• Title/Summary/Keyword: Quinolone alkaloid

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A Quinolone Alkaloid, from the Aleurone Layer of Oryza sativa cv. Mihyangbyo, Inhibits Growth of Cultured Human Leukemia Cell

  • Chung, Ha-Sook
    • Preventive Nutrition and Food Science
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    • v.7 no.2
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    • pp.119-122
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    • 2002
  • Oryza sativa cv. Mihyangbyo is one of several recently developed varieties of rice; characterized by high levels of aromatic components, which may increase its sensory and nutritional properties. In conjunction with our continuing investigation of bioactive components of improved grain varieties, a quinolone alkaloid was isolated from the n-butanol soluble fraction of the aleurone layer of Oryza sativa cv. Mihyangbyo (Gramineae) through activity-guided fractionation and isolation. The compound exhibited moderate antineoplastic activity in a human leukemia cell line (U937) with an $IC_{50}$/ value of 118.1 ug/mL, based on the MTT(3-[4, 5]dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide) cell proliferation assay. The chemical structure of the functional compound was determined, based on physical and spectroscopic characteristics.

Quinolone Alkaloids from the Arctic Bacterium, Pseudomonas aeruginosa (북극해 박테리아, Pseudomonas aeruginosa에서 분리된 퀴놀론 알칼로이드)

  • Youn, Ui Joung;Han, Se Jong;Kim, Il Chan;Yim, Jung Han
    • Korean Journal of Pharmacognosy
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    • v.49 no.2
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    • pp.108-112
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    • 2018
  • Four quinolone alkaloids, 2-heptyl-4-quinolone (1), 2-nonyl-4-quinolone (2), 2-undecyl-4-quinolone (3), and 2-undecen-1'-yl-4-quinolone (4), together with two nitrogen derived benzoic acid derivatives, N-acetylanthranilic acid (5) and o-acetamidobenzamide (6) have been isolated from the Arctic bacterial strain, Pseudomonas aeruginosa. The structures of the compounds were determined by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with published values. To the best of our knowledge, compounds 3-6 were isolated for the first time from P. aeruginosa.

Isolation of Alkaloids with Immune Stimulating Activity from Oryza sativa cv. Heugnambyeo (흑남벼 함유 Alkaloid 분리 및 면역효능 연구)

  • Ryu, Min-Ju;Chung, Ha-Sook
    • Journal of the Korean Chemical Society
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    • v.54 no.1
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    • pp.65-70
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    • 2010
  • We describe the immune stimulatory effects of compounds determined by means of activity-monitored extraction and isolation techniques. As a result, 4-carboethoxy-6-methoxy-2-quinolone (1) and 4-carboethoxy-6-hydroxy-2-quinolone (2) were isolated from the ethyl acetate-soluble fraction of the Oryza sativa cv. Heugnambyeo bran, and were determined to exert significant inhibitory effects in macrophage cell line (murine RAW 264.7) and murine splenocytes. The structures were elucidated on the basis of spectroscopic evidence, particularly the results obtained via hetero nuclear multiple-bond connectivity and high-resolution MS spectroscopy. Up to date, compound (1) was isolated as natural sources for the first time.

Quinolone Alkaloids from Evodiae fructus Inhibit LFA-1/ICAM-1-mediated Cell Adhesion

  • Lee, Seung-Woong;Chang, Jong-Sun;Lim, Ju-Hwan;Kim, Min-Seok;Park, Su-Jin;Jeong, Hyung-Jae;Kim, Min-Soo;Lee, Woo-Song;Rho, Mun-Chual
    • Bulletin of the Korean Chemical Society
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    • v.31 no.1
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    • pp.64-68
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    • 2010
  • Four quinolone alkaloids were isolated by bioactivity-guided fractionation from the methanol extracts of Evodiae fructus fruits. Structures of compounds were elucidated by spectroscopic analysis ($^1H$-, $^{13}$C-NMR and MS), as follows: 1-methyl-2-undecyl-4(1H)-quinolone (1), evocarpine (2), dihydroevocarpine (3) and mixture of [1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone] (4). They inhibited the interaction of sICAM-1 and LFA-1 in THP-1 cells at $IC_{50}$ values of >150 (1), 109.8 (2), >150 (3) and $40.9 {\mu}M$ (4), respectively,

Alkaloids from the Stem Bark of Phellodendron amurense Rupr (황백나무로부터 생리활성물질인 alkaloids 화합물의 분리 및 탐색)

  • Lee Jin Hwan;Lee Byong Won;Kang Nam Suk;Moon Yea Hwang;Yang Min Suk;Park Ki Hun
    • Journal of Life Science
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    • v.15 no.3 s.70
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    • pp.423-426
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    • 2005
  • Two isoquinolines and one quinolone were isolated from the stem bark of Pellodendron amurense Rupr. (Rutaceae). Two isoquinolines were elucidated as thalifoline (2) and pharmacological active berberine (3) has been blocking the release of $Ca^{2+}$ from internal stores. One quinolone was identified as N-methylatanine (1). This is the first report on the isolation of N-methylatanine (1) and thalifoline (2) from this plant.

Viridicatol from Marine-derived Fungal Strain Penicillium sp. SF-5295 Exerts Anti-inflammatory Effects through Inhibiting NF-κB Signaling Pathway on Lipopolysaccharide-induced RAW264.7 and BV2 Cells

  • Ko, Wonmin;Sohn, Jae Hak;Kim, Youn-Chul;Oh, Hyuncheol
    • Natural Product Sciences
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    • v.21 no.4
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    • pp.240-247
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    • 2015
  • Viridicatol (1) has previously been isolated from the extract of the marine-derived fungus Penicillium sp. SF-5295. In the course of further biological evaluation of this quinolone alkaloid, anti-inflammatory effect of 1 in RAW264.7 and BV2 cells stimulated with lipopolysaccharide (LPS) was observed. In this study, our data indicated that 1 suppressed the expression of well-known pro-inflammatory mediators such as inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2, and consequently inhibited the production of iNOS-derived nitric oxide (NO) and COX-2-derived prostaglandin E2 ($PGE_2$) in LPS stimulated RAW264.7 and BV2 cells. Compound 1 also reduced mRNA expression of pro-inflammatory cytokines such as $interleukin-1{\beta}$ ($IL-1{\beta}$), interleukin-6 (IL-6), and tumor necrosis $factor-{\alpha}$ ($TNF-{\alpha}$). In the further evaluation of the mechanisms of these anti-inflammatory effects, 1 was shown to inhibit nuclear factor-kappa B ($NF-{\kappa}B$) pathway in LPS-stimulated RAW264.7 and BV2 cells. Compound 1 blocked the phosphorylation and degradation of inhibitor kappa B $(I{\kappa}B)-{\alpha}$ in the cytoplasm, and suppressed the translocation of $NF-{\kappa}B$ p65 and p50 heterodimer in nucleus. In addition, viridicatol (1) attenuated the DNA-binding activity of $NF-{\kappa}B$ in LPS-stimulated RAW264.7 and BV2 cells.