• Title/Summary/Keyword: ${\beta}-Lactones$

Search Result 15, Processing Time 0.026 seconds

A Regioselectio Synthesis of ${\beta}-Lactones$; Bromolactonization of 2-Substituted-1-Cyclohexenyl-1-acetic acid

  • Jew, Snag-Sup;Lee, Hee-Soon;Koo, Bon-Am
    • Archives of Pharmacal Research
    • /
    • v.17 no.5
    • /
    • pp.327-330
    • /
    • 1994
  • Bromolactonization of 2-substituted-1-cyclohexenyl-1-acetic acids with 1, 3-dibromo-5, 5-dime-thylhydantoin 9DBH) and potsssium tertiary butoxide (t-BuOK0 in anhydrous DMF was found to proceed in a highly regioselective manner. The reaction predominantly resulted in the formation of ${\betha}-lactones$ (greater than 96%).

  • PDF

The study of chemical substances in Hymenoxys brachyactis(II) (Hymenoxys brachyactis의 화학성분에 관한 연구(II))

  • Lee, Sang-Jun;Kim, Sung-Han;Kim, Jung-Han
    • Applied Biological Chemistry
    • /
    • v.38 no.5
    • /
    • pp.473-477
    • /
    • 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.

  • PDF

Development of a Sensitive Bioassay Method for Quorum Sensing Inhibitor Screening Using a Recombinant Agrobacterium tumefaciens

  • Kim Yeon Hee;Kim Young Hee;Kim Jung Sun;Park Sunghoon
    • Biotechnology and Bioprocess Engineering:BBE
    • /
    • v.10 no.4
    • /
    • pp.322-328
    • /
    • 2005
  • Acylhomoserine lactones (AHLs) are known to be the triggering molecules in the quorum sensing mechanism of many gram-negative bacteria. In order to detect AHL inhibitors that are potential biofilm inhibitors, a convenient and sensitive bioassay was developed based on the $\beta$-galactosidase activity ($\beta$-GAL) of a recombinant Agrobacterium tumefaciens strain. A series of commercially available AHLs were tested for inducing $\beta$-GAL at varying concentrations in agar-plate and liquid cultures of the reporter strain. All AHLs tested exhibited a concentration­dependent induction, and octanoyl homoserine lactone (OHL) showed the highest sensitivity with a detection limit of 0.1 nM in the liquid culture assay. When fimbrolide, a known quorum sensing inhibitor, was added, induction of $\beta$-GAL by OHL was repressed. The repression at a constant OHL concentration was dependent on the fimbrolide concentration with the detection limit below 1 ppm, indicating that this assay is a sensitive method for screening AHL inhibitors.

Sesquiterpene Lactones of Artemisia sylvatica (그늘쑥의 Sesquiterpene Lactone 성분)

  • 권학철;최상진;이원빈;민용득;양민철
    • YAKHAK HOEJI
    • /
    • v.45 no.2
    • /
    • pp.147-152
    • /
    • 2001
  • The phytochemical study of the aerial parts of Artemisia sylvatica (Asteraceae) led to the isolation of nine sesquiterpene lactones, l$\alpha$-hydroperoxy-rupicolin A acetate (1), rupicolin B acetate (2), rupicolin A acetate (3), l$\alpha$-hydroxy-4$\alpha$-hydroperoxy-bishopsolicepolide (4), 1$\alpha$-hydroperoxy-4$\beta$-hydroxy-8$\alpha$-acetoxy-guaia-2,9,11 (13)-triene-6$\alpha$,12-oxide (5), 1$\alpha$-hydroperoxy-4$\alpha$-hydroxybishopsolicepolide (6), l$\alpha$,4$\beta$-dihydroxy-8$\alpha$-acetoxy-guaia-2,9,11(13)-triene-6$\alpha$,12-olive (7), rupicolin A (8) and l$\alpha$,4$\alpha$-dihydroxy-bishopsolicepolide (9). Their structures were established by chemical and spectroscopic methods.

  • PDF

Stereochemistry of the Degradation Product of (-)-α-Narcotine and Its Analogs with Ethyl Chloroformate ((-)-α-Narcotine과 유사화합물을 ethyl chloroformate로 반응시 생성된 분해물의 입체화학)

  • Lee Dong-Ung
    • Journal of Life Science
    • /
    • v.15 no.1 s.68
    • /
    • pp.147-151
    • /
    • 2005
  • A$(-)-\alpha$-narcotine from Papaver sommiferum was refluxed with ethyl chloroformate to give the diastereomeric chloro-carbamate mixture and the Z/E-enol lactones as Z:E=1:1.1 ratio in HPLC analysis. After photoisomerization with UV (254 nm), the Z/E ratio was drastically changed to Z:E=7:1, which may indicate that the E-isomer was easily converted to the Z-isomer due to photoisomerization. The photoisomerization of the Z/E-enol lactones and the different stereochemistry of the degradation product of $\beta-narcotine$, deuterated $\beta-narcotine$ and $\beta-narcotine$ with ethyl chloroformate will also be discussed.

Cytotoxic and ACAT-inhibitory Sesquiterpene Lactones from the Root of Ixeris dentata forma albiflora

  • Ahn, Eun-Mi;Bang, Myun-Ho;Song, Myoung-Chong;Park, Mi-Hyun;Kim, Hwa-Young;Kwon, Byoung-Mog;Baek, Nam-In
    • Archives of Pharmacal Research
    • /
    • v.29 no.11
    • /
    • pp.937-941
    • /
    • 2006
  • Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel ($C_{18},\;ODS$) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11 (13)-triene-6, 12-olide(2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian$-4(15), 10(14)-diene-6, 12-olide (3), $3-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguauan$-10(14)-ene-6, 12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adeno-carcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.