Preparative mass-spectrometry profiling of bioactive metabolites in Saudi-Arabian propolis fractionated by high-speed countercurrent chromatography and off-line atmospheric pressure chemical ionization mass-spectrometry injection

Journal of Chromatography A

Volumn 1347, Issue , 2014, Pages 17-29

  Jerz, Gerold ^a   Elnakady, Yasser A ^b,c   Braun, André ^a   Jäckel, Kristin ^a   Sasse, Florenz ^c   Al Ghamdi, Ahmad A ^d   Omar, Mohamed O M ^d   Winterhalter, Peter ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

1D 2D NMR; Diterpene; Off line APCI MS MS injection metabolite profiling; Preparative high speed countercurrent chromatography; Saudi Arabian propolis; Triterpene

Indexed keywords

ATMOSPHERIC PRESSURE; BIOMOLECULES; CHEMICAL DETECTION; CHROMATOGRAPHY; FATTY ACIDS; IONIZATION; MASS SPECTROMETRY; METABOLITES; ORGANIC SOLVENTS;

1D/2D-NMR; DITERPENES; HIGH-SPEED COUNTER CURRENT CHROMATOGRAPHY; METABOLITE PROFILING; SAUDI ARABIAN PROPOLIS; TRITERPENES;

DRUG PRODUCTS;

15 O OLEOYL ISOCUPRESSIC ACID; 15 O PALMITOYL ISOCUPRESSIC ACID; 24 METHYLENE CYCLOARTENOL; 3BETA ACETOXY 19(29) TARAXASTEN 20ALPHA OL; ACETIC ACID DERIVATIVE; ALPHA AMYRIN 3BETA O ACTETATE; BETA AMYRIN 3BETA O ACTETATE; COMMUNIC ACID; CYCLOARTENOL; FATTY ACID ESTER; FERRUGINOL; LINOLEIC ACID; LUPEOL 3BETA O ACTETATE; OLEIC ACID; PALMITIC ACID; PROPOLIS; PSEUDOTARAXASTEROL 3BETA O ACTETATE; SANDARACOPIMARIC ACID; STEARIC ACID; TARAXASTEROL 3BETA O ACTETATE; TERPENOID; TOTAROL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL COMPOSITION; CONTROLLED STUDY; COUNTER CURRENT CHROMATOGRAPHY; HIGH SPEED COUNTERCURRENT CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS;

APOIDEA;

1D/2D-NMR; DITERPENE; OFF-LINE APCI-MS/MS INJECTION METABOLITE PROFILING; PREPARATIVE HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY; SAUDI ARABIAN PROPOLIS; TRITERPENE;

ACETATES; ANIMALS; BEES; CHEMICAL FRACTIONATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUNTERCURRENT DISTRIBUTION; MOLECULAR WEIGHT; PROPOLIS; SAUDI ARABIA; SOLVENTS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 84901048415     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.04.068     Document Type: Article

References (64)

1. Banskota A.H., Tezuka Y., Kadota S. Phytother. Res. 2001, 15:561.
2. Simone-Finstrom M., Spivak M. Apidologie 2010, 41:295.
3. Ghisalberti E. Bee World 1979, 60:59.
4. Parolia A., Thomas M.S., Kundabala M., Mohan M. Int. J. Med. Med. Sci. 2010, 2:210.
5. Sforcin J.M., Bankova V. J. Ethnopharmacol. 2011, 133:253.
6. Pellati F., Orlandini G., Pinetti D., Benvenuti S. J. Pharm. Biomed. Anal. 2011, 55:934.
7. Midorikawa K., Banskota A.H., Tezuka Y., Nagaoka T., Matsushige K., Message D., Huertas A.A.G., Kadota S. Phytochem. Anal. 2001, 12:366.
8. Gardana C., Scaglianti M., Pietta P., Simonetti P. J. Pharm. Biomed. Anal. 2007, 45:390.
9. Volpi N., Bergonzini G. J. Pharm. Biomed. Anal. 2006, 42:354.
10. Sawaya A.C.H.F., Tomazela D.M., Cunha I.B.S., Bankova V.S., Marcucci M.C., Custodio A.R., Eberlin M.N. Analyst 2004, 129:739.
11. Sawaya A.C.H.F., Abdelnur P.V., Eberlin M.N., Kumazawa S., Ahn M.-R., Bang K.-S., Nagaraja N., Bankova V.S., Afrouzan H. Talanta 2010, 81:100.
12. Ito Y. J. Chromatogr. A 2005, 1065:145.
13. High-speed Countercurrent Chromatography. Chemical Analysis 1996, vol. 132. Wiley, New York. Y. Ito, W.D. Conway (Eds.).
14. Duret P., Fakhfakh M.A., Herrenknecht C., Fournet A., Franck X., Figadère B., Hocquemiller R. J. Chromatogr. A 2003, 1011:55.
15. Jerz G., Wybraniec S., Gebers N., Winterhalter P. J. Chromatogr. A 2010, 1217:4544.
16. Jerz G., Murillo-Velásquez J.A., Skrjabin I., Gök R., Winterhalter P. Recent Advances in the Analysis of Food and Flavors. ACS Symposium Series 2012, vol. 1098:145. American Chemical Society, Washington, DC. S. Toth, C. Mussinan (Eds.).
17. Jerz G., Schmalfuß E., Kleinwächter M., Winterhalter P., Selmar D. Planta Med. 2013, 79:PH7. 10.1055/s-0033-1352084.
18. Oetken J., Beuerle T., Knapp H., Giesecke T., Winterhalter P., Jerz G. Planta Med. 2013, 79:PH8. 10.1055/s-0033-1352085.
19. Althaus J.B., Jerz G., Winterhalter P., Kaiser M., Brun R., Schmidt T.J. Planta Med. 2013, 79:PA2. 10.1055/s-0033-1351906.
20. Kuropatnicki A.K., Szliszka E., Krol W. J. Evid.-Based Complement. Altern. Med. 2013, Article ID 964149, 11 pp., http://dx.doi.org/10.1155/2013/964149.
21. Marcucci M.C. Apidologie 1995, 26:83.
22. Bankova V. J. Evid.-Based Complement. Altern. Med. 2005, 2:29.
23. Burdock G.A. Food Chem. Toxicol. 1998, 36:347.
24. Duran G., Duran N., Culha G., Ozcan B., Oztas H., Ozer B. Parasitol. Res. 2008, 102:1217.
25. Prytzyk E., Dantas A.P., Salomão K., Pereira A.S., Bankova V.S., De Castro S.L., Aquino Neto F.R. J. Ethnopharmacol. 2003, 88:189.
26. Stahl E., Kaltenbach U. J. Chromatogr. 1961, 5:351.
27. Berthod A., Ruiz-Angel M.J., Carda-Broch S. Anal. Chem. 2003, 75:5886.
28. Salatino A., Weinstein Teixeira E., Negri G., Message D. J. Evid.-Based Complement. Altern. Med. 2005, 2:33.
29. Mohammadzadeh S., Shariatpanahi M., Hamedi M., Ahmadkhaniha R., Samadi N., Ostad S.N. Food Chem. 2007, 103:1097.
30. Petrova A., Popova M., Kuzmanova C., Tsvetkova I., Naydenski H., Muli E., Bankova V. Fitoterapia 2010, 81:509.
31. Muhammad I., Mossa J.S., Al-Yahya M.A., Ramadan A.F., El-Feraly F.S. Phytother. Res. 1995, 9:584.
32. Carpenter C.D., O'Neill T., Picot N., Johnson J.A., Robichaud G.A., Webster D., Gray C.A. J. Ethnopharmacol. 2012, 143:695.
33. Seca A.M.L., Silva A.M.S. Recent Progress in Medicinal Plants. Phytomedicines 2007, vol. 16:401. Studium Press (India) Pvt. Ltd.
34. Gordien A.Y., Gray A.I., Franzblau S.G., Seidel V. J. Ethnopharmacol. 2009, 126:500.
35. Wenkert E., Buckwalter B.L. J. Am. Chem. Soc. 1972, 94:4367.
36. Mossa J.S., El-Feraly F.S., Muhammad I. Phytother. Res. 2004, 18:934.
37. Muhammad I., Mossa J.S., El-Feraly F.S. Phytother. Res. 1992, 6:261.
38. Honecker F. Phytochemische Untersuchung an der mexikanischen Arzneipflanze Salvia parryi (Lamiaceae) 1997, (Ph.D. thesis), University Erlangen-Nürnberg, Germany.
39. Nishida T., Wahlberg I., Enzell C.R. Org. Magn. Reson. 1977, 9:203.
40. Wehrli F.W., Nishida T. Fortschritte Chem. Org. Naturst. 1979, 36:1.
41. Sankaram A.V.B., Bhaskariah K., Murthi M.M., Subrahmanyam M. Tetrahedron Lett. 1988, 29:4881.
42. Melliou E., Chinou I. Planta Med. 2004, 70:515.
43. Moujir L., Gutiérrez-Navarro A.M., San Andrés L., Luis J.G. Phytother. Res. 1996, 10:172.
44. Muhammad I., Mossa J.S., El-Feraly F.S. Phytother. Res. 1996, 10:604.
45. Chiang Y.-M., Chang J.-Y., Kuo C.-C., Chang C.-Y., Kuo Y.-H. Phytochemistry 2005, 66:495.
46. Herbarium collections Al-Baha region, Dr. Jacob Thomas 2013, Dept. of Botany & Microbiology, College of Science, King Saud University Riyadh, Saudi Arabia. http://www.plantdiversityofsaudiarabia.info/.
47. Popova M.P., Chinou I.B., Marekov I.N., Bankova V.S. Phytochemistry 2009, 70:1262.
48. Feliciano A.S., Caballero E., Del Rey B., Sancho I. Phytochemistry 1991, 30:3134.
49. Seca A.M.L., Silva A.M.S., Bazzocchi I.L., Jimenez I.A. Phytochemistry 2008, 69:498.
50. Klaubert B. Phytochemische Untersuchung der brasilianischen Arzneipflanzen Costus scaber (Costaceae) und Prevostea ferruginea (Convolvulaceae) 1998, (Ph.D. thesis), University Erlangen-Nürnberg, Germany.
51. Benirschke G. Phytochemische Analyse von Cochlospermum-Arten (Cochlospermaceae) und der brasilianischen Arzneipflanze Joannesia princeps (Euphorbiaceae) 1995, (Ph.D. thesis), University Erlangen-Nürnberg, Germany.
52. Sousa da Silva M.S., das Graças Lopes Citó A.M., Chaves M.H., Dantas J.A. Quim. Nova 2005, 28:801.
53. Mahato S.B., Kundu A.P. Phytochemistry 1994, 37:1517.
54. Patra A., Mukhopadhyay A.K., Mitra A.K. Org. Magn. Reson. 1981, 17:166.
55. Reynolds W.F., Sawyer J.F., Enríquez R.G., Escobar L.I., Chavez M.A., Shoolery J.N. Can. J. Chem. 1985, 63:1048.
56. Wenkert E., Baddeley G.V., Burfitt I.R., Moreno L.N. Org. Magn. Reson. 1978, 11:337.
57. Jerz G. Phytochemische Analyse der afrikanischen Arzneipflanze Ongokea gore (Olacaceae) 1999, (Ph.D. thesis), University Erlangen-Nürnberg, Germany.
58. Abd El Hady F.K., Hegazi A.G. Z. Naturforsch. C: Biosci. 2002, 57:386.
59. Furakawa S., Takagi N., Ikeda T., Ono M., Nafady A.M., Nohara T., Sugimoto H., Doi S., Yamada H. Chem. Pharm. Bull. (Tokyo) 2002, 50:439.
60. Al-Musayeib N.M., Mohamed G.A., Ibrahim S.R.M., Ross S.A. Med. Chem. Res. 2013, 22:5297.
61. Muhammad I., El Sayed K.A., Mossa J.S., Al-Said M.S., El-Feraly F.S., Clark A.M., Hufford C.D., Oh S., Mayer A.M.S. J. Nat. Prod. 2000, 63:605.
62. Samoylenko V., Dunbar D.C., Gafur Md.A., Khan S.I., Ross S.A., Mossa J.S., El-Feraly F.S., Tekwani B.L., Bosselaers J., Muhammad I. Phytother. Res. 2008, 22:1570.
63. Sutherland I., Hewitson P., Ignatova S. J. Chromatogr. A 2009, 1216:4201.
64. Sutherland I., Hewitson P., Ignatova S. J. Chromatogr. A 2009, 1216:8787.