Hyperforin

Phytochemistry

Volumn 67, Issue 20, 2006, Pages 2201-2207

  Beerhues, Ludger ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Biosynthesis; Clusiaceae; Hyperforin; Hypericum perforatum; Pharmacology; Structure

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BICYCLO COMPOUND; DRUG DERIVATIVE; HYPERFORIN; NEUROTRANSMITTER UPTAKE INHIBITOR; PHLOROGLUCINOL; TERPENE;

CHEMISTRY; HISTOLOGY; HYPERICUM; METABOLISM; NUCLEAR MAGNETIC RESONANCE; SHORT SURVEY;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BICYCLO COMPOUNDS; HYPERICUM; NEUROTRANSMITTER UPTAKE INHIBITORS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHLOROGLUCINOL; TERPENES;

CLUSIACEAE; HYPERICUM PERFORATUM; POSIBACTERIA;

EID: 33748788822     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.08.017     Document Type: Short Survey

References (75)

1. Adam P., Arigoni D., Bacher A., and Eisenreich W. Biosynthesis of hyperforin in Hypericum perforatum. J. Med. Chem. 45 (2002) 4786-4793
2. Albert D., Zündorf I., Dingermann T., Müller W.E., Steinhilber D., and Werz O. Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. Biochem. Pharmacol. 64 (2002) 1767-1775
3. Bais H.P., Vepachedu R., Lawrence C.B., Stermitz F.R., and Vivanco J.M. 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
4. Berghöfer R., and Hölzl J. Johanniskraut (Hypericum perforatum L.) - Prüfung auf Verfälschung. Dtsch. Apoth. Ztg. 126 (1986) 2569-2573
5. Boubakir Z., Beuerle T., Liu B., and Beerhues L. The first prenylation step in hyperforin biosynthesis. Phytochemistry 66 (2004) 51-57
6. Brondz I., Greibrokk T., Groth P.A., and Aasen A.J. The relative stereochemistry of hyperforin - an antibiotic from Hypericum perforatum L. Tetrahedron Lett. 23 (1982) 1299-1300
7. Brondz I., Greibrokk T., Groth P.A., and Aasen A.J. The absolute configuration of hyperforin, an antibiotic from Hypericum perforatum L., based on the crystal structure determination of its p-bromobenzoate ester. Acta Chem. Scand. A37 (1983) 263-265
8. Butterweck V. Mechanism of action of St. John's wort in depression. CNS Drugs 17 (2003) 539-562
9. Bystrov N.S., Chernov B.K., Dobrynin V.N., and Kolosov M.N. The structure of hyperforin. Tetrahedron Lett. 32 (1975) 2791-2794
10. Bystrov N.S., Gupta S.R., Dobrynin V.N., Kolosov M.N., and Chernov B.K. Chemistry of hyperforin. IX. Structure of hyperforin. Bioorg. Khim. 4 (1978) 948-955
11. Cantoni L., Rozio M., Mangolini A., and Caccia S. Hyperforin contributes to the hepatic CYP3A-inducing effect of Hypericum perforatum extract in the mouse. Toxicol. Sci. 75 (2003) 25-30
12. Chatterjee S.S., Nöldner M., Koch E., and Erdelmeier C. Antidepressant activity of Hypericum perforatum and hyperforin: the neglected possibility. Pharmacopsychiatry 31 Suppl (1998) 7-15
13. Ciochina R., and Grossman R.B. A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols. Org. Lett. 5 (2003) 4619-4621
14. Dias A.C.P. The potential of in vitro cultures of Hypericum perforatum and of Hypericum androsaemum to produce interesting pharmaceutical compounds. In: Ernst E. (Ed). Hypericum: The genus Hypericum (2003), Taylor and Francis, New York 137-154
15. Donà M., Dell'Aica I., Pezzato E., Sartor L., Calabrese F., Barbera M.D., Donella-Deana A., Appendino G., Borsarini A., Caniato R., and Garbisa S. Hyperforin inhibits cancer invasion and metastasis. Cancer Res. 64 (2004) 6225-6232
16. Erdelmeier C.A.J. Hyperforin, possibly the major non-nitrogenous secondary metabolite of Hypericum perforatum L. Pharmacopsychiat. 31 Suppl (1998) 2-6
17. Erdelmeier, C.A.J., Klessing, K., Renzl, S., Hauer, H., 1999. New hyperforin analogues from Hypericum perforatum and a stable dicyclohexylammonium salt of hyperforin. In: 2000 Years of Natural Products Research - Past, Present and Future, Luijendijk, T.J.C., Verpoorte, R., (Eds.), p. 432.
18. Fellermeier M., and Zenk M.H. Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett. 427 (1998) 283-285
19. Gartner M., Müller T., Simon J.C., Giannis A., and Sleeman J.P. Aristoforin, a novel stable derivative of hyperforin, is a potent anticancer agent. ChemBioChem 6 (2005) 171-177
20. Gronquist M., Bezzerides A., Attygalle A., Meinwald J., Eisner M., and Eisner T. Attractive and defensive functions of the ultraviolet pigments of a flower (Hypericum calycinum). PNAS 98 (2001) 13745-13750
21. Gurevich A.I., Dobrynin V.N., Kolosov M.N., Popravko S.A., Ryabova I.D., Chernov B.K., Derbentseva N.A., Aizenman B.E., and Gargulya A.D. Hyperforin, an antibiotic from Hypericum perforatum. Antibiotiki 16 (1971) 510-513
22. Gutmann H., Poller B., Berger Büter K., Pfrunder A., Schaffner W., and Drewe J. Hypericum perforatum: Which constituents may induce intestinal MDR1 and CYP3A4 mRNA expression?. Planta Med. 72 (2006) 685-690
23. Hostanska K., Reichling J., Bommer S., Weber M., and Saller R. Hyperforin a constituent of St. John's wort (Hypericum perforatum L.) extract induces apoptosis by triggering activation of caspases and with hypericin synergistically exerts cytotoxicity towards human malignant cell lines. Eur. J. Pharm. Biopharm. 56 (2003) 121-132
24. Jensen A.G., Hansen S.H., and Nielsen E.O. Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity. Life Sci. 68 (2001) 1593-1605
25. Kirakosyan A.B., Vardapetyan R.R., and Charchoglyan A.G. Initation of callus and suspension cell cultures of Hypericum perforatum L. for obtaining hypericin and pseudohypericin. Russ. J. Plant Physiol. 47 (2000) 270-274
26. Klingauf P., Beuerle T., Mellenthin A., El-Moghazy S.A.M., Boubakir Z., and Beerhues L. Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures. Phytochemistry 66 (2004) 139-145
27. Košuth J., Koperdáková J., Tolonen A., Hohtola A., and Cellárová E. The content of hypericins and phloroglucinols in Hypericum perforatum L. seedlings at early stage of development. Plant Sci. 165 (2003) 515-521
28. Kraus G.A., Nguyen T.H., and Jeon I. Synthesis of the core bicyclic system of hyperforin and nemorosone. Tetrahedron Lett. 44 (2003) 659-661
29. Lang F., Biber A., and Erdelmeier C. Hyperforin in Johanniskraut-Droge, -Extrakten und -Präparaten. Pharm. Unserer Zeit 5 (2002) 512-514
30. Liu B., Falkenstein-Paul H., Schmidt W., and Beerhues L. 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
31. Liu F., Pan C., Drumm P., and Ang C.Y.W. Liquid chramatography-mass spectrometry studies of St. John's wort methanol extraction: active constituents and their transformation. J. Pharm. Biomed. Anal. 37 (2005) 303-312
32. Madabushi R., Frank B., Drewelow B., Derendorf H., and Butterweck V. Hyperforin in St. John's wort drug interactions. Eur. J. Clin. Pharmacol. 62 (2006) 225-233
33. Maisenbacher P., and Kovar K.A. Analysis and stability of Hyperici oleum. Planta Med. 58 (1992) 351-354
34. Maisenbacher P., and Kovar K.A. Adhyperforin: A homologue of hyperforin from Hypericum perforatum. Planta Med. 58 (1992) 291-293
35. Marti{dotless}́nez-Poveda B., Quesada A.R., and Medina M.A. Hyperforin, a bio-active compound of St. John's wort, is a new inhibitor of angiogenesis targeting several key steps of the process. Int. J. Cancer 117 (2005) 775-780
36. Mathijssen R.H.J., Verweij J., de Bruijn P., Loos W.J., and Sparreboom A. Effects of St. John's wort on irinotecan metabolism. J. Natl. Cancer Inst. 94 (2002) 1247-1249
37. Medina M.A., Marti{dotless}́nez-Poveda B., Amores-Sánchez M.I., and Quesada A.R. Hyperforin: More than an antidepressant bioactive compound?. Life Sci. 79 (2006) 105-111
38. Moore L.B., Goodwin B., Jones S.A., Wisely G.B., Serabjit-Singh C.J., Willson T.M., Collins J.L., and Kliewer S.A. St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. PNAS 97 (2000) 7500-7502
39. Müller W.E. Current St. John's wort research from mode of action to clinical efficacy. Pharmacol. Res. 47 (2003) 101-109
40. Nicolaou K.C., Carenzi G.E.A., and Jeso V. Construction of highly functionalized medium-sized rings: Synthesis of hyperforin and perforatumone model systems. Angew. Chem. Int. Ed. 44 (2005) 3895-3899
41. Okada Y., and Ito K. Cloning and analysis of valerophenone synthase gene expressed specifically in lupulin gland of hop (Humulus lupulus L.). Biosci. Biotech. Biochem. 65 (2001) 150-155
42. Orth H.C.J., Hauer H., Erdelmeier C.A.J., and Schmidt P.C. Orthoforin: The main degradation product of hyperforin from Hypericum perforatum. Pharmazie 54 (1999) 76-77
43. Piovan A., Filippini R., Caniato R., Borsarini A., Maleci L.B., and Cappelletti E.M. Detection of hypericins in the "red glands" of Hypericum elodes by ESI-MS/MS. Phytochemistry 65 (2004) 411-414
44. Piscitelli S.C., Burstein A.H., Chaitt D., Alfaro R.M., and Falloon J. Indinavir concentrations and St. John's wort. Lancet 355 (2000) 547-548
45. Pojer F., Wemakor E., Kammerer B., Chen H., Walsh C.T., Li S.M., and Heide L. CloQ, a prenyltransferase involved in clorobiocin biosynthesis. PNAS 100 (2003) 2316-2321
46. Reichling J., Weseler A., and Saller R. A current review of the antibacterial activity of Hypericum perforatum L. Pharmacopsychiatry 34 Suppl (2001) 116-118
47. Repčák M., and Mártonfi P. The localization of secondary substances in Hypericum perforatum flowers. Biologia 52 (1997) 91-94
48. Robson N.K.B. Hypericum botany. In: Ernst E. (Ed). Hypericum: The genus Hypericum (2003), Taylor and Francis, New York 1-22
49. Rücker G., Manns D., Hartmann R., and Bonsels U. Peroxides as constituents of plants. 19. A C(50)-hydroperoxide from Hypericum perforatum. Arch. Pharm. 328 (1995) 725-730
50. Ruschitzka F., Meier P.J., Turina M., Luscher T.F., and Noll G. Acute heart transplant rejection due to Saint John's wort. Lancet 355 (2000) 548-549
51. Schempp C.M., Pelz K., Wittmer A., Schöpf E., and Simon J.C. Antibacterial activity of hyperforin from St. John's wort, against multiresistant Staphylococcus aureus and gram-positive bacteria. Lancet 353 (1999) 2129
52. Schempp C.M., Winghofer B., Lüdtke R., Simon-Haarhaus B., Schöpf E., and Simon J.C. Topical application of St. John's wort (Hypericum perforatum L.) and of its metabolite hyperforin inhibits the allostimulatory capacity of epidermal cells. Br. J. Dermatol. 142 (2000) 979-984
53. Schempp C.M., Kirkin V., Simon-Haarhaus B., Kersten A., Kiss J., Termeer C.C., Gilb B., Kaufmann T., Borner C., Sleeman J.P., and Simon J.C. Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis. Oncogene 21 (2002) 1242-1250
54. Shan M.D., Hu L.H., and Chen Z.L. Three new hyperforin analogues from Hypericum perforatum. J. Nat. Prod. 64 (2001) 127-130
55. +. J. Pharmacol. Exp. Ther. 290 (1999) 1363-1368
56. Sirvent T.M., Krasnoff S.B., and Gibson D.M. Induction of hypericins and hyperforins in Hypericum perforatum in response to damage by herbivores. J. Chem. Ecol. 29 (2003) 2667-2681
57. Smelcerovic A., and Spiteller M. Phytochemical analysis of nine Hypericum L. species from Serbia and the F.Y.R. Macedonia. Pharmazie 61 (2006) 251-252
58. Spessard S.J., and Stoltz B.M. Progress toward the synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core. Org. Lett. 4 (2002) 1943-1946
59. Tekel'ová D., Repčák M., Zemková E., and Tóth J. Quantitative changes of dianthrones, hyperforin and flavonoids content in the flower ontogenesis of Hypericum perforatum. Planta Med. 66 (2000) 778-780
60. Treiber K., Singer A., Henke B., and Müller W.E. Hyperforin activates nonselective cation channels (NSCCs). Br. J. Pharmacol. 145 (2005) 75-83
61. Trifunović S., Vajs V., Macura S., Juranić N., Djarmati Z., Jankov R., and Milosavljević S. Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry 49 (1998) 1305-1310
62. Tsai H.F., Wang H., Gebler J.C., Poulter C.D., and Schardl C.L. The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis. Biochem. Biophys. Res. Commun. 216 (1995) 119-125
63. Umek A., Kreft S., Kartnig T., and Heydel B. Quantitative phytochemical analyses of six Hypericum species growing in Slovenia. Planta Med. 65 (1999) 388-390
64. Usuda H., Kanai M., and Shibasaki M. Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A. Tetrahedron Lett. 43 (2002) 3621-3624
65. Vajs V., Vugdelija S., Trifunović S., Karadžić I., Juranić N., Macura S., and Milosavljević S. Further degradation product of hyperforin from Hypericum perforatum (St. John's wort). Fitoterapia 74 (2003) 439-444
66. Verotta L., Appendino G., Belloro E., Jakupovic J., and Bombardelli E. Furohyperforin, a prenylated phloroglucinol from St. John's wort (Hypericum perforatum). J. Nat. Prod. 62 (1999) 770-772
67. Verotta L., Appendino G., Jakupovic J., and Bombardelli E. Hyperfoirn analogues from St. John's wort (Hypericum perforatum). J. Nat. Prod. 63 (2000) 412-415
68. Verotta L., Appendino G., Belloro E., Bianchi F., Sterner O., Lovati M., and Bombardelli E. Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety. J. Nat. Prod. 65 (2002) 433-438
69. Verotta L., Lovaglio E., Sterner O., Appendino G., and Bombardelli E. Oxidative fragmentation of the bridged ß-triketone core of hyperforin. Eur. J. Org. Chem. (2004) 1193-1197
70. Wang E.J., Lew K., Barecki M., Casciano C.N., Clement R.P., and Johnson W.W. Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem. Res. Toxicol. 14 (2001) 1596-1603
71. Watkins R.E., Maglich J.M., Moore L.B., Wisely G.B., Noble S.M., Davis-Searles P.R., Lambert M.H., Kliewer S.A., and Redinbo M.R. 2.1 Å Crystal structure of human PXR in complex with the St. John's wort compound hyperforin. Biochemistry 42 (2003) 1430-1438
72. Whiskey E., Werneke U., and Taylor D. A systematic review and meta-analysis of Hypericum perforatum in depression: a comprehensive clinical review. Int. Clin. Psychopharmacol. 16 (2001) 239-252
73. Young D.G.J., and Zeng D. A preliminary approach to nonenolizable ß,ß-tricarbonyls: Assembly of a hyperevolutin prototype. J. Org. Chem. 67 (2002) 3134-3137
74. Zobayed S.M.A., Murch S.J., Rupasinghe H.P.V., and Saxena P.K. Elevated carbon supply altered hypericin and hyperforin contents of St. John's wort (Hypericum perforatum) grown in bioreactors. Plant Cell, Tissue Organ Culture 75 (2003) 143-149
75. Zuurbier K.W.M., Fung S.Y., Scheffer J.J.C., and Verpoorte R. In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in Humulus lupulus. Phytochemistry 49 (1998) 2315-2322