scholarly journals Spirostane-type Saponins from Dracaena fragrans « Yellow Coast »

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Abdelmalek Rezgui ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
Marie-Aleth Lacaille-Dubois
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Steroidal Glycosides ◽  
Nmr Data ◽  
First Time

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

Two new taxane-glycosides from the needles of Taxus canadensis

2015 ◽  
Vol 70 (11) ◽  
pp. 829-835 ◽  
Author(s):  
Nan Li ◽  
Jin Wang ◽  
Hui-Min Yan ◽  
Man-li Zhang ◽  
Qing-Wen Shi ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Data Analysis ◽  
High Resolution ◽  
Fast Atom Bombardment ◽  
2D Nmr ◽  
Taxus Canadensis ◽  
Nmr Data ◽  
First Time

AbstractTwo minor taxane glycosides were isolated for the first time from the needles of Taxus canadensis. Their structures were characterized as 2α,5α-diacetoxy-10β-(6′-O-acetyl-β-d-glucopyranosyl)oxy-14β-[(2′R,3′S)-3′-hydroxy-2′-methylbutanoyl]oxytaxa-4(20),11-diene (1) and 2α,14β-diacetoxy-10β-(β-d-glucopyranosyl)oxytaxa-4(20),11-dien-5β-ol (2) on the basis of 1D and 2D NMR data analysis and confirmed by high-resolution fast atom bombardment mass spectrometry.

scholarly journals A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL Anthelia sp.

2013 ◽  
Vol 13 (3) ◽  
pp. 216-220 ◽  
Author(s):  
Anggia Murni ◽  
Novriyandi Hanif ◽  
Junichi Tanaka
Keyword(s):  
Mass Spectrometry ◽  
Drug Development ◽  
Ethyl Acetate ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Cancer Drug ◽  
Nmr Data ◽  
Anti Cancer

One new dolabellane (1) and two known diterpenoids stolonidiol (2) and clavinflol B (3) have been isolated from the ethyl acetate extract of the Indonesian soft coral Anthelia sp. A new compound 1 exhibited a moderate cytotoxicity against NBT-T2 cells at 10 µg/mL, while known compounds 2 and 3 showed cytotoxicity at 1 and 0.5 µg/mL, respectively. Structure of the new compound 1 was elucidated by interpretation of NMR spectroscopic data (1D and 2D NMR data) and mass spectrometry (ESIMS data) as well as comparison with those of related ones. This finding should be useful for anti cancer drug development of the promising dolabellane-types compound.

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.

Synthesis of metal-free tetraazaisobacteriochlorin and via template condensation of phthalogenes

2020 ◽  
Vol 24 (05n07) ◽  
pp. 878-886
Author(s):  
Semyon V. Dudkin ◽  
Takahiro Kawata ◽  
Svetlana A. Belova ◽  
Yusuke Okada ◽  
Nagao Kobayashi
Keyword(s):  
Mass Spectrometry ◽  
Quantum Chemical ◽  
2D Nmr ◽  
Metal Free ◽  
Tert Butyl ◽  
H Nmr ◽  
Nmr Data ◽  
Template Condensation ◽  
Td Dft ◽  
Low Symmetry

The indium(III) complexes of (4-(tert-butyl)phenyl)-substituted tetraazaisobacteriochlorin (TAiBC) and tetraazachlorin (TAC) were synthesized by direct template condensation of bis(4-(tert-butyl)phenyl)fumaronitrile and tetramethylsuccinonitrile using indium(III) ion as a matrix. The corresponding metal-free tetraazaisobacteriochlorin and tetraazachlorin were obtained by demetallation of their indium(III) complexes. These metal-free complexes were characterized using elemental analysis, mass-spectrometry, 1H and [Formula: see text]C{1H}NMR spectroscopy, UV-vis and MCD spectroscopy as well as DFT and TD-DFT calculations. Due to the low symmetry of the molecules, the NMR data were complex, but could be assigned by collecting 1D- and 2D NMR data and comparing with the results of quantum chemical calculations. From the position of the pyrrole proton signal (6.78 ppm), it was found that the diatropic current of TAiBC is much weaker than that of TAC, and plausibly the weakest among porphyrinoids so far reported. Absorption and MCD spectra were reasonably interpreted using the calculated absorption spectra.

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 Steroidal Glycosides from Veronica chamaedrys L. Part I. The Structures of Chamaedrosides C, C1, C2, E, E1 and E2

2012 ◽  
Vol 7 (5) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Alexandra Marchenko ◽  
Pavel Kintya ◽  
Bozena Wyrzykiewicz ◽  
Elena Gorincioi
Keyword(s):  
2D Nmr ◽  
Spectroscopic Methods ◽  
Steroidal Glycosides ◽  
Ms Analysis ◽  
The Given ◽  
First Time ◽  
Chemical Evidence

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time.

scholarly journals A Deeper Investigation of Drug Degradation Mixtures Using a Combination of MS and NMR Data: Application to Indapamide

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1764 ◽  
Author(s):  
Cécile Palaric ◽  
Roland Molinié ◽  
Dominique Cailleu ◽  
Jean-Xavier Fontaine ◽  
David Mathiron ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Degradation Products ◽  
Multivariable Analysis ◽  
Active Pharmaceutical Ingredient ◽  
2D Nmr ◽  
Forced Degradation ◽  
Drug Degradation ◽  
Uniform Sampling ◽  
Nmr Data ◽  
Data Application

A global approach that is based on a combination of mass spectrometry (MS) and nuclear magnetic resonance (NMR) data has been developed for a complete and rapid understanding of drug degradation mixtures. We proposed a workflow based on a sample preparation protocol that is compatible to MS and NMR, the selection of the most appropriate experiments for each technique, and the implementation of prediction software and multivariable analysis method for a better interpretation and correlation of MS and NMR spectra. We have demonstrated the efficient quantification of the remaining active pharmaceutical ingredient (API). The unambiguous characterization of degradation products (DPs) was reached while using the potential of ion mobility-mass spectrometry (IM-MS) for fragment ions filtering (HDMSE) and the implementation of two-dimensional (2D) NMR experiments with the non-uniform sampling (NUS) method. We have demonstrated the potential of quantitative NMR (qNMR) for the estimation of low level DPs. Finally, in order to simultaneously monitor multi-samples, the contribution of partial least squares (PLS) regression was evaluated. Our methodology was tested on three indapamide forced degradation conditions (acidic, basic, and oxidative) and it could be easily transposed in the drug development field to assist in the interpretation of complex mixtures (stability studies, impurities profiling, and biotransformation screening).

scholarly journals Oleanane-type Triterpene Glycosides from Glycyrrhiza Uralensis

2007 ◽  
Vol 2 (3) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Jinwei Li-Yang ◽  
Jun-ichiro Nakajima ◽  
Nobuhito Kimura ◽  
Kazuki Saito ◽  
Shujiro Seo
Keyword(s):  
Natural Products ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Mass Spectrometric ◽  
Triterpene Glycosides ◽  
Glycyrrhiza Uralensis ◽  
Nmr Data ◽  
Nmr Methods ◽  
First Time ◽  
C Nmr

Chemical investigation of the roots of Glycyrrhiza uralensis resulted in the isolation of six oleanane-type triterpene glycosides (1 – 6), including one new saponin (1) and two (2 and 3) obtained as natural products for the first time. The new licorice saponin (1) was identified as 22β–acetoxylglycyrrhizin from [α]D, mass spectrometric, and UV, IR, and NMR spectroscopic data.. Full assignments of 1H and 13C-NMR data for compounds 2, 3, 4, 5 and 6 were made for the first time according to 2D NMR methods.

scholarly journals PHENOLIC COMPOUNDS FROM STEM OF BOERHAVIA ERECTA L. GROWING IN VIETNAM

2011 ◽  
Vol 14 (2) ◽  
pp. 58-65
Author(s):  
Lien Thi My Do ◽  
Dung Thi My Nguyen ◽  
Phung Kim Phi Nguyen
Keyword(s):  
Breast Cancer ◽  
Breast Cancer Resistance Protein ◽  
2D Nmr ◽  
Hepatoprotective Activity ◽  
Cancer Resistance ◽  
New Class ◽  
Nmr Data ◽  
Medicinal Properties ◽  
Resistance Protein ◽  
First Time

Plants of Boerhavia genus (Nyctaginaceae family) are known to have medicinal properties as antidiabetic, immunomodulatory effect, anticonvulsant, antistress, adaptogenic, hepatoprotective activity. Rotenoids in plants of this genus are reported as a new class of potent breast cancer resistance protein inhibitors.[5] Boerhavia erecta L. was used in traditional African medicine but there are still no scientific research in Vietnam where it is widely grown. In this paper, we report the isolation of four compounds: 2,6-dimethoxybenzoquinone (1), (+)-catechin (2), isorhamnetin 3-O-β- D-glucopyranoside (3) and rutin (4). The structure of these compounds were determined through the interpretation of their MS and 1D, 2D-NMR data. This is the first time that these compounds are isolated from Boerhavia erecta L.

Isolation, Structure Elucidation and Activity of Anthracycline Acetates from a Terrestrial Streptomyces sp.

2003 ◽  
Vol 58 (12) ◽  
pp. 1242-1246 ◽  
Author(s):  
Serge Fotso ◽  
Rajendra P. Maskey ◽  
Iris Grün-Wollny ◽  
Hartmut Laatsch
Keyword(s):  
Molecular Weight ◽  
Natural Product ◽  
Structure Elucidation ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Streptomyces Sp ◽  
Naturally Occurring ◽  
Nmr Data ◽  
New Antibiotics ◽  
First Time

The red coloured ethyl acetate extract of the Streptomyces sp. isolate GW37/3236 delivered the two new antibiotics 13-O-acetyl-bisanhydro-13-dihydrodaunomycinone (3c) and 4,13-O-diacetylbisanhydro- 4-O-demethyl-13-dihydrodaunomycinone (3d) and additionally several known compounds. The quinones 3c and 3d are the first naturally occurring quinone acetates. Their structures were derived by comparison of the NMR data with those of bisanhydro-13-dihydrodaunomycinone (3b) and by interpretation of the 2D NMR data accompanied by the molecular weight and formula. 2-Acetamido-3-hydroxybenzamide (5) was also isolated from the extract and was identified by comparison of the NMR data with those of 2-acetamidobenzamide and by 2D NMR correlations. 6,9,11- Trihydroxy-4-methoxy-5,12-naphthacenedione (4) is isolated for the first time as a natural product.

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