SpringerProtocols: Abstract: Isolation of Natural Products by Low-Pressure Column Chromatography

Isolation of Natural Products by Low-Pressure Column Chromatography

By: Raymond G. Reid⁴, Satyajit D. Sarker⁵

Abstract

Full Text

Download PDF (441K)

This chapter deals with the isolation of natural products using low-pressure liquid column chromatography (LPLC). A brief summary of the adsorption and size-exclusion processes involved in the LPLC is presented. Different types of stationary phases used in both adsorption and size-exclusion LPLC are described along with examples of each type used in LPLC. Operational parameters are also discussed in detail in relation to column packing (both wet and dry), column equilibration, sample application, and column development. An outline of generic procedures for adsorption and size-exclusion LPLC is provided. Sixty-one specific examples of the use of LPLC for the isolation of various natural products, including flavones, coumarins, alkaloids, and triterpenoid saponins from various plants are given. Many of these examples incorporate a combination of adsorption and size-exclusion chromatography to obtain specific compounds.

Affiliation(s): (4) Phytopharmaceutical Research Laboratory, School of Pharmacy, The Robert Gordon University, Aberdeen, Scotland, UK
(5) Pharmaceutical Biotechnology Research Group, School of Biomedical Sciences, University of Ulster at Coleraine, Coleraine, Northern Ireland, UK

Book Title: Natural Products Isolation

Series: Methods in Biotechnology | Volume: 20 | Pub. Date: Sep-19-2005 | Page Range: 117-157 | DOI: 10.1385/1-59259-955-9:117

Subject: Biochemistry

Key Words: Natural products - low-pressure column chromatography - adsorption - size exclusion - packing materials

References

Download References

1.	Brown, P. R. (1990) High performance liquid chromatography—past developments, present status, and future trends. Anal. Chem. 62, A995–A1014.

2.	Warner, M. (1990) Pioneers in gas chromatography. Anal. Chem. 62, A1015–A1017.

3.	Issaq, H. J. (2001) (ed.) A Century of Separation Science. Marcel Dekker, New York.

4.	Ettre, L. S. (2001) (ed.) Milestones in the Evolution of Chromatography. ChromSource Inc., Portland.

5.	Gehrke, C. W. (2001) (ed.) Chromatography—a century of discovery 1900–2000, in Journal of Chromatography Series. vol. 64, Elsevier, Amsterdam.

6.	Brown, P. and Hartwick, R. A. (1989) High Performance Liquid Chromatography Wiley, New York.

7.	de Neue, U. (1997) HPLC Columns: Theory, Technology and Practice. Wiley, New York.

8.	Robards, K., Haddad, P., and Jackson, P. (1994). Principles and Practice of Modern Chromatographic Methods. Academic, Elsevier, Amsterdam.

9.	Snyder, L. R., Kirkland, J. J., and Glajch, J. L. (1997). Practical HPLC Method Development. Wiley, New York.

10.	Wu, C.-S. (2003) Handbook of Size Exclusion Chromatography and Related Techniques. Marcel Dekker, New York.

11.	Braithwaite, A. and Smith, F. J. (1995) Chromatographic Methods. 5 ed., Kluwer Academic Publishers.

12.	Kazakevich, Y. and McNair, H. (1996) Basic Liquid Chromatography. Available on-line at http://hplc.chem.shu.edu/NEW/HPLC_Book/index.html.

13.	Unger, K. K. (1990) (ed.) Packings and stationary phases in chromatographic techniques, in Chromatographic Science Series. vol. 47, Dekker, New York.

14.	Scott, R. P. W. (1993). Silica Gel and Bonded Phases: Their Production, Properties and use in LC. Wiley, New York.

15.	Sarker, S. D., Bartholomew, B., Nash, R. J., and Simmonds, M. (2001) Sideroxylin and 8-demethylsideroxylin from Eucalyptus saligna (Myrtaceae) Biochem. Syst. Ecol. 29, 759–762.

16.	Sharp, H., Latif, Z., Bartholomew, B. et al. (2001) Emodin and syringaldehyde from Rhamnus pubescens (Rhamnaceae). Biochem. Syst. Ecol. 29, 113–115.

17.	Sharp, H., Bartholomew, B., Bright, C., Latif, Z., Sarker, S. D., and Nash, R. J. (2001) 6-Oxygenated flavones from Baccharis trinervis. Biochem. Syst. Ecol. 29, 105–107.

18.	Sharp, H., Latif, Z., Bright, C., Bartholomew, B., Sarker, S. D., and Nash, R. J. (2001) Totarol, totaradiol and ferruginol: three diterpenes from Thuja plicata (Cupressaceae). Biochem. Syst. Ecol. 29, 215–217.

19.	Sharp, H., Thomas, D., Currie, F. et al. (2001) Pinoresinol and syringa-resinol: two lignans from Avicennia germinans (Avicenniaceae). Biochem. Syst. Ecol. 29, 325–327.

20.	Cowan, S., Bartholomew, B., Bright, C. et al. (2001) Lignans from Cupressus lusitanica (Cupressaceae). Biochem. Syst. Ecol. 29, 109–111.

21.	Turnock, J., Cowan, S., Watson, A. A. et al. (2001) N-trans-feruloyltyramine from two species of the Solanaceae. Biochem. Syst. Ecol. 29, 209–211.

22.	Cowan, S., Stewart, M., Latif, Z., Sarker, S. D., and Nash, R. J. (2001) Lignans from Strophanthus gratus. Fitoterapia 72, 80–82.

23.	Murphy, E. M., Nahar, L., Byres, M. et al. (2004) Coumarins from the seeds of Angelica sylvestris (Apiaceae) and their distribution within the genus Angelica. Biochem. Syst. Ecol. 32, 203–207.

24.	Sarker, S. D., Armstrong, J. A., and Waterman, P. G. (1995) (−)-1,12-Oxaguai-10(15)-ene: a sesquiterpene from Eriostemon fitzgeraldii. Phytochemistry 40, 1159–1162.

25.	Sarker, S. D., Waterman, P. G., and Armstrong, J. A. (1995) Coumarin glycosides from 2 species of Eriostemon. J. Nat. Prod.-Lloydia 58, 1109–1115.

26.	Sarker, S. D., Armstrong, J. A., and Waterman, P. G. (1995) An alkaloid, coumarins and a triterpene from Boronia algida. Phytochemistry 39, 801–804.

27.	Sarker, S. D., Waterman, P. G., and Armstrong, J. A. (1995) 3,4,8-Trimethoxy-2-quinolone—a new alkaloid from Eriostemon gardneri. J. Nat. Prod.-Lloydia 58, 574–576.

28.	Sarker, S. D., Gray, A. I., Waterman, P. G., and Armstrong, J. A. (1994) Coumarins from Asterolasia trymalioides. J. Nat. Prod.-Lloydia 57, 1549–1551.

29.	Sarker, S. D., Gray, A. I., Waterman, P. G., and Armstrong, J. A. (1994) Coumarins from 2 Asterolasia species. J. Nat. Prod.-Lloydia 57, 324–327.

30.	Sarker, S. D., Armstrong, J. A., and Waterman, P. G. (1994) Sesquiterpenyl coumarins and geranyl benzaldehyde derivatives from the aerial parts of Eriostemon myoporoides. Phytochemistry 37, 1287–1294.

31.	Sarker, S. D., Armstrong, J. A., and Waterman, P. G. (1994) Angular pyranocoumarins from Eriostemon thryptomenoides (Rutaceae). Biochem. Syst. Ecol. 22, 863–864.

32.	Sarker, S. D., Armstrong, J. A., Gray, A. I., and Waterman, P. G. (1994) Coumarins from Asterolasia phebalioides (Rutaceae). Biochem. Syst. Ecol. 22, 433.

33.	Sarker, S. D., Armstrong, J. A., Gray, A. I., and Waterman, P. G. (1994) Pyrano coumarins from Eriostemon apiculatus. Biochem Syst. Ecol. 22, 641–644.

34.	Shoeb, M., Jaspars, M., MacManus, S. M., Majinda, R. R. T., and Sarker, S. D. (2004) Epoxylignans from the seeds of Centaurea cyanus. Biochem. Syst. Ecol. 32, 1201–1204.

35.	Egan, P., Middleton, P., Shoeb, M. et al. (2004) GI5, a dimer of oleoside, from Fraxinus excelsior (Oleaceae). Biochem. Syst. Ecol. 32, 1069–1071.

36.	Kumarasamy, Y., Byres, M., Cox, P. J. et al. (2004) Isolation, structure elucidation and biological activity of flavone C-glycosides from the seeds of Alliaria petiolata. Chem. Nat. Compounds 40, 106–110.

37.	Kumarasamy, Y., Cox, P. J., Jaspars, M., Nahar, L., and Sarkar, S. D. (2003) Isolation, structure elucidation and biological activity of two unique alkaloids, hederacine A and B, from Glechoma hederaceae. Tetrahedron 59, 6403–6407.

38.	Kumarasamy, Y., Cox, P. J., Jaspars, M., Nahar, L., and Sarker, S. D. (2003) Bioactivity of secoiridoid glycosides from Centaurium erythraea. Phytomedicine 10, 344–347.

39.	Kumarasamy, Y., Nahar, L., Cox, P. J. et al. (2003) Biological activities of lignans from Centaurea scabiosa. Pharm. Biol. 41, 203–206.

40.	Kumarasamy, Y., Cox, P. J., Jaspars, M., Rashid, M. A., and Sarker, S. D. (2003) Bioactive flavonoid glycosides from the seeds of Rosa canina. Pharm. Biol. 41, 237–242.

41.	Kumarasamy, Y., Cox, P. J., Jaspars, M., Nahar, L., and Sarker, S. D. (2003) Cyanogenic glycosides from Prunus spinosa (Rosaceae). Biochem. Syst. Ecol. 31, 1063–1065.

42.	Sarker, S. D., Whiting, P., Dinan, L., Sik, V., and Rees, H. H. (1999) Identification and ecdysteroid antagonist activity of three resveratrol trimers (suffruticosol A, B and C) from Paeonia suffruticosa. Tetrahedron 55, 513–524.

43.	Sarker, S. D., Whiting, P., Sik, V., and Dinan, L. (1999) Ecdysteroid antagonists (Cucurbitacins) from Physocarpus opulifolius (Rosaceae). Phytochemistry 50, 1123–1128.

44.	Dinan, L., Sarker, S. D., Bourne, P., Whiting, P., Sik, V., and Rees, H. H. (1999) Phytoecdysteroids in seeds and plants of Rhagodia baccata (Labill.) Moq. (Chenopodiaceae). Arch. Insect Biochem. Physiol. 41, 18–23.

45.	Sarker, S. D., Dinan, L., Sik, V., Underwood, E., and Waterman, P. G. (1998) Moschamide: an unusual alkaloid from the seeds of Centaurea moschata. Tetrahedron Lett. 39, 1421–1424.

46.	Sarker, S. D., Sik, V., Rees, H. H., and Dinan, L. (1998) 2-Dehydro-3-epi-20-hydroxy ecdysone from Froelichia floridana. Phytochemistry 49, 2311–2314.

47.	Sarker, S. D., Sik, V., Rees, H. H., and Dinan, L. (1998) (20R)-1α,20-Dihy-droxy ecdysone from Axyris amaranthoides. Phytochemistry 49, 2305–2310.

48.	Sarker, S. D., Sik, V., Dinan, L., and Rees, H. H. (1998) Moschatine: an unusual steroidal glycoside from Centaurea moschata. Phytochemistry 48, 1039–1043.

49.	Sarker, S. D., Girault, J. P., Lafont, R., and Dinan, L (1998) (20R) 15α-Hydroxy-8β,9α,14α,17α-pregn-4-en-3-one 20-O-β-d-glucopyranoside from Centaurea moschata. Pharm. Biol. 36, 202–206.

50.	Sarker, S. D., Savchenko, T., Whiting, P., Sik, V., and Dinan, L. N. (1997) Two limonoids from Turraea obtusifolia (Meliaceae), prieurianin and rohitukin, antagonise 20-hydroxyecdysone action in a Drosophila cell line. Arch. Insect Biochem. Physiol. 35, 211–217.

51.	Sarker, S. D., Girault, J. P., Lafont, R., and Dinan, L. (1997) Ecdysteroid xylosides from Limnanthes douglasii. Phytochemistry 44, 513–521.

52.	Sarker, S. D., Dinan, L., Sik, V., and Rees, H. H. (1997) 9ξ-O-β-d-Glucopyr-anosyloxy-5-megastigmen-4-one from Lamium album. Phytochemistry 45, 1435–1439.

53.	Sarker, S. D., Savchenko, T., Whiting, P., Sik, V., and Dinan, L. N. (1997) Moschamine, cis-moschamine, moschamindole and moschamindolol: four novel indole alkaloids from Centaurea moschata. Nat. Prod. Lett. 9, 189–199.

54.	Sarker, S. D., Dinan, L., Girault, J. P., Lafont, R., and Waterman, P. G. (1996) Punisterone [(20R, 24S)-25-deoxy-11α,20,24-trihydroxyecdysone]: a new phytoecdysteroid from Blandfordia punicea. J. Nat. Prod. Lloydia 59, 789–793.

55.	Diaz, J. G., Ruiz, J. G., and de la Fuente, G. (2000) Alkaloids from Delphinium staphisagria. J. Nat. Prod. 63, 1136–1139.

56.	Grandez, M., Madinaveitia, A., Gavin, J. A., Alva, A., and de la Fuente, G. (2002) Alkaloids from Consolida oliverianna. J. Nat. Prod. 65, 513–516.

57.	Zhu, N., Jiang, Y., Wang, M., and Ho, C-T. (2001) Cycloartane triterpene saponins from the roots of Cimicfuga foetida. J. Nat. Prod. 64, 627–629.

58.	Yoshikawa, K., Tanaka, M., Arihara, S. et al. (2000) New oleanene triterpenoid saponins from Madhuca longifolia. J. Nat. Prod. 63, 1679–1681.

59.	Yoshikawa, K., Morikawa, T., Nakano, K., Pongpiriyadacha, Y., Murakami, T., and Matsuda, H. (2002) Characterisation of new sweet triterpene saponins from Albizia myriophylla. J. Nat. Prod. 65, 1638–1642.

60.	Ma, W., Wei, X., Ling, T., Xie, H., and Zhou, W. (2003) New phenolics from Polygala fallax. J. Nat. Prod. 66, 441–443.

61.	Nunez, M. J., Guadano, A., Jiminez, I. A., Ravelo, A. G., Gonzalez-Coloma, A., and Bazzocchi, I. L. (2004) Insecticidal sesquiterpene pyridine alkaloids from Maytenus chiapensis. J. Nat. Prod. 67, 14–18.

62.	Wright, A. D., Osterhage, C., and König, G. M. (2003) Epicoccamide, a novel secondary metabolite from a jellyfish-derived culture of Epicoccum purpurascens. Org. Biomol. Chem. 1, 507–510.

63.	Ferguson, C. A., Nahar, L., Finnie, D. et al. (2003) Centaurea scabiosa: a source of dibenzylbutyrolactone lignans. Biochem. Syst. Ecol. 31, 303–305.

64.	Middleton, M., Cox, PJ., Jaspars, M. et al. (2003) Dibenzylbutyrolactone lignans and indole alkaloids from the seeds of Centaurea nigra (Asteraceae). Biochem. Syst. Ecol. 31, 653–656.

65.	Kumarasamy, Y., Middleton, M., Reid, R. G., Nahar, L., and Sarker, S. D. (2003) Biological activity of serotonin conjugates from the seeds of Centaurea nigra. Fitoterapia 74, 609–612.

66.	Tomlinson, C. T. M., Nahar, L., Copland, A. et al. (2003) Flavonol glycosides from the seeds of Agrimonia eupatoria (Rosaceae). Biochem. Syst. Ecol. 31, 439–441.

67.	Jin, J-M., Zhang, Y. J., and Yang, C.-R. (2004) Spirostanol and furostanol glycosides from the fresh tubers of Polianthes tuberosa. J. Nat. Prod. 67, 5–9.

68.	Groweiss, A., Cardellina, J. H., and Boyd, M. R. (2000) HIV-inhibitory prenylated xanthones and flavones from Maclura tinctoria. J. Nat. Prod. 63, 1537–1539.

69.	Al-Howiriny, T. A., Zemaitis, M. A., Gao, C.-Y., et al. (2001) Thalibealine, a novel tetrahydroprotoberberine-aporphine dimeric alkaloid from Thalictrum wangii. J. Nat. Prod. 64, 819–822.

70.	Levison, P. R. (2003) Large-scale ion-exchange column chromatography of proteins: comparison of different formats. J. Chromatogr. B 790, 17–33.

71.	Roman, R. B., Alvarez-Pez, J. M., Fernandez, F. G. A., and Grima, E. M. (2002) Recovery of pure β-phycoerythrin from the microalga Porphyridium cruentum. J. Biotechnol. 93, 73–85.

72.	Orozco-Villafuerte, J., Cruz-Sosa, F., Ponce-Alquicira, E., and Vernon-Carter, E. J. (2003) Mesquite gum: fractionation and characterisation of the gum exuded from Prosopis laevigata obtained from plant tissue culture and from wild trees. Carbohydr. Polymers 54, 327–333.

73.	Froytlog, C., Slimestad, R., and Andersen, O. M. (1998) Combination of chromatographic techniques for the preparative isolation of anthocyanins-applied on blackcurrant (Ribes nigrum) fruits. J. Chromatogr. A 825, 89–95.

74.	Adamson G. E., Lazarus, S. A., Mitchell A. E., et al. (1999) HPCL method for the qualification of procyanidins in cocoa and chocolate samples and correlation to total antioxidant capacity. J. Agric. Food Chem. 47, 4184–4188.

75.	Salituro, G. M. and Dufresne, C. (1998) Isolation by low-pressure column chromatography, in Natural Products Isolation, 1 ed. (Cannell, R. J. P., ed.), Humana Press, New Jersey.

Comments (Loading...)

Post comment/View all comments