Two New Sulfated Furostanol Saponins from Tribulus terrestris

2002 ◽  
Vol 57 (1-2) ◽  
pp. 33-38 ◽  
Author(s):  
Ivanka Kostova ◽  
Dragomir Dinchev ◽  
Gudrun Hopp Rentsch ◽  
Vladimir Dimitrov ◽  
Antoaneta Ivanova
Keyword(s):  
Chemical Transformation ◽  
Sodium Salt ◽  
Mass Spectra ◽  
Tribulus Terrestris ◽  
Furostanol Saponins ◽  
Aerial Parts ◽  
Nmr Data ◽  
New Compounds

The known furostanol saponins methylprotodioscin and protodioscin and two new sulfated saponins, sodium salt of 26-O-β-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol- 3-O-α-rhamnopyranosyl-(1→2)-β-4-O-sulfo-glucopyranoside (methylprototribestin) and sodium salt of 26-O-β-glucopyranosyl-22α-hydroxy-(25R)-furost-5-ene-3β,26-diol-3-O-α-rhamnopyranosyl-( 1→2)-β-4-O-sulfo-glucopyranoside (prototribestin) have been isolated from the aerial parts of Tribulus terrestris L. growing in Bulgaria. The structures of the new compounds were elucidated on the basis of 1D and 2D (DQF-COSY, TOCSY, HSQC-TOCSY, HSQC, HMBC, ROESY) NMR data, ESI mass spectra and chemical transformation.

scholarly journals neo-Clerodane Diterpenoids from Scutellaria galericulata

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Josep Coll
Keyword(s):  
Acetone Extract ◽  
Aerial Parts ◽  
Nmr Data ◽  
Clerodane Diterpenoids ◽  
New Compounds ◽  
First Time

Four neo-clerodane diterpenoids, neoajugapyrin A, scutegalerins A and B and scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata. Neoajugapyrin A and scutecolumnin C are reported in this species for the first time, whereas scutegalerins A and B are new compounds. NMR data of neoajugapyrin A are discussed in detail to support the proposed revised structure of ajugapyrin A.

scholarly journals Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum

2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Yoshihiro Mimaki ◽  
Tsukasa Aoki ◽  
Maki Jitsuno ◽  
Akihito Yokosuka ◽  
Ceyda Sibel Kiliç ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Promyelocytic Leukemia ◽  
Leukemia Cells ◽  
Steroidal Saponins ◽  
Furostanol Saponins ◽  
Nmr Data ◽  
Spirostanol Saponins ◽  
New Compounds ◽  
Chemical Evidence

Phytochemical screening of the rhizomes of Ruscus hypophyllum (Liliaceae) has resulted in the isolation of five spirostanol saponins (1-5) including a new saponin (4) and nine furostanol saponins (6–14) including three new saponins (9–11), together with a known cholestane glycoside (15) and a new cholestane glycoside (16). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence. The spirostanol saponins 1, 2, and 5 showed moderate cytotoxic activity against HL-60 human promyelocytic leukemia cells.

Unexpected Keto-enol Tautomerism in the Cyclopyridinophane Class Direct and indirect proofs

2008 ◽  
Vol 59 (10) ◽  
Author(s):  
Paul Ionut Dron ◽  
Neculai Doru Miron ◽  
Gheorghe Surpateanu
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Stable Conformer ◽  
Ph Measurements ◽  
Theoretical Methods ◽  
Nmr Data ◽  
Tautomeric Forms ◽  
New Compounds

The paper presents the synthesis of cyclo (bis-paraquat p-phenylene p-phenylene-carbonyl) tetrakis (hexafluorophosphate), named �CETOBOX�, and the closely related structural determinations. This compound exists in three tautomeric forms. These forms were evidentiated by NMR-data (1H-NMR, TOCSY, COSY, NOESY), UV-Vis spectra coupled with pH measurements and by synthesis. As the �CETOBOX� gives �in situ� only the corresponding monoylide, the synthesis of a new fluorescent indolizine cyclophane has been performed by a 3+2 cycloaddition. All structures of the new compounds presented herein have been established by NMR spectroscopy. Also, theoretical methods (MM3, AM1, AM1-COSMO and B88LYPDFT) have been used to determine the most stable conformer structures.

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

New soluble 4-(4-formyl-2,6-dimethoxyphenoxy) substituted phthalocyanines: Synthesis, characterization, photophysical and photochemical properties

2021 ◽  
pp. 1-10
Author(s):  
Ibrahim Erden ◽  
Betül Karadoğan ◽  
Fatma Aytan Kılıçarslan ◽  
Göknur Yaşa Atmaca ◽  
Ali Erdoğmuş
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Fluorescence Quantum Yield ◽  
Metal Ion ◽  
Mass Spectra ◽  
Quantum Yields ◽  
Therapeutic Outcomes ◽  
Ft Ir ◽  
Photochemical Properties ◽  
New Compounds

This work describes the synthesis, spectral and fluorescence properties of bis 4-(4-formyl-2,6-dimethoxyphenoxy) substituted zinc (ZnPc) and magnesium (MgPc) phthalocyanines. The new compounds have been characterized by elemental analysis, UV-Vis, FT-IR, 1H-NMR and mass spectra. Afterward, the effects of including metal ion on the photophysicochemical properties of the complexes were studied in biocompatible solvent DMSO to analyze their potential to use as a photosensitizer in photodynamic therapy (PDT). The fluorescence and singlet oxygen quantum yields were calculated as 0.04–0.15 and 0.70–0.52 for ZnPc and MgPc, respectively. According to the results, MgPc has higher fluorescence quantum yield than ZnPc, while ZnPc has higher singlet oxygen quantum yield than MgPc. The results show that the synthesized complexes can have therapeutic outcomes for cancer treatment.

scholarly journals Derivatives of 2-Aminopyridines as Inhibitors of Multidrug Resistant Staphylococcus Aureus Strains

2018 ◽  
Vol 10 (1) ◽  
pp. 153
Author(s):  
Iniobong E. Ante ◽  
Sherifat A Aboaba ◽  
Hina Siddiqui ◽  
Muhammad A Bashir ◽  
Muhammad I Choudhary
Keyword(s):  
Staphylococcus Aureus ◽  
Mass Spectra ◽  
Multidrug Resistant ◽  
Drug Resistant ◽  
Acid Chlorides ◽  
Alamar Blue ◽  
Standard Drug ◽  
Starting Point ◽  
New Compounds ◽  
Derivatives Of

A new series of 2-aminopyridine derivatives were synthesised. N-acylation of 2-amino-3-chloro-5-(trifluoromethyl) pyridine and 2-amino-5-(trifluoromethyl) pyridine with series of acid chlorides afforded a total of fourteen (14) amide compounds. The structures of the new compounds have been established by their IR, NMR and mass spectra data. All the compounds were tested for their activity against four (4) multi-drug resistant (MDR) bacteria Staphylococcus aureus strains using microplate alamar blue assay. The MDR-Staphylococcus aureus strains employed for this study were Epidermic Methicilin Resistant Staphylococcus aureus (EMRSA-17), Methicilin Resistant Staphylococcus aureus (MRSA-252), Epidermic Methicilin Resistant Staphylococcus aureus (EMRSA-16) and Pakistani Drug resistant clinical isolate of Staphylococcus aureus (PRSA). Other bacteria strains also used include Escherichia coli (ATCC 2592), Shigella flexenari (ATCC 12022), Staphylococcus aureus (NCTC 6571) and Pseudomonas aeruginosa (NCTC 10662). The synthesised compounds exhibited very good activity against the four MDR-Staphylococcus aureus strains of which most of the compounds showed higher potencies for inhibiting the growth of the strains than vancomycin, the standard drug employed. The compounds reported here may serve as the starting point for the design and development of MDR-S.aureus inhibitors as antibacterial agents.

scholarly journals Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Quantum Mechanics-Based Structure Analysis of Cyclic Monoterpene Glycosides from Rhodiola Rosea

2020 ◽  
Author(s):  
Yu Tang ◽  
J. Brent Friesen ◽  
David C. Lankin ◽  
James McAlpine ◽  
Dejan Nikolić ◽  
...  
Keyword(s):  
Quantum Mechanics ◽  
Spectroscopic Analysis ◽  
Spatial Arrangement ◽  
Spin Coupling ◽  
Rhodiola Rosea ◽  
Analysis Software ◽  
Nmr Data ◽  
Biological Studies ◽  
Spin Analysis ◽  
New Compounds

NMR- and MS-guided metabolomic mining for new phytoconstituents from a widely used dietary supplement, <i>Rhodiola rosea</i>, yielded two new (+)-myrtenol glycosides, <b>1</b> and <b>2</b>, and two new cuminol glycosides (<b>3</b> and <b>4</b>), along with three known analogues (<b>5</b>–<b>7</b>). The structures of the new compounds were determined by extensive spectroscopic analysis. Quantum Mechanics-driven <sup>1</sup>H iterative Full Spin Analysis (QM-HiFSA) decoded the spatial arrangement of the methyl groups in <b>1</b> and <b>2</b>, as well as other features not recognizable by conventional methods, including higher order spin-coupling effects. The application of QM-HiFSA will provide a definitive reference point for future phytochemical and biological studies of <i>R. rosea</i> as a resilience botanical. Application of a new NMR data analysis software package, CT, for QM-based iteration of NMR spectra is also discussed.

scholarly journals Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1518-1525 ◽  
Author(s):  
Hamid Reza Jaberi ◽  
Hadi Noorizadeh
Keyword(s):  
Acetic Acid ◽  
Sodium Acetate ◽  
Carbon Disulphide ◽  
Thiazole Derivatives ◽  
H Nmr ◽  
Nmr Data ◽  
Elemental Analyses ◽  
New Compounds ◽  
Isoxazole Derivatives ◽  
C Nmr

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

scholarly journals Further Guaianolides from Amphoricarpos neumayeri ssp. murbeckii from Montenegro

2006 ◽  
Vol 61 (11) ◽  
pp. 1437-1442 ◽  
Author(s):  
Iris Djordjević ◽  
Milka Jadranin ◽  
Vlatka Vajs ◽  
Nebojša Menković ◽  
Vele Tešević ◽  
...  
Keyword(s):  
Double Bond ◽  
Aerial Parts ◽  
New Compounds

The aerial parts of Amphoricarpos neumayeri ssp. murbeckii afforded eleven guaianolides with the same relative (1αH,4β H,5αH,7αH) configuration of the basic skeleton. All of them contained a CH2OX (X = H, acetyl or isovaleroyl) group in 4α-position, typical for amphoricarpolides. Four compounds (1 - 4) were isolated before from the same species, originating from different localities. Guaianolides 5 - 11 are new compounds. Compounds 7 and 8 were epoxidized at the 10α(14)-position. Instead of the Δ11(13)-double bond, observed in all previously isolated guaianolides from the same species, the four lactones contained 11α,13-diol (8 - 10) or 11α-OH,13-chloro (11) moieties respectively.

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