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Isolation of Flavonoids from Piper delineatum Leaves by Chromatographic Techniques

采用色谱技术从胡椒属叶分离类黄酮

Isabel L. Bazzocchi Isabel L. Bazzocchi
Juan C. Ticona Juan C. Ticona
Ignacio A. Jiménez Ignacio A. Jiménez
Ninoska Flores Ninoska Flores

发布: 2016年07月20日第6卷第14期 DOI: 10.21769/BioProtoc.1867 浏览次数: 18179

评审: Arsalan DaudiAnonymous reviewer(s)

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Jun 2015

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Abstract

The genus Piper (Piperaceae) is widely distributed in the tropical and subtropical regions of the world, and species belonging to this genus are included in the Ayurvedic system of medicine and in folklore medicine of Latin America. Phytochemical investigations of Piper species have led to the isolation of several classes of physiologically active compounds such as alkaloids, amides, pyrones, dihydrochalcones, flavonoids, phenylpropanoids, lignans and neolignans. In an ongoing investigation of bioactive secondary metabolites from Piper species, herein, we describe the isolation procedure of nine flavonoids, including two chalcones and two flavanones from the leaves of Piper delineatum Trel. (Piperaceae), a shrub native to tropical regions of the Americas. All compounds were elucidated by spectroscopic and spectrometric methods, and comparison with data reported in the literature.

Keywords: Piper (派珀) search Flavonoids (黄酮类化合物) search Isolation (隔离) search Chromatography (色谱法) search

Materials and Reagents

  1. Silica gel 60 (particle size 63-200 mm) (Macherey-Nagel, catalog number: 815330 )
  2. Silica gel 60 (particle size 15-40 mm) (Macherey-Nagel, catalog number: 815650 )
  3. TLC silica gel 60 F254 plates (Merck Millipore Corporation, catalog number: 105735 )
  4. SIL G/UV254 (20 x 20 cm), Macherey-Nagel, catalog number: 805023 )
  5. Pre-coated TLC-plates UV254 20 x 20 cm (Macherey-Nagel, catalog number: 821030 )
  6. Round-bottom tubes (40 ml, 200 x 20 mm) (Simax, Alamo, catalog number: 00684800 )
  7. Round-bottom tubes (8 ml, 120 x 12 mm) (Simax, Alamo, catalog number: 00684400 )
  8. Microcapillary tube 1-5 μl (Sigma-Aldrich, catalog number: P0549-1PAK )
  9. NMR simple tubes 5 mm (Wilmad® LabGlass, catalog number: 528-PP-7 )
  10. Leaves of the plant species (Piper delineatum) at the mature stage were collected in Iquitos, Maynas Province, Department of Loreto, Perú in November 2009. A voucher specimen (10484) was identified by botanist Juan Ruiz Macedo and was deposited at the Amazonense Herbarium of Universidad Nacional de la Amazonia Peruana, Iquitos, Perú.
  11. Ethanol absolute (Panreac, catalog number: 141086 )
  12. Dichloromethane (CH2Cl) (Panreac, catalog number: 131254 )
  13. Ethyl acetate (Panreac, catalog number: 141318.1212 )
  14. Hexanes (Panreac, catalog number: 121347.1612 )
  15. Chloroform (Panreac, catalog number: 161252 )
  16. Diethyl ether (Panreac, catalog number: 142770.0311 )
  17. Acetone (Panreac, catalog number: 131007.1212 )
  18. Methanol (Panreac, catalog number: 141091.1211 )
  19. Isopropanol (Panreac, catalog number: 131090 )
  20. Acetone deuterated [(CD3)2CO] (Sigma-Aldrich, catalog number: 151793-25G )
  21. Magnesium sulfate anhydrous (Panreac, catalog number: 212486 )
  22. Sulfuric acid (Panreac, catalog number: 141058 )
  23. Acetic acid glacial (Panreac, catalog number: 141008 )
  24. Sea sand washed thin grain QP (Panreac, catalog number: 211160.0416 )
  25. Sephadex LH-20 (Sigma-Aldrich, catalog number: LH20100 )
  26. Oleum: Acetic acid-water-sulfuric acid (20:4:1) (see Recipes)
  27. Coating rotor with sorbent for the CPTLC (4 mm thickness) (see Recipes)

Equipment

  1. Rotary cutter mill (Mateu and Sole, S.L., Constructores, MATSO, model: B-2, nº 258 )
  2. Soxhlet extraction apparatus (ANORSA, catalog number: 322060 )
  3. Rotary R-210 evaporator (Sigma- Aldrich, Büchi® Rotavapor®, catalog number: Z565466 )
  4. Separating funnel, 2 L (Sigma-Aldrich, catalog number: Z330663 )
  5. Erlenmeyer flasks (100 ml and 500 ml) (Duran, catalog numbers: Z232793-1EA and Z232831-1EA , respectively)
  6. Teflon funnel holder
  7. Solvent-pouring funnel (stem L, O.D. 0.65 x 22 mm) (Sigma-Aldrich, catalog number: 548804 )
  8. Evaporating flask (pear-shaped, 1L) (Sigma-Aldrich, catalog number: Z402990 )
  9. Round-bottom flask (5 L) (Sigma-Aldrich, catalog number: Z302872 )
  10. Glass Pasteur pipets 225 mm (BRAND, catalog number: 747720 )
  11. Pasteur pipette rubber bulbs, 2 ml (Sigma-Aldrich, catalog number: Z111597-12EA )
  12. Heating bath (Sigma-Aldrich, catalog number: Z563544 )
  13. Heating mantle 5 L (Selecta, catalog number: 3031450 )
  14. Hot plate (Selecta, catalog number: 1000443 )
  15. Liebig Condenser (Sigma-Aldrich, catalog number: Z531006 )
  16. Glass chromatography column (CC) for silica gel (50 x 9 cm) (Fisher Scientific, catalog number: 12058880 )
  17. Glass chromatography column (CC) for Sephadex (60 x 4.5 cm) (Fisher Scientific, catalog number: 12011550 ).
  18. Centrifugal preparative thin layer chromatography system (CPTLC) (Chromatotron, Harrison Research Inc., model: 7924T )
  19. Silica gel PF254 disks (Merck Millipore Corporation, catalog number: 107749 2500 )
  20. TLC Chamber rectangular for TLC plates (7.5 x 15.5 x 8.0 cm) (Sigma-Aldrich, catalog number: Z204226 )
  21. TLC Chamber rectangular for PTLC plates (27.0 x 26.5 x 7.0 cm) (Sigma-Aldrich, catalog number: Z126195-1EA )
  22. Glass atomizer reagent sprayer (125 ml) (Sigma-Aldrich, catalog number: Z529737-1EA )
  23. Glass vacuum filter (Fisher Scientific, catalog number: 11979659 )
  24. Micro-spatula (8 in) (Sigma-Aldrich, catalog number: Z513342-1PAK )
  25. Analytical balance, semi-micro balance (Fisher Scientific, Mettler ToledoTM, catalog number: 11142062 ; model: NewClassic MS105DU)
  26. Nuclear Magnetic Resonance (NMR) Spectrometers (Bruker, model: Bruker Avance 400 ; Bruker Avance 500 ).
  27. Optical rotations polarimeter (CHCl3 at 25 °C) (PerkinElmer, model: 241 automatic polarimeter )
  28. Ultraviolet (UV) spectrophotometer (JASCO, model: V-560 )
  29. Infrared (IR) spectrophotometer (Bruker, model: IFS 55 , IFS 28/55 )
  30. High resolution electron impact (HREI) mass spectrometer (MS) (MasSpec, model: Micromass VG Autospec magnetic sector , M series)

Procedure

English
中文翻译

文章信息

版权信息

© 2016 The Authors; exclusive licensee Bio-protocol LLC.

如何引用

Bazzocchi, I. L., Ticona, J. C., Jiménez, I. A. and Flores, N. (2016). Isolation of Flavonoids from Piper delineatum Leaves by Chromatographic Techniques. Bio-protocol 6(14): e1867. DOI: 10.21769/BioProtoc.1867.

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分类

植物科学 > 植物生物化学 > 其它化合物

植物科学 > 植物新陈代谢 > 其它化合物

生物化学 > 其它化合物 > 类黄酮

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