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Hyperforin
Hyperforin 3D projection
IUPAC name
Identifiers
CAS number 11079-53-1
SMILES
Properties
Molecular formula C35H52O4
Molar mass 536.78 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort).

Contents

Occurrence

Hyperforin has only been found in significant amounts in Hypericum perforatum (St John's wort).[1] Other Hypericum species contain low amounts of hyperforin.[2]

Chemistry

The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975.[3][4 ] Hyperforin is a prenylated phloroglucinol derivative. Total synthesis of hyperforin has not yet been accomplished, despite attempts by several research groups.[5]

Hyperforin is unstable in the presence of light and oxygen.[6]

Pharmacology

Hyperforin is believed to be the primary active constituent responsible for the antidepressant and anxiolytic properties of the extracts of St. John's wort.[7] It acts as a reuptake inhibitor of monoamines, including serotonin, norepinephrine, dopamine, and of GABA and glutamate, with IC50 values of 0.05-0.10 mcg/ml for all compounds, with the exception of glutamate, which is in the 0.5 mcg/ml range.[8] It appears to exert these effects by activating the transient receptor potential ion channel TRPC6.[9] Activation of TRPC6 induces the entry of sodium and calcium into the cell which causes inhibition of monoamine reuptake.[9]

Hyperforin is also thought to be responsible for the induction of the cytochrome P450 enzymes CYP3A4 and CYP2C9 by binding to and activating the pregnane X receptor (PXR).[10]

Antibiotic

Hyperforin has antibiotic properties and is active against methicillin-resistant strains of Staphylococcus aureus (MRSA) with a minimal inhibitory concentration (MIC) value of 1.0 μg/ml,[11] as well as against other gram-positive bacteria.[12]

See also

Further reading

References

  1. ^ Umek A, Kreft S, Kartnig T, Heydel B (May 1999). "Quantitative phytochemical analyses of six hypericum species growing in slovenia". Planta medica 65 (4): 388–90. doi:10.1055/s-2006-960798. PMID 17260265.  
  2. ^ Smelcerovic A, Spiteller M (March 2006). "Phytochemical analysis of nine Hypericum L. species from Serbia and the F.Y.R. Macedonia". Die Pharmazie 61 (3): 251–2. PMID 16599273.  
  3. ^ Bystrov NS, Gupta ShR, Dobrynin VN, Kolosov MN, Chernov BK (January 1976). "[Structure of the antibiotic hyperforin]" (in Russian). Doklady Akademii Nauk SSSR 226 (1): 88–90. PMID 1248360.  
  4. ^ Bystrov NS, Chernov BK, Dobrynin VN, Kolosov MN (1975). "[The structure of hyperforin]". Tetrahedron Letters 16 (32): 2791–2794. doi:10.1016/S0040-4039(00)75241-5.  
  5. ^ Nicolaou KC, Carenzi GE, Jeso V (June 2005). "Construction of highly functionalized medium-sized rings: synthesis of hyperforin and perforatumone model systems". Angewandte Chemie (International ed. In English) 44 (25): 3895–9. doi:10.1002/anie.200500776. PMID 15892032.  
  6. ^ Liu F, Pan C, Drumm P, Ang CY (February 2005). "Liquid chromatography-mass spectrometry studies of St. John's wort methanol extraction: active constituents and their transformation". Journal of pharmaceutical and biomedical analysis 37 (2): 303–12. doi:10.1016/j.jpba.2004.10.034. PMID 15708671.  
  7. ^ Newall, Carol A.; Joanne Barnes; Anderson, Linda R. (2002). Herbal medicines: a guide for healthcare professionals. London: Pharmaceutical Press. ISBN 0-85369-474-5.  
  8. ^ Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Müller WE (1998). "Hyperforin as a possible antidepressant component of hypericum extracts". Life Sci. 63 (6): 499–510. doi:10.1016/S0024-3205(98)00299-9. PMID 9718074.  
  9. ^ a b Leuner K, Kazanski V, Müller M, et al. (December 2007). "Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels". The FASEB journal : official publication of the Federation of American Societies for Experimental Biology 21 (14): 4101–11. doi:10.1096/fj.07-8110com. PMID 17666455.  
  10. ^ Moore LB, Goodwin B, Jones SA, et al. (June 2000). "St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor". Proceedings of the National Academy of Sciences of the United States of America 97 (13): 7500–2. doi:10.1073/pnas.130155097. PMID 10852961.  
  11. ^ Reichling J, Weseler A, Saller R (July 2001). "A current review of the antimicrobial activity of Hypericum perforatum L". Pharmacopsychiatry 34 Suppl 1: S116–8. doi:10.1055/s-2001-15514. PMID 11518059.  
  12. ^ Schempp CM, Pelz K, Wittmer A, Schöpf E, Simon JC (June 1999). "Antibacterial activity of hyperforin from St John's wort, against multiresistant Staphylococcus aureus and gram-positive bacteria". Lancet 353 (9170): 2129. doi:10.1016/S0140-6736(99)00214-7. PMID 10382704.  







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