Analyses of chlorogenic acids and related cinnamic acid derivatives from Nicotiana tabacumtissues with the aid of UPLC-QTOF-MS/MS based on the in-source collision-induced dissociation method
Tóm tắt
Chlorogenic acids (CGAs) are a class of phytochemicals that are formed as esters between different derivatives of cinnamic acid and quinic acid molecules. In plants, accumulation of these compounds has been linked to several physiological responses against various stress factors; however, biochemical synthesis differs from one plant to another. Although structurally simple, the analysis of CGA molecules with modern analytical platforms poses an analytical challenge. The objective of the study was to perform a comparison of the CGA profiles and related derivatives from differentiated tobacco leaf tissues and undifferentiated cell suspension cultures.
Using an UHPLC-Q-TOF-MS/MS fingerprinting method based on the in-source collision induced dissociation (ISCID) approach, a total of 19 different metabolites with a cinnamic acid core moiety were identified. These metabolites were either present in both leaf tissue and cell suspension samples or in only one of the two plant systems. Profile differences point to underlying biochemical similarities or differences thereof.
Using this method, the
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Clifford MN: Chlorogenic acids and other cinnamates- nature, occurrence and dietary burden. J Sci Food Agr. 1999, 79: 362-372. 10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
Clifford MN: Chlorogenic acids and other cinnamates nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agr. 2000, 80: 1033-1042. 10.1002/(SICI)1097-0010(20000515)80:7<1033::AID-JSFA595>3.0.CO;2-T.
Marques V, Farah A: Chlorogenic acids and related compounds in medicinal plants and infusions. Food Chem. 2012, 113: 1370-1376. 10.1016/j.foodchem.2008.08.086.
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.
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.
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. 10.1111/j.1750-3841.2011.02213.x.
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. 10.1021/jf203104k.
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),
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. 10.1021/jf4053989.
Clifford M-N, Johnston K-L, Knight S, Kuhnert N: A hierarchical scheme for LC-MSn identification of chlorogenic acid. J Agr Food Chem. 2003, 53: 3821-3832. 10.1021/jf050046h.
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. 10.1021/jf050046h.
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. 10.1016/j.foodchem.2007.05.081.
Kuhnert N, Karaköse H, Jaiswal R: Analysis of chlorogenic acids and other hydroxycinnamates in food, plants and pharmacokinetic studies. Handbook of Analysis of Active Compounds in Functional Foods, Volume 1. Edited by: Nollet ML L, Toldra F. 2012, CRC Press, United States, 461-10.1201/b11653-26.
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. 10.2298/JSC091109055W.
Ramachandra RS, Ravishankar GA: Plant cell cultures: Chemical factories of secondary metabolites. Biotechnol Adv. 2002, 20: 101-153. 10.1016/S0734-9750(02)00007-1.
Verpoorte R, Contin A, Memelink J: Biotechnology for the production of plant secondary metabolites. Phytochem Rev. 2002, 1: 13-25. 10.1023/A:1015871916833.
Kolewe ME, Gaurav V, Roberts SC: Pharmaceutically active natural product synthesis and supply via plant cell culture technology. Mol Pharm. 2008, 5: 243-256. 10.1021/mp7001494.
Atkinson MM, Huang J, Knopp JA: Hypersensitivity of suspension-cultured tobacco cells to pathogenic bacteria. Phytopathology. 1985, 75: 1270-1274. 10.1094/Phyto-75-1270.
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. 10.1006/pmpp.1995.1008.
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. 10.1016/j.plaphy.2011.05.009.
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. 10.1093/aob/mcl080.
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. 10.1016/j.bbrc.2006.03.216.
Hossain MB, Rai D-K, Brunton NP, Martin-Diana AB, Barry-Ryan C: Characterization of phenolics composition in Lamiaceae spices by LC-ESI-MS/MS. J Agr Food Chem. 2010, 58: 10576-10581. 10.1021/jf102042g.
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. 10.1016/j.foodchem.2010.04.030.
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. 10.1007/BF02040093.
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. 10.1007/s00442-001-0826-z.
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. 10.1021/jf900625r.
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. 10.3945/jn.108.095554.
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. 10.1590/S0100-204X2001000900001.
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-MS n. Phytochemistry 2014, 10.1016/j.phytochem.2014.08.023,
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. 10.1016/j.phytochem.2014.07.018.
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. 10.1007/s11418-011-0563-5.
Mhlongo MI, Piater LA, Steenkamp PA, Madala NE, Dubery IA: Priming agents of plant defence stimulate the accumulation of mono - and di -acylated chlorogenic acids in cultured tobacco cells. Physiol Molec Plant Pathol 2014 (in press),
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. 10.1016/j.plantsci.2011.02.009.
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.