• Korean Journal of Pharmacognosy
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• v.42 no.4
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• pp.302-308
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• 2011

As a part of our ongoing program on finding biologically active components from natural source we found three known constituents from the EtOH extract of the wheat bran. The known compounds were identified as tachioside (1), pinellic acid (2) and tryptophan (3). The structure and relative stereochemistry were determined from MS, 1D and extensive 2D NMR techniques as well as by comparison of their data with the published values. All isolates were tested their inhibitory effects on the adipogenesis in 3T3-L1 cells. The effect of compounds from wheat bran on 3T3-L1 adipocyte differentiation were measured by Oil Red O staining. These results demonstrate that tachioside (1) and pinellic acid (2) decreased lipid content in 3T3-L1 adipocytes by inhibiting lipogenesis. These compounds had shown antiobesity activities.

• The Korean Journal of Physiology and Pharmacology
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• v.14 no.6
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• pp.441-447
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• 2010

B13, a ceramide analogue, is a ceramidase inhibitor and induces apoptosis to give potent anticancer activity. A series of thiourea B13 analogues was evaluated for their in vitro cytotoxic activities against human renal cancer Caki-2 and leukemic cancer HL-60 in the MTT assay. Some compounds (12, 15, and 16) showed stronger cytotoxicity than B13 and C6-ceramide against both tumor cell lines, and compound (12) gave the most potent activity with $IC_{50}$ values of 36 and $9\;{\mu}M$, respectively. Molecular modeling of thiourea B13 analogues was carried out by comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). We obtained highly reliable and predictive CoMSIA models with cross-validated $q^2$ values of 0.707 and 0.753 and CoMSIA contour maps to show the structural requirements for potent activity. These data suggest that the amide group of B13 could be replaced by thiourea, that the stereochemistry of 1,3-propandiol may not be essential for activity and that long alkyl chains increase cytotoxicity.

• The Korean Journal of Physiology and Pharmacology
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• v.15 no.6
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• pp.423-429
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• 2011

B13 analogues are being considered as therapeutic agents for cancer cells, since B13 is a ceramide analogue and inhibits ceramidase to promote apoptosis in cancer cells. B13 sulfonamides are assumed to have biological activity similar to B13, since they are made by bioisosterically substituting the carboxyl moiety of B13 with sulfone group. Twenty B13 sulfonamides were evaluated for their in vitro cytotoxicities against human colon cancer HT-29 and lung cancer A549 cell lines using MTT assays. Replacement of the amide group with a sulfonamide group increased cytotoxicity in both cancer cell lines. The sulfonamides with long alkyl chains exhibited activities two to three times more potent than that of B13 and compound (15) had the most potent activity with $IC_{50}$ values of 27 and $28.7{\mu}M$ for HT-29 and A549, respectively. The comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used to carry out QSAR molecular modeling of these compounds. The predictive CoMSIA models for HT-29 and A549 gave cross-validated q2 values of 0.703 and 0.830, respectively. From graphical analysis of these models, we suppose that the stereochemistry of 1,3-propandiol is not important for activity and that introduction of a sulfonamide group and long alkyl chains into B13 can increase cytotoxicity.

• Bulletin of the Korean Chemical Society
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• v.26 no.4
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• pp.594-598
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• 2005

Treatment of a solution of $CuCl_2$ in dimethyl phosphate (DMP) with DMSO under nitrogen atmosphere afforded to a light blue fluorescence powder. Slow evaporation of $H_2O$-DMSO solution of this powder resulted in blue-sky crystals of a new polymeric Cu(II) complex, with a unit cell composed of $Cu_2(DMP)_4$(DMSO), (1). The crystal and molecular structure of the complex acquired crystallographically. Compound (1) crystallizes in the monoclinic space group $P2_1$/n with a = 12.8920(11) $\AA$, b = 13.1966(11) $\AA$, c = 14.7926(13) $\AA$, $\alpha$ = 90$^{\circ}$, $\beta$ = 98.943(2)$^{\circ}$, $\gamma$ = 90$^{\circ}$, V= 2486.1(4) ${\AA}^3$, and Z = 4. A square pyramidal environment for the metal center was established by coordination of oxygen atoms of four bridging DMP ligands in the basal positions and binding a tri-centered oxygen atom of DMSO in the apical disposition of Cu(II). The sixth position was also affected by a weak interaction with the sulfur atom of another DMSO. The phosphorous atom in the bridging DMP was arranged in a deformed tetrahedron with (gg) conformation for methyl esters with $C_{2v}$ symmetry.

• Korean Journal of Pharmacognosy
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• v.33 no.3 s.130
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• pp.173-176
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• 2002

In search for the plant-derived antioxidant compound, it was found that the EtOAc, BuOH extracts obtained from the leaves parts of Oryza sativa L. which exhibited a significant antioxidant activity from 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical cleavage. Activity-guided fractionation on the basis of the inhibitory activity upon the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical cleavage. and repeated column chromatography afforded several antioxidant compounds from Oryza sativa L. The structures and stereochemistry of these compounds were established on the basis of analysis of spectra and some chemical transformations as follows: 5,7-dihydroxy- 8-methoxyflavone, $acacetin-7-O-{\beta}-rutinoside$, $pectolinarigenin-7-O-{\beta}-rutinoside$. At antioxidant activity test for isolated three compounds, antioxidant activity was showed too.

• Natural Product Sciences
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• v.26 no.2
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• pp.151-157
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• 2020

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B₅ (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B₂ (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

• Journal of the Korean Chemical Society
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• v.27 no.6
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• pp.441-448
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• 1983

A wide variety of vinylic bromides such as (Z)-1-bromopropene, 1-bromo-2-methylpropene, 2-bromo-3-methyl-2-butene, (E)-ethyl 2-methyl-3-bromo-2-propenoate, 1-bromo-cyclohexene has been found to react with ethyl acrylate, ethyl 3-butenoate, allyl cyanide, (E)-ethyl crotonate, ethyl 4-pentenoate, methyl 10-undecenoate and methyl methacrylate in the presence of triethylamine and a palladium acetate-triorthotolylphosphine catalyst. In general, 2,4-dienoic acid derivatives were obtained in good yield and stereochemistry of the products was determined. Using this method, four, five and eleven carbon-carbon extension with ethyl 3-butenoate, ethyl 4-pentenoate and methyl 10-undecenoate was also possible.

• Bulletin of the Korean Chemical Society
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• v.31 no.6
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• pp.1551-1554
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• 2010

Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic ${\alpha}$-amino methyl esters, ${\alpha}$-amino N,N-diethylamides and ${\alpha}$-amino N-propylamides. The CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of ${\alpha}$-amino N-propylamides. Some of ${\alpha}$-amino methyl esters and ${\alpha}$-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.

• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2381-2386
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• 2013

A new series of Mn(II) and Mo(VI) complexes containing the Schiff bases hydrazinecarbothioamide and hydrazinecarboxamide of 5,6-dimethyl-1H-indol-2,3-dione have been synthesized. The nature of bonding and the stereochemistry of the complexes have been deduced from elemental analyses, molecular weight determinations and spectral studies viz. electronic IR, ESR, $^1H$ NMR and $^{13}C$ NMR and X-ray diffraction spectral studies. The magnetic moment values of the manganese(II) complexes are in the range of 5.80-6.15 B.M. suggesting a high spin state of manganese in these complexes. The spectral data are consistent with a tetrahedral geometry around Mn(II) and an octahedral geometry for Mo(VI), in which the ligands act as bidentate chelating agents, coordinated through the nitrogen and sulfur/oxygen atoms. The ligands and their metal complexes have been tested against a number of pathogenic fungi and bacteria at different concentrations and were found to possess sufficient fungicidal and bactericidal properties. Further, the complexes were also tested for their antifertility activity in male albino rats and the results were indeed positive.

• Korean Journal of Pharmacognosy
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• v.31 no.4
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• pp.449-454
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• 2000

In search for plant-derived cytotoxic compounds, it was found that the $CHCl_3$ and EtOAC extracts obtained from the flowers of Paulownia coreana Uyeki (Scrophulariaceae) exhibited significant cytotoxic activity against human tumor cell lines, A549, SK-OV-3, SK-MEL-2, XF498, and HCT15. Activity-guided fractionation on the basis of the inhibitory activity against the growth of human tumor cell lines, in vitro, and repeated column chromatography afforded several cytotoxic compounds from P. coreana. The structures and stereochemistry of these compounds were established, on the basis of analysis of spectra including IR, UV, EI-MS, $^{1}H-NMR,\;^{13}C-NMR$ and some chemical transformations, as Compound PCCl $(2-hydroxy-4(15),11(13)-eudesmadien-8{\beta},12-olide)$, Compound $PCC2(2,3-dihydro-4-hydroxy-1(15),11(13)-xanthadien-8{\beta},12-olide)$, Compound PCE1 (chrysophanol), Compound PCE2 (emodin), Compound PCE3 (physcion). Cytotoxic activity of compounds obtained from P. coreana. on five tumor cells lines was evaluated by procedure of SRB methods.