Bark ◽  
First Time

Abstract A method has been developed for the characterization of biologically active silver birch (Betula pendula) inner bark phenolics based on high-performance liquid chromatography/diode array detector (HPLC-DAD)/electrospray ionization-mass spectrometry (ESI-MS). It was demonstrated that the inner bark contains high amounts of flavonoids, arylbutanoids, diarylheptanoids, simple phenolic compounds, phenolic acids, lignans, and procyanidins. Altogether, 30 individual compounds were characterized based on their ultraviolet (UV) and MS data. Structures of 22 compounds were confirmed by nuclear magnetic resonance (NMR) spectroscopy. In addition to previously reported phenolic compounds, 12 compounds were identified in silver birch inner bark for the first time; two of them are novel compounds: 3-β-glucopyranosyloxy-2-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-one and 1,7-bis-(4-hydroxyphenyl)-3-heptanol 3-O-β-ap-iofuranosyl-(1→2)-β-glucopyranoside.

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