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Hyperforin
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==Occurrence== Hyperforin has only been found in significant amounts in ''[[Hypericum perforatum]]'' with other related species such as ''[[Hypericum calycinum]]'' containing lower levels of the phytochemical.<ref name=pubchem/> It accumulates in oil glands, [[pistil]]s, and fruits, probably as a [[plant defense against herbivory|plant defensive compound]].<ref>{{cite journal | vauthors = Beerhues L | title = Hyperforin | journal = Phytochemistry | volume = 67 | issue = 20 | pages = 2201–2207 | date = October 2006 | pmid = 16973193 | doi = 10.1016/j.phytochem.2006.08.017 | bibcode = 2006PChem..67.2201B }}</ref> The first natural extractions were done with ethanol and afforded a 7:1 yield of crude extract to phytochemical however, this technique produced a mixture of hyperforin and [[adhyperforin]].<ref name=j3/><ref name=j2>{{cite journal | vauthors = Vajs V, Vugdelija S, Trifunović S, Karadzić I, Juranić N, Macura S, Milosavljević S | title = Further degradation product of hyperforin from Hypericum perforatum (St John's Wort) | journal = Fitoterapia | volume = 74 | issue = 5 | pages = 439–444 | date = July 2003 | pmid = 12837358 | doi = 10.1016/S0367-326X(03)00114-X }}</ref><ref name=j1>{{cite journal | vauthors = Verotta L, Appendino G, Belloro E, Jakupovic J, Bombardelli E | title = Furohyperforin, a prenylated phloroglucinol from st. John's wort (Hypericumperforatum) | journal = Journal of Natural Products | volume = 62 | issue = 5 | pages = 770–772 | date = May 1999 | pmid = 10346967 | doi = 10.1021/np980470v }}</ref> The extraction technique has since been modernized using lipophilic liquid CO<sub>2</sub> extraction to afford a 3:1 crude to phytochemical extraction which is then further purified away from adhyperforin.<ref name=j3/><ref name=j2/><ref name=j1/> This CO<sub>2</sub> extraction is rather tricky still because typical 'supercritical' conditions extract less material whereas anything over 40 °C (100 °F) will degrade hyperforin.<ref name=j3/><ref name=j2/><ref name=j1/> Other ''Hypericum'' species contain low amounts of hyperforin.<ref name="pmid16599273">{{cite journal | vauthors = Smelcerovic A, Spiteller M | title = Phytochemical analysis of nine Hypericum L. species from Serbia and the F.Y.R. Macedonia | journal = Die Pharmazie | volume = 61 | issue = 3 | pages = 251–252 | date = March 2006 | pmid = 16599273 }}</ref>
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