• Title/Summary/Keyword: Lactone

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Isolation of Guaianolides with ACAT Inhibitory Activity from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 ACAT 저해활성을 가지는 Guaianolides의 분리)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1275-1284
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    • 2017
  • Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

Syntheses of New Lactones Containing Phenyl or Methyl Groups (페닐기 및 메틸기를 포함하는 새로운 lactone의 합성)

  • Chang, Seung Hyun;Moon, Sang Chil;Kim, Hak Hee;Lee, Kap Duk;Chung, Kwang Bo
    • Applied Chemistry for Engineering
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    • v.9 no.6
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    • pp.842-845
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    • 1998
  • Four new lactones and one dibenzo crown ether were synthesized by reaction of dihydroxy compound with oxalyl chloride and with ${\alpha}$,${\omega}$-dibromo compound, respectively. 5,6,11,12-Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclodode- cane(1), 5,6,11,12-tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16-tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), and 5,6,11,12-tetracarbonyl- 2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4) were prepared by reaction of oxalyl chloride with benzopinacol, pinacol, 2,2'-dihydroxybiphenyl and hydrobenzoin, respectively, in the presence of pyridine. Dibenzo-13-crown-4 (5) was obtained by reaction of catechol with 1,3-dibromopropane/1,2-dibromoethane.

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Fertilization Effects on Growth, Foliar Nutrients and Extract Concentrations in Ginkgo Seedlings (은행나무 묘목(苗木)에 대(對)한 시비(施肥)가 생장(生長) 및 엽내(葉內) 양분(養分)과 유용(有用) 추출물(抽出物) 농도(濃度)에 미치는 영향(影響))

  • Son, Yowhan;Kim, Zin-Suh;Hwang, Jae Hong;Park, Jung Soo
    • Journal of Korean Society of Forest Science
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    • v.87 no.1
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    • pp.98-105
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    • 1998
  • We measured seedling growth, foliar nutrient and extract concentrations of 3-year-old Ginkgo biloba seedlings growing in a nursery following a single fertilization with nitrogen (N), phosphorus (P) and nitrogen plus phosphorus (N+P) fertilizers. Fertilization did not change foliage, stem and root biomass of the seedlings except for the high N+P treatment, Foliar N and P concentrations following fertilization varied according to the amount of fertilizers. In general, foliar N and P concentrations increased with fertilization, but fertilization with 400kg N/ha and 100kg P/ha decreased foliar N and P concentrations, respectively. Seedling growth and foliar nutrient concentrations showed that N and P were the growth-limiting nutrients in our study site. It was found that fertilization reduced the concentrations of secondary metabolites (Ginkgo flavon glycosides and terpene lactones) in foliages. It seemed there was a relationship between foliage biomass production and secondary chemicals in G. biloba seedlings.

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Inhibition of Cellular Proliferation by p53 dependent Apoptosis and G2M Cell Cycle Arrest of Saussurea lappa CLARKE in AGS Gastric Cancer Cell Lines

  • Jeong Han Su;Kim Dong Jo;Heo Geum Jeong;Nam Chang Gyu;Go Seong Gyu
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.18 no.4
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    • pp.1186-1191
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    • 2004
  • The root of Saussurea lappa includes sesquiterpene lactones such as costunolide and dehydrocostus lactone, and has been shown to be anti-tumorigenic with being used in traditional medicinal therapy in the Eastern Asia. However, the molecular basis of the effects of Saussurea lappa on fate of gastric carcinoma, which incur very frequently in the area, has not been well identified. In this study, the cytostatic effects of Saussurea lappa were examined using gastric AGS cancer cells. Cell viability was dramatically reduced by Saussurea lappa, in a dose-dependent manner. As time passed after its treatment, apoptotic population was increased and clearly showed G2-arrest. Being consistent, its treatment resulted in maintaining of G1 and S-phase cyclins D1, E, and A even until a significant apoptotic population was observed, for example, at 24h after treatment. However, G2/M phase cyclin B1 was reduced even at 12 h after treatment. In addition, its treatment increased expression of p53, p21/sup Wafl / cyclin dependent kinase inhibitor (CKI), and Bax, resulted in cleavages of procaspase 3 and poly ADP-ribose polymerase(PARP), indicating that such G2 arrest- and apoptosis-related molecules are involved. Therefore, these suggest that extracts of Saussurea lappa root may be a safer and effective reagent to deal with gastric cancers either by traditional herbal therapy or combinational therapy with conventional chemotherapy.

Anti-cancer Effects of Costunolide in Estrogen Receptor Positive MCF-7 Breast Cancer Cells (에스트로겐 수용체 양성 MCF-7 유방암 세포주에 대한 costunolide의 항암효과)

  • Kim, Woon Ji;Choi, Youn Kyung;Woo, Sang Mi;Park, Nam Gyu;Jung, Hye In;Kim, Yong Gook;Shin, Yong Cheol;Ko, Seong Gyu
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.27 no.3
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    • pp.306-312
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    • 2013
  • Costunolide ($C_{15}H_{20}O_2$) is a sesquiterpene lactone that was isolated from many herbal medicines and it has diverse effects (anti-viral, anti-fungal, and anti-inflammatory) according to previous reports. However, the anti-cancer effects of Costunolide and its mechanism of actions are not well known in estrogen receptor positive breast cancer. In this study, we observed that costunolide suppresses cell growth in estrogen receptor positive MCF-7 breast cancer cells as shown by MTT assay and soft agar colony formation assay. To examine the mechanism by which costunolide inhibits MCF-7 cell growth, we performed FACS analysis. We found that costunolide induced G2/M and S cell cycle arrest, and regulated cycle-related protein expression. In addition, costunolide inhibited ERK signaling pathway and induced autophagy. Therefore, costunolide might be a good and useful chemotherapy agent for estrogen receptor positive breast cancer patients.

Development of the Standard Analytical Methods for Compound Hawthorn Berry 60% Ethanol Extract, Ginkgo Biloba Leaf Extract and Garlic Oil Capsules (복방서양산사60%에탄올엑스.은행엽엑스.마늘유캡슐의 기준 및 시험법과 규격 설정)

  • Cho, Chang-Hee;Kim, Ji-Sun;Whang, Ji-Sang;Baek, Ju-Hyun;Park, Ju-Young;Shim, Young-Hoon;Seong, Rack-Seon;Kim, Dong-Sup;Lee, Jong-Phill;Lee, Joo-Hyeun;Sohn, Su-Jung
    • Korean Journal of Pharmacognosy
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    • v.41 no.1
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    • pp.67-72
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    • 2010
  • In the recent version of the Korea Pharmacopoeia(KP) and the Korean Herbal Pharmacopoeia(KHP), there are 563 items(181 in KP, 381 in KHP) of herbal medicines including finished drugs. Also, approximately 507 items including herbal extracts and herbal medicinal products was published in the 3th edition of Korea Pharmaceutical Codex (KPC). These items help the persons working in the pharmaceutical manufacturing field to register the drug and in research fields to develop the new drug considering as a standard specifications. This study was carried out to establish standard analytical methods for 'Compound Hawthorn Berry 60% Ethanol Extract, Ginkgo Biloba Leaf Extract and Garlic Oil Capsules' in the 3th edition of Korea Pharmaceutical Codex. Ginkgo flavonoid and terpene lactone were employed as reference compounds for analytical method. Analytical methods established in this study could be applied to a reasonable and unified quality control of G. biloba leaf extract and hawthorn berry extract.

Biodegradation of Aromatic Compounds by Nocardioform Actinomycetes

  • CHA CHANG-JUN;CERNIGLIA CARL E.
    • Proceedings of the Microbiological Society of Korea Conference
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    • 2001.11a
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    • pp.157-163
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    • 2001
  • Mycolic acid-containing gram-positive bacteria, so called nocardioform actinomycetes, have become a great interest to environmental microbiologists due to their metabolic versatility, multidegradative capacity and potential for bioremediation of priority pollutants. For example, Rhodococcus rhodochrous N75 was able to metabolize 4-methy1catechol via a modified $\beta$-ketoadipate pathway whereby 4-methylmuconolactone methyl isomerase catalyzes the conversion of 4-methylmuconolactone to 3-methylmuconolactone in order to circumvent the accumulation of the 'dead-end' metabolite, 4-methylmuconolactone. R. rhodochrous N75 has also shown the ability to transform a range of alkyl-substituted catechols to the corresponding muconolactones. A novel 3-methylmuconolactone-CoAsynthetase was found to be involved in the degradation of 3-methylmuconolactone, which is not mediated in a manner analogous to the classical $\beta$-ketoadipate pathway but activated by the addition of CoA prior to hydrolysis of lactone ring, suggesting that the degradative pathway for methylaromatic compounds by gram-positive bacteria diverges from that of proteobacteria. Mycobacterium sp. Strain PYR-l isolated from oil-contaminated soil was capable of mineralizing various polyaromatic hydrocarbons (PAHs), such as naphthalene, phenanthrene, pyrene, fluoranthrene, 1-nitropyrene, and 6-nitrochrysene. The pathways for degradation of PAHs by this organism have been elucidated through the isolation and characterization of chemical intermediates. 2-D gel electrophoresis of PAH-induced proteins enabled the cloning of the dioxygenase system containing a dehydrogenase, the dioxygenase small ($\beta$)-subunit, and the dioxygenase large ($\alpha$)-subunit. Phylogenetic analysis showed that the large a subunit did not cluster with most of the known sequences except for three newly described a subunits of dioxygenases from Rhodococcus spp. and Nocardioides spp. 2-D gel analysis also showed that catalase-peroxidase, which was induced with pyrene, plays a role in the PAH metabolism. The survival and performance of these bacteria raised the possibility that they can be excellent candidates for bioremediation purposes.

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Production of Cell Mass and Monacolin K from Monascus sp. on Rice Solid Culture (Monascus 속 균주의 균체 생산 및 고체배양에 의한 Monacolin K 생산)

  • 정혁준;유대식
    • Korean Journal of Microbiology
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    • v.40 no.2
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    • pp.160-166
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    • 2004
  • The optimal conditions for production of Monascus sp. KM100l cell mass on submerged culture and production of monacolin K on rice solid culture were investigated. An overproducing mutant of Monascus pigments, KM 1001 mutant, from Monascus purpureus KCCM60016 was selected by NTG treatment. The optimal medium for the production of KM100l mutant cell mass is instructed to be composed of 3% glucose, 2% yeast extract, 0.1 % KH$_2$PO$_4$, 0.05% The optimal conditions for production of Monascus sp. KM100l cell mass on submerged culture and production of monacolin K on rice solid culture were investigated. An overproducing mutant of Monascus pigments, KM 1001 mutant, from Monascus purpureus KCCM60016 was selected by NTG treatment. The optimal medium for the production of KM100l mutant cell mass is instructed to be composed of 3% glucose, 2% yeast extract, 0.1 % KH$_2$The optimal conditions for production of Monascus sp. KM100l cell mass on submerged culture and production of monacolin K on rice solid culture were investigated. An overproducing mutant of Monascus pigments, KM 1001 mutant, from Monascus purpureus KCCM60016 was selected by NTG treatment. The optimal medium for the production of KM100l mutant cell mass is instructed to be composed of 3% glucose, 2% yeast extract, 0.1 % $(KH_2PO_4$, 0.05% $MgSO_4{\cdot}7H_2O$, 0.2% L-asparagine, pH 4.5, and the optimal inoculum size and shaking speed were $1.5{\times}10^6$ spores/50 m1 medium and 150 rpm, respectively. On optimal conditions, 4.1 g/l of the cell mass was obtained at 28$^{\circ}C$ for 3 days. The mycelium were inoculated on 500 g of steamed rice using vinyl bag ($30.6{\times}44$ cm) and incubated at $30^{\circ}C$, 85% humidity for 21 days. Lactone form monacolin K was rapidly increased for 2 days and reached highest concentration of monacolin K (2,930 mg/kg) for 15 days, and monacolin K was decreased after 15 days.

Disease-resistant Transgenic Arabidopsis Carrying the expI Gene from Pectobacterium carotovorum subsp. carotovorum SL940

  • Lee, Joo-Hee;Hong, Ja-Bin;Hong, Sang-Bin;Choi, Min-Seon;Jeong, Ki-Yong;Park, Hyoung-Joon;Hwang, Duk-Ju;Lee, Seung-Don;Ra, Dong-Soo;Heu, Sung-Gi
    • The Plant Pathology Journal
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    • v.24 no.2
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    • pp.183-190
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    • 2008
  • Plant-cell-wall-degrading enzymes (PCWDEs) of Pectobacterium carotovorum subsp. carotovorum are the key virulence factor in pathogenesis of soft rot disease of vegetables. The production of PCWDEs is controlled in a cell density dependent manner to avoid the premature production of PCWDEs and subsequent activation of plant defense. N-oxoacyl-homoserine lactone (OHL) is essential for quorum sensing in the soft rot pathogen and the expI gene is responsible for OHL production. The ExpI homolog isolated from P. carotovorum subsp. carotovorum SL940 had 94% identity with ExpI of E. carotovora subsp. carotovora scc3193 and 74% identity with Carl of E. carotovora subsp. atroseptica. The transgenic plants that express exp I uner the control of CaMV35S promoter were able to produce diffusible OHL. Transgenic plants producing OHL were very resistant to the infection of P. carotovorum subsp. carotovorum. Since the PR1 gene was strongly induced and NPR1 and NPR4 were induced weakly in transgenic plants compared to the wild type, salicylic acid-dependent pathways is likely involved in the resistance to the soft rot pathogen P. carotovorum subsp. carotovorum in ExpI transgenic plants.

Anti-inflammatory effect of zaluzanin C on lipopolysaccharide-stimulated murine macrophages (지방질다당류로 자극한 마우스 대식세포에 있어서 zaluzanin C의 항염증 효과)

  • Kang, Ye Rim;Lee, Hee Won;Kim, Yoon Hee
    • Korean Journal of Food Science and Technology
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    • v.48 no.4
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    • pp.392-397
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    • 2016
  • Zaluzanin C is a sesquiterpene lactone isolated from Ainsliaea acerifolia, a Korean medicinal plant. In the present study, the anti-inflammatory effects of zaluzanin C were demonstrated in lipopolysaccharide (LPS)-stimulated murine macrophages (RAW264.7 cells). Zaluzanin C inhibited the release of nitric oxide (NO) by alleviating the protein expression of inducible NO synthase in LPS-treated RAW264.7 cells. Furthermore, it suppressed the release of interleukin-6 induced by LPS. Zaluzanin C was also found to block the translocation of the p65 subunit of nuclear factor-kB from the cytosol to the nucleus, which is one of the underlying mechanisms of the anti-inflammatory action of zaluzanin C. These data suggest the potential of zaluzanin C in the treatment of inflammatory diseases.