Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Verotta L (2003) Hypericum perforatum, a source of neuroactive lead structures. Current Topics Med Chem 3: 187–201
Barnes J, Anderson LA, Phillipson JD (2001) St John’s Wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties. J Pharm Pharmacol 53: 583–600
Bombardelli E, Morazzoni P (1995) Hypericum perforatum. Fitoterapia 56: 43–68
Roth L (1990) Hypericum, Hypericin: Botanik, Inhaltsstoffe, Wirkung. Vol Ecomed, Landsberg/Lech
Buchner A (1830) Buchner’s Report. Pharm 34: 217
Siersch E (1927) Anatomie und Mikrochemie der Hypericum Drüsen (Chemie des Hypericins). Plants 3: 481
Brockmann H, Sanne W (1953) Pseudohypericin, ein neuer Hypericum-Farbstoff. Naturwissenschaften 40: 461
Brockmann H (1957) Photodynamisch wirksame Pflanzenfarbstoffe. Fortschritt Chem Org Naturstoff 14: 141–177
Brockmann H, Franssen U, Spitzner D, Augustiniak H (1974) Zur Isolierung und Konstitution des Pseudohypericins. Tetrahedron Lett 15: 1991–1994
Brockmann H, Haschad MN, Maier K, Pohl F (1939) Über das Hypericin, den photodynamisch wirksamen Farbstoff aus H. perforatum. Naturwissenschaften 27: 550
Brockmann H, Kluge F (1951) Zur Synthese des Hypericins. Naturwissenschaften 38: 141
Brockmann H, Sanne W (1957) Zur Kenntnis des Hypericins und Pseudohypericins. Chem. Berichte 90: 2480–2491
Brockmann H, Spitzner D (1975) Die Konstitution des Pseudohypericins. Tetrahedron Lett 16: 37–40
Cameron D, Raverty WD (1976) Pseudohypericin and other phenanthroperlyne quinones. Aust J Chem 29: 1523–1533
Mathis C, Ourisson G (1963) Etude chimio-taxonomique du genre hypericum I. Repartition de l’hypericine. Phytochemistry 2: 157–171
Tolonen A, Uusitalo J, Hohtola A, Jalonen J (2002) Determination of naphthodianthones and phloroglucinols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry. Rap Comm Mass Spectrom 16: 396–402
Freeman D, Kapinus E, Lavie D, Lavie G, Meruelo D, Mazur Y (1994) Acidic properties of hypericin and its octahydroxy analog in the ground and excited-states. J Chem Soc Chem Commun 7: 891–892
Lavie G, Mazur Y, Lavie D, Meruelo D (1995) The chemical and biological properties of Hypericin: a compound with a broad spectrum of biological activities. Med Res Rev 15: 111–119
Suzuki O, Katsumata Y, Oya M, Bladt S, Wagner H (1984) Inhibition of monoamine oxydase by hypericin. Planta Med 50: 272–274
Bladt S, Wagner H (1993) MAO-Hemmung durch Fraktionen und Inhaltsstoffen von Hypericum-Extrakt. Nervenheilkunde 12: 349–352
Yang KC, Prusti RK, Walker EB, Song P-S, Watanabe M, Furuya M (1986) Photodynamic action in Stentor coeruleus sensitized by endogenous pigment stentorin. Photochem Photobiol 43: 305–310
Barnard DL, Huffman JH, Wood SG (1990) Characterization of the anti human cytomegalovirus (HCMV) activity of three anthraquinone compounds 30th Interscience Conference on Antimicrobial Agents and Chemotherapy,{ Atlanta, October 21–24}: 1093
Hudson JB, Lopez-Bazzocchi I, Towers GHN (1991) Antiviral activities of Hypericum Antivir Res 15: 101–112
Moraleda G, Wu TT, Jilbert AR, Aldrich CE, Condreay LD, Larsen SH, Tang JC, Colacino JM, Mason WS (1993) Inhibition of duck hepatitis B virus replication by hypericin. Antivir Res 20: 235–247
Tang J, Colacino JM, Larsen SH, Spitze W (1990) Virucidal activity of Hypericum against enveloped and non-enveloped DNA and RNA virus. Antivir Res 13: 313–325
Kraus GA, Pratt D, Tossberg J, Carpenter S (1990) Antiretroviral activity of synthetic hypericin and related analogs. Biochem Biophys Res Commun 172: 149–153
Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D (1989) Studies of the mechanism of action of the antiretroviral agents hypericin and pseudohypericin. Proc Natl Acad Sci USA 86: 5963–5967
Lenard J, Rabson A, Vanderoef R (1993) Photodynamic inactivation of infectivity of human immunodeficiency virus and enveloped viruses using hypericin and rose bengal: inhibition of fusion and syncytia formation. Proc Natl Acad Sci USA 90: 158–162
Lopez-Bazzocchi I, Hudson JB, Towers GHN (1991) Antiviral activity of the photoactive plant pigment hypericin. Photochem Photobiol 54: 95
Meruelo D, Lavie G, Lavie D (1988) Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: aromatic polycyclic diones Hypericin and Pseudohypericin. Proc Natl Acad Sci USA 85: 5230–5234
Vlietinck AJ, De Bruyne T, Apers S, Pieters LA (1998) Plant-derived lead compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med 64: 97–109
Gulick RM, McAuliffe V, Holden-Wiltse J, Crumpacker C, Liebes L, Stein DS, Meehan P, Hussey S, Forcht J, Valentine FT (1999) Phase I studies of hypericin, the active compound in St. John’s Wort, as an antiretroviral agent in HIV-infected adults — AIDS clinical trials group protocols 150 and 258. Ann Intern Med 130: 510–514
Vanhaelen M, Vanhaelen-Fastre R (1983) Quantitative determination of biologically active constituents in medicinal plant crude extracts by thin layer chromatography-densitometry. J Chromatogr 281: 263–271
Gurevich AI, Dobrynin VN, Kolosov MN, Popravko SA, Ryabova ID, Chernov BK, Derbents NA, Aizenman BE, Garaguly AD (1971) Hyperforin, an antibiotic from Hypericum perforatum L. Antibiotiki 16: 510–513
Roz N, Mazur Y, Hirshfeld A, Rehavi M (2002) Inhibition of vesicular uptake of monoamines by hyperforin. Life Sciences 71: 2227–2237
Bystrov NS, Chernov BK, Dobrynin VN, Kolosov MN (1975) Structure of hyperforin. Tetrahedron Lett 32: 2791–2794
Bystrov NS, Dobrynin VN, Kolosov MN, Chernov BK, Chervin, II, Yakovlev GI (1975) Structure of chromophoric moiety of hyperforin. Doklady Akademii Nauk Sssr 225: 1327–1328
Bystrov NS, Dobrynin VN, Kolosov MN, Chernov BK, Chervin, II, Yakovlev GI (1976) Stoichiometry of antibiotic hyperforin. Doklady Akademii Nauk Sssr 226: 338–341
Bystrov NS, Gupta SR, Dobrynin VN, Kolosov MN, Chernov BK, Chervin, II, Yakovlev GI, Aizenman BE, Derbentseva NA (1976) Structure of antibiotic hyperforin. Doklady Akademii Nauk Sssr 226: 88–90
Brondz I, Greibrokk T, Groth P, Aasen AJ (1983) The absolute-configuration of hyperforin, an antibiotic from Hypericum-perforatum L, based on the crystal-structure determination of its para-bromobenzoate ester. Acta Chem Scan 37: 263–265
Maisenbacher P, Kovar KA (1992) Adhyperforin — a homolog of hyperforin from Hypericum-perforatum. Planta Med 58: 291–293
Shan MD, Hu LH, Chen ZL (2001) Three hyperforin analogues from Hypericum perforatum. J Nat Prod 64: 127–130
Fuzzati N, Gabetta N, Strepponi I, Villa F (2001) High-performance liquid chromatography—electrospray ionization mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products. J Chromatogr A 926: 187–198
Trifunovic S, Vajs V, Macura S, Juranic N, Djarmati Z, Jankov R, Milosavljevic S (1998) Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry 49: 1305–1310
Vajs V, Vugdelija S, Trifunovic S, Karadzic I, Juranic N, Macura S, Milosavljevic S (2003) Further degradation products of hyperforin from Hypericum perforatum (St. John’s Wort). Fitoterapia 74: 439–444
Verotta L, Appendino G, Belloro E, Jakupovic J, Bombardelli E (1999) Furohyperforin, a prenylated phloroglucinol from St. John’s Wort (Hypericum perforatum). J Nat Prod 62: 770–772
Verotta L, Appendino G, Belloro E, Jakupovic J, Bombardelli E (2000) Hyperforin analogues from St. John’s Wort (Hypericum perforatum). J Nat Prod 63: 412–415
Wolfender J-L, Verotta L, Fuzzati N, Strepponi I, Hostettmann K (2003) Structural investigations of isomeric oxidised forms of hyperforin by LC/NMR and LC/MSn. Phytochem Anal 14: 290–297
Verotta L, Appendino G, Belloro E, Bianchi F, Sterner O, Lovati M, Bombardelli E (2002) Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety. J Nat Prod 65: 433–438
Jerzmanowska Z (1937) Über das Hypericin, ein Glukosid von Hypericum perforatum L. Wiadomusci Farm 64: 527
Sprecher P, Casparis F, Müller HJ (1946) Untersuchungen über natürliche Flavonolglykoside. Pharm Acta Helvetiae 21: 341
Dorossiev I (1985) Determination of flavonoids in Hypericum perforatum. Pharmazie 40: 585–586
Berghofer R, Holzl J (1987) Biflavonoids in Hypericum-perforatum.1. Isolation of I3,Ii8-Biapigenin. Planta Med 53: 216–217
Berghofer R, Holzl J (1989) Biflavonoids from Hypericum-perforatum L.2. Isolation of I3’,Ii8-Biapigenin (Amentoflavone) from Hypericum perforatum. Planta Med 55: 91
Demisch L, Hölzl J, Golnik B, Kaczmarczyk P (1989) Identification of selective MAO-type-A inhibitors in Hypericum perforatum L. (Hyperforat®). Pharmacopsychiatry 22: 194
Melzer R, Fricke U, Holzl J (1991) Vasoactive properties of procyanidins from Hypericum-perforatum-L in isolated porcine coronary-arteries. Arzneimittel-Forschung/Drug Research 41: 481–483
Akhtardzhiev K, Kitanov G (1974) Catechin composition of Hypericum perforatum. Farmatsiya 24: 17–20
Gunatilaka AAL, Balasubramaniam S, Kumar V (1979) Studies on medicinal and related plants of Sri-Lanka.1. 2,3-dimethoxyxanthone from Hypericum-mysorense. Phytochemistry 18: 182–183
Suzuki O, Katsumata Y, Oya M, Chari VM, Klapfenberger R, Wagner H, Hostettmann K (1981) Inhibition of type A and type B monoamine oxidases by naturally occurring xanthones. Planta Med 42: 17–21
Sparenberg B, Demisch L, Hölzl J (1993) Untersuchungen über antidepressive Wirkstoffe von Johanniskraut. J Pharm Ztg Wiss 6: 50–54
Ollivier B, Balansard G, Maillard C, Vidal E (1985) Separation and identification of phenolic-acids by HPLC and UV spectral-analysis — Application to parietary (Parietaria officinalis L) and to Saint-Johns Wort (Hypericum perforatum L). J Pharm Bel 40: 173–177
Mathis C, Ourisson G (1964) Etude chimio-taxonomique du genre Hypericum II. Identification de constituents de diverses huiles essentielles d’Hypericum. Phytochemistry 3: 115–131
Mathis C, Ourisson G (1964) Etude chimio-taxonomique du genre Hypericum III. Répartition des carbures saturés et des monoterpènes dans les huiles essentielles d’Hypericum. Phytochemistry 3: 133–141
Mathis C, Ourisson G (1964) etude chimio-taxonomique du genre Hypericum IV. Répartition des sesquiterpenes, des alcools monoterpeniques et des aldehydes saturés dans les huiles essentielles d’Hypericum. Phytochemistry 3: 377–378
Schwob I, Bessiere JM, Viano J (2002) Composition of the essential oils of Hypericum perforatum L. from southeastern France. CR Biologies 325: 781–785
Mimica-Dukic N, Ivancev-Tumbas I, Igic R, Popovic M, Gasic O (1997) The content and composition of the essential oil of Hypericum perforatum from Serbia. Pharm Pharmacol Let 8: 26–28
Hölzl J, Ostrowski E (1987) Johanniskraut (Hypericum perforatum L.). HPLC-Analyse der wichtigen Inhaltstoffe und deren Variabilität in einer Population. Dtsch Apoth Ztg 127: 1227–1230
Brondz I, Greibrokk T, Aasen AJ (1983) Normal-alkanes of Hypericum perforatum — a revision. Phytochemistry 22: 295–296
Brondz I, Greibrokk T (1983) N-l-alkanols of Hypericum perforatum. J Nat Prod 46: 940–941
Commission_E_of_the_German_Federal_Public_Health_Departement (1984) Monograph Hyperici herba, Johanniskraut, Berlin
Berghofer R (1987) Dissertation, Universität Marburg
von Eggelklaaut-Gottanka SG, Abu Abed S, Muller W, Schmidt PC (2002) Quantitative analysis of the active components and the by-products of eight dry extracts of Hypericum perforatum L. (St John’s Wort). Phytochem Anal 13: 170–176
Holz J, Ostrowski E (1987) Dtsch Apoth Ztg 23
Kartnig T, Göbel I (1992) Determination of hypericin and pseudohypericin by thin-layer chromatography-densitometry. J Chromat 609: 423–426
Southwell IA, Campbell MH (1991) Hypericin content variation in Hypericum perforatum in Australia. Phytochemistry 30: 475–478
Brolis M, Gabetta B, Fuzzati N, Pace R, Panzeri F, Peterlongo F (1998) 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: 9–16
Poutaraud A, Lobstein A, Girardin P, Weniger B (2001) Improved procedure for the quality control of Hypericum perforatum L. Phytochem Anal 12: 355–362
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2005 Birkhäuser Verlag/Switzerland
About this chapter
Cite this chapter
Hostettmann, K., Wolfender, JL. (2005). Phytochemistry. In: Müller, W.E. (eds) St. John’s Wort and its Active Principles in Depression and Anxiety. Milestones in Drug Therapy MDT. Birkhäuser Basel. https://doi.org/10.1007/3-7643-7338-5_2
Download citation
DOI: https://doi.org/10.1007/3-7643-7338-5_2
Publisher Name: Birkhäuser Basel
Print ISBN: 978-3-7643-6160-0
Online ISBN: 978-3-7643-7338-2
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)