Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures

Phytochemistry

Volumn 66, Issue 2, 2005, Pages 139-145

  Klingauf, Petra ^a   Beuerle, Till ^a   Mellenthin, Annett ^b   El Moghazy, Safaa A M ^a   Boubakir, Zakia ^a   Beerhues, Ludger ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Benzophenone synthase; Cell cultures; Chalcone synthase; Hyperforins; Hypericum calycinum; Isobutyrophenone synthase

Indexed keywords

ADHYPERFORIN; BENZOPHENONE SYNTHASE; CHALCONE SYNTHASE; COENZYME A; FLAVONOID; HYPERFORIN; ISOBUTYROPHENONE SYNTHASE; ISOBUTYRYL COENZYME A; MALONYL COENZYME A; POLYKETIDE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; CELL GROWTH; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ISOLATION; ENZYME MECHANISM; HYPERICUM CALYCINUM; MEDICINAL PLANT; NONHUMAN; PLANT CELL CULTURE; POLYMERIZATION;

ACYLTRANSFERASES; BICYCLO COMPOUNDS; CARBON-CARBON LIGASES; CELLS, CULTURED; HYPERICUM; MOLECULAR STRUCTURE; PHLOROGLUCINOL; POLYKETIDE SYNTHASES; TERPENES; TIME FACTORS;

HYPERICUM; HYPERICUM CALYCINUM; HYPERICUM PERFORATUM;

EID: 11844276458     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.11.003     Document Type: Article

References (25)

1. A.M.A. Abd El-Mawla, and L. Beerhues Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum Planta 214 2002 727 733
2. I. Abe, Y. Utsumi, S. Oguro, and H. Noguchi The first plant type III polyketide synthase that catalyzes formation of aromatic heptaketide FEBS Lett. 562 2004 171 176
3. M.I. Amer, B.L. Booth, G.F.M. Noori, and M.F.J.R.P. Proenca The chemistry of nitrilium salts. Part 3. The importance of triazinium salts in Houben-Hoesch reactions catalyzed by trifluoromethanesulphonic acid J. Chem. Soc., Perkin Trans. I 5 1983 1075 1083
4. H.P. Bais, R. Vepachedu, C.B. Lawrence, F.R. Stermitz, and J.M. Vivanco 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 2003 32413 32422
5. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254
6. V. Butterweck Mechanism of action of St John's wort in depression CNS Drugs 17 2003 539 562
7. L.A. Decosterd, H. Stoeckli-Evans, J.C. Chapuis, B. Sordat, and K. Hostettmann New cell growth-inhibitory cyclohexadienone derivatives from Hypericum calycinum L Helv. Chim. Acta 72 1998 1833 1845
8. C.A.J. Erdelmeier Hyperforin, possibly the major non-nitrogenous secondary metabolite of Hypericum perforatum L Pharmacopsychiatry 31 Suppl. 1 1998 2 6
9. O.L. Gamborg, and D.E. Eveleigh Culture methods and detection of glucanases in suspension cultures of wheat and barley Can. J. Biochem. 46 1968 417 421
10. M. Gronquist, A. Bezzerides, A. Attygalle, J. Meinwald, M. Eisner, and T. Eisner Attractive and defensive functions of the ultraviolet pigments of a flower Hypericum calycinum PNAS 98 2001 13745 13750
11. A.G. Jensen, S.H. Hansen, and E.O. Nielsen Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity Life Sci. 68 2001 1593 1605
12. J.M. Jez, M.E. Bowman, and J.P. Noel Expanding the biosynthetic repertoire of plant type III polyketide synthases by altering starter molecule specificity PNAS 99 2002 5319 5324
13. E.M. Linsmaier, and F. Skoog Organic growth factor requirements of tobacco tissue cultures Physiol. Plant. 18 1965 100 127
14. B. Liu, T. Beuerle, T. Klundt, and L. Beerhues Biphenyl synthase from yeast-extract-treated cell cultures of Sorbus aucuparia Planta 218 2004 492 496
15. B. Liu, H. Falkenstein-Paul, W. Schmidt, and L. Beerhues Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional expression, and site-directed mutagenesis of two polyketide synthases Plant J. 34 2003 847 855
16. P. Maisenbacher, and K.A. Kovar Adhyperforin: a homologue of hyperforin from Hypericum perforatum Planta Med. 58 1992 291 293
17. T. Murashige, and F. Skoog A revised medium for rapid growth and bioassays with tobacco tissue cultures Physiol. Plant. 15 1962 473 497
18. A.V. Muruganandam, S. Ghosal, and S.K. Bhattacharya The role of xanthones in the antidepressant activity of Hypericum perforatum involving dopaminergic and serotoninergic systems Biog. Amines 15 2000 553 567
19. W.E. Müller Current St. John's wort research from mode of action to clinical efficacy Pharmacol. Res. 47 2003 101 109
20. Y. Okada, and K. Ito Cloning and analysis of valerophenone synthase gene expressed specifically in lupulin gland of hop (Humulus lupulus L.) Biosci. Biotechnol. Biochem. 65 2001 150 155
21. N.B. Paniego, K.W.M. Zuurbier, S.Y. Fung, R. v.d.Heijden, J.J.C. Scheffer, and R. Verpoorte Phlorisovalerophenone synthase, a novel polyketide synthase from hop (Humulus lupulus L.) cones Eur. J. Biochem. 262 1999 612 616
22. S. Peters, W. Schmidt, and L. Beerhues Regioselective oxidative phenol couplings of 2,3′,4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L Planta 204 1998 64 69
23. W. Schmidt, A.M.A. Abd El-Mawla, J.L. Wolfender, K. Hostettmann, and L. Beerhues Xanthones in cell cultures of Hypericum androsaemum Planta Med. 66 2000 380 381
24. J. Schröder The chalcone/stilbene synthase-type family of condensing enzymes U. Sankawa Comprehensive Natural Products Chemistry vol. 1 1999 Elsevier Amsterdam 749 771
25. J.W. van Klink, J.J. Brophy, N.B. Perry, and R.T. Weavers β-Triketones from Myrtaceae: isoleptospermone from Leptospermum scoparium and papuanone from Corymbia dallachiana J. Nat. Prod. 62 1999 487 489