scholarly journals (6R,9S)-6″-(4″-Hydroxybenzoyl)-Roseoside, a New Megastigmane Derivative from Ouratea polyantha and its Effect on Hepatic Glucose-6-phosphatase

2012 ◽  
Vol 7 (8) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Jairo Bermúdez ◽  
María Rodríguez ◽  
Masahisa Hasegawa ◽  
Freddy González-Mujica ◽  
Sandra Duque ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Column Chromatography ◽  
High Speed ◽  
Inhibitory Effect ◽  
Countercurrent Chromatography ◽  
Analytical Column ◽  
H Nmr ◽  
Hepatic Glucose ◽  
Counter Current ◽  
C Nmr

A new megastigmane derivative, (6 R,9 S)–6′-(4″-hydroxybenzoyl)-roseoside (1) and two known compounds, the biflavoneagathisflavone (2) and 4-hydroxy-benzoic acid (3) were isolated and purified from leaves and stems of Ouratea polyantha Engl. Agathisflavone was isolated in a single high-speed counter-current chromatography run, while the megastigmane was purified in two steps, by using a combination of high-speed countercurrent chromatography and analytical column chromatography. All structures were elucidated on the basis of spectral evidence and comparison with literature data. Compound 1 was characterized by [α]D20, UV-Vis, IR, MS, 1H NMR, 13C NMR, HMQC, HMBC, COSY and NOESY. Compounds 1 and 2 showed an inhibitory effect of 63.6 and 13.7% on the G-6-Pase intact microsomes, respectively.

scholarly journals Preparative Separation of Four Major Bufadienolides from the Chinese Traditional Medicine, Chansu, Using High-Speed Counter-Current Chromatography

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Xiu Lan Xin ◽  
Junying Liu ◽  
Xiao Chi Ma ◽  
Qing Wei ◽  
Li Lv ◽  
...  
Keyword(s):  
High Speed ◽  
Solvent System ◽  
Two Phase ◽  
Isolation And Purification ◽  
H Nmr ◽  
Chemical Structures ◽  
One Step ◽  
Counter Current ◽  
Chloroform Methanol ◽  
C Nmr

A preparative, high-speed, counter-current chromatographic (HSCCC) method for the isolation and purification of bufadienolides from Chansu was successfully developed by using stepwise elution with a two-phase solvent system composed of n-hexane: chloroform: methanol: water (4:1:2.5:5 and 4:1:4:5, v/v). A total of 7.5 mg of cinobufotalin (1), 8.0 mg of bufalin (2), 14.0 mg of cinobufagin (3) and 9.5 mg of resibufogenin (4) were obtained in a one-step separation from 80 mg of the crude extract with purities of 93.2%, 98.7%, 99.2%, and 99.4%, respectively. The chemical structures were determined from 1H NMR and 13C NMR spectroscopic data.

Cardenolide aus Ornithogalum nutans (2 n = 28), 1. Mitteilung / Cardenolides from Ornithogalum nutans (2 n = 28), Part

1992 ◽  
Vol 47 (10) ◽  
pp. 1444-1458 ◽  
Author(s):  
Roland Ferth ◽  
Andreas Baumann ◽  
Wolfgang Robien ◽  
Brigitte Kopp
Keyword(s):  
Acid Hydrolysis ◽  
Column Chromatography ◽  
Structure Elucidation ◽  
European Species ◽  
H Nmr ◽  
First Time ◽  
Hydrolysis Of ◽  
C Nmr

From leaves and bulbs of Ornithogalum nutans L. (2 n = 28), seventeen cardenolides were isolated by column chromatography, DCCC and TLC. The structure elucidation was performed by means of 1H NMR, 13C NMR, HH-Cosy, HC-Cosy and FAB-MS studies and identification of the sugar moieties by GLC after acid hydrolysis of the cardenolides. Sugar compounds were identified as digitoxose, 3-acetyl-digitoxose, 2-deoxy-allose, 6-deoxy-allose, rhamnose, xylose and apiose. Glycosides of 7β,15β, 16 α-trihydroxy-uzarigenin, 8β,16 α-dihy-droxy, 15-oxo-uzarigenin, 3 β, 11β-dihydroxy, 12-oxo, 18-nor-5 α-card-13-enolid, 11 α-hydroxygitoxigenin, 12-oxo,8, 14β-epoxy-uzarigenin, 8β-hydroxy, 15-oxo-uzarigenin and 12β-hydroxy-oleandrigenin are described for the first time, the presence of oleandrigenin-glycosides in the genus Ornithogalum was not known until now. Ornithogalum nutans L. shows a different cardenolide pattern from the second European species of the section Myogalum (LINK) PETERM. - Ornithogalum boucheanum (KUNTH) ASCHERS.

scholarly journals Design, Synthesis and Antibacterial Activity of Novel Pyrimidine-Containing 4H-Chromen-4-one Derivatives

2020 ◽  
Author(s):  
Shijun Su ◽  
Mei Chen ◽  
Xuemei Tang ◽  
Feng Peng ◽  
Tingting Liu ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Inhibitory Effect ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
H Nmr ◽  
Half Maximal Effective Concentration ◽  
Bacterial Cell Membrane ◽  
Better Than ◽  
C Nmr

Abstract A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. All compounds were characterized using 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary biological activity results showed that most of title compounds displayed significant inhibitory activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). In particular, compound 4c demonstrated a good inhibitory effect against Xac and Xoo, with half-maximal effective concentration(EC50) values of 15.5 and 14.9 μg/mL respectively, and that of compound 4h showed the best antibacterial activity against Rs with an EC50 value of 14.7 μg/mL, These results were better than both bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative(42.4%) and protective (49.2%) activities for reducing rice bacterial leaf blight than both BT (35.2, 39.1%) and TC (30.8, 27.3%). The mechanism of compound 4c against Xoo was analysed through scanning electron microscopy (SEM). Results showed that the compound destroied the bacterial cell membrane structure. These results indicated that pyrimidine-containing 4H-chromen-4-one derivatives are valuable in the research of new agrochemicals.

scholarly journals The isolation of (6S, 9S)-cyclo (prolylvalyl) from marine actinomycete, by use of high speed contercurrent chromatography

2002 ◽  
Vol 67 (1) ◽  
pp. 27-30
Author(s):  
Andrija Smelcerovic ◽  
Mirko Schiebel ◽  
Sinisa Djordjevic
Keyword(s):  
Silica Gel ◽  
Column Chromatography ◽  
High Speed ◽  
Countercurrent Chromatography ◽  
Marine Research ◽  
Gel Fraction ◽  
Marine Actinomycete

The marine actinomycete B 1758 came from the actinomycete collection of the Alfred Wegener Institute for Polar and Marine Research in Bremerhafen Germany. 1.079 g of raw extract was obtained by fermentation. Seven fractions were separated by column chromatography on silica gel. Fraction 4 was separated by high speed countercurrent chromatography. Fraction 4.6 yielded 5.2 mg of (6S, 9S)-cyclo(prolylvalyl).

Reaction of 3,5-dicyano-2,4,4,6-tetramethyl-1,4-dihydropyridine with nitric acid

1984 ◽  
Vol 49 (11) ◽  
pp. 2620-2627 ◽  
Author(s):  
Antonín Kurfürst ◽  
Josef Kuthan
Keyword(s):  
Nitric Acid ◽  
Column Chromatography ◽  
Title Compound ◽  
Mass Spectra ◽  
Probable Mechanism ◽  
Mechanism Of Formation ◽  
H Nmr ◽  
C Nmr

Reaction of the title compound I with nitric acid in acetic afforded a mixture of products which on column chromatography afforded 5-cyano-4,4,6-trimethyl-2-nitromethylene-3-oxo-1,2,3,4-tetrahydropyridine (II), (Z)-5-(1-acetoxy-2-nitrovinyl)-3,5-dicyano-4,4-dimethyl-2-pyrazoline (III) and 3-acetoxy-3-cyano-4,4,6-trimethyl-5-oxo-2,3,4,5-tetrahydropyridazine (IV). Reaction of I with nitrating mixture in chloroform gave only the compound II. The probable mechanism of formation of compounds II, III and IV, together with their 1H NMR, 13C NMR, IR and mass spectra, is discussed.

Progesterone Hydroxylation with Colletotrichum Lini AS3. 4486

2011 ◽  
Vol 343-344 ◽  
pp. 1070-1073 ◽  
Author(s):  
Yan Jun Shen ◽  
Hua Sun ◽  
Yu Wan Fu ◽  
Chu Yang Xu ◽  
Min Wang
Keyword(s):  
Silica Gel ◽  
Column Chromatography ◽  
Broth Culture ◽  
H Nmr ◽  
Culture Supernatants ◽  
C Nmr

The biotransformation of progesterone by Colletotrichum lini AS3. 4486 was studied. The formation of the product was monitored by HPLC. Product was purified from broth culture supernatants by silica gel column chromatography and identified as 7β,12β-dihydoxylprogesterone with MS, 1H NMR, 13C NMR and NOE.

scholarly journals An integrated 2H and 13C NMR study of gluconeogenesis and TCA cycle flux in humans

2001 ◽  
Vol 281 (4) ◽  
pp. E848-E856 ◽  
Author(s):  
John G. Jones ◽  
Michael A. Solomon ◽  
Suzanne M. Cole ◽  
A. Dean Sherry ◽  
Craig R. Malloy
Keyword(s):  
Hepatic Glucose Production ◽  
Glucose Production ◽  
Tca Cycle ◽  
H Nmr ◽  
Nmr Study ◽  
Hepatic Glucose ◽  
Glucose Synthesis ◽  
Acetaminophen Glucuronide ◽  
Pep Carboxykinase ◽  
C Nmr

Hepatic glucose synthesis from glycogen, glycerol, and the tricarboxylic acid (TCA) cycle was measured in five overnight-fasted subjects by 1H,2H, and 13C NMR analysis of blood glucose, urinary acetaminophen glucuronide, and urinary phenylacetylglutamine after administration of [1,6-13C2]glucose,2H2O, and [U-13C3]propionate. This combination of tracers allows three separate elements of hepatic glucose production (GP) to be probed simultaneously in a single study: 1) endogenous GP, 2) the contribution of glycogen, phospho enolpyruvate (PEP), and glycerol to GP, and 3) flux through PEP carboxykinase, pyruvate recycling, and the TCA cycle. Isotope-dilution measurements of [1,6-13C2] glucose by 1H and 13C NMR indicated that GP in 16-h-fasted humans was 10.7 ± 0.9 μmol · kg−1 · min−1.2H NMR spectra of monoacetone glucose (derived from plasma glucose) provided the relative 2H enrichment at glucose H-2, H-5, and H-6 S, which, in turn, reflects the contribution of glycogen, PEP, and glycerol to total GP (5.5 ± 0.7, 4.8 ± 1.0, and 0.4 ± 0.3 μmol · kg−1 · min−1, respectively). Interestingly, 13C NMR isotopomer analysis of phenylacetylglutamine and acetaminophen glucuronide reported different values for PEP carboxykinase flux (68.8 ± 9.8 vs. 37.5 ± 7.9 μmol · kg−1 · min−1), PEP recycling flux (59.1 ± 9.8 vs. 27.8 ± 6.8 μmol · kg−1 · min−1), and TCA cycle flux (10.9 ± 1.4 vs. 5.4 ± 1.4 μmol · kg−1 · min−1). These differences may reflect zonation of propionate metabolism in the liver.

Preparative Separation and Purification of Lancifodilactone C from Schisandra Chinensis (Turcz.) Baill by High-Speed Counter-Current Chromatography

2013 ◽  
Vol 634-638 ◽  
pp. 1502-1505
Author(s):  
Bin Li ◽  
Xian Jun Meng ◽  
Li Jie Zhu ◽  
Xin Yao Jiao
Keyword(s):  
High Speed ◽  
Solvent System ◽  
Butyl Alcohol ◽  
Structure Identification ◽  
Schisandra Chinensis ◽  
Preparative Separation ◽  
Separation And Purification ◽  
Two Phase ◽  
H Nmr ◽  
Counter Current

High-speed counter-current chromatography (HSCCC) was successfully applied to the preparative separation and purification of lancifodilactone C from the crude extracts of Schisandra chinensis (Turcz.) Baill. Following an initial cleaning-up step on the AB-8 macroporous resin, a preparative high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of Chloroform- n-Butyl alcohol- methanol -water(10:0.5:8:4，v/v) was used to isolate and separate lancifodilactone C from Schisandra Chinensis(Turcz.) Baill. A total of 101 mg lancifodilactone C with purities of 98.2% were obtained from 1000 mg crude extract in one-step elution and less than 1 h, and the structure identification was performed by UV, IR, MS,1H NMR and13C NMR.

scholarly journals Silver Ion-Complexation High-Speed Countercurrent Chromatography Coupled with Prep-HPLC for Separation of Sesquiterpenoids from Germacrene A Fermentation Broth

Fermentation ◽  
2021 ◽  
Vol 7 (4) ◽  
pp. 230
Author(s):  
Huanzhu Zhao ◽  
Xiangyun Song ◽  
Iftikhar Ali ◽  
Manzoor Hussain ◽  
Andleeb Mehmood ◽  
...  
Keyword(s):  
Metal Ion ◽  
High Speed ◽  
Fermentation Broth ◽  
Solvent System ◽  
Silver Ion ◽  
Preparative Hplc ◽  
Countercurrent Chromatography ◽  
Geometrical Isomers ◽  
Crude Sample ◽  
Counter Current

A silver ion high-speed counter-current chromatography ([Ag+]-HSCCC) was developed to separate and purify five sesquiterpenoids from germacrene A fermentation broth. The solvent system was consisted of n-hexane-methanol-silver nitrate (3 mol/L) solution (10:9.5:0.5, v/v). By employing this chromatographic protocol, five sesquiterpenoids named β-elemene (1; 54.1 mg), germacrene A (2; 28.5 mg), γ-selinene (3; 4.6 mg), β-selinene (4; 3.4 mg), and α-selinene (5; 1.3 mg) were obtained successfully from 500 mg extracted crude sample with purities of 97.1%, 95.2%, 98.2%, 96.3% and 98.5%, respectively, combined with preparative HPLC. The results reveal that the addition of metal ion in biphasic solvent system significantly improved the HSCCC separation factor of sesquiterpenoids. Meanwhile, our study also provided an alternate approach to separate the compounds with less polarity, also geometrical isomers and various natural product classes.

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