• Title/Summary/Keyword: Lactones

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Structural Analysis and Biological Activities of Sesquiterpene Lactones Isolated from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 분리한 Sesquiterpene Lactone들의 구조규명 및 생리활성)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1285-1295
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    • 2017
  • Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.

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
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    • v.10 no.4
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    • pp.322-328
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    • 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.

Cytotoxic Effects of Sesquiterpene Lactones from the Flowers of Hemisteptia Iyrata B.

  • Ha, Tae-Joung;Jang, Dae-Sik;Lee, Jong-Rok;Lee, Kyung-Dong;Lee, Jun;Hwang, Seon-Woo;Jung, Hwa-Jin;Nam, Sang-Hae;Park, Ki-Hun;Yang, Min-Suk
    • Archives of Pharmacal Research
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    • v.26 no.11
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    • pp.925-928
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    • 2003
  • Four guaia-12,6-olide type sesquiterpene lactones, aguerin B (1), 8$\alpha$-acetoxyzaluzanin C (2), cynaropicrin (3), and deacylcynaropicrin (4), were isolated from the flowers of Hemisteptia Iyrata Bunge. It is the first report on the isolation of compounds 1-4 from Hemisteptia species. All the isolates (1-4) were examined for their cytotoxic activity against SK-OV-3, LOX-IMVI, A549, MCF-7, PC-3, and HCT-15 human cancer cell lines.

Aroma Components of Chicory (Cichorium intybus L.) Te and Its Model System

  • Park, Sung-Hee
    • Preventive Nutrition and Food Science
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    • v.4 no.2
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    • pp.88-91
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    • 1999
  • Aroma components of tea processed from Korean chicory roots were isolated and identified. The model system of amino-carbonyl reaction was carried out to study the formation mechanism of aroma compounds of chicory tea during manufacturing process. The concentration extracts from chicory tea and model system were analyzed and identified by gas chromatography(GC) and GC-mass spectrometry. Twenty-nine compounds, including pyrazines, furans, acids, alcohols, pyrroles and lactones were isolated and identified in chicory tea. The main compounds were pyrazines including methyl pyrazine, 2,5-dimethyl pyrazine, 2, 6-dimethyl pyrazine, 2-ethyl-6-methyl pyrazine, 2-ethyl-3-methyl pyrazine, thrimethyl pyrazine, 3-ethyl-2-5-dimenthyl pyrazine, 5-ethyl-2-3-dimenthyl pyrazine, and 2-acetyl-3-methy pyrazine and pyrroles including acethl pyrrole and formlyl pyrrole ; and furans including furfural , acetyl furan, 5-methyl furan, 5-methyl furfuralm, and furfuryl alcohol. These pyrazine compounds of a roasted and nutty aroma may be important contributors to the flavor of chicory tea. The aroma concentrate of model system also had a roasted and nutty aroma and the main compounds were methyl pyrazine, 2, 5-dimetyl pyrazine, 2, 6-dimethyl pyrazine and trimethyl pyrazine.

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Antifungal Activities of Hemistepsin A and B Isolated from Hemistepita lyrata Bunge against Dandruff-causing Microbe Malassezia obutusa (지칭개에서 분리한 Hemistepsin A와 B의 비듬균에 대한 항균효과)

  • Lee, Jong Rok;Jung, Dae Hwa;Park, Moon Ki
    • KSBB Journal
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    • v.28 no.2
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    • pp.74-79
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    • 2013
  • There are a large number of bioactive sesquiterpene lactones from compositae plants including Hemistepita lyrata Bunge. In the present study, we purified two sesquiterpene lactones, Hemistepsin A and B, from H. lyrata and evaluated their antimicrobial activities against Malassezia obutusa. Chromatographic separation was used for the preparation of Hemistepsin A and B, and the identity of these compounds was confirmed by NMR. Strong inhibition of growth of M. obutusa was obtained with all doses of Hemistepsin A tested. Moreover, antifungal activity of Hemistepsin A occurred in a dose-dependent manner. Hemistepsin B also showed potent antifungal activity at the dose of $800{\mu}m/disc$. From these results, it was suggested that Hemistepsin A and B be beneficial for the preparation of the useful agent for treating scalp diseases occurred by dandruff-causing Malassezia species.

Cytotoxity of Sesquiterpene Lactones from Leaves of Helianthus tuberosus L. (돼지감자로부터 분리된 Sesquiterpene Lactone의 세포독성)

  • Choi, Hyun-Gyu;Jiang, Yanfu;Ryu, Shi-Yong;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.43 no.1
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    • pp.6-9
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    • 2012
  • The $CH_2Cl_2$ soluble part of the leaves of Helianthus tuberosus L. (Compositae) exhibited a potent cytotoxic activity against the cultured human tumor cell lines including A-549, SK-OV-3, SK-MEL-2, XF498 and HCT-15 in vitro. Bioassaydirected fractionation of the $CH_2Cl_2$ soluble part of this plant led to the isolation of four cytotoxic sesquiterpene lactones having ${\alpha}$-methylene-${\gamma}$-lactone ring in the molecule. On the basis of physical and spectral evidences, their structures were characterized as ${\Delta}^{4,15}$-isoatripliciolide tiglate (1), ${\Delta}^{4,15}$-isoatripliciolide methacrylate (2), budlein A isobutylate (3) and budlein A tiglate (4). The ${\Delta}^{4,15}$-isoatripliciolide tiglate (1) showed the most potent cytotoxic activity ($0.26{\mu}M<ED_{50}<2.16{\mu}M$) against all of the cell lines tested.

Anti-inflammatory Activity of Standardized Fraction from Inula helenium L. via Suppression of NF-κB Pathway in RAW 264.7 Cells

  • Chun, Jaemoo;Song, Kwangho;Kim, Yeong Shik
    • Natural Product Sciences
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    • v.25 no.1
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    • pp.16-22
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    • 2019
  • Inula helenium L. is rich source of eudesmane-type sesquiterpene lactones, mainly alantolactone and isoalantolactone, which have the various pharmacological functions. In this study, we examined the inhibitory effects of nitric oxide (NO) production of hexane, methylene chloride, ethyl acetate, butanol, and water fractions from I. helenium and investigated the anti-inflammatory effect of hexane fraction of I. helenium (HFIH) in LPS-induced RAW 264.7 cells. Quantification of alantolactone and isoalantolactone from HFIH was carried out for the standardization by multiple reaction monitoring using triple quadrupole mass spectrometer. HFIH significantly inhibited inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) protein as well as their downstream products NO and prostaglandin $E_2$ ($PGE_2$) in LPS-stimulated RAW 264.7 cells. Moreover, HFIH suppressed $NF-{\kappa}B$ transcriptional activity by decreasing the translocation of p65 to the nucleus. The in vivo study further confirmed that HFIH attenuated the paw edema induced by carrageenan in an acute inflammation model. These findings suggest that HFIH may be useful as a promising phytomedicine for inflammatory-associated diseases.

Antimicrobial Activities of Sesquiterpene Lactones Isolated from the Flower of Chrysanthemum coronarium L. (쑥갓의 꽃에서 분리한 sesquiterpene lactones의 항균활성)

  • Ha, Tae-Jung;Han, Hyo-Shim;Jang, Ki-Chang;Jang, Dae-Sik;Cho, Dong-Young;Yang, Min-Suk;Lee, Kyung-Dong
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.235-239
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    • 2003
  • Thirteen sesquiterpene lactones isolated from the flower of Chrysanthemum coronarium L., which has been widely cultivated in Korea as a vegetable for a long time, were investigated their antimicrobial activities against eight bacteria and five phytopathogenic fungi. The antimicrobial activities of dihydrochrysanolide (6) and 1-epi-dihydrochrysanolide (7) showed strong activities against all the bacteria such as Bacillus subtilis, Bacillus cereus, Staphylococcus aureus and Vibrio parahaemolyticus. Especially, Staphylococcus aureus was investigated that have very strong antibacterial activity to $1.56\;{\mu}g{\cdot}disc^{-1}$, respectively. Also, most of sesquiterpene lactones, which have ${\alpha}-methylene-{\gamma}-butyrolactone$ group, were exhibited strong activity to Gram(+) bacteria than Gram(-) bacteria. In the antifungal test, Rhizoctonia solani and Phytophthora capsici known as phytopathogenic fungi have exhibited all extensive activity about compounds that have ${\alpha}-methylene-{\gamma}-butyrolactone$ group.