Acyl spermidines in inflorescence extracts of elder (Sambucus nigra L., Adoxaceae) and elderflower drinks

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 14, 2013, Pages 3501-3508

  Kite, Geoffrey C ^a   Larsson, Sonny ^a   Veitch, Nigel C ^a   Porter, Elaine A ^a   Ding, Ning ^a   Simmonds, Monique S J ^a  

^a ROYAL BOTANIC GARDENS   (United Kingdom)

Author keywords

elderflower; feruloylspermidine; LC MS; NMR; Sambucus nigra

Indexed keywords

BEVERAGES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; STEREOCHEMISTRY; VEGETATION;

ELDERFLOWER; FERULOYLSPERMIDINE; LC-MS; N ACETYLS; SAMBUCUS NIGRA;

ISOMERS;

PLANT EXTRACT; SPERMIDINE;

ACETYLATION; ACYLATION; ANALOGS AND DERIVATIVES; ANALYSIS; BEVERAGE; CHEMISTRY; INFLORESCENCE; POLLEN; SAMBUCUS NIGRA; UNITED KINGDOM;

ACETYLATION; ACYLATION; BEVERAGES; GREAT BRITAIN; INFLORESCENCE; PLANT EXTRACTS; POLLEN; SAMBUCUS NIGRA; SPERMIDINE;

EID: 84876128557     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf304602q     Document Type: Article

References (36)

1. Prendergast, H. D. V.; Sanderson, H. Britain's Wild Harvest; Royal Botanic Gardens, Kew: Richmond, UK, 2004.
2. Barnes, J.; Anderson, L. A.; Phillipson, J. D. Herbal Medicines, 3 rd ed.; Pharmaceutical Press: London, UK, 2007.
3. Prendergast, H. D. V.; Dennis, F. Superior merits of a troublesome weed-elder in the 1990s Br. Wildlife 1997, 8, 281-286
4. Milliken, W.; Bridgewater, S. Flora Celtica: Sustainable Development of Scottish Plants; Scottish Executive Central Research Unit: Edinburgh, UK, 2001.
5. Sanderson, H.; Prendergast, H. D. V. Commercial Uses of Wild and Traditionally Managed Plants in England and Scotland; Royal Botanic Gardens, Kew: Richmond, UK, 2002, (available from http://www.kew.org/science/ecbot/ commusesreport.pdf).
6. Jørgensen, U.; Hansen, M.; Christensen, L. P.; Jensen, K.; Kaack, K. Olfactory and quantitative analysis of aroma compounds in elder flower (Sambucus nigra L.) drink processed from five cultivars J. Agric. Food Chem. 2000, 48, 2376-2395
7. Christensen, L. P.; Kaack, K.; Fretté, X. C. Selection of elderberry (Sambucus nigra L.) genotypes best suited for the preparation of elderflower extracts rich in flavonoids and phenolic acids Eur. Food Res. Technol. 2008, 227, 293-305
8. Council of Europe. Elder flower (Sambuci flos). Ph Eur monograph 1217. European Pharmacopoeia, 6 th ed.; Council of Europe: Strasbourg, France, 2007.
9. Scopel, M.; Mentz, L. A.; Henriques, A. T. Comparative analysis of Sambucus nigra and Sambucus australis flowers. Development and validation of an HPLC method for raw material quantification and preliminary stability study Planta Med. 2010, 76, 1026-1031
10. Martin-Tanguy, J.; Cabanne, F.; Perdrizet, E.; Martin, C. The distribution of hydroxycinnamic acid amides in flowering plants Phytochemistry 1978, 17, 1927-1928
11. Bassard, J.-E.; Ullmann, P.; Bernier, F.; Werck-Reichhart, D. Phenolamides: bridging polyamines to the phenolic metabolism Phytochemistry 2010, 71, 1808-1824
12. Dictionary of Natural Products, on-line, v. 19.2; CRC Press: Boca Raton, FL, 2011, (http://dnp.chemnetbase.com).
13. Youhnovski, N.; Bigler, L.; Werner, C.; Hesse, M. On-line coupling of high-performance liquid chromatography to atmospheric pressure chemical ionization mass spectrometry (HPLC/APCI-MS and MS/MS). The pollen analysis of Hippeastrum × hortorum (Amaryllidaceae) Helv. Chim. Acta 1998, 81, 1654-1671
14. Meurer, B.; Wray, V.; Wiermann, R.; Strack, D. Hydroxycinnamic acid spermidine amides from pollen of Alnus glutinosa, Betula verrucosa and Pterocarya fraxinifolia Phytochemistry 1988, 27, 839-843
15. Sobolev, V. S.; Sy, A. A.; Gloer, J. B. Spermidine and flavonoid conjugates from peanut (Arachis hypogaea) flowers J. Agric. Food Chem. 2008, 56, 2960-2969
16. Youhnovski, N.; Werner, C.; Hesse, M. N, N ′, N ″-Triferuloylspermidine, a new UV absorbing polyamine derivative from pollen of Hippeastrum × hortorum Z. Naturforsch., C: J. Biosci. 2001, 56, 526-530
17. 10-Tris(4-hydroxycinnamoyl) spermidines from Microdesmis keayana roots Chem. Biodiversity 2006, 3, 982-989
18. Bokern, M.; Witte, L.; Wray, V.; Nimtz, M.; Meurer-Grimes, B. Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen Phytochemistry 1995, 39, 1371-1375
19. Meurer, B.; Wray, V.; Grotjahn, L.; Wiermann, R.; Strack, D. Hydroxycinnamic acid spermidine amides from pollen of Corylus avellana L Phytochemistry 1986, 25, 433-435
20. Meurer, B.; Wiermann, R.; Strack, D. Phenylpropanoid patterns in Fagales pollen and their phylogenetic relevance Phytochemistry 1988, 27, 823-828
21. Nimtz, M.; Bokern, M.; Meurer-Grimes, B. Minor hydroxycinnamic acid spermidines from pollen of Quercus dentata Phytochemistry 1996, 43, 487-489
22. Davídek, J. Isolation of chromatographically pure rutin from flowers of elder Nature 1961, 189, 487-488
23. Lamaison, J. L.; Petitjean-Freytet, C.; Carnat, A. Présence de 3-glucoside et de 3-rutinoside d'isorhamnétine dans les fleurs de Sambucus nigra L Ann. Pharm. Fr. 1991, 49, 258-262
24. Bigler, L.; Schnider, C. F.; Hu, W.; Hesse, M. Acid-catalyzed isomerization of N, N ′-bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl] spermidines by the zip reaction Helv. Chim. Acta 1996, 79, 2152-2163
25. Ponchet, M.; Martin-Tanguy, J.; Marais, A.; Martin, C. Hydroxycinnamoyl acid amides and aromatic amines in the inflorescences of some Araceae species Phytochemistry 1982, 21, 2865-2869
26. Abdel Sattar, E.; Glasl, H.; Nahrstedt, A.; Hilal, S. H.; Zaki, A. Y.; El-Zalabani, S. M. H. Hydroxycinnamic acid amides from Iochroma cyaneum Phytochemistry 1990, 29, 3931-3933
27. Strack, D.; Eilert, U.; Wray, V.; Wolff, J.; Jaggy, H. Tricoumaroylspermidine in flowers of Rosaceae Phytochemistry 1990, 29, 2893-2896
28. Werner, C.; Hu, W.; Lorenzi-Riatsch, A.; Hesse, M. Di- coumaroylspermidines and tri-coumaroylspermidines in anthers of different species of the genus Aphelandra Phytochemistry 1995, 40, 461-465
29. Lin, S.; Mullin, C. A. Lipid, polyamide, and flavonol phagostimulants for adult Western corn rootworm from sunflower (Helianthus annuus L.) pollen J. Agric. Food Chem. 1999, 47, 1223-1229
30. Hanhineva, K.; Rogachev, I.; Kokko, H.; Mintz-Oron, S.; Venger, I.; Kärenlampi, S.; Aharoni, A. Non-targeted analysis of spatial metabolite composition in strawberry (Fragaria × ananassa) flowers Phytochemistry 2008, 69, 2463-2481
31. Fellenberg, C.; Böttcher, C.; Vogt, T. Phenylpropanoid polyamine conjugate biosynthesis in Arabidopsis thaliana flower buds Phytochemistry 2009, 70, 1392-1400
32. Mercier, A. J.; Farragher, S.; Schmor, B.; Kamau, M.; Atkinson, J. Effect of a plant-derived spider toxin analogue on crayfish neuromuscular junctions Can. J. Zool. 1998, 76, 2103-2107
33. Klose, M. K.; Atkinson, J. K.; Mercier, A. J. Effects of a hydroxy-cinnamoyl conjugate of spermidine on arthropod neuromuscular junctions J. Comp. Physiol., A 2002, 187, 945-952
34. Fixon-Owoo, S.; Levasseur, F.; Williams, K.; Sabado, T. N.; Lowe, M.; Klose, M.; Mercier, A. J.; Fields, P.; Atkinson, J. Preparation and biological assessment of hydroxycinnamic acid amides of polyamines Phytochemistry 2003, 63, 315-334
35. Ma, C.; Nakamura, N.; Hattori, M. Inhibitory effects on HIV-1 protease of tri- p -coumaroylspermidine from Artemisia caruifolia and related amides Chem. Pharm. Bull. 2001, 49, 915-917
36. Zhao, G.; Qin, G.-W.; Gai, Y.; Guo, L.-H. Structural identification of a new tri- p -coumaroylspermidine with serotonin transporter inhibition from safflower Chem. Pharm. Bull. 2010, 58, 950-952