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Alkyl Glycosides from the Flowers of Magnolia obovata

황목련 꽃으로부터 Alkyl Glycoside의 분리 동정

  • Oh, Eun-Ji (Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Seo, Kyeong-Hwa (Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Kwon, Jung-Hwa (Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Lee, Dae-Young (Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Baek, Nam-In (Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung Hee University)
  • Received : 2015.04.28
  • Accepted : 2015.06.01
  • Published : 2015.09.30

Abstract

The flowers of Magnolia obovata were extracted with aqueous MeOH and fractionated into EtOAc, n-BuOH, and $H_2O$ fractination. Three alkyl glycosides were isolated from the EtOAc fraction through repeated silica gel and ODS column chromatography. The structures were identified to be 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galacto-pyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), and 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3) on the basis of spectroscopic analyses such as fast atom bombardment mass spectrometry, infrared spectroscopy, 1D nuclear magnetic resonance (NMR) ($^1H$ and $^{13}C-NMR$), and 2D NMR (gCOSY, gHSQC, and gHMBC). These compounds were isolated for the first time from the flower of M. obovata in this study.

황목련 꽃으로부터 3개의 alkyl glycoside 화합물을 분리, 동정하였다. 황목련 꽃을 80% MeOH에 추출하여 이를 EtOAc, n-BuOH, 그리고 $H_2O$ 층으로 계통분획을 실시하였다. 이중 EtOAc 분획에 대하여 silica gel과 ODS column chromatography를 반복 실시하여 3종의 화합물을 분리, 정제하였다. Nuclear magnetic resonance, infrared spectroscopy 및 mass spectrometry의 spectroscopic data를 해석하여 이 화합물들을 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galactopyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3)로 각각 동정하였다. 동정된 화합물 모두 황목련 꽃에서는 이번 연구에서 처음으로 분리, 동정되었다.

Keywords

References

  1. Elzaawely AA, Xuan TD, Koyama H, and Tawata S (2007) Antioxidant activity and contents of essential oil and phenolic compounds in flowers and seeds of A. zerumbet (Pers.). Food Chem 104, 1648-53. https://doi.org/10.1016/j.foodchem.2007.03.016
  2. Ishikawa T, Sega Y, and Kitajima J (2001) Water-soluble constituents of Glehnia littoralis fruit. Chem Pharm Bull 49, 584-8 https://doi.org/10.1248/cpb.49.584
  3. Kim CH, Shin MK, Ahn DG, and Lee GS (1999) The unabridged dictionary of chinese medicine. Jeongdam, Korea.
  4. Kim YK and Ryu SY (1999) Cytotoxic components from stem bark of Magnolia obovata. Planata Med 65, 291-2. https://doi.org/10.1055/s-2006-960784
  5. Lee TB (2003) In Colored Florea of Korea. Hyangmunsa, Korea.
  6. Matsuda H, Kageura T, Oda M, Morikawa T, Sakamoto Y, and Yosikawa M (2001) Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide activated macrophages. Chem Pharm Bull 49, 716-20. https://doi.org/10.1248/cpb.49.716
  7. Pyo MK, Yun-Choi HS, and Hong YJ (2003) Antiplatelet activities of aporphine alkaloids isolated from leaves of Magnolia obovata. Planata Med 69, 267-9. https://doi.org/10.1055/s-2003-38493
  8. Schwab W and Schreier P (1990) Glycosidic conjugates of aliphatic alcohols from apple fruit (Malus sylvestris Mill cult. Jonathan). J Agric Food Chem 38, 757-63 https://doi.org/10.1021/jf00093a037
  9. Seo KH, Lee DY, Lee DS, Park JH, Jeong RH, Jung YJ et al. (2013) Neolignans from the fruits of Magnolia obovata and their inhibition effect on NO production in LPS-induced RAW 264.7 cells. Planta Med 79, 1335-40 https://doi.org/10.1055/s-0033-1350673
  10. Trincone A, Nicolas B, Lama L, Morzillo P, and De Rosa M (1991) Enzymecatalyzed synthesis of alkyl ${\beta}$-D-glycosides with crude homogenate of Sulfolobus solfataricus. Biotechnology Letters 13, 235-40. https://doi.org/10.1007/BF01041476
  11. Wang Q, Kuang H, Su Yang, Sun Y, Feng J, Guo R et al. (2013) Naturally derived anti-inflammatory compounds from Chinese medicinal plants. J Ethnopharmacol 146, 9-39. https://doi.org/10.1016/j.jep.2012.12.013