• Title/Summary/Keyword: polyacetylene compound

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Chemical Constituents of the Halophyte Glehnia littoralis (염생식물 갯방풍의 화학적 성분연구)

  • Um, Young-Ran;Lee, Jung-Im;Lee, Jin-Hyeok;Kim, Hae-Jin;Yea, Sung-Su;Seo, Young-Wan
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.701-706
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    • 2010
  • Two polyacetylenes (1 and 2), four coumarins (3-6), and one sesquiterpene (7) were isolated from the halophyte Glehnia littoralis. Particularly, compound 6 and 7 were isolated for the first time from Glehnia littoralis. Their chemical structures have been determined by extensive 2-D NMR experiments such as $^1H$, COSY, HMQC and HMBC and by comparison with the reported data in the literature.

Molecular Mechanisms of Cell Cycle Arrest and Apoptosis by Dideoxypetrosynol A, a Polyacetylene from the Sponge Petrosia sp., in Human Monocytic Leukemia Cells

  • Choi, Yung Hyun
    • Journal of Marine Bioscience and Biotechnology
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    • v.1 no.4
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    • pp.243-251
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    • 2006
  • Dideoxypetrosynol A, a polyacetylene from the marine sponge Petrosia sp., is known to exhibit significant selective cytotoxic activity against a small panel of human tumor cell lines, however, the mechanisms of which are poorly understood. In the present study, it was investigated the further possible mechanisms by which dideoxytetrosynol A exerts its anti-proliferative action in cultured human leukemia cell line U937. We observed that the proliferation-inhibitory effect of dideoxypetrosynol A was due to the induction of G1 arrest of the cell cycle and apoptosis, which effects were associated with up-regulation of cyclin D1 and down-regulation of cyclin E without any change in cyclin-dependent-kinases (Cdks) expression. Dideoxypetrosynol A markedly induced the levels of Cdk inhibitor p16/INK4a expression. Furthermore, down-regulation of phosphorylation of retinoblastoma protein (pRB) by this compound was associated with enhanced binding of pRB and the transcription factor E2F-1. The increase in apoptosis was associated with a dose-dependent up-regulation in pro-apoptotic Bax expression and activation of caspase-3 and caspase-9. Dideoxytetrosynol A decreased the levels of cyclooxygenase (COX)-2 mRNA and protein expression without significant changes in the levels of COX-1, which was correlated with a decrease in prostaglandin E2 (PGE2) synthesis. Furthermore, dideoxytetrosynol A treatment markedly inhibited the activity of telomerase, and the expression of human telomerase reverse transcriptase (hTERT), a main determinant of the telomerase enzymatic activity, was progressively down-regulated by dideoxytetrosynol A treatment in a dose-dependent fashion. Taken together, these findings provide important new insights into the possible molecular mechanisms of the anti-cancer activity of dideoxytetrosynol A.

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Phytochemical Study on the Rhizome of Atractylodes japonica from Korea (한국산 창출의 성분연구)

  • Yim, Dong-Sool;Yu, Seung-Cho;Chi, Hyung-Joon
    • Korean Journal of Pharmacognosy
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    • v.19 no.4
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    • pp.228-232
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    • 1988
  • From the rhizome of Atractylodes japonica Koidzumi (Compositae) which is the original plant of oriental medicine 'Cang-Zhu', four essential oil compounds were isolated. Three of them were identified as atractylon, hydroxyatractylon and $5{\alpha}H,\;10{\beta}-selina-4(14),\;7(11)-diene-8-one$, which were already known as the constitutents of Atractylodes Rhizoma. The fourth is a novel polyacetylene type compound, and the structure is postulated as 1, 4-diacetoxytetradeca-6, 12-diene-8, 10-diyne by the spectral data.

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ACAT Inhibition of Polyactylenes from Gymnaster koraiensis

  • Jung, Hyun-Ju;Hung, Tran-Manh;Na, Min-Kyun;Min, Byung-Sun;Kwon, Byoung-Mog;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.15 no.2
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    • pp.110-113
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    • 2009
  • Acyl-coenzyme A: cholesterol acyltransferase (ACAT) catalyzes cholesterol esterification and plays important roles in intestinal absorption of cholesterol, hepatic production of lipoproteins and accumulation of cholesteryl ester within macrophages and smooth muscle cells. In our study, eight polyacetylenes (1 - 8), were isolated from the roots of Gymnaster koraiensis, and their chemical structures were identified on the basis of spectroscopic analysis and mass. Compound 2 with the (10S)-15,16-epoxy group in skeleton strongly inhibited ACAT enzyme with $IC_{50}$ value of 35.8 ${\mu}g$/mL, meanwhile the other compounds displayed significant inhibition of ACAT enzyme with the $IC_{50}$ values from 45.5 to 55.1 ${\mu}g$/mL.

Anti-inflammatory and Immunosuppressive Effects of Panax notoginseng

  • Cao, Thao Quyen;Han, Jae Hyuk;Lee, Hyun-Su;Ha, Manh Tuan;Woo, Mi Hee;Min, Byung Sun
    • Natural Product Sciences
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    • v.25 no.4
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    • pp.317-325
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    • 2019
  • Here, we designed to examine the anti-inflammatory effects on RAW264.7 cells and the immunosuppressive effects by evaluating interleukin-2 (IL-2) production in Jurkat T cells using a MeOH extract of Panax notoginseng roots. The results showed that the MeOH extract inhibited the synthesis of nitric oxide (NO) in a dose-dependent manner (IC50 value of 7.08 ㎍/mL) and displayed effects on T cell activation at a concentration of 400 ㎍/mL. In efforts to identify the potent compounds, bioactivity-guided fractionation of the MeOH extract and chemical investigation of its active CH2Cl2-, EtOAc-, and butanol-soluble fractions led to the successful isolation and identification of eleven compounds, including two polyacetylenes (1, 2), a steroid saponin (3), seven dammarane-type ginsenosides (4 - 10), and an oleanane-type ginsenoside (11). Among them, compound 11 was isolated from this plant for the first time. Compound 2 exhibited potent inhibitory effects on NO synthesis and an immunosuppressive effect with IC50 values of 2.28 and 65.57 μM, respectively.

Inhibitory Effects of the Rhizome Extract of Atractylodes japonica on the Proliferation of Human Tumor Cell Lines (백출 추출물의 암세포증식 저해 효과)

  • Lee, Sung-Ok;Seo, Jee-Hee;Lee, Jung-Won;Yoo, Mi-Young;Kwon, Jee-Woong;Choi, Sang-Un;Kang, Jong-Seong;Kwon, Dae-Young;Kim, Young-Kyoon;Kim, Young-Sup;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.36 no.3 s.142
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    • pp.201-204
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    • 2005
  • The rhizome extract of Atractylodes japonica Koidzumi(Compositae) exhibited a particular inhibition on the proliferation of cultured human tumor cell lines, in vitro. Thus, the intensive phytichemical investigation of the MeOH extract of Atractylodes japonica have been conducted by the way of activity-guided purification. The repeated column chromatographic separation of the n-hexane soluble part of extract resulted in the isolation of four sesquiterpenes (1-4) and a polyacetylene component (5). Chemical structures of them were identified as atractylon (1), atractylenolide Ⅰ(2), atractylenolide Ⅲ(3), eudesma-4(15),7(11)-dien-8-one (4) and 1,3-diacetyl-atractylodiol (5) by spectroscopic means. Among the isolates, compound 2-4 were shown to give moderate inhibitory effect in a dose dependent manner on the proliferation of cultured human tumor cell lines such as A549 (non small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT 15(colon), respectively.

Effects of Red Ginseng Extracts on Hydrogen Peroxide Production of Murine Prtitoneal Macrophages (홍삼추출물이 마우스 복강 대식세포 Hydrogen Peroxide 생산에 미치는 영향)

  • 박란숙
    • The Korean Journal of Food And Nutrition
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    • v.11 no.1
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    • pp.107-113
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    • 1998
  • This experiment has conducted to evaluate whether single injection of red ginseng extract including 50% ethanol extract, crude saponin, and lipid soluble fraction can induce oxidative burst of mouse peritoneal macrophages with use of fluorescence spectrophotometer. To optimize conditions of fluorescent spectrophotometry, concentrations of DCFH-DA(2', 7' -dichlorofluorescin diacetate) was 1.6 ${\mu}{\textrm}{m}$ and control oxidative burst by Zymosan A and PMA(phorbol myristate acetate) were 100$\mu\textrm{g}$, 250ng, respectively. Though in vitro macrophages failed to induce increment of H2O2 production, but 50% ethanol extract group induced significant enhancement of H2O2 production when zymosan A triggered oxidative burst. On the other hand, lipid soluble fraction enhanced significantly H2O2 production than that of control group. These findings consisted with the other reports which showed ginsenosides inhibited nitric oxide production and lipid soluble fraction activated colony stimulating factor(granulocyte - monocyte) activity in bone marrow stem cells. As is well known, lipid soluble fraction contains phenol compound, polyacetylene compound and alkaloids. Further study would unravel which component of it can induce H2O2 production of macrophages. Key words : Red ginseng(Panax ginseng), H2O2 production, macrophages.

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Isolation and Identification of Growth Inhibition Substance on L. monocytogenes from Dystaenia takesimana Kitagawa (섬바디로부터 L. monocytogenes에 대한 생장억제 물질의 분리 및 구조동정)

  • Oh, Jin-Ah;Shin, Dong-Hwa;Baek, Nam-In
    • Korean Journal of Food Science and Technology
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    • v.31 no.4
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    • pp.984-993
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    • 1999
  • The ethanol extracts and its n-hexane fraction of Dystaenia takesimana Kitagawa exhibited growth inhibition on Listeria monocytogenes ATCC 19111, ATCC 19112, ATCC 19113, ATCC 19114 and ATCC 15313. The minimum inhibitory concentration of the ethanol extract and its n-hexane fraction were 50 ppm and below 30 ppm on Listeria monocytogenes respectively. By silica gel column chromatography, the active fraction A8 was obtained from the ethanol extract of Dystaenia takesimana Kitagawa. After three times of column chromatography, the SBD-1 and SBD-2 were separated from the A8 fraction of the ethanol extract of Dystaenia takesimana Kitagawa. Antimicrobial activity of the SBD-l and SBD-2 was lower than that of the A8. And the A8 exhibited growth inhibition on five strains of Listeria monocytogenes at the level of $10{\sim}30$ ppm and the bactericidal effect was confirmed at same the level. The purified antimicrobial active compound was identified as (9z)-heptadeca-l,9-dien-4,6-diyn-3,8-diol, falcarindiol, by EI/MS, $^{1}H-NMR$ and $^{13}C-NMR$.

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