• Title/Summary/Keyword: Piperidine

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Enhancement of Piperidine Alkaloid Contents by Lactic Acid Fermentation of Mulberry Leaves (Morus alba L.) (뽕잎의 유산발효에 의한 Piperidine Alkaloid 함량 증진)

  • Ryu, Il Hwan;Kwon, Tae Oh
    • Korean Journal of Medicinal Crop Science
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    • v.20 no.6
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    • pp.472-478
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    • 2012
  • This study was carried out to investigate solid-state fermentation method using cellulolytic lactic acid bacteria Lactobacillus plantarum TO-2100 in order to increase piperidine alkaloid contents in mulberry leaves. Piperidine alkaloid, one type of which include 1-deoxynojirimycin (1-DNJ), is known to inhibit ${\alpha}$-glycosidase activities. Using this strain, the optimal solid-state fermentation conditions on mulberry leaves powder were found as the following: initial moisture content, temperature and relative humidity were 20%, $30{\sim}35^{\circ}C$ and 60 ~ 70%, respectively, and the fermentation time was 72 hrs. The piperidine alkaloid contents in the fermented mulberry leaves were 2.86% on dry powder, which is 7-fold increase from that of non-fermented mulberry leaves. The 1-deoxynojirimycin contents after applying preparative thin layer chromatography were 2.02% on dry powder, which is 8 times higher than that of non-fermented mulberry leaves. ${\alpha}$-Glycosidase activities was inhibited by 65.7 ~ 84.7% with 3 ~ 5% treatments of hot-water extracts of the fermented mulberry leaves, compared to 16.2 ~ 40.2% with 3 ~ 5% treatments of hot-water extracts of non-fermented mulberry leaves. Therefore, the results suggest that solid-state fermentation method does indeed increase of piperidine alkaloid contents on mulberry leaves.

Solid-phase Parallel Synthesis of a Novel N-[Alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted Amide and Amine Drug-like Libraries

  • Kim, Ji-Hye;Gong, Young-Dae;Lee, Gee-Hyung;Seo, Jin-Soo
    • Bulletin of the Korean Chemical Society
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    • v.33 no.1
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    • pp.128-136
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    • 2012
  • We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivatives were obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions on the resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.

Model Test on the Loss of Experimental Fishy Odor in Tilapia, Oreochromis niloticus, by Sea Water Acclimation (해수순치에 의한 틸라피아의 담수어취 제거에 관한 모델 시험)

  • YOON Ho-Dong;SUH Sang-Bok;KIM Yeong-Sook;LEE Jong-Ho
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.29 no.4
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    • pp.431-437
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    • 1996
  • The efforts of removing the specific fresh water fishy odor were studied by inducing tilapia, Oreochromis niloticus, to sea water in the use of the flavoring chemicals such as pyrrolidine and piperidine as experimental flavors. The amines added to the grinded muscle of tilapia were recovered by $88\%$ for pyrrolidine and $90\%$ for piperidine. When live tilapia were retained in a tank containing 100 ppm solution of the flavor for 30 min and then begun to start the acclimation into sea water with daily increase of $5\%_{\circ}$ salinity within 7days, no amines in the skin and the muscle of tilapia were detected after 4 days of acclimation to sea water. For the purge effects of amino in the skin and the muscle of tilapia, the concentration of pyrrolidine and piperidine lost $73.4\%,\;83.7\%$ in the muscle and $93.6\%,\;90.6\%$ in the skin of tilapia after purging in fresh water for 72 hrs, while $66.2\%,\;73.6\%$ of amines were removed in the muscle and $90.1\%,\;87.7\%$ in the skin of tilapia acclimated to sea water after purging in on sea water for 72hr. Loss rates of pyrrolidine and piperidine were found to be $0.0231h-^{1}\;and\;0.0333\;h^{-1}$ from the muscle and $0.0652h-^{1}\;0.0413\;h^{-1}$from the skin of tilapia in the fresh water, while $0.0131h-^{1}\;and\;0.0354\;h^{-1}$ from the muscle, $0.0674h-^{1}\;and\;0.0549\;h^{-1}$ from the skin of tilapia in the sea water after 24hrs of exposure, respectively.

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The Effect of Functional Group Position of the Piperidine Derivatives on the CO2 Absorption Characteristics in the (H2O-Piperidine-CO2) System ((H2O-Piperidine-CO2) system에서 piperidine 유도체의 작용기 위치에 따른 이산화탄소 흡수특성 연구)

  • Choi, Jeong Ho;Yun, Soung Hee;Kim, Yeong Eun;Yoon, Yeo Il;Nam, Sung Chan
    • Korean Chemical Engineering Research
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    • v.53 no.1
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    • pp.57-63
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    • 2015
  • Absorption characteristics of 2-methylpiperidine (2MPD), 3-methylpiperidine (3MPD) and 4-methylpiperidine (4MPD) absorbents were studied by a vapor-liquid equilibrium (VLE) apparatus and a differential reaction calorimeter (DRC). Using a VLE apparatus, the $CO_2$ loading capacity of each absorbent was estimated. After reaching the absorption equilibrium, nuclear magnetic resonance spectroscopy (NMR) had been conducted to characterize the species distribution of the ($H_2O$-piperidine-$CO_2$) system. Using a DRC, the reaction of heat was confirmed in accordance with the absorption capacity. The unique characteristics of 2MPD, 3MPD and 4MPD absorbents appeared by the position of methyl group. The 2MPD possessing the methyl group at the ortho position showed its hindrance effect during the absorption process; however, piperidine derivatives possessing the meta position and para position did not show its characteristics in $H_2O$-piperidine-$CO_2$ system.

Synthesis and Analytical Application of Piperidine Dithiocarbamate Complex of Copper(II) (피페리딘 디티오카바메이트의 구리(II)의 착물합성과 분석적 응용)

  • Kim, Chan-Woo;Kim, Chang-Su
    • Analytical Science and Technology
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    • v.12 no.1
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    • pp.1-6
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    • 1999
  • Copper(II) complex of piperidine dithiocarbamate (Pipdtc) was synthesized from the reaction of Cu(II) and piperidine dithiocarbamate. The possible structure of the complex was proposed on the basis of elemental analysis, molar conductivity, infrared spectroscopy, electronic absorption spectroscopy, and $^{13}C-NMR$ studies. The extraction of copper(II)-Pipdtc complex by carbon tetrachloride can be achieved in the pH range of 6.0~10. The solution of copper(II) with piperidine dithiocarbamate was bey Beer's law in the concentration up to ${\sim}8.0{\times}10^{-5}M$ at pH 9.0.

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Aminomethylation of 5-Phenylhydantoin (5-Phenylhydantoin의 아미노메칠화 반응)

  • 권순경
    • YAKHAK HOEJI
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    • v.26 no.2
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    • pp.111-116
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    • 1982
  • The behavior of the 5-phenylhydantoin (5-phenyl-2, 4-imidazolidinedione) ring in the aminomethylation reaction was studied in order to determine the orientation of this substitution. In case of monoaminomethylation, 3-morpholinomethyl-5-phenylhydantoin (or 3-piperidinomethyl-5- phenylhydantoin) was synthesized by the condensation of 5-phenylhydantoin with one mole of morpholine (or piperidine) and one mole of formaldehyde. 1, 3-Dimorpholinomethyl- 5-phenylhydantoin was obtained in the attempted condensation of 5-phenylhydantoin with two moles of morpholine and two moles of formaldehyde. Despite the close resemblance to morpholine the attempted condensation of 5-phenylhydantoin with piperidine and formaldehyde under reflux gave no expected 1, 3-dipiperidinomethyl -5-phenylhydantoin. In case of diaminomethylation using piperidine and formaldehyde, only 3, 5-dipiperidinomethyl-5-phenylhydantoin was formed.

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Piperoctadecalindine, a New Piperidine Alkaloid from Piper retrofractum Fruits

  • Ahn Jong Woong;Lee Chong Ock;Kim Eun Joo;Zee Ok Pyo;Kim Hyung Jin
    • Bulletin of the Korean Chemical Society
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    • v.13 no.4
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    • pp.388-391
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    • 1992
  • A chemical investigation of the fruits of Piper retrofractum (Piperaceae) has led to the isolation and characterization of a novel piperidine alkaloid, piperoctadecalidine together with three known alkaloids piperine, pipernonaline and guineensine. The structure of the new compound was detemined to be (2E,4E,14Z)-N-(2,4,14-Octadecatrienoyl) piperidine by spectral and synthetic methods.

Synthesis of ${\beta}$-Acetyl-${\beta}$-benzoylstyrene Derivatives and Their Adducts of Piperidine (${\beta}$-아세틸-${\beta}$-벤조일스티렌 유도체와 그들의 피페리딘 첨가생성물의 합성)

  • Tae-Sung Huh;In-Sook Baek;Tae-Rin Kim
    • Journal of the Korean Chemical Society
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    • v.31 no.4
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    • pp.369-372
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    • 1987
  • Five N-(2-acetyl-2-benzoyl-1-phenylethyl) piperidine derivatives (2a-2e) were synthesized from piperidine, benzoylacetone and benzaldehyde derivatives. Five ${\beta}$-acetyl-${\beta}$-benzoylstyrene derivatives (3a-3e) were synthesized from their adducts of piperidine derivatives. The structures of these compounds were confirmed by means of elemental analyses, ir and nmr spectra.

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Charge Transfer Complex Formation of Amines with Organic Halides (I) (아민과 有機할로겐 化合物間의 Charge Transfer Complex 形成에 關한 硏究 (I))

  • Kim, Yoo-Sun;Oh, Jung-Hee
    • Journal of the Korean Chemical Society
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    • v.11 no.4
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    • pp.121-125
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    • 1967
  • The formation of a charge transfer complex between various amines and organic halogen compounds was closely investigated. A mixture of amine (piperidine, pyridine, diethylamine, ethylamine, triethylamine and triethanolamine) and organic halides(carbon tetrachloride and chloroform) was checked for its UV absorption spectrum in presence of n-hexane solvent. A red shift was observed. The formation of charge transfer complex was observed in the case of triethylamine and diethylamine, whereas the formation of contact complex was distinct in case of piperidine. The relation between the nucleophilicity of amines and their tendency of forming charge transfer complex was discussed.

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Chemical Equilibria of Lanthanides{Ln(III)=Pr, Sm, Gd, Dy}-Macrocyclic Complexes with Monodentate Ligands in $CH_3$OH(Part I) ($CH_3$OH용매에서 란탄족 원소{Ln(III)=Pr, Sm, Gd, Dy}-거대고리 착물과 한자리 리간드 간의 화학평형(제1보))

  • Byun, Jong Chul;Park, Yu Chul;Park, Shin Bok
    • Journal of the Korean Chemical Society
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    • v.43 no.3
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    • pp.257-263
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    • 1999
  • Ln-macrocyclic([20]DOTA) complexes, [Ln([20]DPTA)(NO_{3})(H_{2}O)](NO_{3})_{2} \cdotxH_{2}O{Ln(III)=Pr, Sm, Gd, Dy}, which had been synthesized from 2, 6-diformyl-p-cresol(DFPC), was placed in methanol for 2 days, and $[Ln([20]DPTA)(NO_{3})(CH_{3}OH)]^{2+}$ was formed. The equilibrium constants(L) for the substitution of coordinated $CH_{3}OH$ in the Ln-[20]DOTA complexes by various auxiliary ligands, $L_{a}(=monodentate ligands; pyridine, imidazole, triethylamine, diethylamine, piperidine) were determined spectroscopically at $25^{\circ}C$ and 0.1M. The pKa of auxiliary ligand is in the order of pyridine < imidazole < triethylamine < diethylamine < piperidine, however the K has shown the trend of pyridine < imidzole < diethylamine < piperidine < triethylamine.

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