Editing Hypericum perforatum (section)

=== Phytochemistry ===
[[File:Hypericin2DACS.svg|thumb|Chemical structure of [[hypericin]]|151x151px]]The most common active chemicals in ''Hypericum perforatum'' are [[hypericin]] and [[pseudohypericin]] ([[Anthraquinones|naphthodianthrones]]), and [[hyperforin]] (a [[phloroglucinol]] derivative).<ref name="Mehta" /><ref>{{cite journal |vauthors=Umek A, Kreft S, Kartnig T, Heydel B |year=1999 |title=Quantitative phytochemical analyses of six hypericum species growing in slovenia |journal=Planta Med. |volume=65 |issue=4 |pages=388–90 |doi=10.1055/s-2006-960798 |pmid=17260265 |s2cid=260248637}}</ref><ref>{{cite journal |vauthors=Tatsis EC, Boeren S, Exarchou V, Troganis AN, Vervoort J, Gerothanassis IP |year=2007 |title=Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS |journal=Phytochemistry |volume=68 |issue=3 |pages=383–93 |bibcode=2007PChem..68..383T |doi=10.1016/j.phytochem.2006.11.026 |pmid=17196625 |s2cid=28120366}}</ref> The species contains a host of [[essential oil]]s, the bulk of which are [[sesquiterpene]]s.<ref name="Mehta" /> In the wild, the concentrations of any active chemicals can vary widely among individual plants and populations.<ref name=Ernst-2003>{{Cite book |last=Ernst |first=Edzard |url=https://books.google.com/books?id=dAmr_Ir-WL4C |title=''Hypericum'': the genus ''Hypericum'' |publisher=[[Taylor & Francis]] |year=2003 |series=Medicinal and Aromatic Plants—Industrial Profiles |volume=31 |location=London|isbn=9781420023305 }}
{{hidden begin|style=border:solid 1px #aaa|title={{center|Comparison of selected chemical constituents of ''Hypericum perforatum''}}}}{{Hidden end}}</ref><ref name=HM>{{cite book |author1= Barnes, J. |author2= Anderson, L.A. |author3= Phillipson, J.D. |title= Herbal Medicines |year= 2007 |url= http://file.zums.ac.ir/ebook/366-Herbal%20Medicines,%20Third%20edition-Joanne%20Barnes%20J.%20David%20Phillipson%20Linda%20A.%20Anderson-085369623.pdf |publisher= Pharmaceutical Press |isbn=978-0-85369-623-0 |edition=3rd |location= London, UK |orig-year= 1996 |access-date=7 February 2015 |archive-url= https://web.archive.org/web/20180701140306/http://file.zums.ac.ir/ebook/366-Herbal%20Medicines,%20Third%20edition-Joanne%20Barnes%20J.%20David%20Phillipson%20Linda%20A.%20Anderson-085369623.pdf |archive-date=1 July 2018 |url-status=dead}}</ref><ref name=NS>{{cite web|title=St. John's wort|work=Natural Standard |access-date=13 December 2013 |url=http://www.naturalstandard.com/databases/herbssupplements/stjohnswort.asp |location=Cambridge, MA}}</ref>
{| class = wikitable
! Compound !! Conc.<ref name="HM" /><br /><ref name="Xeno2012">{{cite book | title = Metabolism of Drugs and Other Xenobiotics | year = 2012 | doi = 10.1002/9783527630905 | publisher = Wiley-VCH | isbn = 978-3-527-63090-5 | editor1-last = Anzenbacher | editor2-last = Zanger | editor2-first = Ulrich M. | editor1-first = Pavel | location = Weinheim, Germany }}</ref> !! log ''P'' !! [[Polar surface area|PSA]] !! [[Acid dissociation constant|pK<sub>a</sub>]] !! Formula !! [[Molecular weight|MW]] !! [[CYP1A2]]<br /><ref group = Note>In brackets is the IC<sub>50</sub>/EC<sub>50</sub> value depending on whether it is an inhibitory or inductive action being exhibited, respectively.</ref> !![[CYP2C9]]<br /><ref group = Note name="auto">As with last note</ref> !! [[CYP2D6]]<br /><ref group = Note name="auto" /> !! [[CYP3A4]]<br /><ref group = Note name="auto" /> !! [[P-glycoprotein|PGP]]<br /><ref group = Note name="auto" /> !! t<sub>1/2</sub><ref name="Xeno2012" /> (h) !! T<sub>max</sub><ref name="Xeno2012" /> (h) !! C<sub>max</sub><ref name="Xeno2012" /> (mM) !! C<sub>SS</sub><ref name="Xeno2012" /> (mM) !! Notes/Biological activity<ref group = Note>Values given in brackets are IC<sub>50</sub>/EC<sub>50</sub> depending on whether it is an inhibitory or inductive action the compound displays towards the biologic target in question. If it pertains to bacterial growth inhibition the value is MIC<sub>50</sub></ref>
|-
| colspan="17" style="text-align:center;"| <big>'''[[Phloroglucinol]]s''' (2–5%)</big>
|-
| [[Adhyperforin]] || 0.2–1.9 || 10–13 || 71.4 || 8.51 || C<sub>36</sub>H<sub>54</sub>O<sub>4</sub> || 550.81 || ? || ? || ? || ? || ? || ? || ? || ? || ? || ?
|-
| [[Hyperforin]] || 2–4.5 || 9.7–13 || 71.4 || 8.51 || C<sub>35</sub>H<sub>52</sub>O<sub>4</sub> || 536.78 || + || +/- || – || + || + || 3.5–16 || 2.5–4.4 || 15-235 || 53.7 || –
|-
| colspan="17" style="text-align:center;"| <big>'''[[Naphthodianthrone]]s''' (0.03-3%)</big>
|-
| [[Hypericin]] || 0.003-3 || 7.5–10 || 156 || 6.9±0.2 ||C<sub>30</sub>H<sub>16</sub>O<sub>8</sub> || 504.44 || 0 || – <br />(3.4 μM) || – (8.5 μM) || – <br />(8.7 μM) || ? || 2.5–6.5 || 6–48 || 0.66-46 || ? || ?
|-
| Pseudohypericin || 0.2–0.23 || 6.7±1.8 || 176 || 7.16 || C<sub>30</sub>H<sub>16</sub>O<sub>9</sub> || 520.44 || ? || ? || ? || ? || ? || 24.8–25.4|| 3 || 1.4–16 || 0.6–10.8 || –
|-
| colspan="17" style="text-align:center;"| <big>'''[[Flavonoid]]s''' (2–12%)</big>
|-
| [[Amentoflavone]]<br /> || 0.01–0.05 || 3.1–5.1 || 174 || 2.39 || C<sub>30</sub>H<sub>18</sub>O<sub>10</sub> || 538.46 || ? || – <br />(35 nM) || – (24.3 μM) || – <br />(4.8 μM) || ? || ? || ? || ? || ? || ?
|-
| [[Apigenin]] || 0.1–0.5 || 2.1±0.56 || 87 || 6.63 || C<sub>15</sub>H<sub>10</sub>O<sub>5</sub> || 270.24 || ? || ? || ? || ? || ? || ? || ? || ? || ? || ?
|-
| [[Catechin]] || 2–4 || 1.8±0.85 || 110 || 8.92 || C<sub>15</sub>H<sub>14</sub>O<sub>6</sub> || 290.27 || ? || ? || ? || ? || ?|| ? || ? || ? || ? || ?

|-
| [[Epigallocatechin]] || ? || −0.5–1.5 || 131 || 8.67 || C<sub>15</sub>H<sub>14</sub>O<sub>6</sub> || 290.27 || ? || ? || ? || ? || ? || 1.7±0.4<sup>a</sup> || 1.3–1.6<sup>a</sup> || ? || ? || ?
|-
| [[Hyperoside]] || 0.5-2 || 1.5±1.7 || 174 || 6.17 || C<sub>21</sub>H<sub>20</sub>O<sub>12</sub> || 464.38 || ? || ? || ? || ? || ? || ? || ? || ? || ? ||
|-
| [[Kaempferol]] || ? || 2.1±0.6 || 107 || 6.44 || C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> || 286.24 || ? || ? || ? || +/- || ? || ? || ? || ? || ? || ?
|-
| [[Luteolin]] || ? || 2.4±0.65 || 107 || 6.3 || C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> || 286.24 || – || ? || ? || ? || ? || ? || ? || ? || ? || ?
|-
| [[Quercetin]] || 2–4 || 2.2±1.5 || 127 || 6.44 || C<sub>15</sub>H<sub>10</sub>O<sub>7</sub> || 302.24 || – <br />(7.5 μM)<br /><sup>b</sup> || – (47 μM)<br /><sup>b</sup> || – (24 μM)<br /><sup>b</sup> || – (22 μM)<br /><sup>b</sup> || – || 20–72<sup>c</sup> || 8<sup>c</sup> || ? || ? || ?
|-
| [[Rutin]] || 0.3–1.6 || 1.2±2.1 || 266 || 6.43 || C<sub>27</sub>H<sub>30</sub>O<sub>16</sub> || 610.52 || ? || ? || ? || ? || ? || ? || ? || ? || ? || ?
|-
| colspan="17" style="text-align:center;"| <big>'''Phenolic acids''' (~0.1%)</big>
|-
| [[Caffeic acid]] || 0.1 || 1.4±0.4 || 77.8 || 3.64 || C<sub>9</sub>H<sub>8</sub>O<sub>4</sub> || 180.16 || ? || ? || ? || – || ? || ? || ? || ? || ? || ?

|-
| [[Chlorogenic acid]] || <0.1% || -0.36±0.43 || 165 || 3.33 || C<sub>16</sub>H<sub>18</sub>O<sub>9</sub> || 354.31 || 0 || 0 || 0 || 0 || ? || ? || ? || ? || ? || ?

|}

{| class=wikitable
|+ '''Acronyms and symbols'''
! Acronym/Symbol !! Meaning
|-
| MW || Molecular weight in g•mol<sup>−1</sup>.
|-
| PGP || [[P-glycoprotein]]
|-
| t<sub>1/2</sub> || [[Elimination half-life]] in hours
|-
| T<sub>max</sub> || Time to peak plasma concentration in hours
|-
| C<sub>max</sub> || Peak plasma concentration in mM
|-
| C<sub>SS</sub> || Steady state plasma concentration in mM
|-
| <math>\log{P}</math> || [[Partition coefficient]].
|-
| PSA || [[Polar surface area]] of the molecule in question in square [[angstroms]] (Å<sup>2</sup>). Obtained from [[PubChem]]
|-
| Conc. || These values pertain to the approximation concentration (in %) of the constituents in the fresh plant material
|-
| – || Indicates inhibition of the enzyme in question.
|-
| + || Indicates an inductive effect on the enzyme in question.
|-
| 0 || No effect on the enzyme in question.
|-
| 5-HT || 5-hydroxytryptamine – synonym for serotonin.
|-
| DA || Dopamine
|-
| NE || Norepinephrine
|-
| GABA || γ-aminobutyric acid
|-
| Glu || Glutamate
|-
| Gly || Glycine
|-
| Ch || Choline
|-
| <sup>a</sup> || ?
|-
| <sup>b</sup> || ?
|-
| <sup>c</sup> || ?
|}
'''Notes:'''
{{Reflist|group=Note}}