Dereplication of bioactive constituents of the genus hypericum using LC-(+,-)-ESI-MS and LC-PDA techniques: Hypericum triquterifolium as a case study

Saudi Pharmaceutical Journal

Volumn 17, Issue 4, 2009, Pages 269-274

  Alali, Feras Q ^a   Tawaha, Khaled ^b  

^a ISRA UNIVERSITY   (Jordan)

^b UNIVERSITY OF JORDAN   (Jordan)

Author keywords

Clusiaceae; Dereplication; Hypericum triquetrifolium; Hyphenated techniques; Naphthodianthrones; Phloroglucinols

Indexed keywords

ADHYPERFIRIN; HYPERFIRIN; HYPERICIN; NAPHTHODIANTHRONE DERIVATIVE; PHLOROGLUCINOL DERIVATIVE; PHOTOHYPERICIN; PLANT MEDICINAL PRODUCT; PROTOPSEUDOHYPERICIN; PSEUDOHYPERICIN; RUTOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HYPERICUM; HYPERICUM TRIQUETRIFOLIUM; LIQUID CHROMATOGRAPHY;

EID: 74049094716     PISSN: 13190164     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsps.2009.10.002     Document Type: Article

References (34)

1. Ackermann B.L., Regg B.T., Colombo L., Stella S., and Coutant J.E. Rapid analysis of antibiotic-containing mixtures from fermentation broths by using liquid chromatography-electrospray ionization-mass spectrometry and matrix-assisted laser desorption ionization-time-of-flight-mass spectrometry. J. Am. Soc. Mass Spectrom. 7 (1996) 1227-1237
2. Alali F.Q., Tawaha K., El-Elimat T., Syouf M., El-Fayad M., Abulaila K., Nielsen S.J., Wheaton W.D., Falkinham III J.O., and Oberlies N.H. Antioxidant activity and total phenolic content of aqueous and methanolic extracts of Jordanian plants: an ICBG project. Nat. Prod. Res. 21 (2007) 1121-1131
3. Al-Eisawi, D.M., 1998. Field guide to wild flowers of Jordan and neighbouring countries, first ed., Jordan Press Foundation Al-Rai, Amman.
4. Alvi K.A., Peterson J., and Hofmann B. Rapid identification of elaiophylin and geldanamycin in streptomyces fermentation broths using CPC coupled with a photodiode array detector and LC-MS methodologies. J. Ind. Microbiol. Biotechnol. 15 (1995) 80-84
5. Apaydin S., Zeybek U., Ince I., Elgin G., Karamenderes C., Ozturk B., and Tuglular I. Hypericum triquterifolium Turra extract exhibits antinociceptive activity in the mouse. J. Ethnopharmacol. 67 (1999) 307-312
6. Brolis M., Gabetta B., Fuzzati N., Pace R., Panzeri F., and Peterlongo F. Identification by high-performance liquid chromatography-diode array detection-mass spectrometry and quantification by high-performance liquid-chromatography-UV absorbance detection of active constituents of Hypericum perforatum. J. Chromatogr. A 825 (1998) 9-16
7. Constant H.L., and Beecher C.W.W. A method for the dereplication of natural product extracts using electrospray HPLC/MS. Nat. Prod. Lett. 6 (1995) 193-196
8. Cordell G.A., and Shin Y.G. Finding the needle in the haystack. The dereplication of natural product extracts. Pure Appl. Chem. 71 (1999) 1089-1094
9. Couladis M., Baziou P., Verykokidou E., and Loukis A. Antioxidant activity of polyphenols from Hypericum triquetrifolium Turra. Phytother. Res. 16 (2002) 769-770
10. Exarchou V., Fiamegos Y.C., vanBeek T., Nanos C., and Vervoort J. Hyphenated chromatographic techniques for the rapid screening and identification of antioxidants in methanolic extracts of pharmaceutically used plants. J. Chromatogr. A 1112 (2006) 293-302
11. Fuzzati N., Gabetta B., Streponi I., and Villa F. High performance liquid chromatography-electrospray ionisation mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products. J. Chromatogr. A 926 (2001) 187-198
12. Ghisalberti, E.L., 1993. Detection and isolation of bioactive natural products. In: Colegate, S.M., Molyneux, R.J. (Eds.), Detection, Isolation and Structural Determination, CRC Press Inc., Florida, pp. 9-57.
13. Hostettmann K., Wolfender J., and Terreaux C. Modern screening techniques for plant extracts. Pharm. Biol. 39 (2001) 18-32
14. INA Methods Validation Program, 2000. Determination of Hypericin and Pseudohypericin in St. John's Wort by High Performance Liquid Chromatography, 107.000. Institute for Nutraceutical Advancement, Denver, CO, pp. 1-4.
15. Karim, F., Quraan, S., 1986. Medicinal plants of Jordan, Yarmouk University, Irbid, Jordan.
16. Kingston, D.G.I., 1996. Natural products as pharmaceuticals and sources for lead structures. In: Meyer, P. (Ed.), The Practice of Medicinal Chemistry, Academic Press Limited, London, pp. 101-116.
17. Liu F.F., Ang C.Y.W., Heinze T.M., Rankin J.D., Beger R.D., Freeman J.P., and Lay Jr. J.O. Evaluation of major active components in St. John's Wort dietary supplements by high performance liquid chromatography with photodiode array detection and electrospray mass spectrometric confirmation. J. Chromatogr. A 888 (2000) 85-92
18. Mauri P., and Pietta P. High performance liquid chromatography/electrospray mass spectrometry of Hypericum perforatum extracts. Rapid Commun. Mass Spectrom. 14 (2000) 95-99
19. Nahrstedt A., and Butterweck V. Biologically active and other chemical constituents of the herb Hypericum perforatum L. Pharmacopsychiatry 30 Suppl. (1997) 129-134
20. Newman D.J., and Cragg G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 70 (2007) 461-477
21. Newman D., Cragg G., and Snader K. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66 (2003) 1022-1037
22. Niessen W.M.A. State-of-the-art in liquid chromatography-mass spectrometry. J. Chromatogr. A 856 (1999) 179-197
23. Sarker S., and Nahar L. Hyphenated techniques. In: Sarker S., Latif Z., and Gray A.I. (Eds). Natural Products Isolation (2005), HUMANA Press, Totowa, NJ 233-268
24. Sedlock D.M., Sun H.H., Smith W.F., Kawaoka K., Gillum A.M., and Cooper R. Rapid identification of teleocidins in fermentation broth using HPLC photodiode array and LC/MS methodology. J. Ind. Microbiol. Biotechnol. 9 (1992) 45-52
25. Su Q., Rowley K.G., and Balazs N.D.H. Carotenoids: separation methods applicable to biological samples. J. Chromatogr. B 781 (2002) 393-418
26. Sun L., Rezaei K.A., Temelli F., and Ooraikul B. Supercritical fluid extraction of alkylamides from Echinacea angustifolia. J. Agric. Food Chem. 50 (2002) 3947-3953
27. Suzuki O., Katsumata Y., Oya M., Bladt S., and Wagner H. Inhibition of monoamine oxidase by hypericin. Planta Med. 50 (1984) 272-274
28. Tatsis E.C., Boeren S., Exarchou V., Troganis A.N., Vervoort J., and Gerothanassis I.P. Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry 68 (2007) 383-393
29. Tawaha K., Alali F.Q., Gharaibeh M., Mohammad M., and El-Elimat T. Antioxidant activity and total phenolic content of selected Jordanian plant species. Food Chem. 104 (2007) 1372-1378
30. Tolonen A., Uusitalo J., Hohtola A., and Jalonen J. Determination of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 16 (2002) 396-402
31. Tolonen A., Hohtola A., and Jalonen J. Fast HPLC/PDAanalysis of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts. Phytochem. Anal. 14 (2003) 306-309
32. Tsao R., and Yang R. Optimization of a new mobile phase to know the complex and real polyphenolic composition: towards a total phenolic index using high-performance liquid chromatography. J. Chromatogr. A 1018 (2003) 29-40
33. Wolfender J.L., Verotta L., Belvisi L., Fuzzati N., and Hostettmann K. Structural investigations of isomeric oxidised forms of hyperforin by HPLC-NMR and HPLC-MSn. Phytochem. Anal. 14 (2003) 290-297
34. Wolfender J., Queiroz E.F., and Hostettmann K. The importance of hyphenated techniques in discovery of new lead compounds from nature. Exp. Opin. Drug Discov. 1 (2006) 237-260