Structure of Tyrolobibenzyl D and Biological Activity of Tyrolobibenzyls from Scorzonera humilis

2002 ◽  
Vol 57 (7-8) ◽  
pp. 614-619 ◽  
Author(s):  
Christian Zidorn ◽  
Renate Spitaler ◽  
Ernst-P. Ellmerer-Müller ◽  
Nigel B. Perry ◽  
Clarissa Gerhäuser ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Bacillus Subtilis ◽  
Biological Activity ◽  
Biological Activities ◽  
Trichophyton Mentagrophytes ◽  
2D Nmr ◽  
Bacterial Activity ◽  
2D Nmr Spectroscopy ◽  
Chemopreventive Activity ◽  
Derivatives Of

A novel tyrolobibenzyl derivative, 1→6-β-ᴅ-apiosyl-β-ᴅ-glucopyranosyl 4-[2-(4-hydroxyphenyl) ethyl]benzofuran-2-carboxylate 3 (tyrolobibenzyl D) was isolated from Scorzonera humilis L. and its structure established by mass spectrometry and 1D- and 2D-NMR spectroscopy. The biological activities of the new compound and related tyrolobibenzyls A-C (1-2, 4) and the semi-synthetic peracetyl derivatives of tyrolobibenzyls B (2a) and C (4a) were assessed. The results revealed no cytotoxic activity against P388 cells and neither anti-bacterial activity against Bacillus subtilis nor antifungal activity against Candida albicans and Trichophyton mentagrophytes for any of the investigated compounds. An evaluation of potential chemopreventive activity of 2, 2a, 4, and 4a also revealed no pronounced activity in any of the employed assaying systems.

scholarly journals Fruits of Rosa brunonii – A Source of Antioxidant Phenolic Compounds

2017 ◽  
Vol 12 (11) ◽  
pp. 1934578X1701201
Author(s):  
Muhammad Ishaque ◽  
Yamin BiBi ◽  
Karin M. Valant–Vetschera ◽  
Johann Schinnerl ◽  
Markus Bacher
Keyword(s):  
Mass Spectrometry ◽  
Phenolic Compounds ◽  
Biological Activities ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Flavonol Glycosides ◽  
Northern Pakistan ◽  
Dpph Assay ◽  
2D Nmr Spectroscopy ◽  
Kaempferol Glycosides

Phytochemical examination of matured fruits of Rosa brunonii collected in Northern Pakistan led to the isolation of three flavonol glycosides quercetin-3- O-rhamnoside (1), and the kaempferol glycosides astragalin (2) and tiliroside (3). Their structures were elucidated by 1D– and 2D–NMR spectroscopy and mass spectrometry. Radical scavenging activities of the crude extract and isolated compounds were assessed by a DPPH assay. The results show strong antioxidative activities of tiliroside (3) and lower activities of astragalin (2) and quercetin-3- O-rhamnoside (1). These data confirm previous reports and underline the biological activities of flavonol glycosides.

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.

Identification of promising objects for the synthesis of thiosulphonate derivatives of benzoquinone and hydroquinone

2021 ◽  
Vol 4 (2) ◽  
pp. 47-53
Author(s):  
N. Y. Monka ◽  
◽  
N. E. Stadnytska ◽  
I. R. Buchkevych ◽  
K. O. Kaplia ◽  
...  
Keyword(s):  
Biological Activity ◽  
Biological Activities ◽  
Experimental Studies ◽  
New Drugs ◽  
Reduced Form ◽  
Free Form ◽  
Wide Range ◽  
On Line ◽  
Living Organisms ◽  
Derivatives Of

Benzoquinone and its reduced form hydroquinone belong to phenolic compounds and are found in living organisms in free form or in glycosides. They are active substances of some medicinal plants and have a pharmacological effect on the human body. Accordingly, their derivatives are important objects for chemical synthesis and development of new drugs. This article presents the findings of the structural design of substances with benzoquinone or hydroquinone fragment and sulfur-containing compound. By use of appropriate on-line programs a predictive screening of the biological activity and cytotoxicity of thiosulfonate derivatives of benzoquinone and hydroquinone has been conducted. It has been found that they have immense methodological potential to be synthesized by substances with a wide range of biological activities and a high value of probable activity, which substantiates the feasibility of conducting experimental studies on their biological activity, particularly anticancer.

scholarly journals Insight into the Presence of Stilbenes in Medicinal Plants Traditionally Used in Croatian Folk Medicine

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Ivana Generalić Mekinić ◽  
Danijela Skroza ◽  
Ivica Ljubenkov ◽  
Višnja Katalinić
Keyword(s):  
Biological Activity ◽  
Medicinal Plants ◽  
Biological Activities ◽  
Folk Medicine ◽  
Free Form ◽  
Naturally Occurring ◽  
Derivatives Of ◽  
Insight Into ◽  
Phenolic Extracts

Over the last years, great interest has arisen concerning plant stilbenes, especially resveratrol, which has a whole spectrum of positive biological activities. In this study, we investigated the presence of resveratrol monomers (trans- and cis- form) and naturally occurring derivatives of fraas-resveratrol (piceid, astringin and isorhapontin) in phenolic extracts of twenty medicinal plants traditionally used in Croatian folk medicine. The investigated compounds were present in the samples, in free form or as glucosides, and the highest share was found in immortelle, common yarrow and Lamiaceae plants. The obtained results indicate that biological activity of selected medicinal plants can be related to the presence of this valuable group of phytochemicals.

scholarly journals Pregnane Glycosides

2006 ◽  
Vol 1 (8) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Nilendu Panda ◽  
Sukdeb Banerjee ◽  
Nirup B. Mandal ◽  
Niranjan P. Sahu
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Data Structures ◽  
Biological Activities ◽  
2D Nmr ◽  
Tandem Mass ◽  
Isolation And Purification ◽  
Chromatographic Techniques ◽  
Recent Developments

Pregnane glycosides constitute a class of compounds widely distributed in the plant kingdom. Many of them have shown either anticarcinogenic or cancer inhibitory properties, besides other useful biological activities. New chromatographic techniques and advances in spectroscopic and spectrometric methods have accelerated the purification and structure determination of novel glycosides of this series. A compilation of the pregnane glycosides isolated from 1995 until the middle of 2005, along with their physical data, structures and occurrence are presented in this review, which also summarizes, with suitable examples, recent developments in isolation and purification techniques, and structural elucidation using modern spectrometric methods like ESIMS and tandem mass spectrometry, and 2D NMR spectroscopic strategies. The reported anticancer and other biological activities of pregnane glycosides are also discussed.

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 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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