• Title/Summary/Keyword: $C_8$-methoxy

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Anthraquinone and Stibene Derivatives from the Cultivated Korean Rubbarb Rhizomes

  • Ko, Sung-Kwon;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.18 no.4
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    • pp.282-288
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    • 1995
  • The sutdies were carried out to evaluate the consituents in the rihzomes of the cultivated Korean Rhubarb (Polygonaceae). From the acetone fraction ofl methanol extract Compound I (1, 8-dihydroxy-3-methyl anthraquinone, chrysophanic acid), Compound II($chrysophanol-8-O-{\beta}-D-glucopyranoside$), Compound III ($emodin-8-O-{\beta}-D-glucopyranoside$) and Compound IV ($aloe-emodin-8-O-{\beta}-D-glucopyranoside$), and from the ether fraction Compound V(1, 8-dihydorxy-3-emthyl-6-methoxy anthraquinone, physcion) and Compound VI (1, 6, 8-thitydroxy-3-emthyl anthrauinone, emodin), and also from the n-buthanol fraction Compound VII ($rhapontigenin-3-O-{\beta}-D-glucopyranoside, rhaponticin$) and Compound VIII ($piceatannol-3'-O-{\beta}-D-glucopyranoside$), were isolated and identified on the basis of their physico-chemical and spectroscopic evidences (UV, IR, H-NMR, C-NMR, EI-MS), respectively.

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Understanding the protox inhibition activity of novel 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives using comparative molecular field analysis (CoMFA) methodology (비교 분자장 분석 (CoMFA) 방법에 따른 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluoro-benzene 유도체들의 Protox 저해 활성에 관한 이해)

  • Sung, Nack-Do;Song, Jong-Hwan;Yang, Sook-Young;Park, Kyeng-Yong
    • The Korean Journal of Pesticide Science
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    • v.8 no.3
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    • pp.151-161
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    • 2004
  • Three dimensional quantitative structure-activity relationships (3D-QSAR) studies for the protox inhibition activities against root and shoot of rice plant (Orysa sativa L.) and barnyardgrass (Echinochloa crus-galli) by a series of new A=3,4,5,6-tetrahydrophthalimino, B=3-chloro-4,5,6,7-tetrahydro-2H-indazolyl and C=3,4-dimethylmaleimino group, and R-group substituted on the phenyl ring in 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2chloro-4-fluorobenzene derivatives were performed using comparative molecular field analyses (CoMFA) methodology with Gasteiger-Huckel charge. Four CoMFA models for the protox inhibition activities against root and shoot of the two plants were generated using 46 molecules as training set and the predictive ability of the each models was evaluated against a test set of 8 molecules. And the statistical results of these models with combination (SIH) of standard field, indicator field and H-bond field showed the best predictability of the protox inhibition activities based on the cross-validated value $r^2_{cv.}$ $(q^2=0.635\sim0.924)$, conventional coefficient $(r^2_{ncv.}=0.928\sim0.977)$ and PRESS value $(0.091\sim0.156)$, respectively. The activities exhibited a strong correlation with steric $(74.3\sim87.4%)$, electrostatic $(10.10\sim18.5%)$ and hydrophobic $(1.10\sim8.30%)$ factors of the molecules. The steric feature of molecule may be an important factor for the activities. We founded that an novel selective and higher protox inhibitors between the two plants may be designed by modification of X-subsitutents for barnyardgrass based upon the results obtained from CoMFA analyses.

Polyacetylene Compounds from Panax ginseng C.A. Meyer (인삼의 Polyacetylene 화합물)

  • Shim Sang Chul;Chang Suk-Ku
    • Proceedings of the Ginseng society Conference
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    • 1988.08a
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    • pp.122-128
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    • 1988
  • Several major polyacetylene compounds were isolated from the petroleum-ether fraction of fresh Korean ginseng roots through solvent fractionation. partition and silica gel column chromatography. Further separation of acetylenic compounds was accomplished by bonded normal phase HPLC utilizing a moderately nonpolar microparticulate column. The preparative separation for the various spectral measurements was carried out by low pressure preparative liquid chromatography. The chemical structure of these polyacetylenes separated was determined by UV. IR/FTIR. $^{1}H$ NMR. mass spectral and elemental analysis. These are identified to be heptadeca-1-en-4.6-diyn-3.9.l0.-triol [1] heptadeca-1.9-dien-4.6-diyn-3-ol. heptadeca-1.8-dien-4.6-diyn-3.10-diol and the 4th was denatured polyacetylene. heptadeca-1.4-dien-6.8-diyn-3.10-diol. Two different p-substituted benzoates of panaxynol were synthesized for the determination of exciton chirality. The circular dichroism spectra in the UV region show that panaxynol p-bromobenzoate and p-dimethyl-aminobenzoate constitute negative exciton chirality [2]. Isolated major polyacetylene compounds were irradiated in aerated solution with 300 nm UV light to obtain the oxidized product at the allylic alcohol center to corresponding carbonyl compounds such as heptadeca-1-en-4.6-diyn-9.10-diol-3-one and heptadeca-1.9-dien-4.6-diyn-3-one. These photooxidation compounds have en-on-diyne chromophore and undergo nucleophilic addition reaction with methanol to yield ${\beta}-methoxy$ carbonyl compounds such as heptadeca-9-en-4.6-diyn-1-methoxy-3-one and heptadeca-4.6-diyn-1-methoxy-9.10-diol-3-one.

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Determination of 10${\alpha}$-Methoxy-9,10-dihydrolysergol (MDL), Main Metabolite of Nicergoline, in Human Plasma by HPLC-MS and Applicability to Oral Bioavailability in Korean Healthy Male Volunteers (HPLC-MS를 이용한 생체시료 중 니세르골린의 주대사체인 10${\alpha}$-Methoxy-9,10-dihydrolysergol(MDL)의 분석 및 이를 이용한 한국인 성인 남성에 대한 생체이용률 응용)

  • Lim, Hyon-Kyun;Yoo, Sun-Dong;Kim, Kyeong-Ho;Han, Sang-Beom;Youm, Jeong-Rok
    • YAKHAK HOEJI
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    • v.51 no.2
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    • pp.133-139
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    • 2007
  • A simple and sensitive HPLC-MS method for quantitation of 10${\alpha}$-methoxy-9,10-dihydrolysergol (MDL), the main metabolite of nicergoline, in human plasma was developed and the bioavailability parameters of MDL was assessed in Korean healthy male volunteers. Clomipramine was used as an internal standard. MDL and internal standard in plasma sample were extracted using ethyl acetate. A centrifuged upper layer was then evaporated and reconstituted with mobile phase of 10 mM ammonium acetate-acetonitrile (10 : 90, v/v). The reconstituted samples were injected into a Zorbax SB-C8 column (2.1${\times}$150 mm,5 ${\mu}$m) at a flow-rate of 0.3 ml/min. Using MS with selected ion monitoring (SIM) mode, MDL and clomipramine were detected without severe interference from human plasma matrix. MDL produced a protonated molecular ion ([M+H]$^+$) at m/z 287. Internal standard produced a protonated molecular ion ([M+H]$^+$) at m/z 315. A linear relationship for MDL was found in the range of 2.5${\sim}$100 ng/ml. The lower limit of quantitation (LLOQ) was 2.5 ng/ml with acceptable precision and accuracy. The intra- and inter-day validation for all coefficients of variation (R.S.D.%) were found less than 15%. Main pharmacokinetic parameters of 30 mg of nicergoline were revealed as follows: AUC$_t$ 321.1${\pm}$64.5 ng${\cdot}$hr/ml, C$_{max}$, 51.2${\pm}$25.3 ng/ml, T$_{max}$ 3.6${\pm}$1.5 hr, K$_{el}$ 0.12${\pm}$0.07 hr$^{-1}$ and t$_{1/2}$ 7.6${\pm}$3.4 hr. Inter subject variations and race differences were shown in comparison with the published data in the literature.

A New Compound Isolation and Structure Analysis from Phellodendron Amurense Fruit Extract (황벽나무 열매 추출물로부터 신규 화합물의 분리 및 구조분석)

  • Kim, Young-Hee;Choi, Jung Eun;Hong, Jin-Young;Jo, Chang Wook;Lee, Jeung-Min;Kim, Soo Ji
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.4
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    • pp.269-275
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    • 2013
  • Antifungal and insecticidal activity of Korean traditional medicinal plants was carried out to develop natural material for the development of organic cultural heritage conservation. As a result, Phellodendron amurense fruit was finally selected as a candidate of antifungal and insecticidal natural material. An novel active compound was purified from the ethylacetate fraction of Phellodendron amurense fruits using silica gel and Sephadex LH-20 column chromatography and PTLC. The compound was obtained as yellow oil form; UV ${\lambda}_{max}$(MeOH): 260 nm. The chemical structure of novel compound was determined as (4'-ethyl-2'-methylfuranyl)-6-methoxy-7-methylnona-2E,4E,6Z,8E-tetraenoic acid on the basis of various NMR experiments including $^1H$- and $^{13}C$-NMR, HMQC, HMBC and ESI-mass spectrum.

Structure Activity Relationship of ar-Turmerone Analogues

  • Baik, Kyong-Up;Jung, Sang-Hun;Ahn, Byung-Zun
    • Archives of Pharmacal Research
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    • v.16 no.3
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    • pp.219-226
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    • 1993
  • For the analysis of structure relationship of ar-turmerone analogues, the compounds containing the various substituents on the phenyl ring and 1(or 2)-naphthyl group in the place of phenyl of ar-turmerone were prepared and tested their cytotoxicity against HL-60, K-562, and L1210 leukemia cells in vitro. The substituents at para position are methoxy, phenoxy, methyl, trifluoromethyl, fluoro, and chloro. At meta position methoxy, methyl, trifluoromethyl, or chloro groups at ortho position mathoxy or chloro group were introduced. Against HL-60 and K-562 cells, $ED_{50}$ values of the analogues are ranged from 0.8 to $30.0\;\mu{g/ml}$. Againste L1210 cell, these are located more than $20.0\;\mu{g/ml}$. However, 5-carbone-thoxy-2-methyl-6(1-naphthyl)-2-octen-4-one (5n)possesses $ED_{50}$ valuses 0.8, 2.1, $6.5\;\mu{g/ml}$ against HL-60, L1210 cells, respectively. The electronic nature of the substituents on phenyl ring of ar-tumerone dose not affect the biological activity. Therefore the flat structure of aromatic potion of ar-tumerone analogues is the more important factor for their activity rather than its electronic nature. The potentiation of the cytotoxicity with the enlargement of aromatic ring region also supports the importance of the plane structure of this area. The restriction of the single bond rotation between C-6 and aromatic ring through the introduction of substituents at the ortho position of phenyl ring and the increment of size of alkyl group at C-6 position enhances the activity. Therefore the effective conformation should by the one having the orthogonal arrangement between the aromatic ring and the side chain.

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Preparations of (Yl-xGdx)2O3:Eu3+ Phosphors Particles by. Solvothermal Synthesis Using the 2-Methoxy Ethanol (2-메톡시에탄올을 사용한 용매열 합성법에 의해 합성되어진 (Yl-xGdx)2O3:Eu3+ 형광체입자)

  • Shin, Su-Cheol;Cho, Tae-Hwan
    • Korean Journal of Materials Research
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    • v.13 no.8
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    • pp.537-542
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    • 2003
  • ($Y_{l-x}$ $Gd_{x}$ )$O_2$$_3$: $Eu^{ 3+}$ red phosphors were prepared with the solvothermal synthesis using the 2-methoxy-ethanol solvents and the emission intensity was investigated that applied with the 254 nm wavelength and the maximum excitation wavelength for energy source. The used solvents for the solvothermal synthesis were made of nitrate salt solutions of Y, Gd and Eu. These solutions dropped in autoclave have be reacted with the solvothermal synthesis at $200^{\circ}C$ for 5hrs and the red phosphors prepared here in were showed the pure cubic phase after annealing at $1000∼1200^{\circ}C$. The brightness of ($Y_{l-x}$ $Gd_{x}$)$_2$$O_3$: $Eu^{3+}$ phosphors particles was increased as an increase of Gd ratio. The maximum excitation wavelengths of ($Y_{l-x}$ $Gd_{x}$ )$_2$$O_3$: $Eu^{3+}$ / phosphors particles were increased according to increasing Gd ratio from 253 nm to 259 nm wavelength. The maximum emission intensity of $Gd_2$$O_3$: $Eu^{3+}$ (Y/Gd = 1/0) phosphors particles under UV 259 nm was found to be higher than the commercial product of $Y_2$$O_3$: $Eu^{3+}$ phosphors.

Synthesis of Novel D-Glucose-derived Benzyl and Alkyl 1,2,3-Triazoles as Potential Antifungal and Antibacterial Agents

  • Wei, Jin-Jian;Jin, Lei;Wan, Kun;Zhou, Cheng-He
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.229-238
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    • 2011
  • A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^{13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.

Isolation and Purification of Berberine in Cortex Phellodendri by Centrifugal Partition Chromatography (Centrifugal Partition Chromatography에 의한 황백으로부터 Berberine의 분리 및 정제)

  • Kim, Jung-Bae;Bang, Byung-Ho
    • The Korean Journal of Food And Nutrition
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    • v.27 no.3
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    • pp.532-537
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    • 2014
  • Cortex Phellodendri (CP) is derived from the dried bark of Phellodendron amurense. It has been widely used as a drug in traditional Korea medicine for treating diarrhea, jaundice, swelling pains in the knees and feet, urinary tract infections, and infections of the body surface. Many analytical methods have been used to study oriental herbal medicines, such as thin-layer chromatography, column liquid chromatography, and high performance liquid chromatography (HPLC). In this study, preparative centrifugal partition chromatography (CPC) was successfully carried out in order to separate pure compounds from a CP methanol extract. The optimum two-phase CPC solvent system was composed of n-butanol: acetic acid: water (4:1:5 v/v/v). The flow rate of the mobile phase was 3 mL/min in ascending mode with rotation at 1,000 rpm. The CPC-separated fraction and purification procedures were carried out by preparatory HPLC. The $^1H$ NMR spectrum revealed that the resonances at ${\delta}$ 4.10 and 4.20 ppm corresponded to three protons ($-OCH_3$), whereas those at ${\delta}$ 6.10 ppm corresponded to two protons ($-OCH_2O-$). Further, two aromatic protons (H-11 and H-12) conveys a doublet-doublet pattern. The H-11 doublet and H-12 doublet appear at ${\delta}$ 7.98 and 8.11, respectively. The $^{13}C$ NMR. spectrum showed a tetrasubstituted with a methylenedioxy group at C2 and C3, and two methoxy groups at C9 and C10. The chemical structure of the berberine was identified by $^1H$, $^{13}C$-nuclear magnetic resonance and electrospray ionization-mass spectroscopy spectral data analysis.

Phytochemical and Antioxidant Activity of Spathodea campanulata P. Beauvois. Growing in Egypt

  • Nazif, Naglaa M.
    • Natural Product Sciences
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    • v.13 no.1
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    • pp.11-16
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    • 2007
  • Alcoholic extract of Spathodea campanulata P. aerial parts, and two of the isolated fractions from celite column showed strong antioxidant activity (92, 94 & 89% RSA, Radical Scavenging Activity). Phytochemical investigation of chloroform/EtOAc faction of this column led to the isolation of phenolic acids, caffiec acid (1), and ferulic acid (2), fraction EtOAc/MeOH on further fractionation afforded 3 Flavonoids, kampferol 3-O-glucoside (3), quercetin 3-methyl ether (4) and 8-methoxy kampferol 3-O-glucoside (5). The isolated constituents were identified by co chromatography with authentic samples, TLC, PC., UV, MS and $^1H-NMR$. Also the lipoidal matter of the plant was studied. The unsaponifiable matter was found to be mixture of hydrocarbons from $(C_{14}-C_{28})$, cholesterol, campasterol, stigmasterol, and ${\alpha}-amyrin$. Fatty acid methyl esters were found to contain 12 fatty acids. The fatty acids containing $C_{18}$ farmed ca.65% of the total mixture.