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Supercritical fluid extraction and identification of isoquinoline alkaloids from leaves of Nelumbo nucifera Gaertn

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Abstract

Isoquinoline alkaloids from leaves of Nelumbo nucifera (N. nucifera) were extracted using supercritical CO2. The effects of the parameters such as the dynamic extraction time, temperature, pressure, various modifiers, and flow rate of the modifier on the yield of nuciferine and the ratio of total isoquinoline alkaloids to the total extract were investigated. Nuciferine content of the extract was determined by high-performance liquid chromatography (HPLC). The results indicated that the yield of nuciferine increased with increases in the dynamic extraction time, pressure, temperature, and flow rate of the modifier. The highest nuciferine yield of 325.54 μg/g was obtained when the extraction was carried out for 2 h at 70 °C under 30 MPa, with 10% (v/v) diethylamine and 1% (v/v) water in methanol as the modifier which kept a flow rate of 1.2 mL/min. The ratio of total isoquinoline alkaloids to the extract was 49.85% at the highest nuciferine yield. Five kinds of isoquinoline alkaloids extracted from N. nucifera leaves were identified by high-performance liquid chromatography combined with ion trap/time-of-flight mass spectrometry (LC/MS-ITTOF). They were Dehydronuciferine, N-nornuciferine, O-nornuciferine, Nuciferine, and Roemerine in the order of retention time.

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References

  1. Agnihotri VK, ElSohly HN, Khan SI, Jacob MR, Joshi VC, Smillie T, Khan IA, Walker LA (2008) Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity. Phytochem Lett 1:89–93

    Article  CAS  Google Scholar 

  2. Ono Y, Hattori E, Fukaya Y, Imai S, Ohizumi Y (2006) Anti-obesity effect of Nelumbo nucifera leaves extract in mice and rats. J Ethnopharmacol 106:238–244

    Article  Google Scholar 

  3. Jiangsu New Medical College (1977) Directory of Chinese Materia Medica. Shanghai Scientific and Technological Press, Shanghai

    Google Scholar 

  4. Ho H-H, Hsu L-S, Chan K-C, Chen H-M, Wu C-H, Wang C-J (2010) Extract from the leaf of nucifera reduced the development of atherosclerosis via inhibition of vascular smooth muscle cell proliferation and migration. Food Chem Toxicol 48:159–168

    Article  CAS  Google Scholar 

  5. Huang B, Ban XQ, He JS, Tong J, Tian J, Wang YW (2010) Hepatoprotective and antioxidant activity of ethanolic extracts of edible lotus (Nelumbo nucifera Gaertn.) leaves. Food Chem 120:873–878

    Article  CAS  Google Scholar 

  6. Liu C-P, Tsai W-J, Lin Y-L, Liao J-F, Chena C-F, Kuo Y-C (2004) The extracts from Nelumbo nucifera suppress cell cycle progression, cytokine genes expression, and cell proliferation in human peripheral blood mononuclear cells. Life Sci 75:699–716

    Article  CAS  Google Scholar 

  7. Mukherjee PK, Mukherjee D, Majia AK, Rai S, Heinrich M (2009) The sacred lotus (Nelumbo nucifera)–phytochemical and therapeutic profile. Pharm and Pharmacol 61:407–422

    CAS  Google Scholar 

  8. Xiao GQ, Lu XY, Tian Y, Yi K, Zhou XM (2006) The research advance of alkaloids from lotus leaf. Chem Bioeng 23:1–2

    Google Scholar 

  9. Kashiwada Y, Aoshima A, Ikeshiro Y, Chen Y-P, Furukawa H, Itoigawa M, Fujioka T, Mihashi K, Cosentino LM, Morris-Natschke SL, Lee K-H (2005) Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Bioorg Med Chem 13:443–448

    Article  CAS  Google Scholar 

  10. Miski M, Shen X, Cooper R, Gillum AM, Fisher DK, MiUer RW, Higgins TJ (1995) Aporphine alkaloids, CD45 protein tyrosine phosphatase inhibitors, from Rollinia ulei. Bioorg Med Chem Lett 5:1519–1522

    Article  CAS  Google Scholar 

  11. Luo XB, Chen B, Liu JJ, Yao SZ (2005) Simultaneous analysis of N-nornuciferine, O-nornuciferine, nuciferine, and roemerine in leaves of Nelumbo nucifera Gaertn by high-performance liquid chromatography–photodiode array detection-electrospray mass spectrometry. Anal Chim Acta 538:129–133

    Article  CAS  Google Scholar 

  12. Herrero M, Mendiola JA, Cifuentes A, Ibáñez E (2010) Supercritical fluid extraction: recent advances and applications. J Chromatogr A 1217:2495–2511

    Article  CAS  Google Scholar 

  13. Verma A, Hartonen K, Riekkola M-L (2008) Optimisation of supercritical fluid extraction of indole alkaloids from catharanthus roseus using experimental design methodology-comparison with other extraction techniques. Phytochem Anal 19:52–63

    Article  CAS  Google Scholar 

  14. Saldaña MDA, Mohamed RS, Baer MG, Mazzafera P (1999) Extraction of purine alkaloids from Maté (Ilex paraguariensis) using supercritical CO2. J Agric Food Chem 47:3804–3808

    Article  Google Scholar 

  15. Boselli E, Caboni MF, Lercker G (2001) Extraction and purification of free cholesterol from some egg-containing food by on-line supercritical fluid extraction–solid-phase extraction. Eur Food Res Technol 212:244–246

    Article  CAS  Google Scholar 

  16. Brachet A, Christen P, Gauvrit J-Y, Longeray R, Lanteri P, Veuthey J-L (2000) Experimental design in supercritical fluid extraction of cocaine from coca leaves. J Biochem Biophys Methods 43:353–366

    Article  CAS  Google Scholar 

  17. Choi YH, Chin Y-W, Kim J, Jeon SH, Yoo K-P (1999) Strategies for supercritical fluid extraction of hyoscyamine and scopolamine salts using basified modifiers. J Chromatogr A 863:47–55

    Article  CAS  Google Scholar 

  18. Radcliffe C, Maguire K, Lockwood B (2000) Applications of supercritical fluid extraction and chromatography in forensic science. J Biochem Biophys Methods 43:261–272

    Article  CAS  Google Scholar 

  19. Staub C (1997) Supercritical fluid extraction and hair analysis: the situation in 1996. Forensic Sci Int 84:295–304

    Article  CAS  Google Scholar 

  20. Reverchon E, Marco ID (2006) Supercritical fluid extraction and fractionation of natural matter. J Supercrit Fluids 38:146–166

    Article  CAS  Google Scholar 

  21. Rajaei A, Barzegar M, Yamini Y (2005) Supercritical fluid extraction of tea seed oil and its comparison with solvent extraction. Eur Food Res Technol 220:401–405

    Article  CAS  Google Scholar 

  22. Liu B, Jiang HL, Shen B, Chang YL (2005) Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils. J Chromatogr A 1075:213–215

    Article  CAS  Google Scholar 

  23. Tzeng T-C, Lin Y-L, Jong T-T, Chang YL, Jang CM (2007) Ethanol modified supercritical fluids extraction of scopoletin and artemisinin from Artemisia annua L. Sep Purif Technol 56:18–24

    Article  CAS  Google Scholar 

  24. Liu B, Shen B, Guo F, Chang YL (2008) Optimization of supercritical fluid extraction of dl-tetrahydropalmatine from rhizome of Corydalis yanhusuo W.T.Wang with orthogonal array design. Sep Purif Technol 64:242–246

    Article  CAS  Google Scholar 

  25. Chen Y, Fan GR, Zhang QY, Wu HL, Wu YT (2007) Fingerprint analysis of the fruits of Cnidium monnieri extract by high-performance liquid chromatography–diode array detection–electrospray ionization tandem mass spectrometry. J Pharm Biomed Anal 43:926–936

    Article  CAS  Google Scholar 

  26. Wang DM, Lu JL, Miao AQ, Xie ZY, Yang D (2008) HPLC-DAD-ESI-MS/MS analysis of polyphenols and purine alkaloids in leaves of 22 tea cultivars in China. J Food Compos Anal 21:361–369

    Article  CAS  Google Scholar 

  27. Ding B, Zhou TT, Fan GR, Hong ZY, Wu YT (2007) Qualitative and quantitative determination of ten alkaloids in traditional Chinese medicine Corydalis yanhusuo W.T. Wang by LC–MS/MS and LC–DAD. J Pharm Biomed Anal 45:219–226

    Article  CAS  Google Scholar 

  28. Zhou J-L, Li P, Li H-J, Jiang Y, Ren M-T, Liu Y (2008) Development and validation of a liquid chromatography/electrospray ionization time-of-flight mass spectrometry method for relative and absolute quantification of steroidal alkaloids in Fritillaria species. J Chromatogr A 1177:126–137

    Article  CAS  Google Scholar 

  29. Chen Y, Fan GR, Wu HL, Wu YT, Mitchell A (2007) Separation, identification and rapid determination of liensine, isoliensinine and neferine from embryo of the seed of Nelumbo nucifera GAERTN by liquid chromatography coupled to diode array detector and tandem mass spectrometry. J Pharm Biomed Anal 43:99–104

    Article  Google Scholar 

  30. Deevanhxay P, Suzuki M, Maeshibu N, Li H, Tanak K, Hirose S (2009) Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry. J Pharm Biomed Anal 50:413–425

    Article  CAS  Google Scholar 

  31. AOAC (1984) Official methods of analysis of the association of official analytical chemists, 14th ed. In Williams S (ed) Association of Official Analytical Chemists, Washington DC, p 1018

  32. Li WM, Jin B, Feng YF (2002) Modernization of traditional Chinese medicine with the supercritical fluid extraction technology. China Medical Science and Technology Press, China

    Google Scholar 

  33. Hu M, Skibsted LH (2002) Antioxidative capacity of rhizome extract and rhizome knot extract of edible lotus (Nelumbo nuficera). Food Chem 76:327–333

    Article  CAS  Google Scholar 

  34. Xu HD, Jian QJ (2008) A new benzylisoquinoline alkaloid from stems of Nelumbo nucifera. Chin Chem Lett 19:308–310

    Article  Google Scholar 

  35. del Valle JM, Rogalinski T, Zetzl C, Brunner G (2005) Extraction of boldo (Peumus boldus M.) leaves with supercritical CO2 and hot pressurized water. Food Res Int 38:203–213

    Article  Google Scholar 

  36. Liu ZY, Huang LL, Dai MH, Chen DM, Wang YL, Tao YF, Yuan ZH (2008) Metabolism of olaquindox in rat liver microsomes: structural elucidation of metabolites by high-performance liquid chromatography combined with ion trap/time-of-flight mass spectrometry. Rapid Commun Mass Spectrum 22:1009–1016

    Article  CAS  Google Scholar 

  37. Liu B, Li WJ, Chang YL, Dong WH, Ni L (2006) Extraction of berberine from rhizome of Coptis chinensis Franch using supercritical fluid extraction. J Pharm Biomed Anal 41:1056–1060

    Article  CAS  Google Scholar 

  38. Duarte CMM, Crew M, Casimiro T, Aguiar-Ricardo A, da Ponte MN (2002) Phase equilibrium for capsaicin + water + ethanol + supercritical carbon dioxide. J Supercrit Fluids 22:87–92

    Article  CAS  Google Scholar 

  39. Iwai Y, Nagano H, Lee GS, Uno M, Arai Y (2006) Measurement of entrainer effects of water and ethanol on solubility of caffeine in supercritical carbon dioxide by FT-IR spectroscopy. J Supercrit Fluids 38:312–318

    Article  CAS  Google Scholar 

  40. Jackson K, Bowman LE, Fulton JL (1995) Water solubility measurements in supercritical fluids and high-pressure liquids using near-infrared spectroscopy. Anal Chem 67:2368–2372

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Xueliang Zhu and Zhaoying Liu for providing instruments and also National Scientific and Technological Support Projects of the “Eleventh Five-Year” for financial support (Project No. 2006BAD27B09-4).

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Correspondence to Zhida Sun.

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Xiao, J., Tian, B., Xie, B. et al. Supercritical fluid extraction and identification of isoquinoline alkaloids from leaves of Nelumbo nucifera Gaertn. Eur Food Res Technol 231, 407–414 (2010). https://doi.org/10.1007/s00217-010-1290-y

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  • DOI: https://doi.org/10.1007/s00217-010-1290-y

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