Spatial chemo-profiling of hypericin and related phytochemicals in Hypericum species using MALDI-HRMS imaging Mass Spectrometry Imaging

Analytical and Bioanalytical Chemistry

Volumn 407, Issue 16, 2015, Pages 4779-4791

  Kusari, Souvik ^a   Sezgin, Selahaddin ^a   Nigutova, Katarina ^b   Cellarova, Eva ^b   Spiteller, Michael ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

Biosynthesis; Dark glands; High resolution mass spectrometry; Hypericin; Hypericum olympicum L; Hypericum patulum THUNB; Hypericum perforatum L; Matrix assisted laser desorption ionization (MALDI) high resolution mass spectrometry imaging

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; DESORPTION; ESSENTIAL OILS; GENE EXPRESSION; IMAGING TECHNIQUES; MASS SPECTROMETRY; SECONDARY ION MASS SPECTROMETRY; SPECTROMETRY;

DARK GLANDS; HIGH RESOLUTION MASS SPECTROMETRY; HYPERICINS; HYPERICUM OLYMPICUM L; HYPERICUM PATULUM THUNB; HYPERICUM PERFORATUM L;

MOLECULAR IMAGING;

HYPERICUM; HYPERICUM OLYMPICUM; HYPERICUM PATULUM; HYPERICUM PERFORATUM;

HYPERICIN; PERYLENE; PLANT MEDICINAL PRODUCT;

ANALOGS AND DERIVATIVES; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPERICUM; MASS SPECTROMETRY; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYPERICUM; PERYLENE; PHYTOCHEMICALS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84938078446     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-015-8682-6     Document Type: Article

References (46)

1. Kosuth J, Smelcerovic A, Borsch T, Zuehlke S, Karppinen K, Spiteller M, Hohtola A, Cellarova E (2011) The hyp-1 gene is not a limiting factor for hypericin biosynthesis in the genus Hypericum. Funct Plant Biol 38:35-43
2. Kosuth J, Hrehorova D, Jaskolski M, Cellarova E (2013) Stress-induced expression and structure of the putative gene hyp-1 for hypericin biosynthesis. Plant Cell Tissue Organ Cult 114:207-216
3. Kusari S, Lamshöft M, Zühlke S, Spiteller M (2008) An endophytic fungus from Hypericum perforatum that produces hypericin. J Nat Prod 71:159-162
4. Kusari S, Zühlke S, Kosuth J, Cellarova E, Spiteller M (2009) Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis. J Nat Prod 72:1825-1835
5. Crockett SL, Robson NKB (2011) Taxonomy and chemotaxonomy of the genus Hypericum. Med Aromat Plant Sci Biotechnol 5:1-13
6. Brockmann H, Haschad MN, Maier K, Pohl F (1939) Über das Hypericin, den photodynamisch wirksamen Farbstoff aus Hypericum perforatum. Naturwissenschaften 27:550
7. Brockmann H, Pohl F, Maier K, Haschad MN (1942) Über das Hypericin, den photodynamischen Farbstoff des Johanniskrautes (Hypericum perforatum). Ann Chem 553:1-52
8. Brockmann H, Kluge F, Muxfeldt H (1957) Totalsynthese des Hypericins. Chem Ber 90:2302-2318
9. Nahrstedt A, Butterweck V (1997) Biologically active and other chemical constituents of the herb of Hypericum perforatum L. Pharmacopsychiatry 30:129-134
10. Häberlein H, Tschiersch KP, Stock S, Hölzl J (1992) Johanniskraut (Hypericum perforatum L.): Nachweis eines weiteren Naphthodianthrons. Pharm Ztg Wiss 5(137):169-174
11. Kitanov GM (2001) Hypericin and pseudohypericin in some Hypericum species. Biochem Syst Ecol 29:171-178
12. Makovetska OY (1999) Research of biologically active substances of Hypericum L. species: report II. Farm Zh (Kiev) 1:47-52
13. Crockett SL, Schaneberg B, Khan IA (2005) Phytochemical profiling of New and Old World Hypericum (St. John's Wort) species. Phytochem Anal 16:479-485
14. Kirakosyan A, Gibson DM, Kaufman PB (2008) The production of dianthrones and phloroglucinol derivatives in St. John's Wort. In: Ramawat KG, Merillon JM (eds) Bioactive molecules and medicinal plants. Springer, Berlin, pp 149-164
15. Brockmann H, Falkenhausen EH, Dorlares A (1950) Die Konstitution des Hypericins. Naturwissenschaften 37:540
16. Thomson RH (1957) Naturally occurring quinones. Butterworths Scientific Publications, London
17. Bais HP, Vepachedu R, Lawrence CB, Stermitz FR, Vivanco JM (2003) Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.). J Biol Chem 278:32413-32422
18. Kosuth J, Katkovcinova Z, Olexova P, Cellarova E (2007) Expression of the hyp-1 gene in early stages of development of Hypericum perforatum L. Plant Cell Rep 26:211-217
19. Cellarova E, Daxnerova Z, Kimakova K, Haluskova J (1994) The variability of hypericin content in the regenerants of Hypericum perforatum. Acta Biotechnol 14:267-274
20. Briskin DP, Leroy A, Gawienowski M (2000) Influence of nitrogen on the production of hypericins by St. John's wort. Plant Physiol Biochem 38:413-420
21. Onelli E, Rivetta A, Giorgi A, Bignami M, Cocucci M, Patrignani G (2002) Ultrastructural studies on the developing secretory nodules of Hypericum perforatum. Flora 197:92-102
22. Hölzl J, Petersen M (2003) Chemical constituents of Hypericum ssp. In: Ernst E (ed) Hypericum: the genus Hypericum (series: medicinal and aromatic plants - industrial profiles), vol 31. Taylor and Francis, London, pp 77-93
23. Hadjur C, Richard MJ, Parat MO, Jardon P, Favier A (1996) Photodynamic effects of hypericin on lipid peroxidation and antioxidant status in melanoma cells. Photochem Photobiol 64:375-381
24. Delaey EM, Obermueller R, Zupko I, De Vos D, Falk H, de Witte PA (2001) In vitro study of the photocytotoxicity of some hypericin analogs on different cell lines. Photochem Photobiol 74:164-171
25. Kamuhabwa AR, Agostinis PM, D'Hallewin MA, Baert L, de Witte PA (2001) Cellular photodestruction induced by hypericin in AY-27 rat bladder carcinoma cells. Photochem Photobiol 74:126-132
26. Kubin A, Wierrani F, Burner U, Alth G, Grunberger W (2005) Hypericin - the facts about a controversial agent. Curr Pharm Des 11:233-253
27. Zobayed SMA, Afreen F, Goto E, Kozai T (2006) Plant-environment interactions: accumulation of hypericin in dark glands of Hypericum perforatum. Ann Bot 98:793-804
28. Maggi F, Ferretti G, Pocceschi N, Meneghini L, Ricciutelli M (2004) Morphological, histochemical and phytochemical investigation of the genus Hypericum of the central Italy. Fitoterapia 75:702-711
29. Römpp A, Spengler B (2013) Mass spectrometry imaging with high resolution in mass and space. Histochem Cell Biol 139:759-783
30. Shih C-J, Chen P-Y, Liaw C-C, Lai Y-M, Yang Y-L (2014) Bringing microbial interactions to light using imaging mass spectrometry. Nat Prod Rep. doi: 10.1039/c3np70091g
31. Bjarnholt N, Li B, D'Alvise J, Janfelt C (2014) Mass spectrometry imaging of plant metabolites - principles and possibilities. Nat Prod Rep. doi: 10.1039/c3np70100j
32. Jaeger RJ, Lamshöft M, Gottfried S, Spiteller M, Spiteller P (2013) HR-MALDI-MS imaging assisted screening of β-carboline alkaloids discovered from Mycena metata. J Nat Prod 76:127-134
33. Kusari P, Kusari S, Lamshöft M, Sezgin S, Spiteller M, Kayser O (2014) Quorum quenching is an antivirulence strategy employed by endophytic bacteria. Appl Microbiol Biotechnol 98:7173-7183
34. Kusari S, Lamshöft M, Kusari P, Gottfried S, Zühlke S, Louven K, Hentschel U, Kayser O, Spiteller M (2014) Endophytes are hidden producers of maytansine in Putterlickia roots. J Nat Prod 77:2577-2584
35. Ciccarelli D, Andreucci AC, Pagni AM (2001) Translucent glands and secretory canals in Hypericum perforatum L. (Hypericaceae): morphological, anatomical and histochemical studies during the course of ontogenesis. Ann Bot 88:637-644
36. Łotocka B, Osińska E (2010) Shoot anatomy and secretory structures in Hypericum species (Hypericaceae). Bot J Linn Soc 163:70-86
37. Nürk NM, Crockett SL (2011) Morphological and phytochemical diversity among Hypericum species of the Mediterranean Basin. Med Aromat Plant Sci Biotechnol 5:14-28
38. Perrone R, Rosa PD, Castro OD, Colombo P (2013) Leaf and stem anatomy in eight Hypericum species (Clusiaceae). Acta Bot Croat 72:269-286
39. Soelberg J, Jørgensen LB, Jäger AK (2007) Hyperforin accumulates in the translucent glands of Hypericum perforatum. Ann Bot 99:1097-1100
40. Hölscher D, Shroff R, Knop K, Gottschaldt M, Crecelius A, Schneider B, Heckel DG, Schubert US, Svatos A (2009) Matrix-free UV-laser desorption/ionization (LDI) mass spectrometric imaging at the single-cell level: distribution of secondary metabolites of Arabidopsis thaliana and Hypericum species. Plant J 60:907-918
41. Thunig J, Hansen SH, Janfelt C (2011) Analysis of secondary plant metabolites by indirect desorption electrospray ionization imaging mass spectrometry. Anal Chem 83:3256-3259
42. Kusari S, Zühlke S, Borsch T, Spiteller M (2009) Positive correlations between hypericin and putative precursors detected in the quantitative secondary metabolite spectrum of Hypericum. Phytochemistry 70:1222-1232
43. Harborne JB (1993) Introduction to ecological biochemistry, 4th edn. Academic Press, London
44. Smelcerovic A, Spiteller M (2006) Phytochemical analysis of nine Hypericum L. species from Serbia and the F.Y.R. Macedonia. Pharmazie 61:251-252
45. Izhaki I (2002) Emodin - a secondary metabolite with multiple ecological functions in higher plants. New Phytol 155:205-217
46. Cornett DS, Reyzer ML, Chaurand P, Caprioli RM (2007) MALDI imaging mass spectrometry: molecular snapshots of biochemical systems. Nat Methods 4:828-833