Seasonal variations in the concentrations of lipophilic compounds and phenolic acids in the roots of echinacea purpurea and echinacea pallida

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 49, 2012, Pages 12131-12141

  Thomsen, Maria O ^a   Fretté, Xavier C ^b   Christensen, Kathrine B ^b   Christensen, Lars P ^b   Grevsen, Kai ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

alkamides; cultivation; Echinacea spp.; harvest time; ketoalkenes; ketoalkynes; phenolic acids; plant development

Indexed keywords

ALKAMIDES; ECHINACEA SPP; HARVEST TIME; KETOALKENES; KETOALKYNES; PHENOLIC ACIDS; PLANT DEVELOPMENT;

AMIDES; CHROMATOGRAPHY; CULTIVATION; HARVESTING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTIMIZATION; ORGANIC ACIDS; PLANTS (BOTANY);

PHENOLS;

ALKENE; ALKYNE; CAFFEIC ACID DERIVATIVE; CAFTARIC ACID; CHLOROGENIC ACID; CICHORIC ACID; ECHINACOSIDE; GLYCOSIDE; HYDROXYBENZOIC ACID DERIVATIVE; PHENOL DERIVATIVE; PHENOLIC ACID; PLANT EXTRACT; SUCCINIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; ECHINACEA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; METHODOLOGY; PLANT ROOT; SEASON;

ALKENES; ALKYNES; CAFFEIC ACIDS; CHLOROGENIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ECHINACEA; GLYCOSIDES; HYDROXYBENZOATES; PHENOLS; PLANT EXTRACTS; PLANT ROOTS; SEASONS; SUCCINATES;

ECHINACEA PALLIDA; ECHINACEA PURPUREA;

EID: 84870867381     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf303292t     Document Type: Article

References (32)

1. Grimm, W.; MuÌ̂ller, H. A randomized controlled trial of the effect of fluid extract of Echinacea purpurea on the incidence and severity of colds and respiratory infections Am. J. Med. 1999, 106, 138-143
2. Woelkart, K.; Bauer, R. The role of alkamides as an active principle of Echinacea Planta Med. 2007, 73, 615-623
3. Barnes, J.; Anderson, L.; Gibbons, S.; Phillipson, J. Echinacea species (Echinacea angustifolia (DC.) Hell., Echinacea pallida (Nutt.) Nutt., Echinacea purpurea (L.) Moench): A review of their chemistry, pharmacology and clinical properties J. Pharm. Pharmacol. 2005, 57, 929-954
4. Clifford, L.; Nair, M.; Rana, J.; Dewitt, D. Bioactivity of alkamides isolated from Echinacea purpurea (L.) Moench Phytomedicine 2002, 9, 249-253
5. Chicca, A.; Pellati, F.; Adinolfi, B.; Matthias, A.; Massarelli, I.; Benvenuti, S.; Martinotti, E.; Bianucci, A. M.; Bone, K.; Lehmann, R.; Nieri, P. Cytotoxic activity of polyacetylenes and polyenes isolated from the roots of Echinacea pallida Br. J. Pharmacol. 2008, 153, 879-885
6. Pellati, F.; Benvenuti, S.; Magro, L.; Melagari, M.; Soragni, F. Analysis of phenolic compounds and radical scavenging activity of Echinacea spp J. Pharm. Biomed. Anal. 2004, 35, 289-301
7. Bauer, R.; Remiger, P. TLC and HPLC analysis of alkamides in Echinacea drugs Planta Med. 1982, 55, 367-371
8. 2 production in RAW264.7 mouse macrophage cells J. Agric. Food Chem. 2007, 55, 7314-7322
9. Matthias, A.; Banbury, L.; Stevenson, L. M.; Bone, K. M.; Leach, D. N.; Lehmann, R. P. Alkylamides from Echinacea modulate induced immune responses in macrophages Immunol. Invest. 2007, 36, 117-130
10. Hou, C. C.; Chen, C. H.; Yang, N. S.; Chen, Y. P.; Lo, C. P.; Wang, S. Y.; Tien, Y. J.; Tsai, P. W.; Shyur, L. F. Comparative metabolomics approach coupled with cell- and gene-based assays for species classification and anti-inflammatory bioactivity validation of Echinacea plants J. Nutr. Biochem. 2010, 21, 1045-1059
11. Woelkart, K.; Koidl, C.; Grisold, A.; Gangemi, J. D.; Turner, R. B.; Marth, E.; Bauer, R. Bioavailability and pharmacokinetics of alkamides from the roots of Echinacea angustifolia in humans J. Clin. Pharmacol. 2005, 45, 683-689
12. Binns, S.; Livesey, J.; Arnason, J.; Baum, B. Phytochemical variation in Echinacea from roots and flower heads of wild and cultivated populations J. Agric. Food Chem. 2002, 50, 3673-3687
13. Rinniger, J. A.; Kickner, S.; Chigurupati, P.; McLean, A.; Franck, Z. Immunopharmacolo-gical activity of Echinacea preparations following simulated digestion on murine macrophages and human peripheral blood mononuclear cells J. Leukocyte Biol. 2000, 68, 503-510
14. Geng, X.; Tian, X.; Tu, P.; Pu, X. Neuroprotective effects of echinacoside in the mouse MPTP model of Parkinson's disease Eur. J. Pharmacol. 2007, 564, 66-74
15. Liu, Y.; Zeng, J.; Chen, B.; Yao, S. Investigation of phenolic constituents in Echinacea purpurea grown in China Planta Med. 2007, 73, 1600-1605
16. Stuart, D.; Wills, R. Alkylamide and cichoric acid levels in Echinacea purpurea tissues during plant growth J. Herbs, Spices Med. Plants 2000, 7, 91-101
17. Marquard, R.; Kroth, E. Purpur-Sonnenhut (Echinacea purpurea (L.) Moench), SchmalblaÌ̂ttriger Sonnenhut (E. angustifolia DC) und Blasser Sonnenhut (E. pallida Nutt.). In Anbau und QualitaÌ̂ tsanforderungen ausgewaÌ̂hlter Arzneipflanzen; Buchedition Agrimedia GmbH: Bergen, Germany, 2001; pp 261-274.
18. Callan, N.; Yokelson, T.; Wall-Maclane, S.; Westcott, M. P.; Miller, J. B.; Ponder, G. Seasonal trends and plant density effects on cichoric acid in Echinacea purpurea (L.) Moench J. Herbs, Spices Med. Plants 2005, 11, 35-46
19. Stuart, D.; Wills, R. Factors affecting the extraction of alkylamides and cichoric acid during ethanolic processing of Echinacea purpurea (L.) Moench Aust. J. Exp. Agric. 2000, 40, 873-877
20. Cech, N. B.; Eleazer, M. S.; Shoffner, L. T.; Crosswhite, M. R.; Davis, A. C.; Mortenson, A. M. High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts J. Chromatogr., A 2006, 1103, 219-228
21. Spelman, K.; Wetschler, M. H.; Cech, N. B. Comparison of alkylamide yield in ethanolic extracts prepared from fresh versus dry Echinacea purpurea utilizing HPLC-ESI-MS J. Pharm. Biomed. Anal. 2009, 49, 1141-1149
22. Pellati, F.; Epifano, F.; Contaldo, N.; Orlandini, G.; Cavicchi, L.; Genovese, S.; Bertelli, D.; Benvenuti, S.; Curini, M.; Bertaccini, A.; Bellardi, M. G. Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea J. Agric. Food Chem. 2011, 59, 10425-10434
23. Mudge, E.; Loes-Lutz, D.; Brown, P.; Scheiber, A. Analysis of alkylamides in Echinacea plant materials and dietary supplements by ultrafast liquid chromatography with diode array and mass spectrometric detection J. Agric. Food Chem. 2011, 59, 8086-8094
24. Pellati, F.; Orlandini, G.; Benvenuti, S. Simultaneous metabolite fingerprinting of hydrophilic and lipophilic compounds in Echinacea pallida by high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometry detection J. Chromatogr., A 2012, 1242, 43-58
25. Hiserodt, R. D.; Pope, B. M.; Cossette, M.; Dewis, M. L. Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer J. Am. Soc. Mass Spectrom. 2004, 15, 1462-1470
26. Pellati, F.; CaloÌ, S.; Benvenuti, S.; Adinolfi, B.; Nieri, P.; Melegari, M. Isolation and structure elucidation of cytotoxic polyacetylenes and polyenes from Echinacea pallida Phytochemistry 2006, 67, 1359-1364
27. Laasonen, M.; Wennberg, T.; Harmia-Pulkkinen, T.; Vuorela, H. Simultaneous analysis of alkamides and caffeic acid derivatives for identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Pathenium integrifolium roots Planta Med. 2002, 68, 572-574
28. Luo, X. B.; Chen, B.; Yao, S. Z.; Zeng, J. G. Simultaneous analysis of caffeic acid derivatives and alkamides in roots and extracts of Echinacea purpurea by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry J. Chromatogr., A 2003, 986, 73-81
29. Qu, L.; Chen, Y.; Wang, X.; Scalzo, R. Patterns of variation in alkamides and cichoric acid in roots and aboveground parts of Echinacea purpurea (l.) Moench HortScience 2005, 40, 1239-1242
30. Molgaard, P.; Johnsen, S.; Christensen, P.; Cornett, C. HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products J. Agric. Food Chem. 2003, 51, 6922-6933
31. Lin, S.; Sung, J.; Chen, C. Effect of drying and storage conditions on caffeic acid derivatives and total phenolics of Echinacea purpurea grown in Taiwan Food Chem. 2011, 125, 226-231
32. Stuart, D.; Wills, R. Effect of drying temperature on alkamide and cichoric acid concentrations of Echinacea purpurea J. Agric. Food Chem. 2003, 51, 1608-1610