Analyses of chlorogenic acids and related cinnamic acid derivatives from Nicotiana tabacum tissues with the aid of UPLC-QTOF-MS/MS based on the in-source collision-induced dissociation method

Chemistry Central Journal

Volumn 8, Issue 1, 2014, Pages

  Ncube, Efficient N ^a   Mhlongo, Msizi I ^a   Piater, Lizelle A ^a   Steenkamp, Paul A ^a,b   Dubery, Ian A ^a   Madala, Ntakadzeni E ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

^b DSI CSIR Nanotechnology Innovation Centre   (South Africa)

Author keywords

Cell suspensions; Chlorogenic acid; Cinnamic acid; ISCID; Leaf tissue; Nicotiana tabacum; UPLC qTOF MS MS

Indexed keywords

EID: 84920383569     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/s13065-014-0066-z     Document Type: Article

References (35)

1. Clifford MN: Chlorogenic acids and other cinnamates- nature, occurrence and dietary burden. J Sci Food Agr 1999, 79:362-372.
2. Clifford MN: Chlorogenic acids and other cinnamates nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agr 2000, 80:1033-1042.
3. Marques V, Farah A: Chlorogenic acids and related compounds in medicinal plants and infusions. Food Chem 2012, 113:1370-1376.
4. Koshiro Y, Jackson M-C, Katahiraa R, Wang M, Nagaib C, Ashiharaa H: Biosynthesis of chlorogenic acids in growing and ripening fruits of Coffea arabica and Coffea canephora plants. Z Naturforsch C 2007, 62:731-742.
5. Plazas M, Andújar I, Vilanova S, Hurtado M, Gramazio P, Herraiz FJ, Prohens J: Breeding for chlorogenic acid content in eggplant: interest and prospects. Bot Horti Agrobo 2013, 41:26-35.
6. Lou Z, Wang H, Zhu S, Ma C, Wang Z: Antibacterial activity and mechanism of action of chlorogenic acid. J Food Sci 2011, 76:398-403.
7. Xie C, Yu K, Zhong D, Yuan T, Ye F, Jarrell J-A, Millar A, Chen X: Investigation of isomeric transformations of chlorogenic acid in buffers and biological matrixes by Ultra Performance Liquid Chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight mass spectrometry. J Agr Food Chem 2011, 59:11078-11087.
8. Mhlongo MI, Piater LA, Steenkamp PA, Madala NE, Dubery IA: Metabolomic fingerprinting of primed tobacco cells provide the first evidence for the biological origin of cis-chlorogenic acid. Biotechnol Lett (in press) 9.
9. Jaiswal R, Kuhnert N: Identification and characterization of the phenolic glycosides of Lagenaria siceraria Stand (Bottle Gourd) fruit by liquid chromatography-tandem mass spectrometry. J Agr Food Chem 2014, 62:1261-1271.
10. Clifford M-N, Johnston K-L, Knight S, Kuhnert N: A hierarchical scheme for LCMSn identification of chlorogenic acid. J Agr Food Chem 2003, 53:3821-3832.
11. Clifford MN, Knight S, Kuhnert N: Discriminating between the six isomers of dicaffeoylquinic acid by LC-MSn. J Agr Food Chem 2005, 53:3821-3832.
12. Clifford M-N, Kirkpatrick J, Kuhnert N, Roozendaal H, Salgado PR: LC-MSn analysis of the cis isomers of chlorogenic acids. Food Chem 2008, 106:379-385.
13. Kuhnert N, Karaköse H, Jaiswal R: Analysis of chlorogenic acids and other hydroxycinnamates in food, plants and pharmacokinetic studies. In Handbook of Analysis of Active Compounds in Functional Foods, Volume 1. Edited by Nollet ML L, Toldra F. United States: CRC Press; 2012:461.
14. Wang J, Lu D, Zhao H, Jiang B, Wang J, Ling X, Chai H, Ouyang P: Discrimination and classification of tobacco wastes by identification and quantification of polyphenols with LC-MS/MS. J Serb Chem Soc 2010, 75:875-891.
15. Ramachandra RS, Ravishankar GA: Plant cell cultures: Chemical factories of secondary metabolites. Biotechnol Adv 2002, 20:101-153.
16. Verpoorte R, Contin A, Memelink J: Biotechnology for the production of plant secondary metabolites. Phytochem Rev 2002, 1:13-25.
17. Kolewe ME, Gaurav V, Roberts SC: Pharmaceutically active natural product synthesis and supply via plant cell culture technology. Mol Pharm 2008, 5:243-256.
18. Atkinson MM, Huang J, Knopp JA: Hypersensitivity of suspension-cultured tobacco cells to pathogenic bacteria. Phytopathology 1985, 75:1270-1274.
19. Mozzetti C, Ferraris L, Tamietti G, Matta A: Variation in enzyme activities in leaves and cell suspensions as markers of incompatibility in different Phytophthora pepper interactions. Physiol Mol Plant P 1995, 46:95-107.
20. Franklin G, Dias ACP: Chlorogenic acid participates in the regulation of shoot, root and root hair development in Hypericum perforatum. Plant Physiol Biochem 2011, 49:835-842.
21. Mondolot L, La Fisca P, Buatois B, Talansier E, De Kochko A, Campa C: Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development. Ann Bot 2006, 98:33-40.
22. Sanabria NM, Dubery IA: Differential display profiling of the Nicotiana response to LPS reveals elements of plant basal resistance. Biochem Biophys Res Commun 2006, 344:1001-1007.
23. Hossain MB, Rai D-K, Brunton NP, Martin-Diana AB, Barry-Ryan C: Characterization of phenolics composition in Lamiaceae spices by LCESI- MS/MS. J Agr Food Chem 2010, 58:10576-10581.
24. He W, Liu X, Xu H, Gong Y, Yuan F, Gao Y: On-line HPLC-ABTS screening and HPLC-DAD-MS/MS identification of free radical scavengers in Gardenia (Gardenia jasminoides Ellis) fruit extracts. Food Chem 2010, 123:521-528.
25. Nurmi K, Ossipov V, Haukioja E, Pihlaja K: Variation of total phenolic content and individual low-molecular-weight phenolics in foliage of mountain birch trees (Betula pubescens ssp. tortuosa). J Chem Ecol 1996, 22:2023-2040.
26. Riipi M, Ossipov V, Lempa K, Haukioja E, Koricheva J, Ossipova S, Pihlaja K: Seasonal changes in birch leaf chemistry: are there trade-offs between leaf growth and accumulation of phenolics. Oecologia 2002, 130:380-390.
27. Regos I, Urbanella A, Treutter D: Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia). J Agr Food Chem 2009, 57:5843-5852.
28. Farah A, Monteiro M, Donangelo CM, Lafey S: Chlorogenic acids from green coffee extracts are highly bioavailable in humans. J Nutr 2008, 138:2309-2315.
29. De Mello M-O, De Campos Amaral AF, Melo M: Sucrose metabolizing enzymes in cell suspension cultures of Bauhinia forficata, Curcuma zedoaria and Phaseolus vulgaris. Pesqui Agropecu Bras 2001, 36:1085-1092.
30. Jaiswal R, Muller H, Muller A, Karar MGE, Kuhnert N: Identification and characterisation of chlorogenic acids, chlorogenic acid glycosides and flavonoids from Lonicera henryi L. (Caprifoliaceae) leaves by LC-MSn. Phytochemistry 2014, 10.1016/j.phytochem.2014.08.023.
31. Jaiswal R, Halabi EA, Karar MGE, Kuhnert N: Identification and characterisation of the phenolics of Ilex glabra L. Gray (Aquifoliaceae) leaves by liquid chromatography tandem mass spectrometry. Phytochemistry 2014, 106:141-155.
32. Kashiwada Y, Ahmed FA, Kurimoto S, Kim SY, Shibata H, Fujikota T, Takaishi Y: New alpha-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam. J Nat Med 2012, 66:217-221.
33. Mhlongo MI, Piater LA, Steenkamp PA, Madala NE, Dubery IA: Priming agents of plant defence stimulate the accumulation of mono- and diacylated chlorogenic acids in cultured tobacco cells. Physiol Molec Plant Pathol 2014 (in press).
34. Torras-Claveria L, Jáuregui O, Codinaa C, Tiburcioa AF, Bastidaa J, Viladomat F: Analysis of phenolic compounds by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry in senescent and water-stressed tobacco. Plant Sci 2012, 182:71-78.
35. Parveen I, Threadgill MD, Hauck B, Donnison I, Winters A: Isolation, identification and quantitation of hydroxycinnamic acid conjugates, potential platform chemicals, in the leaves and stems of Miscanthus x giganteus using LC-ESI-MS(n). Phytochemistry 2012, 72:71-78.