• Bulletin of the Korean Chemical Society
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• v.14 no.4
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• pp.428-430
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• 1993

• Bulletin of the Korean Chemical Society
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• v.13 no.3
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• pp.343-344
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• 1992

• Journal of Society of Preventive Korean Medicine
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• v.11 no.1
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• pp.1-8
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• 2007

Curcumin and its analogues(Tetrahydrocurcumin THC, demethoxycurcumin ; BDMC and dimethoxycurcumin DiMC) were compared for their ability to inhibit the growth of human leukemia HL-60 cells. The growth of HL-60 cells was inhibited by curcumin, DeMC and DiMC, but not by THC lacking ${\alpha},{\beta}-unsaturated$ carbonyl groups thus suggesting that ${\alpha},{\beta}-unsaturated$ carbonyl groups are crucial for antiproliferative activity. The order of antiproliferative activity was DiMC, curcumin and BDMC indicating that the number of methoxy groups on the aromatic rings of the active compounds plays an important role in enhancing anti-proliferating activity. In comparison with cellular uptake of the active compounds, uptake capacity was found to be highest with DiMC, followed by curcumin and BDMC. Therefore, it is most likely that the differential antiproliferative activities of DiMC, curcumin and BDMC are associated with their capacities of cellular uptake resulting in building up of enough concentration inside the cells.

• Journal of Ginseng Research
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• v.38 no.1
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• pp.34-39
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• 2014

Cigarette smoke is considered a major risk factor for vascular diseases. There are many toxic compounds in cigarette smoke, including acrolein and other ${\alpha},{\beta}$-unsaturated aldehydes, which are regarded as mediators of inflammation and vascular dysfunction. Furthermore, recent studies have revealed that acrolein, an ${\alpha},{\beta}$-unsaturated aldehyde in cigarette smoke, induces inflammatory mediator expression, which is known to be related to vascular diseases. In this study, we investigated whether Korean Red Ginseng (KRG) water extract suppressed acrolein-induced cyclooxygenase (COX)-2 expression in human umbilical vein endothelial cells (HUVECs). Acrolein-induced COX-2 expression was accompanied by increased levels of phosphorylated p38 in HUVECs and KRG inhibited COX-2 expression in HUVECs. These results suggest that KRG suppresses acrolein-induced COX-2 expression via inhibition of the p38 mitogen-activated protein kinase signaling pathway. In addition, KRG exhibited an inhibitory effect on acrolein-induced apoptosis, as demonstrated by annexin Vepropidium iodide staining and terminal deoxynucleotidyl transferase-mediated dUTP nick end-labeling assay. Consistent with these results, KRG may exert a vasculoprotective effect through inhibition of COX-2 expression in acrolein-stimulated human endothelial cells.

• Applied Biological Chemistry
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• v.38 no.5
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• pp.473-477
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• 1995

The dichloromethane extracts of the above ground parts of Hymenoxys brachyactis afforded three sesquiterpene lactones already reported, one new sesquiterpene lactone, biennin C and hispidulin as known toxic flavone. Structures of all compounds were established by spectroscopy and biennin C was determined as an adduct of the modified pseudoguanolide and hymenoxon by Gas Chromatograpy and MS spectrometer These sesquiterpene lactones have the same ${\alpha},{\beta}$-unsaturated functional group like that of hymenovin which has been known as major toxic constituent of important livestock poison. And biennin C is also considered as toxic compound because of toxic hymenoxon.

• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.742-745
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• 2010

• Archives of Pharmacal Research
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• v.16 no.3
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• pp.254-256
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• 1993

For the evaluation of the role of .alpha., .betha.-unsaturated ketone portion of ar-tumerone for its activity, the structural variation of this structural unit was performed to omit its alkylating propery. Thus compounds 2, 3, and 4 were prepared and their cytotoxicities were determined against three different leukemiz cell lines (HL-60, K-562, and $L_{1210})$ in vitro. The biological inactivity against three different cell lines of these analogues implies that the $\alpha, \beta$-unsaturated ketone of ar-tumerone is the essential pharmacophore for its activity.

• The Korean Journal of Pesticide Science
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• v.2 no.3
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• pp.45-51
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• 1998

A series of bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives with mesaured fungicidal activities in vivo against rice blast(Pyricularia oryzae), tomato leaf blight (Phytophtora infestans) and barley powdery mildew(Erysiphe graminis) were studied by using quantitative structure activity relationship equations. The QSAR model for the activity of phenyl substituents, $1{\sim}11$, clearly reveals three important factors, namely, resonance(R<0), optimal molecular hydrophobicity(${\pi})_{opt.}=0.38$) and optimal distance($((L_{1})_{opt.}=5.69({\AA}))$ of substituent, respectively. But in case of 2-pyridyl substituents, $12{\sim}28$, the activity were governed by optimal molecular refractivity $((M_{R})_{opt.}=8.04{\sim}39cm^{3}/mol)$, steric effect(Es<0) and LUMO energy(e.v). The fungicidal activity relationship of phenyl and 2-pyridyl substituents against Erysiphe graminis have been proportioned.

• Applied Biological Chemistry
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• v.44 no.3
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• pp.191-196
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• 2001

${\alpha},{\beta}$-Unsaturated carboxanilides 5 with trifluromethylated dihydro-1,4-oxathiins were synthesized for the development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}-keto$ ester 6 followed by the reaction with 1,2-mercaptoethanol gave intermediate 1,4-oxathiane 11. Without purification of 11, substitution of hydroxy group by chlorine, followed by dehydrochlorination of 10 in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-oxathiin ethyl ester 9. Acylation of the hydroxy group of the carboxylic acid 12 followed by treatment of various amines gave the corresponding trifluoromethylated dihydro-1,4-oxathiin carboxamides 5. Antifungal screening (in vivo) of the synthesized compounds against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Where meta position of the phenyl group was substituted with isopropoxy or isopropyl group, excellent antifungal activities against rice sheath blight and wheat leaf rust were detected.

• Bulletin of the Korean Chemical Society
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• v.31 no.10
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• pp.2776-2782
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• 2010

Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford $\beta,\gamma$-unsaturated $\alpha$-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/$H_2$ (1 atm) to give the corresponding $\alpha$-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic protocols, and have previously been prepared only from carboxylic acids/acid chlorides. Our new approaches provide excellent alternatives for the synthesis of triphenylphosphorane ylide precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units directly from carbonyl compounds in good to excellent yields.