Hydroxycinnamic acid amide profile of Solanum schimperianum Hochst by UPLC-HRMS

International Journal of Mass Spectrometry

Volumn 408, Issue , 2016, Pages 42-50

  Voynikov, Yulian ^a   Zheleva Dimitrova, Dimitrina ^a   Gevrenova, Reneta ^a   Lozanov, Valentin ^a   Zaharieva, Maya M ^b   Tsvetkova, Iva ^b   Najdenski, Hristo ^b   Yagi, Sakina ^c   Almoulah, Nahla Fadl ^d   Momekov, Georgi ^a  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^b INSTITUTE OF MICROBIOLOGY   (Bulgaria)

^c UNIVERSITY OF KHARTOUM   (Sudan)

^d UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Antimicrobial potential; Antioxidant activity; Hydroxycinnamic acid amides; Orbitrap; Solanum schimperianum; UPLC HRMS

Indexed keywords

EID: 84988565723     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2016.08.008     Document Type: Article

References (39)

1. [1] Abdel-Sattar, E., Harraz, F.M., Al-Ansari, S.M., El-Mekkawy, S., Ichino, C., Kiyohara, H., et al. Antiplasmodial and antitrypanosomal activity of plants from the Kingdom of Saudi Arabia. J. Nat. Med. 63 (2009), 232–239.
2. [2] Al-Oqail, M., Hassan, W.H., Ahmad, M.S., Al-Rehaily, A.J., Phytochemical and biological studies of Solanum schimperianum Hochst. Saudi Pharm. J. 20 (2012), 371–379.
3. [3] Al-Rehaily, A.J., Ahmad, M.S., Mustafa, J., Al-Oqail, M.M., Hassan, W.H., Khan, S.I., et al. Solanopubamine, a rare steroidal alkaloid from Solanum schimperianum: synthesis of some new alkyl and acyl derivatives, their anticancer and antimicrobial evaluation. J. Saudi Chem. Soc. 17 (2013), 67–76.
4. [4] Andrews, F.W., 1952. The flowering plants of the Anglo-Egyptian Sudan. Vol. II (Sterculiac-eae-Dipsacaceae), The flowering plants of the Anglo-Egyptian Sudan, Vol. II (Sterculiac-eae-Dipsacaceae).
5. [5] Baker, C.J., Whitaker, B.D., Mock, N.M., Rice, C.P., Roberts, D.P., Deahl, K.L., et al. Differential induction of redox sensitive extracellular phenolic amides in potato. Physiol. Mol. Plant Pathol. 73 (2008), 109–115.
6. [6] Borges, A., Ferreira, C., Saavedra, M.J., Simões, M., Antibacterial activity and mode of action of ferulic and gallic acids against pathogenic bacteria. Microb. Drug Resist. 19 (2013), 256–265.
7. [7] Chaudhary, S., 1999. Flora of the Kingdom of Saudi Arabia: vol. 1. Riyadh: Ministry of Agriculture and Water, National Herbarium, National Agriculture and Water Research Center 691p.-illus. En Icones, Anatomy and morphology, Keys. Geog 2.
8. [8] Chen, L., Qi, J., Y-x, Chang, Zhu, D., Yu, B., Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC–DAD–ESI–MS/MS. J. Pharm. Biomed. Anal. 50 (2009), 127–137.
9. [9] Choi, S.-S., Kim, O.-B., Fragmentation of deprotonated amino acids in atmospheric pressure chemical ionization. Int. J. Mass spectrom. 338 (2013), 17–22.
10. [10] Dong, X., Gao, Y., Chen, W., Wang, W., Gong, L., Liu, X., et al. Spatiotemporal distribution of phenolamides and the genetics of natural variation of hydroxycinnamoyl spermidine in Rice. Mol. Plant 8 (2015), 111–121.
11. [11] Facchini, P.J., Hagel, J., Zulak, K.G., Hydroxycinnamic acid amide metabolism: physiology and biochemistry. Can. J. Bot. 80 (2002), 577–589.
12. [12] Georgiev, L., Chochkova, M., Ivanova, G., Najdenski, H., Ninova, M., Milkova, T., Radical scavenging and antimicrobial activities of cinnamoyl amides of biogenic monoamines. Riv. Ital. Sost. Grasse 89 (2012), 91–102.
13. [13] Guzman, J.D., Natural cinnamic acids: synthetic derivatives and hybrids with antimicrobial activity. Molecules 19 (2014), 19292–19349.
14. [14] Handrick, V., Vogt, T., Frolov, A., Profiling of hydroxycinnamic acid amides in Arabidopsis thaliana pollen by tandem mass spectrometry. Anal. Bioanal. Chem. 398 (2010), 2789–2801.
15. [15] Hassan, W., Al-Oqail, M., Ahmad, M., Al-Rehaily, A., Bioactive long chain amides from Solanum schimperianum Hochst growing in Saudi Arabia. Biosci. Biotechnol. Res. Asia, 9, 2016.
16. [16] Herald, P., Davidson, P., Antibacterial activity of selected hydroxycinnamic acids. J. Food Sci. 48 (1983), 1378–1379.
17. [17] Hu, W., Werner, C., Hesse, M., The photoisomerization behavior of the (4‐Hydroxycinnamoyl)‐spermidines. Helv. Chim. Acta 81 (1998), 342–352.
18. [18] King, R.R., Calhoun, L.A., Characterization of cross-linked hydroxycinnamic acid amides isolated from potato common scab lesions. Phytochemistry 66 (2005), 2468–2473.
19. [19] Koreishi, M., Asayama, F., Imanaka, H., Imamura, K., Kadota, M., Tsuno, T., et al. Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis. Biosci. Biotechnol. Biochem. 69 (2005), 1914–1922.
20. [20] Liu, X., Luo, J., Kong, L., Phenylethyl cinnamides as potential alpha-glucosidase inhibitors from the roots of Solanum melongena. Nat. Prod. Commun. 6 (2011), 851–853.
21. [21] López-Gresa, M.P., Torres, C., Campos, L., Lisón, P., Rodrigo, I., Bellés, J.M., et al. Identification of defence metabolites in tomato plants infected by the bacterial pathogen Pseudomonas syringae. Environ. Exp. Bot. 74 (2011), 216–228.
22. [22] Ma, X., Li, H., Dong, J., Qian, W., Determination of hydrogen peroxide scavenging activity of phenolic acids by employing gold nanoshells precursor composites as nanoprobes. Food Chem. 126 (2011), 698–704.
23. [23] Macoy, D.M., Kim, W.-Y., Lee, S.Y., Kim, M.G., Biosynthesis physiology, and functions of hydroxycinnamic acid amides in plants. Plant Biotechnol. Rep. 9 (2015), 269–278.
24. +, 19.01.2016 edn.
25. [25] Negrel, J., Javelle, F., Paynot, M., Wound-induced tyramine hydroxycinnamoyl transferase in potato (Solanum tuberosum) tuber discs. J. Plant Physiol. 142 (1993), 518–524.
26. [26] Nikolić, D., Gödecke, T., Chen, S.-N., White, J., Lankin, D.C., Pauli, G.F., et al. Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.). Fitoterapia 83 (2012), 441–460.
27. [27] Panagabko, C., Chenier, D., Fixon‐Owoo, S., Atkinson, J.K., Ion‐pair HPLC determination of hydroxycinnamic acid monoconjugates of putrescine, spermidine and spermine. Phytochem. Anal. 11 (2000), 11–17.
28. [28] Sobolev, V.S., Sy, A.A., Gloer, J.B., Spermidine and flavonoid conjugates from peanut (Arachis hypogaea) flowers. J. Agric. Food Chem. 56 (2008), 2960–2969.
29. [29] Spasova, M., Kortenska‐Kancheva, V., Totseva, I., Ivanova, G., Georgiev, L., Milkova, T., Synthesis of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant activity. J. Pept. Sci. 12 (2006), 369–375.
30. [30] Sun, J., Huo, H.-X., Zhang, J., Huang, Z., Zheng, J., Zhang, Q., et al. Phenylpropanoid amides from the roots of Solanum melongena L. (Solanaceae). Biochem. Syst. Ecol. 58 (2015), 265–269.
31. [31] Sun, J., Song, Y.-L., Zhang, J., Huang, Z., Huo, H.-X., Zheng, J., et al. Characterization and quantitative analysis of phenylpropanoid amides in eggplant (Solanum melongena L.) by high performance liquid chromatography coupled with diode array detection and hybrid ion trap time-of-flight mass spectrometry. J. Agric. Food Chem. 63 (2015), 3426–3436.
32. [32] Tebayashi, S.-I., Ishihara, A., Tsuda, M., Iwamura, H., Induction of clovamide by jasmonic acid in red clover. Phytochemistry 54 (2000), 387–392.
33. [33] Ulrich, E.L., Akutsu, H., Doreleijers, J.F., Harano, Y., Ioannidis, Y.E., Lin, J., et al. BioMagResBank. Nucleic Acids Res., 2015, 2008, 36.
34. [34] Weese, T.L., Bohs, L., A three-gene phylogeny of the genus Solanum (Solanaceae). Syst. Bot. 32 (2007), 445–463.
35. [35] Weissberg, A., Dagan, S., Interpretation of ESI (+)-MS-MS spectra—towards the identification of unknowns. Int. J. Mass spectrom. 299 (2011), 158–168.
36. [36] Wong, W.S., Guo, D., Wang, X.L., Yin, Z.Q., Xia, B., Li, N., Study of cis-cinnamic acid in Arabidopsis thaliana. Plant Physiol. Biochem. 43 (2005), 929–937.
37. [37] Wu, S.-B., Meyer, R.S., Whitaker, B.D., Litt, A., Kennelly, E.J., A new liquid chromatography–mass spectrometry-based strategy to integrate chemistry, morphology, and evolution of eggplant (Solanum) species. J. Chromatogr. A 1314 (2013), 154–172.
38. [38] Zhang, J., Guan, S., Sun, J., Liu, T., Chen, P., Feng, R., et al. Characterization and profiling of phenolic amides from Cortex Lycii by ultra-high performance liquid chromatography coupled with LTQ-orbitrap mass spectrometry. Anal. Bioanal. Chem. 407 (2015), 581–595.
39. [39] Zheleva-Dimitrova, D., Balabanova, V., Antioxidant and acetylcholinesterase inhibitory potential of Arnica montana cultivated in Bulgaria. Turk. J. Biol. 36 (2012), 732–737.