Identification of C21 Steroidal Glycosides from Gymnema sylvestre (Retz.) and Evaluation of Their Glucose Uptake Activities

Gymnema sylvestre (Retz.) Schult is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of G. sylvestre, a chemical investigation was thus performed. In this research, four new C21 steroidal glycosides sylvepregosides A-D (1–4) were isolated along with four known compounds, gymnepregoside H (5), deacetylkidjoladinin (6), gymnepregoside G (7) and gymnepregoside I (8), from the ethyl acetate fraction of G. sylvestre. The structures of the new compounds were established by extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectroscopy data. Compounds 1–6 promoted glucose uptake by the range of 1.10- to 2.37-fold, respectively. Compound 1 showed the most potent glucose uptake, with 1.37-fold enhancement. Further study showed that compounds 1 and 5 could promote GLUT-4 fusion with the plasma membrane in L6 cells. The result attained in this study indicated that the separation and characterization of these compounds play an important role in the research and development of new anti-diabetic drugs and pharmaceutical industry.

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Chemical Constituents from Roots of Sophora davidii (Franch.) Skeels and Their Glucose Transporter 4 Translocation Activities

Molecules ◽

10.3390/molecules26030756 ◽

2021 ◽

Vol 26 (3) ◽

pp. 756

Author(s):

Kangdi Li ◽

Yuanren Ma ◽

Tongxi Zhou ◽

Xinzhou Yang ◽

Ho-Young Choi

Keyword(s):

Nuclear Magnetic Resonance ◽

Nmr Spectra ◽

Glucose Transporter ◽

Chemical Constituents ◽

Ethyl Acetate Fraction ◽

Spectroscopy Data ◽

Glucose Transporter 4 ◽

Sophora Davidii ◽

New Compounds

Sophora davidii (Franch.) Skeels is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of S. davidii, a chemical investigation was thus performed. In this research, two new stilbene oligomers, Davidiol E–F (1–2), one new 4-aryl-substituted isoflavan Davidinin A (3), and one new 2-arylbenzofuran dimer, Shandougenine C (4), as well as six known compounds (5–10) were obtained from the ethyl acetate fraction of Sophora davidii (Franch.) Skeels. The structures of new compounds were established by extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectroscopy data. The absolute configuration of 1–3 was assigned by comparing its experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1–10 promoted glucose transporter 4 (GLUT-4) translocations by the range of 1.28–2.60 folds, respectively. Compound 9 showed the most potent glucose transporter 4 translocations with 1.60 fold enhancement. The result attained in this study indicated that the separation and characterization of these compounds plays an important role in the research and development of new anti-diabetic drugs and pharmaceutical industry.

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Isolation and Characterization of Two New Antimicrobial Acids from Quercus incana (Bluejack Oak)

BioMed Research International ◽

10.1155/2018/3798105 ◽

2018 ◽

Vol 2018 ◽

pp. 1-5

Author(s):

Rizwana Sarwar ◽

Umar Farooq ◽

Sadia Naz ◽

Nadia Riaz ◽

Syed Majid Bukhari ◽

...

Keyword(s):

Ethyl Acetate Fraction ◽

Structural Formula ◽

2D Nmr ◽

Spectroscopic Technique ◽

Pentanoic Acid ◽

One Dimensional ◽

Isolation And Characterization ◽

Nmr Techniques ◽

New Compounds

Two new compounds [1-2] were purified from ethyl acetate fraction of Quercus incana. The structure of these compounds is mainly established by using advanced spectroscopic technique such as UV, IR, one-dimensional (ID) and two-dimensional (2D) NMR techniques, and EI mass. The structural formula was deduced to be 4-hydroxydecanoic acid [1] and 4-hydroxy-3-(hydroxymethyl) pentanoic acid [2]. Both isolated compounds were tested for their antimicrobial potential and showed promising antifungal activity against Aspergillus niger and Aspergillus flavus.

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Darstellung und Charakterisierung substituierter Phosphinoether und -thioether / Preparation and Characterization of Substituted Phosphinoethers and -thioethers

Zeitschrift für Naturforschung B ◽

10.1515/znb-1995-0202 ◽

1995 ◽

Vol 50 (2) ◽

pp. 168-174 ◽

Cited By ~ 2

Author(s):

Werner Wolfsberger ◽

Wolfgang Burkart ◽

Helmut Werner

Keyword(s):

Pure State ◽

Ring Opening ◽

Nmr Spectra ◽

Ir And Nmr Spectra ◽

Elemental Analyses ◽

Alkyl Ethers ◽

New Compounds ◽

Nucleophilic Ring Opening ◽

Secondary Phosphines

The (diorganophosphinopropyl)alkyl ethers 1-7 are prepared by hydrophosphination of allylalkyl ethers with secondary phosphines. The corresponding thioethers cannot be obtained in a pure state by the same route. The nucleophilic ring opening of thiirane with lithium dialkyl phosphides, followed by the reaction with ClSi(CH3)3 or Cl(CH2)2OCH3 produces the thioethers 8-12 and 16. The silylated thioethers 8, 10 and 12 react with CH3OH/H2O to give the phosphinoethyl thiols 13-15. All new compounds have been identified and characterized by elemental analyses, IR and NMR spectra.

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Characterization of Eucalyptus and Chemically Related Exudates by Nuclear Magnetic Resonance Spectroscopy

Australian Journal of Chemistry ◽

10.1071/ch07163 ◽

2007 ◽

Vol 60 (11) ◽

pp. 862 ◽

Cited By ~ 12

Author(s):

Joseph B. Lambert ◽

Yuyang Wu ◽

Michael A. Kozminski ◽

Jorge A. Santiago-Blay

Keyword(s):

Nuclear Magnetic Resonance ◽

Solid State ◽

1H Nmr Spectroscopy ◽

Nmr Spectra ◽

Flowering Plants ◽

Resonance Spectroscopy ◽

The Family ◽

First Time ◽

Genus Eucalyptus

Exudates from six species of the genus Eucalyptus and one of the genus Corymbia (formerly Eucalyptus), from the family Myrtaceae, have been characterized by solid-state 13C and solution 1H NMR spectroscopy for the first time. Although these eucalypt kinos, as these exudates often are called, resemble resin (terpenoid) and gum (carbohydrate) exudates in physical appearance, their NMR spectra are dramatically different. In addition to lacking the characteristic terpene saturated resonances, they exhibit strong unsaturated resonances, which are weak for resins and absent for gums. We additionally report that exudates from genera of several other families of flowering plants (Amyris, Centrolobium, Guaiacum, Liquidambar, and Prosopis) also exhibit part or all of this kino spectroscopic signature.

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Synthesis and Characterization of Some New Benzodiazepinium Salt Derivatives under microwave Irradiation

Baghdad Science Journal ◽

10.21123/bsj.12.4.753-760 ◽

2015 ◽

Vol 12 (4) ◽

pp. 753-760

Author(s):

Baghdad Science Journal

Keyword(s):

Reaction Mechanism ◽

Microwave Irradiation ◽

Benzoic Acid ◽

Nmr Spectra ◽

Synthesis And Characterization ◽

Benzoic Acid Derivatives ◽

Unexpected Reaction ◽

Ft Ir ◽

New Compounds

An attempt to synthesize the benzoimidazol derivatives from the reaction of o-phenylenediamine and benzoic acid derivatives in the presence of ethanol and various ketones under microwave irradiation, 1 , 5 - benzodiazepinum salt derivatives were obtained instead of them. Unexpected reaction was happened for synthesis a new series of benzodiazepinium salt derivatives in a selective yield . The reaction mechanism was also discussed. The new compounds were purified and identified their structures were elucidated using various physical techniques like; FT- IR spectra, micro elemental analysis (C.H.N) and 1H NMR spectra.

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Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

Natural Products and Bioprospecting ◽

10.1007/s13659-019-00227-y ◽

2019 ◽

Vol 9 (6) ◽

pp. 419-423 ◽

Cited By ~ 2

Author(s):

Jun Wang ◽

Xian-Hua Meng ◽

Tian Chai ◽

Jun-Li Yang ◽

Yan-Ping Shi

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Nmr Spectra ◽

Mass Spectrometry Analysis ◽

Diterpenoid Alkaloids ◽

Spectrometry Analysis ◽

Chemical Structures ◽

Lignan Glycoside ◽

New Compounds

Abstract Diterpenoid alkaloids have neroprotective activity. Herein, three napelline-type diterpenoid alkaloids 1–3, two aconitine-type diterpenoid alkaloids 4–5, and one isoquinline-type alkaloid 6, as well as one lignan glycoside 7, have been isolated from the roots of Aconitum pendulum Busch. Compounds 1 and 7 were new compounds, and their chemical structures were determined on the basis of nuclear magnetic resonance (NMR) spectra and mass spectrometry analysis. A ThT assay revealed that compound 2 showed significant disaggregation potency on the Aβ1−42 aggregates. Graphical Abstract

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Cytotoxic and Anti-Inflammatory Effects of Ent-Kaurane Derivatives Isolated from the Alpine Plant Sideritis hyssopifolia

Molecules ◽

10.3390/molecules25030589 ◽

2020 ◽

Vol 25 (3) ◽

pp. 589 ◽

Cited By ~ 1

Author(s):

Axelle Aimond ◽

Kevin Calabro ◽

Coralie Audoin ◽

Elodie Olivier ◽

Mélody Dutot ◽

...

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Structural Characterization ◽

Microbial Activities ◽

Alpine Plant ◽

Planar Structures ◽

Anti Inflammatory ◽

New Compounds

This paper reports the isolation and structural characterization of four new ent-kaurane derivatives from the Lamiaceae plant Sideritis hyssopifolia. Planar structures and relative configurations were determined using both mass spectrometry and nuclear magnetic resonance (1D and 2D). Absolute configurations were determined by comparing experimental and theoretical electronic circular dichroism spectra. The cytotoxic and microbial activities of all new compounds were tested. Compounds that were non-cytotoxic were further evaluated for anti-inflammatory activity.

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Darstellung und Charakterisierung einiger ω -Cyanalkyldiorganophosphane Preparation and Characterization of Some ω - Cyanoalkyldiorgano Phosphines

Zeitschrift für Naturforschung B ◽

10.1515/znb-1992-0201 ◽

1992 ◽

Vol 47 (2) ◽

pp. 155-161 ◽

Cited By ~ 7

Author(s):

Werner Wolfsberger ◽

Wolfgang Burkart ◽

Helmut Werner

Keyword(s):

Nmr Spectra ◽

Ir And Nmr Spectra ◽

Elemental Analyses ◽

New Compounds ◽

Secondary Phosphines

Several routes for the preparation of ω-cyanoalkyldiorgano phosphines RR′P (CH2)nCHR″CN (R = CH3, C2H5, C3H7, i-C3H7, C4H9, i-C4H9, t -C4H9, C5H11, c-C5H9, c-C6H11 ; R′ = i-C3H7, t-C4H9, C6H5; R″ = H, Si(CH3)3; n = 1, 2, 3, 4) have been investigated: (1) reaction of lithium diorganophosphides with ω-chloroalkylnitriles, (2) quaternization of secondary phosphines with co-haloalkylnitriles followed by deprotonation of the resulting H -phosphonium halides with aqueous bases, (3) hydrophosphination of secondary phosphines with unsaturated nitriles, (4) reaction of trimethylsilyl phosphines with (y-chloroalkylnitriles followed by Me3SiCl-elimination, and (5) addition of acrylonitrile to trimethylsilyl phosphines. The reaction of 3-chloropropionitrile with trimethylsilyl phosphines leads to the formation of a mixture of the expected phosphine and the corresponding β-silylated derivative. A mechanistic interpretation of the last reaction is given. All new compounds were characterized by elemental analyses, IR and NMR spectra.

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