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Lee, Charles C.,Kim, Jong Hun,Kim, Ji Seung,Oh, Yun Sil,Han, Seung Min,Yoon Park, Jung Han,Lee, Ki Won,Lee, Chang Yong MDPI AG 2017 INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES Vol.18 No.7
<P>Several metabolomics of polymeric flavan-3-ols have reported that proanthocyanidins are extensively metabolized by gut microbiota. 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone (DHPV) has been reported to be the major microbial metabolite of proanthocyanidins. We demonstrated that DHPV has stronger prevention effect on tumor necrosis factor (TNF)-α-stimulated adhesion of THP-1 human monocytic cells to human umbilical vein endothelial cells compared to its potential precursors such as procyanidin A1, A2, B1 and B2, (+)catechin, (−)epicatechin and its microbial metabolites such as 3-(3,4-dihydroxyphenyl)propionic acid and 2-(3,4-dihydroxyphenyl)acetic acid. Mechanism study showed that DHPV prevents THP-1 monocyte-endothelial cell adhesion by downregulating TNF-α-stimulated expressions of the two biomarkers of atherosclerosis such as vascular cell adhesion molecule-1 and monocyte chemotactic protein-1, activation of nuclear factor kappa B transcription and phosphorylation of I kappa-B kinase and IκBα. We suggested that DHPV has higher potentiality in prevention of atherosclerosis among the proanthocyanidin metabolites.</P>
Lee, Charles C.,Dudonné,, Sté,phanie,Kim, Jong Hun,Kim, Ji Seung,Dubé,, Pascal,Kim, Jong-Eun,Desjardins, Yves,Park, Jung Han Yoon,Lee, Ki Won,Lee, Chang Yong Applied Science Publishers 2018 Food chemistry Vol.240 No.-
<P><B>Abstract</B></P> <P>Among many functional foods and their phytochemicals, ingestion of soybean (<I>Glycine max</I>) is highly correlated to reduced risk of cardiovascular diseases. Validation of potential health benefits of functional foods requires information about the bioavailability and metabolism of bioactive compounds. In this context, several phase I and II metabolites of isoflavones were target-analyzed in the plasma of rats acutely supplemented with soybean embryo extract. A daidzein metabolite, 7,8,4′-trihydroxyisoflavone (7,8,4′-THI), was found to have the highest average area under curve value (574.3±112.8). Therefore, its potential prevention effect on atherosclerosis was investigated using monocyte-endothelial cell adhesion assay. Different from its precursor daidzein or daidzin, 7,8,4′-THI attenuated adhesion of THP-1 monocytes to tumor necrosis factor-alpha (TNF-α) stimulated human umbilical vein endothelial cells (HUVECs). In addition, 7,8,4′-THI significantly downregulated TNF-α stimulated the expression of vascular cell adhesion molecule-1 and monocyte chemotactic protein-1 and phosphorylation of IκB kinase and IκBα involved in the initiation of atherosclerosis in HUVECs. Therefore, 7,8,4′-THI, a highly bioavailable hydroxylated isoflavone metabolite, has potential anti-atherosclerotic effect via inhibiting monocyte-endothelial adhesion.</P> <P><B>Highlights</B></P> <P> <UL> <LI> 7,8,4′-Trihydroxyisoflavone was found in the rat plasma after soybean intake. </LI> <LI> The highest average AUC of 7,8,4′-THI was 10 times higher than its precursor daidzein. </LI> <LI> 7,8,4′-THI inhibited TNF-α stimulated monocyte-endothelial cell adhesion. </LI> </UL> </P>
Lee, Charles C.,Dudonné,, Sté,phanie,Dubé,, Pascal,Desjardins, Yves,Kim, Jong Hun,Kim, Ji Seung,Kim, Jong-Eun,Park, Jung Han Yoon,Lee, Ki Won,Lee, Chang Yong Elsevier 2017 Food chemistry Vol.234 No.-
<P><B>Abstract</B></P> <P>Yak-Kong (YK) (<I>Glycine max</I>), a small black soybean cultivar with a green embryo, was evaluated for functional constituents with a focus on atherosclerosis prevention. In comparison to common yellow and black soybean cultivars, YK contains significantly higher concentrations of antioxidants, particularly in its seed coat. A comprehensive phenolic composition analysis revealed that proanthocyanidins were the major phenolic group in YK. In contrast to other proanthocyanidin-rich foods, YK was rich in bioavailable proanthocyanidins (with a degree of polymerization ≤3) specifically with A-type dimers. Significant concentrations of phloridzin and coumestrol were also exclusively found in YK seed coat and the embryo, respectively. Extracts of both the proanthocyanidin-rich seed coat and isoflavonoid-rich embryo of YK attenuated adhesion of THP-1 to LPS-stimulated human umbilical vascular endothelial cells, suggesting that they are important sources of coronary heart disease-preventive phenolics. YK has promising potential for further development as a functional food source targeted at atherosclerosis prevention.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Yak-Kong, a small black soybean with a green embryo, is rich in proanthocyanidins. </LI> <LI> Procyanidin A dimers and phloridzin are newly found in soybean seed coat. </LI> <LI> Significant amount of coumestrol is found in Yak-Kong soybean embryo. </LI> <LI> Both Yak-Kong seed coat and embryo attenuated monocyte-endothelial cell adhesion. </LI> </UL> </P>
김정균,이억석,두렌보스,Jack C. Kim,Lee Euk-suk,Charles C. Chang,Norman J. Doorenbos Korean Chemical Society 1975 대한화학회지 Vol.19 No.3
The intermediate, 17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(Ⅸ) required for the synthesis of 4-(${\beta}$-guanidinoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(V) was obtained through a reaction of 17${\alpha}$-methyl-3,5-seco-4-norandrostan-17${\beta}$-ol-5-on-3-oic acid(VI) with ammonium hydroxide followed by two reductions(platinum dioxide with hydrogen and lithium aluminium hydride). Condensation of Ⅸ with chloroacetonitrile under anhydrous condition, followed by reduction of the nitrile with lithium aluminium hydride gave 4-(${\beta}$-aminoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(XI). The reaction of XI with 2-methyl-2-thiopseudourea or 3,5-dimethylpyrazole-1-carboxamidine, or cyanamide provided the title compound, V. Relaxation of the nictitating membrane, in the absence of mydriasis, is considered to be evidence of adrenergic neurone blockade. Thus the test compound(V) resembles that of the classical adrenergic neurone blocking agents. 4-(${\beta}$-Guanidinoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(V)을 합성하는데에 필요한 중간화합물인 17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(IX)은 4단계를 거쳐 합성하였으며 IX을 chloroacetonitrile과 축합반응을 한후 $LiAlH_4$로서 환원하여 4-(${\beta}$-aminoethyl)-17${\alpha}$-methyl-4-aza-5${\alpha}$-androstan-17${\beta}$-ol(XI)을 얻었다. Tktle compound인 V은 3가지의 시약, 2-methyl-2-thiopseudourea,3,5-dimethylpyrazole-1-carboxamidine, cyanamide를 각각 XI와 반응시켜 좋은 수득률을 얻었다. 약리작용의 실험결과 V은 classical한 adrenergic neurone blocking agents와 유사하며 혈압강하제로서의 전망은 좋다고 예상된다.
PKCι Is a Promising Target Suppressing UVB-Induced MMP- 1 Expression by 7,8,4’-Trihydroxyisoflavone
Juyong Kim,Younghyun Lee,Jong-Eun Kim,Sohee Baek,Charles C. Lee,Ki Won Lee,Jun Seong Park,Deok-kun Oh,Zigang Dong,Chang Yong Lee,Ann M Bode,Hanyong Chen 한국식품영양과학회 2014 한국식품영양과학회 학술대회발표집 Vol.2014 No.10
Ehsan Dowlati,Kory B. Dylan Pasko,Jiaqi Liu,Charles A. Miller,Daniel R. Felbaum,Samir Sur,Jason J. Chang,Ai-Hsi Liu,Rocco A. Armonda,Jeffrey C. Mai 대한신경중재치료의학회 2021 Neurointervention Vol.16 No.3
In-stent stenosis is a feared complication of flow diversion treatment for cerebral aneurysms. We present 2 cases of patients treated with pipeline flow diversion for unruptured cerebral aneurysms. Initial perioperative dual antiplatelet therapy (DAPT) consisted of standard aspirin plus clopidogrel. At 6-month follow-up cerebral angiography, the patients were noted to have developed significant in-stent stenosis (63% and 53%). The patients were treated with cilostazol and clopidogrel for at least 6 months. Subsequent angiography at 1-year post-treatment showed significant improvement of the in-stent stenosis from 63% to 34% and 53% to 21%. The role of cilostazol as treatment of intracranial in-stent stenosis has not been previously described. Cilostazol’s vasodilatory effect and suppression of vascular smooth muscle proliferation provides ideal benefits in this setting. Cilostazol plus clopidogrel may be a safe and effective alternative to standard DAPT for treatment of in-stent stenosis following flow diversion and warrants further consideration and investigation.