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      • SCOPUSKCI등재

        Reaction of Thianthrene Cation Radical Perchlorate with Cumene Hydroperoxides

        신종헌,김경태,Jongheon Shin,Kyongtae Kim Korean Chemical Society 1983 대한화학회지 Vol.27 No.2

        아세토니트릴용액중의 티안트렌 양이온 라디칼 과염소산 염(1)은 Cumene hydroperoxide(4), p-chlorocumene hydroperoxide(2), p-nitrocumene hydroperoxide(3)와 상온에서 반응한다. 이 반응의 공통 생성물로서 티안트렌을 얻었으며 4로 부터 5-(4'-hydroxyphenyl) thianthrenium perchlorate (5), 2로부터 5-(5'-chloro-2'-hydroxyphenyl) thianthrenium perchlorate (7)와 5-acetonylthianthrenium perchlorate (6), 그리고 3으로부터 6만을 얻었다. 이 반응의 양관계는 1의 2몰이 티안트렌 1몰과 티안트렌이움 염(또는 염들) 1몰을 생성한다. 1에 대한 친핵성 활성도는 페놀 > > p-클로로페놀 ${\sim}$아세톤 > > p-니트로페놀 순서임이 밝혀졌다. Hydroperoxide의 산촉매 불균일 분해반응외에도 소량의 균일분해 반응생성물이 3과 4로부터 생성됨을 알았다. Reaction of thianthrene cation radical perchlorate (1) with cumene (4), p-chlorocumene (2), and p-nitrocumene (3) hydroperoxides in acetonitrile at room temperature afforded, inter alia, thianthrene as a common product and 5-(4'-hydroxyphenyl) thianthrenium perchlorate (5) for 4, 5-(5'-chloro-2'-hydroxyphenyl) thianthrenium perchlorate (7) and 5-acetonylthianthrenium perchlorate (6) for 2 and 6 for 3, respectively. Stoichiometry of these reactions showed that 2 moles of 1 gave rise to 1mole of thianthrene and 1 mole of thianthrenium salt (or salts). Nucleophilic reactivity to 1 was found to be in the order of phenol > > p-chlorophenol ${\sim}$ acetone > > p-nitrophenol. Apart from acid-catalyzed heterolytic decomposition of hydroperoxides, small amount of homolytic decomposition products were found from 3 and 4.

      • KCI등재

        Two Biophenolic Glycosides from Portulaca oleracea

        서영완,신종헌,이범종,이동석,Youngwan Seo,Jongheon Shin,Burm Jong Lee,Dong Seok Lee Korean Chemical Society 2003 대한화학회지 Vol.47 No.1

        우리나라에 널리 분포하며 오래 동안 약용으로 사용되어 온 쇠비름으로부터 페놀 글리코시드인 3-hydroxy-1(2-hydroxyethyl)phenyl-4-O-${\beta}$-D-glucopyranoside(1)과 2-(3,4-dihydroxyphenyl)ethyl-O-${\beta}$-D-glucopyranoside (2)를 칼럼 크로마토그래피 및 역상 HPLC로 분리하였으며, NOESY, HMQC, HMBC와 같은 이차원적인 NMR 분광실험에 의해서 이 물질들의 $^{13}C$ NMR 분광 데이터 값의 지정이 수정되었다. DPPH를 이용하여 이 물질들의 항산화 활성을 측정한 결과 주목할 만한 활성을 나타내었다. From Portulaca oleracea which is widely distributed in Korea and has long been used as a folk medicine, two biophenolic glycosides, 3-hydroxy-1-(2-hydroxyethyl)phenyl-4-O-${\beta}$-D-glucopyranoside (1) and 2-(3,4-dihydroxyphenyl) ethyl-O-${\beta}$-D-glucopyranoside (2) were isolated using column chromatography and reversed-phase HPLC. $^{13}C$ NMR spectral assignment for these compounds was revised by the extensive 2-D NMR experiments such as NOESY, HMQC, and HMBC. These compounds showed a considerable antioxidant effect in DPPH assay system.

      • KCI우수등재
      • KCI등재

        HPLC-DAD-ion trap-MS를 이용한 인동 생리활성 물질의 동시분석

        유성광(Sungkwang Ryu),원태형(Tae Hyung Won),강삼식(Sam Sik Kang),신종헌(Jongheon Shin) 대한약학회 2010 약학회지 Vol.54 No.3

        A high-performance liquid chromatography (HPLC) with DAD detector and electrospray ionization mass spectrometry (ESI-MS) was established for the simultaneous determination of coniferin (1), loganic acid (2), demethylsecologanol (3), sweroside (4) and loganin (5) from caulis Lonicera joponica. The optimal chromatographic conditions were obtained on an ODS column (5 μm, 4.6×150 mm) with the column temperature 35oC. The mobile phase was composed of (A) water with 0.1% formic acid and (B) methanol with 0.1% formic acid using a gradient elution, the flow rate was 0.3 ml/min. Detection wavelength was set at 254 nm. All calibration curves showed good linear regression (r2>0.998) within test ranges. The developed method provided satisfactory precision and accuracy with overall intra-day and interday variations of 0.16~3.28% and 0.14~1.99%, respectively, and the overall recoveries of 99.39~105.89% for the five compounds analyzed. The verified method was successfully applied to quantitative determination of the two types (phenolic compounds and iridoids) of bioactive compounds in 24 commercial caulis L. japonica samples from different markets in Korea and China. The analytical results demonstrated that the contents of the five analytes vary significantly with sources.

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