• Title/Summary/Keyword: coumarinolignan

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Lignan Derivatives from Fraxinus rhynchophylla and Inhibitory Activity on Pancreatic Lipase

  • Ahn, Jong-Hoon;Shin, Eun-Jin;Liu, Qing;Kim, Seon-Beom;Choi, Kyeong-Mi;Yoo, Hwan-Soo;Hwang, Bang-Yeon;Lee, Mi-Kyeong
    • Natural Product Sciences
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    • v.18 no.2
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    • pp.116-120
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    • 2012
  • Pancreatic lipase digests dietary fats by hydrolysis, which is a key enzyme for lipid absorption. Therefore, reduction of fat absorption by the inhibition of pancreatic lipase is suggested to be a therapeutic strategy for obesity. We previously reported coumarins and secoiridoids of Fraxinus rhynchophylla as inhibitory constituents on adipocyte differentiation. Further investigation on F. rhynchophylla led to the isolation of lignan derivatives such as lignans (1 - 10), sesquilignans (11 - 14) and coumarinolignans (15 - 17). Among them, coumarinolignans and sesquilignans were first reported from Fraxinus species. Among the constituents isolated, sesquilignans showed the significant inhibition on pancreatic lipase, whereas lignans and coumarinolignans exerted weak effects.

Simultaneous Quantitation of Nine Constituents of Fraxinus rhynchophylla using High Performance Liquid Chromatography - Diode Array Detector

  • Ahn, Jong Hoon;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.236-241
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    • 2013
  • A high-performance liquid chromatography-diode array detector (HPLC-DAD) method was established for quantitative evaluation of nine constituents of Fraxinus rhynchophylla such as four coumarins, esculin (1), fraxin (2), esculetin (3), fraxetin (4), three lignans, syringaresinol 4,4'-O-${\beta}$-diglucoside (5), pinoresinol 4-O-${\beta}$-glucoside (6), pinoresinol (9), one secoiridoid, oleuropein (7), and one coumarinolignan, cleomiscosin C (8). The preferred chromatographic condition was obtained on Phenomenex Gemini-NX (3 ${\mu}m$, C18 110A, $150{\times}4.60$ mm) and the mobile phase was composed of water and acetonitrile using a gradient elution. The wavelength was set at 220 nm. Extraction condition of these constituents in F. rhynchophylla was also optimized through extraction time, extraction solvent and extraction method using established method. From this study, extraction at $70^{\circ}C$ with the mixture of ethanol and water for more than 12 h was suggested to be good extraction condition for these constituents. Quantitation of nine constituents in different F. rhynchophylla samples was also successfully accomplished with the newly established method.

Anti-Proliferative Effects of β-Cyclodextrin Inclusion Complexes with Coumarinolignans from Acer mono (고로쇠 Coumarinolignan의 β-Cyclodextrin 포접화합물 제조 및 암세포증식 억제활성)

  • Yim, Soon-Ho;Jung, Da-Woon;Williams, Darren R.;Geckeler, Kurt E.;Kim, Kyung Keun;Shin, Boo Ahn;Lee, Ik-Soo;Kim, Huyn Jung
    • Korean Journal of Pharmacognosy
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    • v.46 no.2
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    • pp.133-139
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    • 2015
  • Two coumarinolignans, cleomiscosins C (1) and D (2) were isolated from the heartwood of Acer mono, together with four compounds, 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (3), 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-apiofuranosyl-(1$\rightarrow$6)-${\beta}$-D-glucopyranoside (4), scopoletin (5), and (E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (6). Of them, cleomiscosins C (1) and D (2) were applied to preparing inclusion complex molecules with ${\beta}$-cyclodextrin (${\beta}$-CD) to improve the very poor solubility in cell media. The CD complexes of 1 and 2 exhibited an enhancement of water solubility which is feasible to measure their cytotoxicity using a spectrophotometer in a cell-based assay. Anti-proliferative activity of these complex molecules was successfully estimated on HCT116 human colon cancer cells, and cleomiscosin D (2) showed anti-proliferative effects at the concentration of 1.95~31.2 ${{\mu}g}$/mL in a dose-dependent manner.