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Biomedical subjects

Jinwoong Kim

Publications and source records attributed to Jinwoong Kim.

At least 19 recordsLinked to original sources

Concise synthesis of rodgersinol and determination of the C-10 absolute configuration.

Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.

Alkenes↗

A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography.

Centrifugal partition chromatography was applied to separate arctigenin and matairesinol from Forsythia koreana extract with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (5:5:5:5 v/v). Using this method, arctigenin and matairesinol were successfully separated from partially purified F. koreana extracts in only one step. The purities of isolated compounds were determined to be over 90% by HPLC analysis.

Chromatography, High Pressure Liquid↗

Steroidal saponins from the rhizomes of Polygonatum sibiricum.

Four new steroidal saponins, named neosibiricosides A-D (1-4), were isolated from the rhizomes of Polygonatum sibiricum, along with two known spirostanol glycosides. The structures of the new glycosides were elucidated by spectroscopic methods and acid hydrolysis as (23S,24R,25R)-1-O-acetylspirost-5-ene-1beta,3beta,23,24-tetrol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranoside (1), (25S)-1-O-acetylspirost-5-ene-1beta,3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (2), (25S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-2-O-acetyl-beta-D-galactopyranoside (3), and (25R,S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated with human MCF-7 breast cancer cells.

Antineoplastic Agents, Phytogenic↗

Three new flavonol glycosides from the aerial parts of Rodgersia podophylla.

Three new flavonol glycosides were isolated together with five known flavonoids and six bergenin derivatives from the aerial parts of Rodgersia podophylla. The structures of these new compounds were elucidated by spectral methods as kaempferol-3-O-alpha-L-5''-acetyl-arabinofuranoside (1), kaempferol 3-O-alpha-L-3''-acetyl-arabinofuranoside (2), and quercetin-3-O-alpha-L-3'',5''-diacetyl-arabinofuranoside (3).

Carbohydrates↗

Idesolide: a new spiro compound from Idesia polycarpa.

[structure: see text]. Idesolide, a new spiro compound possessing tetrahydrobenzodioxole structure, was isolated from the fruits of Idesia polycarpa Maxim. Its structure was established by NMR and MS spectroscopic analysis with single-crystal X-ray experiments. Idesolide significantly reduced nitric oxide production induced by lipopolysaccharide in BV2 microglial cells.

Anti-Inflammatory Agents↗

Identification and quantification of steroidal saponins in Polygonatum species by HPLC/ESI/MS.

An HPLC/ESI/MS method has been developed to identify and quantify the spirostanol glycosides in the rhizomes of five Polygonatum species. The relative distribution of two steroidal saponins in each extract was established using the selective ion monitoring (SIM) mode via an electrospray ionization (ESI) source. It was found that there were significant differences in the amount of spirostanol glycosides among the Polygonatum species. The results showed that this method could be used to identify the steroidal saponins in the extracts and differentiate Polygonatum species with high sensitivity and reproducibility in a short time. Fragmentation patterns of the two reference compounds were also discussed with the electrospray ionization multi-stage tandem mass spectroscopy (ESI-MSn).

Chromatography, High Pressure Liquid↗

Potentially hepatoprotective glycolipid constituents of Lycium chinense fruits.

Further investigation of Lycium chinense fruits gave a mixture of (6'-O-palmitoyl)- and (6'-O-stearoyl)-beta-sitosterol-3-O-beta-D-glucopyranoside (1) and two glycolipids, 1-O-(9Z,12Z, 15Z-octadecatrienoyl)-2-O-(9Z, 12Z, 15Z-octadecatrienoyl)-3-O-beta-D-galactopyranosyl glycerol (2) and 1-O-(9Z, 12Z-octadecadienoyl)-2-O-(9Z, 12Z, 15Z-octadecatrienoyl)-3-O-beta-D-galactopyranosyl glycerol (3). These compounds were newly isolated as constituents of L. chinense.

Animals↗

Labdane diterpenes from Aster spathulifolius and their cytotoxic effects on human cancer cell lines.

Three new labdane diterpenes (1-3), together with eight known diterpenoids, were isolated from a methanol extract of the aerial parts of Aster spathulifolius. The structures of 1-3 were determined as (13R)-labda-7,14-diene 13-O-beta-d-(4'-O-acetyl)fucopyranoside (1), (13R)-labda-7,14-diene 13-O-beta-d-(3'-O-acetyl)fucopyranoside (2), and (13R)-labda-14(15)-en-8,13-diol 13-O-beta-d-fucopyranoside (3), on the basis of spectroscopic and chemical methods. Compounds 1, 2, and four of the known compounds exhibited generally nonspecific cytotoxicity against human A549, SK-OV-3, SK-MEL-2, XF498, and HCT15 tumor cells.

Antineoplastic Agents, Phytogenic↗

Meso-dihydroguaiaretic acid and licarin A of Machilus thunbergii protect against glutamate-induced toxicity in primary cultures of a rat cortical cells.

1 We previously reported that four lignans isolated from the bark of Machilus thunbergii Sieb. et Zucc. (Lauraceae) protected primary cultures of rat cortical neurons from neurotoxicity induced by glutamate. 2 Among the lignans, meso-dihydroguaiarectic acid (MDGA) and licarin A significantly attenuated glutamate-induced neurotoxicity when added prior to or right after the excitotoxic glutamate challenge. 3 The neuroprotective activities of two lignans appeared to be more effective in protecting neurons against neurotoxicity induced by NMDA than that induced by kainic acid. 4 MDGA and licarin A diminished the calcium influx that routinely accompanies with the glutamate-induced neurotoxicity, and inhibited the subsequent overproduction of cellular nitric oxide and peroxide to the level of control cells. They also preserved cellular activities of antioxidative enzymes such as superoxide dismutase, glutathione peroxidase and glutathione reductase reduced in the glutamate-injured neuronal cells. 5 Thus, our results suggest that MDGA and licarin A significantly protect primary cultured neuronal cells against glutamate-induced oxidative stress, via antioxidative activities.

Animals↗

Inhibition of phospholipase Cgamma1 and cancer cell proliferation by lignans and flavans from Machilus thunbergii.

Thirteen compounds were isolated from the CH2Cl2 fraction of Machilus thunbergii as phospholipase Cgamma1 (PLCgamma1) inhibitors. These compounds were identified as nine lignans, two neolignans, and two flavans by spectroscopic analysis. Of these, 5,7-di-O-methyl-3',4'-methylenated (-)-epicatechin (12) and 5,7,3'-tri-O-methyl (-)-epicatechin (13) have not been reported previously in this plant. In addition, seven compounds, machilin A (1), (-)-sesamin (3), machilin G (5), (+)-galbacin (9), licarin A (10), (-)-acuminatin (11) and compound 12 showed dose-dependent potent inhibitory activities against PLCgamma1 in vitro with IC50 values ranging from 8.8 to 26.0 microM. These lignans, neolignans, and flavans are presented as a new class of PLCgamma1 inhibitors. The brief study of the structure activity relationship of these compounds suggested that the benzene ring with the methylene dioxy group is responsible for the expression of inhibitory activities against PLCgamma1. Moreover, it is suggested that inhibition of PLCgamma1 may be an important mechanism for an antiproliferative effect on the human cancer cells. Therefore, these inhibitors may be utilized as cancer chemotherapeutic and chemopreventive agents.

Animals↗

Lignans of Rosa multiflora roots.

Five known lignans, (+)-pinoresinol (1), (+)-8-hydroxypinoresinol (2), (-)-dehydrodiconiferyl alcohol (3), (+)-trans-dehydrodiconiferyl alcohol (4), and (-)-olivil (5), were isolated from the roots of Rosa multiflora for the first time. Their structures were determined using spectroscopic data.

Lignans↗

Flavonoids of Crotalaria sessiliflora.

Phytochemical investigation of the whole plants of Crotalaria sessiliflora L. led to the isolation of four flavonoids. The structures of these compounds were identified as 2',4',5,7-tetrahydroxyisoflavone (1), 2',4',7-trihydroxyisoflavone (2), 4',7-dihydroxyflavone (3), and isovitexin (4) using spectroscopic analysis. Among these, compounds 2, and 3 have not been reported from Crotalaria species, whereas compounds 1, and 4 were reported from this plant for the first time.

Crotalaria↗

Norisoprenoids and hepatoprotective flavone glycosides from the aerial parts of Beta vulgaris var. cicla.

(+)-Dehydrovomifoliol (1), 3-hydroxy-5alpha,6alpha-epoxy-beta-ionone (2), vitexin 7-O-beta-D-glucopyranoside (3), and vitexin 2''-O-beta-D-glucopyranoside (4) were isolated as new constituents from the aerial parts of Beta vulgaris var. cicla. Compounds 3 and 4 demonstrated hepatoprotective activity with values of 65.8 and 56.1%, respectively, in primary cultured rat hepatocytes with CCl4-induced cell toxicity, compared to controls. This was comparable to that of silibinin (69.8 %) which was used as a positive control.

Animals↗

Analysis of strychnine from detoxified Strychnos nux-vomica [corrected] seeds using liquid chromatography-electrospray mass spectrometry.

The content of strychnine from Strychnos nux-vomica [corrected] seeds was analyzed and compared to processed seeds by the HPLC-ESI/MS method. Using this technique, levels as low as 1 ng of strychnine were detected. In contrast to conventional UV detectors, this method also made it possible to discriminate brucine. This study resulted in finding the content of strychnine in detoxified seeds to be one tenth of unprocessed Strychnos nux-vomica [corrected] seeds.

Plant Extracts↗

Hepatoprotective flavonol glycosides from the aerial parts of Rodgersia podophylla.

A new acylated flavonoid, quercetin 3- O-alpha- L-(5"- O-acetyl)-arabinofuranoside ( 1), along with six known flavonoids ( 2 - 7) were isolated from the aerial parts of Rodgersia podophylla. The new flavonoid 1 exhibited 50.1 % hepatoprotective activity at a concentration of 100 microM, and the three known compounds 3, 5 and 6 showed hepatoprotective activities at a concentration of 50 microM (45.7, 50.8 and 57.3 %, respectively) by using the primary cultures of rat hepatocytes injured by H (2)O (2).

Animals↗

Inhibition of HIV-1 reverse transcriptase and protease by phlorotannins from the brown alga Ecklonia cava.

The bioassay-directed isolation of a marine brown alga, Ecklonia cava, afforded four phlorotannin derivatives, eckol (1), 8,8'-bieckol (2), 8,4"'-dieckol (3), and phlorofucofuroeckol A (4). Among these compounds, 2 and 3 exhibited an inhibitory effect on human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) and protease. Specifically, they inhibited the RT more potently than the protease. The inhibitory activity of compound 2 (IC(50), 0.51 microM) against HIV-1 RT was comparable to that of nevirapine (IC(50), 0.28 microM), a reference compound. An enzyme kinetic assay showed that this compound inhibited the RNA-dependent DNA synthesis activity of HIV-1 RT noncompetitively against dUTP/dTTP with a K(i) value of 0.78 microM. With respect to the homopolymeric template/primer, (rA)n(dT)15, 8,8'-bieckol (2) displayed an uncompetitive type of inhibition (K(i), 0.23 microM).

HIV Protease↗