scholarly journals Isolation of Pyranocoumarins from Angelica Gigas

2008 ◽  
Vol 3 (5) ◽  
pp. 1934578X0800300
Author(s):  
V.L. Niranjan Reddy ◽  
Atul N. Jadhav ◽  
Bharathi Avula ◽  
Ikhlas A. Khan
Keyword(s):  
Acid Hydrolysis ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Preparative Hplc ◽  
Racemic Compound ◽  
Angelica Gigas ◽  
Nmr Data ◽  
Hydrolysis Products ◽  
Decursinol Angelate ◽  
Coumarin Glycoside

A mixture of diastereomers of the coumarin glycoside 3′- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (1), along with six known pyranocoumarins, columbianoside (4), marmesin (5), 3′-hydroxy-3′,4′-dihydroxanthyletin (6), decursin (7), decursinol angelate (8), and isoimperatorin (9), were isolated from the roots of Angelica gigas Nakai. The racemic compound 1 was successfully separated by preparative HPLC to obtain a new isomer 3′( S)- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (2), and a known isomer 3′( R)- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (3). The absolute configuration of compounds 2 and 3 was determined by comparison of optical rotation and NMR data of their acid hydrolysis products.

scholarly journals New dibenzocyclooctadiene lignan from Schisandra chinensis (Turcz.) Baill. fruits

2021 ◽  
Vol 64 (1) ◽  
Author(s):  
Trong Nguyen Nguyen ◽  
Yeong-Geun Lee ◽  
Hyoung-Geun Kim ◽  
Dahye Yoon ◽  
Jin Tae Jeong ◽  
...  
Keyword(s):  
Silica Gel ◽  
Column Chromatography ◽  
Absolute Configuration ◽  
Preparative Hplc ◽  
Schisandra Chinensis ◽  
Axial Chirality ◽  
Chemical Structures ◽  
Data Analyses ◽  
Nmr Data ◽  
Hplc Column

AbstractRepeated column chromatography using Sephadex LH-20, silica gel (SiO2), and octadecyl SiO2 (ODS) as well as preparative HPLC column chromatography led to isolation of a new dibenzocyclooctadiene lignan along with four known ones, gomisin L2 (1), L1 (2), M1 (3), and M2 (4). Their chemical structures were fixed based on MS, IR, and NMR data analyses. In addition, the stereochemistry of atropisomers, the absolute configuration of the axial chirality in a biphenyl structure, was confirmed by a CD experiment. The new lignan was named gomisin M3 (5).

Synthesis and characteristics of ethylenediamine-N,N'-di-S-α-isovalerate and isomers of its cobalt(III) complexes

1982 ◽  
Vol 47 (1) ◽  
pp. 210-216 ◽  
Author(s):  
Milan Strašák ◽  
František Bachratý ◽  
Jaroslav Majer
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Electronic Absorption ◽  
Electronic Absorption Spectra ◽  
Chemical Parameters ◽  
Methyl Group ◽  
Nmr Data ◽  
Physico Chemical ◽  
Natural Amino Acids ◽  
C Nmr

The synthesis and physico-chemical parameters are described of a new complexone based on natural amino acids, viz. ethylenediamine-N,N'-di-S-α-isovalerate (SS-EDDIV). 1H- and 13C-NMR data revealed that the methyl group in the substance are not equivalent. The isomers of the cobalt(III) complex with the asymmetric tetradentate SS-EDDIV ligand were prepared and separated; their characteristics are given. The absolute configuration of two of the five theoretically feasible isomers was determined based on their electronic absorption spectra and circular dichroism data.

scholarly journals Two New Phomaligols from the Marine-Derived Fungus Aspergillus flocculosus and Their Anti-Neuroinflammatory Activity in BV-2 Microglial Cells

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 65
Author(s):  
Byeoung-Kyu Choi ◽  
Duk-Yeon Cho ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
Hee Jae Shin
Keyword(s):  
Nitric Oxide ◽  
Mass Spectrometry ◽  
Optical Rotation ◽  
Chemical Oxidation ◽  
Culture Broth ◽  
Membered Ring ◽  
Microglial Cells ◽  
No Production ◽  
Nmr Data ◽  
Ic50 Value

Two new phomaligols, deketo-phomaligol A (1) and phomaligol E (2), together with six known compounds (3–8) were isolated from the culture broth of the marine-derived fungus Aspergillus flocculosus. Compound 1 was first isolated as a phomaligol derivative possessing a five-membered ring. The structures and absolute configurations of the new phomaligols were determined by detailed analyses of mass spectrometry (MS), nuclear magnetic resonance (NMR) data, optical rotation values and electronic circular dichroism (ECD). In addition, the absolute configurations of the known compounds 3 and 4 were confirmed by chemical oxidation and comparison of optical rotation values. Isolated compounds at a concentration of 100 μM were screened for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Among the compounds, 4 showed moderate anti-neuroinflammatory effects with an IC50 value of 56.6 μM by suppressing the production of pro-inflammatory mediators in activated microglial cells without cytotoxicity.

scholarly journals Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

Chemosensors ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 154
Author(s):  
Stefania Vergura ◽  
Stefano Orlando ◽  
Patrizia Scafato ◽  
Sandra Belviso ◽  
Stefano Superchi
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Environmental Pollutants ◽  
Red Shift ◽  
Electronic Circular Dichroism ◽  
Configuration Assignment ◽  
Clear Sign ◽  
The Absolute ◽  
Circular Dichroïsm

The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, the 4,4′-biphenyl substitution gives rise to a red shift of the diagnostic electronic circular dichroism signal of the biphenyl A band employed for the configuration assignment, removing its overlap with other interfering dichroic bands and allowing its clear sign identification. The largest A band red shift, and thus the most reliable results, are obtained by employing as a probe the 4,4′-dinitro substituted biphenylazepine 3c. The method was applied to the absolute configuration assignment of 2-arylpropionic acids ibuprofen (1a), naproxen (1b), ketoprofen (1c) and flurbiprofen (1d), as well as to the 2-aryloxypropionic acids 2-phenoxypropionic acid (2a) and 2-naphthoxypropionic acid (2b). This approach, allowing us to reveal the sample’s absolute configuration by simple optical rotation measurements, is potentially applicable to online analyses of both the enantiomeric composition and absolute configuration of these chiral pollutants.

scholarly journals Leptogorgins A–C, Humulane Sesquiterpenoids from the Vietnamese Gorgonian Leptogorgia sp.

Marine Drugs ◽  
2020 ◽  
Vol 18 (6) ◽  
pp. 310 ◽  
Author(s):  
Irina I. Kapustina ◽  
Tatyana N. Makarieva ◽  
Alla G. Guzii ◽  
Anatoly I. Kalinovsky ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Prostate Cancer ◽  
South China Sea ◽  
Cancer Cells ◽  
South China ◽  
Absolute Configuration ◽  
Marine Invertebrates ◽  
Drug Resistant ◽  
Prostate Cancer Cells ◽  
First Report ◽  
Nmr Data

Leptogorgins A–C (1–3), new humulane sesquiterpenoids, and leptogorgoid A (4), a new dihydroxyketosteroid, were isolated from the gorgonian Leptogorgia sp. collected from the South China Sea. The structures were established using MS and NMR data. The absolute configuration of 1 was confirmed by a modification of Mosher’s method. Configurations of double bonds followed from NMR data, including NOE correlations. This is the first report of humulane-type sesquiterpenoids from marine invertebrates. Sesquiterpenoids leptogorgins A (1) and B (2) exhibited a moderate cytotoxicity and some selectivity against human drug-resistant prostate cancer cells 22Rv1.

scholarly journals Antifungal Activity of Decursinol Angelate Isolated from Angelica gigas Roots Against Puccinia recondita

2011 ◽  
Vol 17 (1) ◽  
pp. 25-31 ◽  
Author(s):  
Mi-Young Yoon ◽  
Young-Sup Kim ◽  
Gyung-Ja Choi ◽  
Kyoung-Soo Jang ◽  
Yong-Ho Choi ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Puccinia Recondita ◽  
Angelica Gigas ◽  
Decursinol Angelate

scholarly journals Restricticin B from the Marine Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

2020 ◽  
Author(s):  
Byeonung-Kyu Choi ◽  
Shin-Young Park ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Marine Fungus ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Data Comparison ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2-5) were obtained from the EtOAc extract of the marine fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via analyses of NOESY spectroscopy data, comparison of optical rotation values with those of restricticin derivatives reported and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals HPTLC determination of diosgenin in fenugreek seeds

2018 ◽  
Vol 68 (1) ◽  
pp. 97-107 ◽  
Author(s):  
Barbara Król-Kogus ◽  
Khenifi Mohammed Lamine ◽  
Piotr Migas ◽  
Messaoud Boudjeniba ◽  
Mirosława Krauze-Baranowska
Keyword(s):  
Ethyl Acetate ◽  
Acid Hydrolysis ◽  
Methanolic Extract ◽  
Soxhlet Extraction ◽  
African Origin ◽  
Fenugreek Seeds ◽  
Hydrolysis Products ◽  
Hydrolysis Of

Abstract A new HPTLC-densitometric method for diosgenin determination in fenugreek seeds was established after optimization of the conditions for efficient saponin extraction and acid hydrolysis. Several procedures were tested, the best of which was a three-step Soxhlet extraction, followed by hydrolysis of the obtained methanolic extract with 2 mol L-1 H2SO4. Best diosgenin separation from other hydrolysis products was obtained on HPTLC Si60F254 plates u sing a mixture of n-heptane/ethyl acetate (7:3, V/V) and modified anisaldehyde as a spraying reagent. The method was preliminarily validated and the determined amounts of diosgenin in fenugreek seeds of Polish and African origin were found to be similar and ranged from 0.12-0.18 %.

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