scholarly journals Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

2012 ◽  
Vol 8 ◽  
pp. 763-775 ◽  
Author(s):  
Elena A Khatuntseva ◽  
Vladimir M Men’shov ◽  
Alexander S Shashkov ◽  
Yury E Tsvetkov ◽  
Rodion N Stepanenko ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
Methanol Extract ◽  
Keyhole Limpet Hemocyanin ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Triterpenoid Saponins ◽  
Pure Compounds ◽  
Ester Linkage ◽  
Quillaic Acid

Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents.

Topical Anti-inflammatory Activity of Flavonoids and a New Xanthone from Santolina insularis

2005 ◽  
Vol 60 (1-2) ◽  
pp. 63-66 ◽  
Author(s):  
Filippo Cottiglia ◽  
Laura Casu ◽  
Leonardo Bonsignore ◽  
Mariano Casu ◽  
Costantino Floris ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Methanol Extract ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
2D Nmr Spectroscopy ◽  
Equimolar Dose ◽  
Propenoic Acid ◽  
Mouse Ear ◽  
Anti Inflammatory ◽  
Ear Oedema

Bioactivity-guided fractionation of the methanol extract from the leaves of Santolina insularis led to the isolation of one new xanthone, (E)-3-{6-[(E)-3-hydroxy-3-oxo-1-propenyl]-9- oxo-9H-xanthen-2-yl}-2-propenoic acid, together with six known flavonoids: hispidulin, nepetin, cirsimaritin, rhamnocitrin, luteolin and luteolin 7-O-β-ᴅ-glucopyranoside. The structures were elucidated by means of 1D-, 2D-NMR spectroscopy and mass spectrometry. The topical anti-inflammatory activity of all isolated compounds and extracts was investigated employing the croton oil-induced dermatitis in mouse ear. The most active compound, luteolin, showed an ID50 of 0.3 μmol/cm2 and prevented ear oedema more effectively than an equimolar dose of indomethacin within 24 h.

scholarly journals Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine

Molbank ◽  
10.3390/m1250 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1250
Author(s):  
Diana Becerra ◽  
Justo Cobo ◽  
Juan-Carlos Castillo
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ambient Temperature ◽  
Magnesium Sulfate ◽  
Elemental Analysis ◽  
Condensation Reaction ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Temperature Synthesis ◽  
Tert Butyl

We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. The N-pyrazolyl imine 3 was full characterized by IR, 1D, and 2D NMR spectroscopy, mass spectrometry, and elemental analysis.

scholarly journals Exploring the Phytochemicals of Acacia melanoxylon R. Br.

Plants ◽  
2021 ◽  
Vol 10 (12) ◽  
pp. 2698
Author(s):  
Diana Alves ◽  
Sidónio Duarte ◽  
Pedro Arsénio ◽  
Joana Gonçalves ◽  
Cecília M. P. Rodrigues ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Mass Spectrometry ◽  
Methyl Ester ◽  
Nmr Assignments ◽  
2D Nmr ◽  
Human Colorectal Cancer ◽  
2D Nmr Spectroscopy ◽  
Acacia Melanoxylon ◽  
Colorectal Cancer Cells ◽  
Human Colorectal Cancer Cells

Invasive species are currently a world menace to the environment, although the study of their chemistry may provide a means for their future beneficial use. From a study of Portuguese Acacia melanoxylon R. Br. five known compounds were isolated: lupeol, 3β-Z-coumaroyl lupeol, 3β-E-coumaroyl lupeol (dioslupecin A), kolavic acid 15-methyl ester and vomifoliol (blumenol A). Their structures were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry, and as a result some corrections are made to their previous 13C NMR assignments. Cytotoxicity of 3β-E-coumaroyl lupeol (dioslupecin A) and kolavic acid 15-methyl ester was evaluated against HCT116 human colorectal cancer cells although biological activity was not evident.

scholarly journals Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa

2015 ◽  
Vol 10 (10) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Manne Sumalatha ◽  
Rachakunta Munikishore ◽  
Aluru Rammohan ◽  
Duvvuru Gunasekar ◽  
Kotha Anil Kumar ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Methanol Extract ◽  
2D Nmr ◽  
Docking Studies ◽  
Selective Inhibitor ◽  
Pueraria Tuberosa ◽  
Nmr Techniques ◽  
Cox 2 ◽  
Plant Sources ◽  
Cox 1

Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.

scholarly journals Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986394
Author(s):  
David Pertuit ◽  
Mpuza Kapundu ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins

Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments in combination with mass spectrometry as 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosylhederagenin.

scholarly journals Lanostane-Type Saponins from Vitaliana primuliflora

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1606 ◽  
Author(s):  
Włodarczyk ◽  
Szumny ◽  
Gleńsk
Keyword(s):  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Resonance Spectroscopy ◽  
Tandem Mass ◽  
Triterpenoid Saponins ◽  
The Family ◽  
Chemotaxonomic Markers ◽  
First Time

The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.

Structural Studies of Chelirubine and Chelilutine Free Bases

1998 ◽  
Vol 63 (7) ◽  
pp. 1045-1055 ◽  
Author(s):  
Jiří Dostál ◽  
Jiří Slavík ◽  
Milan Potáček ◽  
Radek Marek ◽  
Otakar Humpa ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Quantum Chemical ◽  
2D Nmr ◽  
Molecular Symmetry ◽  
Structural Studies ◽  
Free Base ◽  
2D Nmr Spectroscopy ◽  
Sanguinaria Canadensis ◽  
First Time

The structures of chelirubine and chelilutine free bases have been examined by 2D NMR spectroscopy and mass spectrometry. Chelirubine chloride (1a) upon treatment with Na2CO3 yielded free base which possessed the constitution of bis(5,6-dihydrochelirubin-6-yl) ether (2a). The free base of chelilutine (1b) was determined to be bis(5,6-dihydrochelilutin-6-yl) ether (2b). The aqueous NH3 treatment of chelilutine (1b) produced bis(5,6-dihydrochelilutin-6-yl)amine (3b). 6-Hydroxy-5,6-dihydrochelirubine (4a) and 6-hydroxy-5,6-dihydrochelilutine (4b) were detected only in CDCl3 solution by NMR spectroscopy. In CDCl3, the compound 2b underwent hydrolysis to 4b that was immediately followed by the reverse condensation to a diastereomer of 2b. Pseudokinetics of this reaction was followed by NMR spectroscopy and quantum chemical calculations were carried out to support the suggested type of molecular symmetry alteration. The known alkaloid dihydrochelirubine (5) was isolated for the first time from Sanguinaria canadensis.

scholarly journals Triterpenoid Glycosides from Olax imbricata

2019 ◽  
Vol 22 (3) ◽  
pp. 324-334
Author(s):  
Nga Thi Vo ◽  
Suong Thi Minh Huynh ◽  
Huong Thi My Nguyen ◽  
Huy Thuc Duong ◽  
Phung Kim Phi Nguyen
Keyword(s):  
Oleanolic Acid ◽  
Inhibitory Activity ◽  
Methanol Extract ◽  
Colorimetric Method ◽  
2D Nmr ◽  
Pure Compound ◽  
Ic50 Value ◽  
2D Nmr Spectra ◽  
Pure Compounds ◽  
Triterpenoid Glycosides

Introduction: Olax imbricata, owning antibacterial, antioxidant, and anti-inflammatory activities, has been investigated as one of traditional diabetic plants in Vietnam. In our previous publications on Olax imbricata, the structure analysis of the isolated compounds were reported, including two phenolic compounds, three phenolic glycosidic compounds, a sesquiterpenoid tropolone and 1,2,3,4-tetrahydronaphthalene derivatives. This article described the isolation and structure elucidation of three triterpenoid glycosides isolated from the methanol extract of Olax imbricata growing in Phu Yen province. Additionally, the evaluation of inhibitory activity for a-glucosidase was performed on a pure compound. Method: The methanol extract of this plant applied the chromatographic techniques, including thin-layer chromatography and silica gel column chromatography, led to the isolation of three pure compounds. The structures of three isolated compounds were elucidated by the spectroscopic data, including 1D and 2D NMR spectra in a combination of HRESIMS, and the sugar moieties were elucidated by acid hydrolysis. The a-glucosidase inhibitory assay was applied to a pure compound by the colorimetric method. Results: Three triterpenoid glycosides, namely 3-O-a-L-rhamnopyranosyl-(1->4)-b -D-glucopyranosyl-(1->3)-6′- O-ethyl-b -Dglucuronyl oleanolic acid (1), oleanolic acid 28-O-b -D-glucopyranoside (2) and spergulacin (3) were isolated and elucidated. The compound 2 showed its strong potentiala-glucosidase inhibitory activity with the IC50 value of 56.15+/-1.31 mM. Conclusion: Among them, compound 1 is a new one, the compounds 2 and 3 were isolated for the first time from the genus Olax. The compound 2 exhibited the potential a-glucosidase inhibition activity, contributing to demonstrating the diabetes treatment ability of Olax imbricata in the folklore.  

scholarly journals 2-Oxo-2H-chromen-7-yl 4-chlorobenzoate

Molbank ◽  
10.3390/m1279 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1279
Author(s):  
Diana Becerra ◽  
Jaime Portilla ◽  
Juan-Carlos Castillo
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
2D Nmr ◽  
Acylation Reaction ◽  
2D Nmr Spectroscopy ◽  
Slight Excess

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy.

scholarly journals A New Glucuronolactone Glycoside Phoenixoside B from the Seeds of Phoenix Dactylifera

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Sumbul Azmat ◽  
Rehana Ifzal ◽  
Faryal Vali Mohammad ◽  
Viqar Uddin Ahmad ◽  
Aqib Zahoor
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
High Resolution Mass Spectrometry ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Phoenix Dactylifera ◽  
2D Nmr Spectroscopy ◽  
High Resolution Mass ◽  
Resolution Mass

A new glucuronolactone glycoside, phoenixoside B (1), has been isolated from the n-butanol soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as 1-(1-ethyl-β-D-glucosyl)-4,5-diethyl-[α-D-glucofuranourono-6,3-lactone] on the basis of 1D and 2D-NMR spectroscopy and high-resolution mass spectrometry.

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