• 약학회지
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• 제38권5호
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• pp.544-554
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• 1994

Pyrrolidine-2,3-dione derivative A was synthesized from oxalylation of chiral enamine Ba. The stereostructure of its major diastereomer $(A_{maj})$ was determined as octahydro-2,3-dioxo-6aS-hyd roxy-1-(1S-methoxycarbonyl-2-phenylethyl)-cyclopenta[b]pyrrole-3aR-carboxylic acid ethyl ester Aa by means of NMR spectrum. This result implied that the asymmetric carbon-carbon bond forming reaction occurred preferentially at the ${\beta}-face$ of Ba.

• Archives of Pharmacal Research
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• 제19권6호
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• pp.551-553
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• 1996

A genuine dammarane glycoside, named ginsenoside $Rg_{5}$, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside$ Rg_{5}$ was determined as $3-O-[{\beta}-D-glucopyranosyl (1{\rightarrow}2)-{\beta}-D-glucopyranosyl]$ dammar-20(22), $24-diene-3{\beta},12{\beta}-diol$ by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside $Rg_{5}$ was characterized as (E) from the chemical shift of C-21 in the $^{13}C-NMR $and a NOESY experiment in the $^{1}H-NMR$.

• Natural Product Sciences
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• 제9권1호
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• pp.28-30
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• 2003

A sesquiterpene lactone, 1-O-acetyl-4R,6S-britannilactone (1) which has a new stereochemistry was isolated from the flowers of Inula britannica L. var.chinensis (Rupr.) Reg. Its stereostructure was determined by a x-ray crystallography.

• 약학회지
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• 제39권3호
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• pp.268-275
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• 1995

A novel polyacetylene was isolated from Cirsium spp., as well as five known ones, and its chemical structure was determined as heptadeca-1-en-11.13-diyne-8R, 9S, 10R-triol(1) on the basis of spectral data and chemical reactions. $^{1}$H-and $^{13}$C-NMR data of these polyacetylenes were completely assigned by the appfication of 2D-NMR techniques.

• Journal of Microbiology and Biotechnology
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• 제20권6호
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• pp.985-987
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• 2010

The biological transformation of the bioactive dihydroisocoumarin, (-)-mellein, isolated from the marinederived fungus Cladosporium sp., was studied. The preparativescale culture of (-)-mellein with a marine isolate of a bacterium Stappia sp. resulted in the isolation of its oxidized metabolite, (3R,4S)-4-hydroxymellein. The stereostructure of the metabolite obtained was assigned on the basis of detailed physicochemical data analyses.

• Natural Product Sciences
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• 제22권3호
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• pp.216-219
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• 2016

The microbial transformation of anthranilic acid (1) by the marine-mudflat-derived fungus Thielavia sp. produced an antibacterial polycyclic quinazoline alkaloid, thielaviazoline (2). The stereostructure of the metabolite was assigned based on detailed spectroscopic data analyses including comparison of the NMR ($^1H$ and $^{13}C$) data with those of reported compound (2). Compound 2 displayed in vitro antimicrobial activity against methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA), with minimum inhibitory concentrations (MICs) of 6.25 and $12.5{\mu}g/mL$, respectively. Compound 2 also showed potent radical-scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) with an $IC_{50}$ of $11{\mu}M$, which was more active than the positive control, L-ascorbic acid ($IC_{50}$, $20.0{\mu}M$).

• 한국섬유공학회:학술대회논문집
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• 한국섬유공학회 2003년도 가을 학술발표회 논문집
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• pp.177-178
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• 2003

Many researchers have made efforts to control the stereoregularity in radical polymerization of vinyl monomers because the physical and chemical properties of the polymer are significantly affected by the stereostructure.[1]-[4] In general, monomer design, reaction conditions(e.g. solvent, temperature, and monomer concentration), and additives can alter the stereochemistry of the radical polymerization of acrylic monomer. (omitted)

• Journal of Ginseng Research
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• 제44권5호
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• pp.690-696
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• 2020

Background: As the main metabolites of ginsenosides, 20(S, R)-protopanaxadiol [PPD(S, R)] and 20(S, R)-protopanaxatriol [PPT(S, R)] are the structural basis response to a series of pharmacological effects of their parent components. Although the estrogenicity of several ginsenosides has been confirmed, however, the underlying mechanisms of their estrogenic effects are still largely unclear. In this work, PPD(S, R) and PPT(S, R) were assessed for their ability to bind and activate human estrogen receptor α (hERα) by a combination of in vitro and in silico analysis. Methods: The recombinant hERα ligand-binding domain (hERα-LBD) was expressed in E. coli strain. The direct binding interactions of ginsenosides with hERα-LBD and their ERα agonistic potency were investigated by fluorescence polarization and reporter gene assays, respectively. Then, molecular dynamics simulations were carried out to simulate the binding modes between ginsenosides and hERα-LBD to reveal the structural basis for their agonist activities toward receptor. Results: Fluorescence polarization assay revealed that PPD(S, R) and PPT(S, R) could bind to hERα-LBD with moderate affinities. In the dual luciferase reporter assay using transiently transfected MCF-7 cells, PPD(S, R) and PPT(S, R) acted as agonists of hERα. Molecular docking results showed that these ginsenosides adopted an agonist conformation in the flexible hydrophobic ligand-binding pocket. The stereostructure of C-20 hydroxyl group and the presence of C-6 hydroxyl group exerted significant influence on the hydrogen bond network and steric hindrance, respectively. Conclusion: This work may provide insight into the chemical and pharmacological screening of novel therapeutic agents from ginsenosides.