• Ocean and Polar Research
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• v.39 no.2
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• pp.115-124
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• 2017

The objective of this study is to evaluate the antioxidant activity of the fruits of Ligustrum japonicum. The crude extract was successively fractionated into n-hexane, 85% aqueous methanol (85% aq.MeOH), n-butanol (n-BuOH), and water fractions by means of solvent polarity. The crude extract and its solvent fractions were evaluated for their antioxidant effect by four different assay systems: scavenging power on peroxynitrite and intralcellular ROS produced in HT-1080 cells; DNA oxidation inhibition; ferric reducing antioxidant power (FRAP). The n-BuOH fraction exhibiting potent antioxidant activity was further purified by C18 silica gel column chromatography and RP-HPLC to give tyrosol (1) and salidroside (2). The structure of isolated compounds was determined by extensive 2 D NMR experiments such as $^1H$ COSY, NOESY, HSQC and HMBC as well as by comparison with the published spectral data.

• Korean Journal of Plant Resources
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• v.19 no.6
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• pp.655-659
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• 2006

Two dineolignans (1,2) with nitric oxide inhibitory activities were isolated from Saururus chinensis (Saururaceae) using silica gel column chromatography. Although the structures, saucernetin-7 (1) and -8 (2), have been already reported, NMR assignment of the two compounds was completed aided by 2D-NMR spectroscopy including $^1H-^1H$ COSY, $^1H-^{13}C$ COSY, HMBC and NOESY NMR spectra. Compounds 1 and 2 exhibited significant nitride oxide inhibitory activity in LPS-induced RAW 264.7 cells with $IC_{50}$ values of $11.3{\mu}M\;and\;7.1{\mu}M$, respectively.

• Bulletin of the Korean Chemical Society
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• v.28 no.6
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• pp.990-994
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• 2007

Bioassay-guided fractionation of the MeOH extract from the sponge Discodermia calyx collected off the coast of Jeju Island, South Korea, led to the isolation of a polyketide, icadamide C (1), along with previously reported theopederin K (3). Structure elucidation was performed by a combination of high resolution mass and 2D-NMR (principally COSY, HMBC, HSQC, and NOESY) spectroscopy. Stereochemistry of compound 1 was determined as 2R*, 3R*, 6R*, 10S*, 11S*, 12R*, 13S*, 15R* and 2'S by NMR data and Marfey analysis. Isolated metabolites displayed potent cytotoxic activity against a small panel of five human solid tumor cell lines with ED50 values of less than 0.1 μg/mL.

• Journal of the Korean Magnetic Resonance Society
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• v.25 no.2
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• pp.24-32
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• 2021

Two new sesterterpenes, including a known sesterterpene, were isolated from the marine sponge Haliclona sp. collected in the Gageo island, Korea. One of the new sesterterpenes (1) was an unusual compound possessing a spiroketal moiety and the other (2) represented a four ring-fused skeleton. The planar structure of compound 1 was identical to gombaspiroketals A and B isolated from the marine sponge Clathria gombawuiensis, but the configuration for the two chiral centers was different each other. On the other hand, the skeletal structure of compound 2 was similar to that of phorone A isolated from Phorbas sp. and a compound from C. gombawuiensis, except for one configuration at C-8. However, in comparing the ¹H and ¹³C NMR spectral data, the proton and carbon chemical shifts for the three compounds were almost consistent. The NOESY spectrum revealed that the C-8 configuration of 2 was reversed to that of the two reported compounds. The configuration for compound 2 was supported by quantum mechanical calculation for the carbon chemical shifts and DP4+ probability for the protons and carbons of 2.

• Journal of the Korean Magnetic Resonance Society
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• v.2 no.1
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• pp.33-40
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• 1998

The cross peak intensities versus mixing times of 2D NOESY spectrum for a corepressor L-trp were simulated for the case of a ligand exchanging between free (AX) and bound (A'X') forms in protein/DNA complex. The direct NOE (I(AX)) of the free ligand exhibited a small positive intensity indicative of the strong dominant influence of the bound ligand. The exchange-mediated NOE peak (I(AX')) was very sensitive to corepressor exchange. However, both diagonal (I(A'A')) and direct NOE (I(A'X')) intensities of the bound ligand were not affected much at initial stage. Both peaks were severely influenced by exchange at mixing times of greater than 100 ms. In conclusion, since the NOE intensity is a function of exchange rate, the exchange effect should be considered to properly extract accurate distance information for bound ligand in the presence of conformational exchange.

• Journal of the Korean Magnetic Resonance Society
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• v.2 no.1
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• pp.50-58
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• 1998

The systematic chirality investigations were made on the basic of the fact that zinc-binding tallysomycin (ZnTLMA) could have chiral centers (Zn, NC3, C6) at possible 4-, 5-, and 6-coordination models. Although our NMR data exhibit that the ligation sites are ${\beta}$-aminoalanine, ${\beta}$-hydroxyhistidine, and pyrimidine moiety, all possible coordination modes were tested out to see what kind of chiralities on NC3-C6 are favorable to each coordination mode. Tests were also made that take into account the specific configuration of functional groups, including ${\beta}$-aminoalanine, sugar ring, and ${\beta}$-hydroxyhistidine. Tests were finally extended to zinc-water binding and specific conformational studies by introducing various hydrogen bonding networks associated with the propionamide side chain and the carbamide group of mannose. Results of systematic chirality investigations exhibit that the S-S configuration of NC3-C6 is favorable to all of coordination models, but the R-S configuration, if exists at all, should have internal strain on C6 chiral center.

• Archives of Pharmacal Research
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• v.25 no.4
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• pp.438-440
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• 2002

A new unsaturated hydroxy fatty acid was isolated from the leaves of Cucurbita moschata through repeated silica gel column chromatography and chemical methods. The structure of the new fatty acid was determined as 13-hydroxy-9, 11, 15-octadecatrienoic acid on the basis of several spectral data including 2D-NMR. The stererostructures of double bonds were determined to be 9Z, 11 E and 15E by coupling patterns of related proton signals in the $^1H-NMR$ and NOESY experiments.

• Journal of Applied Biological Chemistry
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• v.49 no.1
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• pp.16-20
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• 2006

The flowers of Hemisteptia lyrata B. afforded two known acylglycerylgalactosides, 2',3'-di-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (1) and 2'-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (2), and a new sesquiterpene galactopyranoside, 7-eudesmene-1${\beta}$,4${\beta}$-diol-1-O-${\beta}$-D-galactopyranoside (3). This is the first time that galactopyranosides (1-3) have been isolated from the genus Hemisteptia. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY and HMBC experiments.

• Archives of Pharmacal Research
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• v.19 no.6
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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 $^{1}H-NMR$.

• Journal of the Korean Magnetic Resonance Society
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• v.23 no.4
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• pp.87-92
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• 2019

Allium hookeri (Liliaceae) has been received the increasing attention as a bioactive resource due to its potent biological activities including anti-oxidant, anti-obesity, anti-microbial and lipid-regulating activities. The beneficial effects of A. hookeri are known contributed from the high content of organosulfur compounds in A. hookeri. Though a variety of articles demonstrated that A. hookeri contains 'saponin' as a bioactive constituent, the scientific evidence to prove it was limited. In the present study, we have attempted to identify saponin contained in A. hookeri through chromatographic isolation and NMR spectroscopic methods. As a result, a spirostane-type steroidal saponin (1) has been successfully isolated from the methanolic extract of A. hookeri roots. The structure of 1 was elucidated by extensive 1D and 2D spectroscopic methods including ¹H-NMR, ¹³C-NMR, ¹H-¹H COSY, HSQC, HMBC and NOESY; identified as (3β, 22R, 25S)-spirost-5-en-3yl O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-[6-deoxy-α-L-mannopyranosyl-(1→2)]-β-D-gluco pyranoside. 1 showed the significant inhibitory activity on mushroom tyrosinase with IC₅₀ values of 248.7 μM while the inhibition on alpha-glucosidase was not significant.