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| {{Redirect|St John's wort}}
| | My name is George (32 years old) and my hobbies are Herping and American football.<br><br>Also visit my webpage ... get help for your health ([http://www.getconstipationhelp.com hop over to this web-site]) |
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| {{Taxobox
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| |image = Saint johns wart flowers.jpg
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| |regnum = [[Plant]]ae
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| |unranked_divisio = [[Angiosperms]]
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| |unranked_classis = [[Eudicots]]
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| |unranked_ordo = [[Rosids]]
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| |ordo = [[Malpighiales]]
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| |familia = [[Hypericaceae]]
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| |genus = ''[[Hypericum]]''
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| |species = '''''H. perforatum'''''
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| |binomial = ''Hypericum perforatum''
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| |binomial_authority = [[Carl Linnaeus|L.]]
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| }}
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| '''''Hypericum perforatum''''', also known as '''St John's wort''', is a [[flowering plant]] species of the genus ''[[Hypericum]]'' and a [[herbal medicine|medicinal herb]] that is sold [[over-the-counter drug|over-the-counter]] as a treatment for [[Depression (mood)|depression]].<ref name="Mehta" /><ref name="MEDRS Neuropharmacology" /> Other names for it include '''Tipton's weed''', '''rosin rose''', '''goatweed''', '''chase-devil''', or '''Klamath weed'''.<ref name="Mehta">[http://pharmaxchange.info/press/2012/12/pharmacognosy-of-st-johns-wort/ Pharmacognosy of St. John's Wort]</ref> With qualifiers, St John's wort is used to refer to any species of the genus ''[[Hypericum]]''. Therefore, ''H. perforatum'' is sometimes called ''common St John's wort'' or ''perforate St John's wort'' to differentiate it. ''Hypericum'' is classified in the family [[Hypericaceae]], having previously been classified as [[Clusiaceae|Guttiferae or Clusiaceae]].<ref>{{cite web | url=http://apps.rhs.org.uk/plantselector/plant?plantid=1004 | title = ''Hypericum perforatum'' data sheet at the ''Royal Horticultural Society'' | accessdate=2011-03-24}}</ref><ref>{{cite web | url = http://www.floridata.com/ref/H/hype_fro.cfm | title = #914: Hypericum frondosum - Floridata.com | accessdate = 2008-11-02}}</ref> Approximately 370 species of the genus ''Hypericum'' exist worldwide with a native geographical distribution including temperate and subtropical regions of [[Europe]], [[Turkey]], [[Ukraine]], [[Russia]], Middle East, [[India]], and [[China]].
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| ==Botanical description==
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| [[File:StJohnswort-leaves.jpg|thumb|Translucent dots on the leaves]]
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| ''Hypericum perforatum'' is a yellow-flowering, [[stoloniferous]] or [[sarmentose (botany)|sarmentose]], [[perennial plant|perennial]] [[herb]] indigenous to [[Europe]]. It has been introduced to many temperate areas of the world and grows wild in many meadows. The herb's common name comes from its traditional flowering and harvesting on [[John the Baptist|St John]]'s day, 24 June. The [[genus]] name ''Hypericum'' is derived from the [[Greek language|Greek]] words ''hyper'' (above) and ''eikon'' (picture), in reference to the plant's traditional use in warding off evil by hanging plants over a religious icon in the house during St John's day. The [[species]] name ''perforatum'' refers to the presence of small oil glands in the leaves that look like windows, which can be seen when they are held against the light.<ref name="Mehta" />
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| St John's wort is a [[perennial plant]] with extensive, creeping [[rhizomes]]. Its stems are erect, branched in the upper section, and can grow to 1 m high. It has opposing, stalkless, narrow, oblong leaves that are 12 mm long or slightly larger. The leaves are yellow-green in color, with transparent dots throughout the tissue and occasionally with a few black dots on the lower surface.<ref name="Mehta" /> Leaves exhibit obvious translucent dots when held up to the light, giving them a ‘perforated’ appearance, hence the plant's [[Latin]] name.
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| Its flowers measure up to 2.5 cm across, have five petals, and are colored bright yellow with conspicuous black dots. The flowers appear in broad [[inflorescence|cymes]] at the ends of the upper branches, between late spring and early to mid summer. The [[sepals]]are pointed, with glandular dots in the tissue. There are many [[stamens]], which are united at the base into three bundles. The pollen grains are ellipsoidal.<ref name="Mehta" />
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| When flower buds (not the flowers themselves) or seed pods are crushed, a reddish/purple liquid is produced.
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| <gallery>
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| File:Hypericum perforatum 09.jpg|Full plant
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| File:Hypericum perforatum plantlets.jpg|Seedlings
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| File:Hypericum-perforatum-frutos.jpg|Fruit
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| File:Hypericum-perforatum-250605-1.jpg|Blossom
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| </gallery>
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| ==Ecology==
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| St John's wort reproduces both vegetatively and sexually. It thrives in areas with either a winter- or summer-dominant rainfall pattern; however, distribution is restricted by temperatures too low for seed germination or seedling survival. Altitudes greater than 1500 m, rainfall less than 500 mm, and a daily mean January (in Southern hemisphere) temperature greater than 24 degrees C are considered limiting thresholds. Depending on environmental and climatic conditions, and rosette age, St John's wort will alter growth form and habit to promote survival. Summer rains are particularly effective in allowing the plant to grow vegetatively, following defoliation by insects or grazing.
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| The seeds can persist for decades in the [[soil seed bank]], germinating following disturbance.<ref name="feis" />
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| ===Invasive species===
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| Although ''Hypericum perforatum'' is grown commercially in some regions of south east Europe, it is listed as a [[noxious weed]] in more than twenty countries and has introduced populations in South and North America, [[India]], [[New Zealand]], [[Australia]], and South Africa.<ref name="feis">{{cite web | url = http://www.invasive.org/weedcd/pdfs/feis/Hypericumperforatum.pdf | work = Fire Effects Information System | title = SPECIES: Hypericum perforatum }}</ref> In pastures, St John’s wort acts as both a toxic and invasive weed.<ref name="autogenerated1">[http://www.northwestweeds.nsw.gov.au/st_johns_wort.htm St John's wort<!-- Bot generated title -->]</ref> It replaces [[native plant|native]] [[plant community|plant communities]] and [[forage]] vegetation to the dominating extent of making productive land nonviable or becoming an [[invasive species]] in natural [[habitat]]s and [[ecosystem]]s. Ingestion by livestock can cause photosensitization, central nervous system depression, spontaneous abortion, and can lead to death. Effective herbicides for control of ''Hypericum'' include [[2,4-D]], picloram, and [[glyphosate]]. In western [[North America]] three beetles ''[[Chrysolina quadrigemina]]'', ''[[Chrysolina hyperici]]'' and ''[[Agrilus hyperici]]'' have been introduced as [[biocontrol]] agents.
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| {{-}}
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| ==Medical uses==
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| ===Major depressive disorder===
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| St John's wort is widely known as a herbal treatment for [[Depression (mood)|depression]]. In some countries, such as [[Germany]], it is commonly prescribed for mild to moderate depression, especially in children and adolescents.<ref name="pmid16553540">{{cite journal|author=Fegert, JM; Kölch, M; Zito, JM; Glaeske, G; Janhsen, K |title=Antidepressant use in children and adolescents in Germany |journal=Journal of Child and Adolescent Psychopharmacology |volume=16 |issue=1–2 |pages=197–206 |date=February–April 2006 |pmid=16553540 |doi=10.1089/cap.2006.16.197 |url=}}</ref> It is proposed that the mechanism of action of St. John's wort is due to the inhibition of reuptake of certain neurotransmitters.<ref name="Mehta" />
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| An analysis of twenty-nine clinical trials with more than five thousand patients was conducted by [[Cochrane Collaboration]]. The review concluded that extracts of St John's wort were superior to placebo in patients with [[major depressive disorder|major depression]]. St John's wort had similar efficacy to standard antidepressants. The rate of side-effects was half that of newer [[Selective serotonin reuptake inhibitor|SSRI]] antidepressants and one-fifth that of older [[tricyclic antidepressants]].<ref name="pmid18843608">{{cite journal |author=Linde, K; Berner, MM; Kriston, L |title=St John's wort for major depression |journal=Cochrane Database of Systematic Reviews|volume=|issue=4 |pages=CD000448 |year=2008 |pmid=18843608 |doi=10.1002/14651858.CD000448.pub3 |url= |editor1-last=Linde |editor1-first=Klaus}}</ref>
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| A report<ref name="pmid18843608"/> from the [[Cochrane Review]] states:
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| <blockquote>
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| The available evidence suggests that the ''Hypericum'' extracts tested in the included trials a) are superior to placebo in patients with major depression; b) are similarly effective as standard antidepressants; and c) have fewer side-effects than standard antidepressants.<br/>There are two issues that complicate the interpretation of our findings:<br/>1) While the influence of precision on study results in placebo-controlled trials is less pronounced in this updated version of our review compared to the previous version (Linde 2005a), results from more precise trials still show smaller effects over placebo than less precise trials.<br/>2) Results from German-language countries are considerably more favourable for Hypericum than trials from other countries.
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| </blockquote>
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| ===Other medical uses===
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| St John's wort is being studied for effectiveness in the treatment of certain [[somatoform disorders]]. Results from the initial studies are mixed and still inconclusive; some research has found no effectiveness, other research has found a slight lightening of symptoms. Further study is needed and is being performed.
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| A major constituent chemical, [[hyperforin]], may be useful for treatment of [[alcoholism]], although dosage, safety and efficacy have not been studied.<ref>{{cite journal |author=Kumar, V; Mdzinarishvili, A; Kiewert, C; Abbruscato, T; Bickel, U; van der Schyf, CJ; Klein, J |title=NMDA receptor-antagonistic properties of hyperforin, a constituent of St. John's Wort |journal=Journal of Pharmacological Sciences |volume=102 |issue=1 |pages=47–54 |date=September 2006 |pmid=16936454 |doi= 10.1254/jphs.FP0060378|url=https://www.jstage.jst.go.jp/article/jphs/102/1/102_1_47/_pdf|format=PDF}}</ref><ref name=Reutera/> Hyperforin has also displayed antibacterial properties against [[gram-positive bacteria]], although dosage, safety and efficacy has not been studied.<ref>{{cite journal |author=Cecchini, C; Cresci, A; Coman, MM; Ricciutelli, M; Sagratini, G; Vittori, S; Lucarini, D; Maggi, F |title=Antimicrobial activity of seven hypericum entities from central Italy |journal=Planta Medica |volume=73 |issue=6 |pages=564–6 |date=June 2007 |pmid=17516331|doi=10.1055/s-2007-967198 |url=}}</ref> [[Herbal medicine]] has also employed lipophilic extracts from St John's wort as a topical remedy for wounds, abrasions, burns, and [[myalgia|muscle pain]].<ref name=Reutera>{{cite journal|last=Reutera|first=J|coauthors=Huykea, C; Scheuvensa, H; Plochc, M; Neumannd, K; Jakobb, T; Schemppa, CM|title=Skin tolerance of a new bath oil containing St. John's wort extract|journal=Skin pharmacology and physiology|year=2008|volume=21|issue=6|pages=306–311|doi=10.1159/000148223|pmid=18667843}}</ref> The positive effects that have been observed are generally attributed to hyperforin due to its possible antibacterial and anti-inflammatory effects.<ref name=Reutera/> For this reason hyperforin may be useful in the treatment of infected wounds and inflammatory skin diseases.<ref name=Reutera/> In response to hyperforin's incorporation into a new bath oil, a study to assess potential skin irritation was conducted which found good skin tolerance of St John's wort.<ref name=Reutera/>
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| A [[randomized controlled trial]] of St John's wort found no [[Statistical significance|significant]] difference between it and placebo in the management of [[ADHD]] symptoms over eight weeks. However, the St John's wort extract used in the study, originally confirmed to contain 0.3% hypericin, was allowed to degrade to levels of 0.13% hypericin and 0.14% hyperforin. Given that the level of hyperforin was not ascertained at the beginning of the study, and levels of both hyperforin and hypericin were well below that used in other studies, little can be determined based on this study alone.<ref name='JAMA_ADHD'>{{cite journal |author=Weber, W; Vander Stoep, A; McCarty, RL; Weiss, NS; Biederman, J; McClellan, J |title=A Randomized Placebo Controlled Trial Of Hypericum perforatum For Attention Deficit Hyperactivity Disorder In Children And Adolescents |journal=JAMA |volume=299 |issue=22 |pages=2633–41 |date=June 2008|pmid=18544723 |pmc=2587403 |doi=10.1001/jama.299.22.2633 |url=}}</ref>
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| Hypericin and pseudohypericin have shown both antiviral and antibacterial activities. It is believed that these molecules bind non-specifically to viral and cellular membranes and can result in photo-oxidation of the pathogens to kill them.<ref name="Mehta" />
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| A research team from the [[Universidad Complutense de Madrid]] (UCM) published a study entitled "''Hypericum perforatum''. Possible option against Parkinson's disease", which suggests that St John's wort has [[antioxidant]] active ingredients that could help reduce the neuronal degeneration caused by the disease.<ref>http://www.sciencedaily.com/releases/2009/05/090511181252.htm</ref><ref>[http://www.diariocritico.com/general/147916 www.diariocritico.com/general/147916]</ref><ref>[http://www.ucm.es/info/otri/cult_cient/infocientifica/noti_feb_09_01.htmwww.ucm.es/info/otri/cult_cient/infocientifica/noti_feb_09_01.htm]</ref><ref>[http://www.madrimasd.org/noticias/-i-Hypericum-perforatum--i---y-Parkinson/38181 www.madrimasd.org/noticias/-i-Hypericum-perforatum--i---y-Parkinson/38181]</ref>
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| Recent evidence suggests that daily treatment with St John's wort may improve the most common physical and behavioural symptoms associated with [[premenstrual syndrome]].<ref name="Canning et al.">{{cite journal |author=Canning, S; Waterman, M; Orsi, N; Ayres, J; Simpson, N; Dye, L |title=The efficacy of Hypericum perforatum (St John's wort) for the treatment of premenstrual syndrome: a randomized, double-blind, placebo-controlled trial |journal=CNS Drugs |volume=24 |issue=3 |pages=207–25 |date=March 2010 |pmid=20155996|doi=10.2165/11530120-000000000-00000 |url=}}</ref>
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| St John's wort was found to be less effective than [[placebo]], in a randomized, double-blind, [[placebo-controlled trial]], for the treatment of [[irritable bowel syndrome]].<ref>{{cite journal |author=Saito, YA; Rey, E; Almazar-Elder, AE; Harmsen, WS; Zinsmeister, AR; Locke, GR; Talley, NJ |title=A randomized, double-blind, placebo-controlled trial of St John's wort for treating irritable bowel syndrome|journal=Am. J. Gastroenterol. |volume=105 |issue=1 |pages=170–7 |date=January 2010 |pmid=19809408 |doi=10.1038/ajg.2009.577|url=}}</ref>
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| St John's wort alleviated age-related long-term memory impairment in rats.<ref>{{cite journal|title=Hypericum perforatum alleviates age-related forgetting in rats|author=Trofimiuk, E; Braszko, JJ|journal=Current Topics in Nutraceutical Research|volume=8|issue=2-3|pages=103–107|date=August 2010}}</ref>
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| ==Adverse effects and drug interactions==
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| St John's wort is generally well tolerated, with an adverse effect profile similar to [[placebo]].<ref name="ernst_et_al_1998">{{cite journal | author = Ernst, E; Rand, JI; Barnes, J; Stevinson, C | year = 1998 | title = Adverse effects profile of the herbal antidepressant St. John's wort (Hypericum perforatum L.) | url = | journal = European Journal of Clinical Pharmacology | volume = 54 | issue = 8| pages = 589–94 | doi = 10.1007/s002280050519 | pmid = 9860144 }}</ref> The most common adverse effects reported are gastrointestinal symptoms, dizziness, confusion, tiredness and sedation.<ref>{{cite book|title=Herbal Medicines: A guide for healthcare professionals|author=Barnes, J; Anderson, LA; Phillipson, JD|year=2002|edition=2nd|location=London, UK|publisher=Pharmaceutical Press|isbn=9780853692898}}</ref><ref>{{cite journal |author=Parker, V; Wong, AH; Boon, HS; Seeman, MV |title=Adverse reactions to St John's Wort |journal=Canadian Journal of Psychiatry |volume=46 |issue=1 |pages=77–9 |date=February 2001|pmid=11221494 |doi= |url=}}</ref> It also decreases the levels of estrogens, such as estradiol, by speeding up its metabolism, and should not be taken by women on [[COCP#Drug interactions|contraceptive pills]] as it upregulates the CYP3A4 cytochrome of the [[P450]] system in the [[liver]].<ref name=etetusp>{{cite web | url=http://www.wcrx.com/pdfs/pi/pi_estrace_wc_imprint.pdf |title=ESTRACE TABLETS, (estradiol tablets, USP) | author=Barr Laboratories, Inc. | authorlink=Barr Laboratories |date=March 2008| publisher=wcrx.com |format=PDF | accessdate=27 January 2010 }}</ref>
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| St John's wort may rarely cause [[photodermatitis|photosensitivity]]. This can lead to visual sensitivity to light and to sunburns in situations that would not normally cause them.<ref name="ernst_et_al_1998" /> Related to this, recent studies concluded that the extract reacts with light, both visible and ultraviolet, to produce [[free radical]]s, molecules that can damage the cells of the body. These can react with vital proteins in the eye that, if damaged, [[precipitate]] out, causing [[cataract]]s.<ref>{{cite journal |author=Schey, KL; Patat, S; Chignell, CF; Datillo, M; Wang, RH; Roberts, JE |title=Photooxidation of lens alpha-crystallin by hypericin (active ingredient in St. John's Wort) |journal=Photochemistry and Photobiology |volume=72 |issue=2 |pages=200–3 |date=August 2000 |pmid=10946573 |doi= 10.1562/0031-8655(2000)0720200POLCBH2.0.CO2}}</ref> This finding is contradicted by the results of another recent study, which found that St John's wort inhibits free radical production in both cell-free and human vascular tissue, revealing antioxidant properties of the compound.<ref>{{cite journal |author=Hunt, EJ; Lester, CE; Lester, EA; Tackett, RL |title=Effect of St. John's wort on free radical production |journal=Life Sci. |volume=69 |issue=2 |pages=181–90|date=June 2001 |pmid=11441908 |doi= 10.1016/S0024-3205(01)01102-X|url=http://www.ncbi.nlm.nih.gov/pubmed/11441908?genre=article&sid=nlm:lifesci&issn=11441908&date=2001&volume=69&issue=2&spage=181}}</ref>
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| St John's wort is associated with aggravating [[psychosis]] in people who have [[schizophrenia]].<ref>{{cite book|author=[[Singh, Simon]] and [[Edzard Ernst]]|title=[[Trick or Treatment: The Undeniable Facts About Alternative Medicine]]|page=218|year=2008|publisher=W. W. Norton & Company|isbn=978-0-393-33778-5}}</ref>
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| Do not take St. John's wort if you have [[bipolar disorder]]. There is concern that people with [[major depression]] taking St. John’s wort may be at a higher risk for mania.<ref name="ummdotedu">{{cite web |url=http://umm.edu/health/medical/altmed/herb/st-johns-wort |title= St. John's wort - University of Maryland Medical Center|author=<!--Staff writer(s); no by-line.--> |date=June 24, 2013 |website=University of Maryland Medical Center |publisher=umm.edu |accessdate=January 3, 2014}}</ref>
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| Never give your child St. John’s wort without medical supervision.
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| <ref name="ummdotedu" />
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| ===Pharmacokinetic interactions===
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| St John's wort has been shown to cause multiple drug interactions through [[Enzyme induction and inhibition|induction]] of the [[cytochrome P450]] enzymes [[CYP3A4]] and [[CYP2C19]]. This drug-metabolizing enzyme induction results in the increased metabolism of certain drugs, leading to decreased plasma concentration and potential clinical effect.<ref>{{cite journal|title=Effect of St John's wort on the activities of CYP1A2, CYP3A4, CYP2D6, N-acetyltransferase 2, and xanthine oxidase in healthy males and females|journal=British Journal of Clinical Pharmacology|date=April 2004|volume=57|issue=4|pages=495–499|doi=10.1111/j.1365-2125.2003.02049.x|pmid=15025748|pmc=1884478|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884478/pdf/bcp0057-0495.pdf|format=PDF|author=Wenk, M; Todesco, L; Krähenbühl, S}}</ref> The principal constituents thought to be responsible are [[hyperforin]] and [[amentoflavone]].
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| St John's wort has also been shown to cause drug interactions through the [[Enzyme induction and inhibition|induction]] of the [[P-glycoprotein|P-glycoprotein (P-gp)]] efflux transporter. Increased [[P-glycoprotein|P-gp]] expression results in decreased absorption and increased clearance of certain drugs, leading to lower plasma concentration and potential clinical efficacy.<ref>{{cite journal|author=Gurley, BJ; Swain, A; Williams, DK; Barone, G; Battu, SK |title=Gauging the clinical significance of P-glycoprotein-mediated herb-drug interactions: Comparative effects of St. John's wort, echinacea, clarithromycin, and rifampin on digoxin pharmacokinetics|journal=Mol Nutr Food Res|volume=52 |issue=7 |pages=772–9 |date=July 2008 |pmid=18214850 |pmc=2562898 |doi=10.1002/mnfr.200700081|url=}}</ref>
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| <center>
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| {| class="wikitable"
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| |+'''Examples of drugs causing clinically significant interactions with St John's wort'''
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| |-
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| !Class
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| !Drugs
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| |-
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| |[[Antiretroviral]]s
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| |[[Non-nucleoside reverse transcriptase inhibitor]]s, [[protease inhibitor (pharmacology)|protease inhibitor]]s
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| |-
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| |[[Benzodiazepine]]s
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| |[[Alprazolam]], [[midazolam]]
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| |-
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| |[[Hormonal contraception]]
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| |[[Oral contraceptive formulations#Combined oral contraceptive pills|Combined oral contraceptive]]s
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| |-
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| |[[Immunosuppressant]]s
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| |[[Calcineurin inhibitor]]s, [[cyclosporine]], [[tacrolimus]]
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| |-
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| |[[Antiarrhythmic]]s
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| |[[Amiodarone]], [[flecainide]], [[mexiletine]]
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| |-
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| |[[Beta-blocker]]s
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| |[[Metoprolol]], [[carvedilol]]
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| |-
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| |[[Calcium channel blockers]]
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| |[[Verapamil]], [[diltiazem]], [[amlodipine]]
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| |-
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| |[[Statin]]s (cholesterol-reducing medications)
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| |[[Lovastatin]], [[simvastatin]], [[atorvastatin]]
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| |-
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| |Others
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| |[[Digoxin]], [[methadone]], [[omeprazole]], [[phenobarbital]], [[theophylline]], [[warfarin]], [[levodopa]], [[buprenorphine]], [[irinotecan]]
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| |-
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| | colspan="2" | <small>Reference: Rossi, 2005; [[Micromedex]]</small>
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| |}
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| </center>
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| For a complete list, see [[CYP3A4#CYP3A4 ligands|CYP3A4 ligands]] and [[CYP2C9#CYP2C9 Ligands|CYP2C9 ligands]]. For further updating on interactions and appropriate management, see [http://www.herbological.com/images/SJW_table.pdf Herbological.com – St John's Wort Interactions table] (outdated since 2005).
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| ===Pharmacodynamic interactions===
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| In combination with other drugs that may elevate [[5-HT]] (serotonin) levels in the [[central nervous system]] (CNS), St John's wort may contribute to [[serotonin syndrome]], a potentially life-threatening adverse drug reaction.<ref name = AMH>{{cite isbn|9780980579093}}</ref>
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| <center>
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| {| class="wikitable"
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| |+'''Drugs that may contribute to serotonin syndrome with St John's wort'''
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| |-
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| !Class
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| !Drugs
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| |-
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| |[[Antidepressant]]s
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| |[[MAOI]]s,<ref>Including the harmala alkaloids - components of the Passion flower (Passiflora), Syrian rue (Peganum harmala) and Banisteriopsis caapi.</ref> [[Tricyclic antidepressant|TCA]]s, [[SSRI]]s, [[SNRI]]s, [[mirtazapine]]
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| |-
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| |[[Opioid]]s
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| |[[Tramadol]], [[meperidine]] ([[pethidine]]), [[Levorphanol]]
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| |-
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| |CNS [[stimulant]]s
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| |[[Phentermine]], [[diethylpropion]], [[amphetamine]]s, [[sibutramine]], [[cocaine]]
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| |-
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| |[[5-HT receptor|5-HT<sub>1</sub>]] agonists
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| |[[Triptan]]s
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| |-
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| |Psychedelic drugs
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| |[[Methylenedioxymethamphetamine]] (MDMA), [[lysergic acid diethylamide]] (LSD), [[psilocybin]] / [[psilocin]], [[Mescaline]] and virtually every [[serotonergic psychedelic]].
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| |-
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| |Others
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| |[[Selegiline]], [[tryptophan]], [[buspirone]], [[Lithium pharmacology|lithium]], [[linezolid]], [[5-HTP]], [[dextromethorphan]]
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| |-
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| | colspan="2" | <small>Reference:<ref name = AMH/></small>
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| |}
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| </center>
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| ==Detection in body fluids==
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| Hypericin, pseudohypericin, and hyperforin may be quantitated in plasma as confirmation of usage and to estimate the dosage. These three active substituents have plasma elimination half-lives within a range of 15–60 hours in humans. None of the three has been detected in urine specimens.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man, 8th edition'', Biomedical Publications, Foster City, CA, 2008, pp. 1445–1446.</ref>
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| ==Chemical constituents==
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| The plant contains the following:<ref name = HM>{{cite isbn|9780853696230}}</ref><ref name = Comp>{{cite journal|title=St. John’s wort (Hypericum perforatum): a review of the current pharmacological, toxicological, and clinical literature|journal=Psychopharmacology (Berl)|volume=153|issue=4|pages=402–414date=February 2001|doi=10.1007/s002130000625|pmid=11243487|author=Greeson, JM; Sanford, B; Monti, DA|url=http://sites.duke.edu/greesonlab/files/2011/07/Greeson_etal_2001_Psychopharm-St.-Johns-Wort.pdf|format=PDF}}</ref>
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| * Flavonoids (e.g. [[epigallocatechin]], [[rutin]], [[hyperoside]], [[isoquercetin]], [[quercitrin]], [[quercetin]], [[amentoflavone]], biapigenin, [[astilbin]], [[myricetin]], [[miquelianin]], [[kaempferol]], [[luteolin]])
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| * Phenolic acids (e.g. [[chlorogenic acid]], [[caffeic acid]], [[p-coumaric acid]], [[ferulic acid]], [[p-hydroxybenzoic acid]],[[vanillic acid]])
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| * [[Naphthodianthrone]]s (e.g. [[hypericin]], pseudohypericin, protohypericin, protopseudohypericin)
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| * [[Phloroglucinol]]s (e.g. [[hyperforin]], [[adhyperforin]])
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| * Tannins (unspecified, proanthocyanidins reported)
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| * Volatile oils (e.g. 2-methyloctane, [[nonane]], 2-methyldecane, [[undecane]], [[alpha-pinene|α-pinene]], [[beta-pinene|β-pinene]],[[alpha-terpineol|α-terpineol]], [[geraniol]], [[myrcene]], [[limonene]], [[caryophyllene]], [[humulene]])
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| * [[Saturated fatty acid]]s (e.g. [[isovaleric acid]] (3-methylbutanoic acid), [[myristic acid]], [[palmitic acid]], [[stearic acid]])
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| * [[Alkanol]]s (e.g. [[1-Tetracosanol|1-tetracosanol]], [[1-hexacosanol]])
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| * Vitamins & their analogues (e.g. [[carotenoids]], [[choline]], [[nicotinamide]], [[nicotinic acid]])
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| * Miscellaneous others (e.g. [[pectin]], [[β-sitosterol]], [[hexadecane]], [[triacontane]], kielcorin, norathyriol)
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| The naphthodianthrones hypericin and pseudohypericin along with the phloroglucinol derivative hyperforin are thought to be among the numerous active constituents.<ref name="Mehta" /><ref>{{cite journal |pmid=17260265 |year=1999 |last1=Umek |first1=A|last2=Kreft|first2=S |last3=Kartnig |first3=T |last4=Heydel |first4=B |title=Quantitative phytochemical analyses of six hypericum species growing in slovenia |volume=65 |issue=4 |pages=388–90 |doi=10.1055/s-2006-960798 |journal=Planta medica}}</ref><ref>{{cite journal |pmid=17196625|year=2007 |last1=Tatsis |first1=EC |last2=Boeren |first2=S |last3=Exarchou |first3=V |last4=Troganis |first4=AN|last5=Vervoort|first5=J |last6=Gerothanassis |first6=IP |title=Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS |volume=68 |issue=3 |pages=383–93 |doi=10.1016/j.phytochem.2006.11.026 |journal=Phytochemistry}}</ref><ref>Schwob I, Bessière JM, Viano J.Composition of the essential oils of Hypericum perforatum L. from southeastern France.C R Biol. 2002;325:781-5.</ref> It also contains essential oils composed mainly of [[sesquiterpene]]s.<ref name="Mehta" />
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| {{collapse top|title=Selected chemical constituents of ''Hypericum perforatum''|bg=#F0FFF0}}
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| {| border="1" align = center
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| | [[Image:Hypericin2DACS.svg|thumb|center|160px|[[Hypericin]]]] ||[[Image:Pseudohypericin2DACS2.svg|thumb|center|190px|Pseudohypericin]]|| [[Image:Adhyperforin2DACS.svg|thumb|center|180px|[[Adhyperforin]]]] || [[Image:Hyperforin2DACS.svg|thumb|center|220px|[[Hyperforin]]]]
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| | [[Image:Amentoflavone2DACS.svg|thumb|center|260px|[[Amentoflavone]]]] || [[Image:Hyperoside2DACS.svg|thumb|center|200px|[[Hyperoside]]]] || [[Image:Rutin2DACS.svg|thumb|center|220px|[[Rutin]]]] || [[Image:Kaempferol2DACS.svg|thumb|center|200px|[[Kaempferol]]]] ||
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| | [[Image:Myricetin2DACS.svg|thumb|center|200px|[[Myricetin]]]] || [[Image:Quercetin2DACS.svg|thumb|center|200px|[[Quercetin]]]] ||[[Image:Quercetrin2DACS.svg|thumb|center|200px|[[Quercetrin]]]] || [[Image:Isoquercitrin2DACS.svg|thumb|center|200px|[[Isoquercitrin]]]]
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| | [[Image:Luteolin2DACS.svg|thumb|center|200px|[[Luteolin]]]] || [[Image:Catechin2DACS.svg|thumb|center|200px|[[Catechin]]]] || [[Image:Epicatechin2DACS.svg|thumb|center|200px|[[Epicatechin]]]] || [[Image:Epigallocatechin2DACS.svg|thumb|center|200px|[[Epigallocatechin]]]]
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| | [[Image:Chlorogenic acid2DACS.svg|thumb|center|220px|[[Chlorogenic acid]]]] || [[Image:Caffeic acid2DACS.svg|thumb|center|160px|[[Caffeic acid]]]] || [[Image:Kielcorin2DACS.svg|thumb|center|220px|Kielcorin]] || [[Image:Norathyriol2DACS.svg|thumb|center|180px|Norathyriol]]
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| |}
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| {{collapse bottom}}
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| ==Mechanism of action==
| |
| St. John's wort (SJW), similarly to other herbal products, contains a whole host of different chemical constituents that may be pertinent to its therapeutic effects.<ref name = HM/> [[Hyperforin]] and [[adhyperforin]], two [[phloroglucinol]] constituents of SJW, is a [[TRPC6]] [[receptor agonist]] and, consequently, it induces noncompetitive [[reuptake inhibitor]] of [[monoamine reuptake inhibitor|monoamines]] (specifically, [[Dopamine reuptake inhibitor|dopamine]], [[Norepinephrine reuptake inhibitor|norepinephrine]], and [[Serotonin reuptake inhibitor|serotonin]]), [[GABA reuptake inhibitor|GABA]], and [[glutamate]] when it activates this receptor.<ref name="MEDRS Neuropharmacology" /><ref name="DB-Hyp-Biomed">{{cite web|title=Hyperforin|url=http://www.drugbank.ca/drugs/DB01892#pharmacology|work=Drugbank|publisher=University of Alberta|accessdate=5 December 2013|section=Pharmacology|section=Biomedical Effects and Toxicity}}</ref><ref name="PC-Hyp-Effects">{{cite web|title=Hyperforin|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=441298#x332|work=Pubchem Compound|publisher=National Center for Biotechnology Information|section=Biomedical Effects and Toxicity|accessdate=5 December 2013}}</ref> It inhibits reuptake of these [[neurotransmitters]] by increasing [[intracellular]] sodium ion concentrations.<ref name="MEDRS Neuropharmacology">{{cite journal|last=Nathan|first=PJ|title=Hypericum perforatum (St John's Wort): a non-selective reuptake inhibitor? A review of the recent advances in its pharmacology|journal=Journal of psychopharmacology (Oxford, England)|date=March 2001|volume=15|issue=1|pages=47–54|pmid=11277608|doi=10.1177/026988110101500109}}</ref> Moreover, SJW is known to [[Downregulation and upregulation|downregulate]] the [[beta-1 adrenergic receptor|β<sub>1</sub> adrenoceptor]] and [[Downregulation and upregulation|upregulate]] postsynaptic [[5-HT1A receptor|5-HT<sub>1A</sub>]] and [[5-HT2A receptor|5-HT<sub>2A</sub>]] receptors, both of which are a type of [[serotonin receptor]].<ref name="MEDRS Neuropharmacology" /> Other compounds may also play a role in SJW's antidepressant effects such compounds include: [[Condensed tannins|oligomeric procyanidines]], [[flavonoids]] ([[quercetin]]), [[hypericin]], and pseudohypericin.<ref name="MEDRS Neuropharmacology" /><ref name="pmid9342774">{{cite journal|author=Nahrstedt, A; Butterweck, V |title=Biologically active and other chemical constituents of the herb of Hypericum perforatum L|journal=Pharmacopsychiatry |volume=30 |issue=Suppl 2 |pages=129–34 |date=September 1997 |pmid=9342774 |doi=10.1055/s-2007-979533|url=}}</ref><ref name="pmid12775192">{{cite journal |author=Butterweck, V |title=Mechanism of action of St John's wort in depression : what is known? |journal=CNS Drugs |volume=17 |issue=8 |pages=539–62 |year=2003 |pmid=12775192|url=http://link.springer.com/content/pdf/10.2165/00023210-200317080-00001.pdf|doi=10.2165/00023210-200317080-00001}}</ref><ref name="pmid12543057">{{cite journal |author=Müller, WE |title=Current St John's wort research from mode of action to clinical efficacy|journal=Pharmacology Research |volume=47 |issue=2 |pages=101–9 |date=February 2003 |pmid=12543057|url=http://linkinghub.elsevier.com/retrieve/pii/S1043661802002669|doi=10.1016/S1043-6618(02)00266-9}}</ref>
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| In humans, the active ingredient [[hyperforin]] is a [[monoamine reuptake inhibitor]] which also acts as an inhibitor of [[PTGS1]], [[Arachidonate 5-lipoxygenase]], [[SLCO1B1]] and an inducer of [[cMOAT]]. Hyperforin is also a powerful [[anti-inflammatory]] compound with [[anti-angiogenic]], [[antibiotic]], and [[neurotrophic]] properties.<ref name="DB-Hyp-Biomed" /><ref name="PC-Hyp-Effects" /><ref name="Hyperforin pubchem">{{cite web | title=Hyperforin | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=441298#x94 |work=PubChem Compound | publisher = National Center for Biotechnology Information | accessdate=3 December 2013 | section=Pharmacology and Biomolecular Interactions and Pathways}}</ref><ref name="Hyperforin Drugbank">{{cite web|title=Hyperforin|url=http://www.drugbank.ca/drugs/DB01892|work=DrugBank|publisher=University of Alberta|accessdate=4 December 2013|section=Targets}}</ref> Hyperforin also has an antagonistic effect on [[NMDA receptor]]s, a type of glutamate receptor.<ref name="Hyperforin pubchem" /> According to one study, [[hyperforin]] content correlates with therapeutic effect in mild to moderate depression.<ref name="ncbi.nlm.nih.gov">http://www.ncbi.nlm.nih.gov/pubmed/9684948</ref> Moreover, a hyperforin-free extract of St John's wort (Remotiv) may still have significant antidepressive effects.<ref name="Woelk 2000">{{cite journal |author=Woelk, H |title=Comparison of St John's wort and imipramine for treating depression: randomised controlled trial |journal=BMJ |volume=321 |issue=7260 |pages=536–9|date=September 2000 |pmid=10968813 |pmc=27467 |url=http://bmj.com/cgi/pmidlookup?view=long&pmid=10968813|doi=10.1136/bmj.321.7260.536}}</ref><ref name="schrader_et_al_2000">{{cite journal |author=Schrader, E|title=Equivalence of St John's wort extract (Ze 117) and fluoxetine: a randomized, controlled study in mild-moderate depression|journal=Int Clin Psychopharmacol |volume=15 |issue=2 |pages=61–8 |date=March 2000 |pmid=10759336 |doi=10.1097/00004850-200015020-00001}}</ref> The limited existing literature on adhyperforin suggests that, like hyperforin, it is a reuptake inhibitor of monoamines, GABA, and glutamate.<ref>{{cite journal|last=Jensen|first=AG|coauthors=Hansen, SH; Nielsen, EO|title=Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity.|journal=Life Sciences|date=Feb 23, 2001|volume=68|issue=14|pages=1593–605|pmid=11263672|doi=10.1016/S0024-3205(01)00946-8}}</ref>
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| {{collapse top|title=Comparison of selected active chemical constituents of ''Hypericum perforatum''<ref name = HM/><ref name = NS>{{cite web|title=St. John's wort|work=Natural Standard|accessdate=13 December 2013|url=http://www.naturalstandard.com/databases/herbssupplements/stjohnswort.asp?|location=Cambridge, MA}}</ref>|bg=#F0FFF0}}
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| {| class = wikitable
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| ! Compound !! Conc.<ref name = HM/><br><ref name = Comp/><ref name = Xeno2012>{{cite isbn|9783527630905}}</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 its an inhibitory or inductive action being exhibited, respectively.</ref> !![[CYP2C9]]<br><ref group = Note>As with last note</ref> !! [[CYP2D6]]<br><ref group = Note>As with last note</ref> !! [[CYP3A4]]<br><ref group = Note>As with last note</ref> !! [[P-glycoprotein|PGP]]<br><ref group = Note>As with last note</ref> !! 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's 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>
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| | colspan="17" align=center | <big>'''[[Phloroglucinol]]s''' (2-5%)</big>
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| | [[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 || ? || ? || ? || ? || ? || ? || ? || ? || ? || Inhibits reuptake of: [[serotonin|5-HT]], [[Dopamine|DA]], [[Norepinephrine|NE]], [[gamma-aminobutyric acid|GABA]] and [[Glutamate|Glu]] via [[TRPC6]] activation<ref>{{cite journal | doi = 10.1016/S0024-3205(01)00946-8 | author = Jensen, AG; Hansen, SH; Nielsen, EO | title = Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity. | journal = Life Sciences | volume = 68 | issue = 14 | pages = 1593–1605 | date = February 2001 | pmid = 11263672 }}</ref>
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| | [[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 || +<ref name = SJWH2005>{{cite journal|title=St. John's wort and its constituent hyperforin concordantly regulate expression of genes encoding enzymes involved in basic cellular pathways|journal=Pharmacogenetics and Genomics|date=November 2005|volume=15|issue=11|pages=817–829|pmid=16220113|author=Krusekopf, S; Roots, I|doi=10.1097/01.fpc.0000175597.60066.3d}}</ref> || +<ref name = SJWH2005/>/-<ref name =JPET2000>{{cite journal|title=Inhibition of human cytochrome P450 enzymes by constituents of St. John's Wort, an herbal preparation used in the treatment of depression|journal=Journal of Pharmacology and Experimental Therapeutics|date=July 2000|volume=294|issue=1|pages=88–95|pmid=10871299|author=Obach, RS|url=http://jpet.aspetjournals.org.elibrary.jcu.edu.au/content/294/1/88.full.pdf|format=PDF}}</ref> || -<ref name = JPET2000/> || + || + || 3.5-16 || 2.5-4.4 || 15-235 || 53.7 || Serves as a [[TRPC6]] and [[Pregnane X receptor|PXR]] agonist. Reuptake inhibitor of 5-HT (205nM), DA (102nM), NE (80nM), GABA (184nM), Glu (829nM), Gly and Ch (8.5μM). Angiogenesis, [[COX-1]] (300nM), [[5-LO]] (90nM), [[SIRT1]] (15μM), [[SIRT2]] (28μM) and [[Methicillin resistant staphylococcus aureus|MRSA]] (1.86μM) inhibitor.
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| | colspan = "17" align = center | <big>'''[[Naphthodianthrone]]s''' (0.03-3%)</big>
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| | [[Hypericin]]<ref name = H2005>{{cite journal|title=Hypericin - The Facts About a Controversial Agent|journal=Current Pharmaceutical Design|year=2005|volume=11|issue=2|pages=233–253|doi=10.2174/1381612053382287|pmid=15638760|author=Kubin, A; Wierrani, F; Burner, U; Alth, G; Grünberger, W|url=http://www.benthamscience.com/cpd/sample/cpd11-2/0007B.pdf|format=PDF}}</ref> || 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 || ? || Is a [[topoisomerase II]],<ref>{{cite journal|title=Catalytic inhibition of human DNA topoisomerase IIalpha by hypericin, a naphthodianthrone from St. John's wort (Hypericum perforatum)|journal=Biochemical Pharmacology|volume=62|issue=8|pages=1059–1070|doi=10.1016/S0006-2952(01)00759-6|pmid=11597574|author=Peebles, KA; Baker, RK; Kurz, EU; Schneider, BJ; Kroll, DJ}}</ref> [[protein kinase A|PKA]] (10μM), [[protein kinase C|PKC]] (27nM), [[Casein kinase 1|CK1]] (3μM),[[Casein kinase 2|CK2]] (6nM), [[Mitogen-activated protein kinase|MAPK]] (4nM), [[Epidermal growth factor receptor|EGFR]] (35nM),[[Insulin receptor|InsR]] (29nM), [[Phosphoinositide 3-kinase|PI3K]] (180nM), [[dopamine β-hydroxylase|DBH]] (12.4μM), [[DNA polymerase|DNA polymerase A]] (14.7μM), [[Reverse transcriptase|HIV-1 RT]] (770nM), [[Catechol-O-methyl transferase|COMT]], [[Monoamine oxidase A|MAO<sub>A</sub>]] (68μM) and [[Monoamine oxidase B|MAO<sub>B</sub>]] (420μM), succinoxidase (8.2μM), [[Glutathione reductase|GSR]] (2.1nM), [[Glutathione peroxidase|GPx]] (5.2μM),[[glutathione S-transferase|GST]] (6.6μM) and [[Superoxide dismutase|CuZnSOD]] (5.25μM) inhibitor.<ref name = Xeno2012/><ref name = H2005/> Binds to the [[NMDA receptor]] (K<sub>i</sub>=1.1μM), [[Mu opioid receptor|μ-opioid]], [[Kappa opioid receptor|κ-opioid]], [[Delta opioid receptor|δ-opioid]], [[5-HT6 receptor|5-HT<sub>6</sub>]], [[Corticotropin releasing hormone receptor 1|CRF1]], [[Neuropeptide Y receptor Y1|NPY-Y1]], [[Neuropeptide Y receptor Y2|NPY-Y2]] and [[Sigma receptor|σ]] receptors.<ref name = H2005/> Exhibits light-dependent inhibitory effects on [[HIV-1]] and cancers.<ref name = H2005/>
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| | 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<ref>{{cite journal|title=Single-dose and steady-state pharmacokinetics of hypericin and pseudohypericin|journal=Antimicrobial Agents and Chemotherapy|date=September 1996|volume=40|issue=9|pages=2087–2093|pmid=8878586|pmc=163478|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC163478/pdf/402087.pdf|format=PDF|author=Kerb, R; Brockmöller, J; Staffeldt, B; Ploch, M; Roots, I}}</ref> || Photosensitiser and [[antiretroviral]] like [[hypericin]].<ref>{{cite journal|title=Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin|journal=Proceedings of the National Academy of Sciences|date=July 1988|volume=85|issue=14|pages=5230–5234|pmid=2839837|pmc=281723|author=Meruelo, D; Lavie, G; Lavie, D|url=http://www.pnas.org/content/85/14/5230.full.pdf|format=PDF}}</ref><ref>{{cite journal|title=Studies of the mechanisms of action of the antiretroviral agents hypericin and pseudohypericin|journal=Proceedings of the National Academy of Sciences|date=August 1989|pmid=2548193|pmc=297751|url=http://www.pnas.org/content/86/15/5963.full.pdf|format=PDF|volume=86|issue=15|pages=5963–5967|author=Lavie, G; Valentine, F; Levin, B; Mazur, Y; Gallo, G; Lavie, D; Weiner, D; Meruelo, D}}</ref> [[Protein kinase C|PKC]] inhibitory effects ''in vitro''.<ref>{{cite journal|title=Hypericin and pseudohypericin specifically inhibit protein kinase C: Possible relation to their antiretroviral activity|journal=Biochemical and Biophysical Research Communications|volume=165|issue=3|pages=December 1989|doi=10.1016/0006-291X(89)92730-7|pmid=2558652|author=Takahashi, I; Nakanishi, S; Kobayashi, E; Nakano, H; Suzuki, K; Tamaoki, T}}</ref>
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| | colspan = 17 align = center | <big>'''[[Flavonoid]]s''' (2-12%)</big>
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| | [[Amentoflavone]]<br><ref>{{cite journal|title=Inhibition of human cytochromes P450 by components of Ginkgo biloba|journal=The Journal of Pharmacy and Pharmacology|volume=56|issue=8|pages=1039–1044|doi=10.1211/0022357044021|pmid=15285849|date=August 2004|author=von Moltke, LL; Weemhoff, JL; Bedir, E; Khan, IA; Harmatz, JS; Goldman, P; Greenblatt, DJ}}</ref> || 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) || ? || ? || ? || ? || ? || Serves as a [[fatty acid synthase]] (FASN) inhibitor,<ref>{{cite journal|title=Fatty acid synthase inhibition by amentoflavone induces apoptosis and antiproliferation in human breast cancer cells|journal=Biological & Pharmaceutical Bulletin|date=August 2009|volume=32|issue=8|pages=1427–1432|doi=10.1248/bpb.32.1427|pmid=19652385|author=Lee, JS; Lee, MS; Oh, WK; Sul, JY|url=https://www.jstage.jst.go.jp/article/bpb/32/8/32_8_1427/_pdf|format=PDF}}</ref><ref>{{cite journal|title=Inhibition of fatty acid synthase by amentoflavone reduces coxsackievirus B3 replication|journal=Archives of Virology|volume=157|issue=2|pages=259–269|doi=10.1007/s00705-011-1164-z|pmid=22075919|author=Wilsky, S; Sobotta, K; Wiesener, N; Pilas, J; Althof, N; Munder, T; Wutzler, P; Henke, A|date=February 2012}}</ref><ref>{{cite journal|title=Fatty Acid Synthase Inhibition by Amentoflavone Suppresses HER2/neu(erbB2) Oncogene in SKBR3 Human Breast Cancer Cells|journal=Phytotherapy Research|date=May 2013|volume=27|issue=5|pages=713–720|doi=10.1002/ptr.4778|pmid=22767439|author=Lee, JS; Sul, JY; Park, JB; Lee, MS; Cha, EY; Song, IS; Kim, JR; Chang, ES}}</ref> opioid antagonist,<ref>{{cite journal |author=Katavic, PL; Lamb, K; Navarro, H; Prisinzano, TE |title=Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships |journal=J Nat Prod. |volume=70 |issue=8 |pages=1278–82 |date=August 2007 |pmid=17685652 |url= |doi=10.1021/np070194x |pmc=2265593}}</ref> and a negative allosteric modulator at the [[benzodiazepine]] site of the [[GABAA receptor|GABA<sub>A</sub>]] receptor.<ref>{{cite journal | pmid = 12824018 | year = 2003 | last1 = Hanrahan | first1 = JR | last2 = Chebib |first2 = M | last3 = Davucheron | first3 = NL | last4 = Hall | first4 = BJ | last5 = Johnston |first5 = GA | title = Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors | volume = 13 | issue = 14 |pages = 2281–4 | journal = Bioorganic & Medicinal Chemistry Letters}}</ref>
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| | [[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 || ? || ? || ? || ? || ? || ? || ? || ? || ? || [[Benzodiazepine]] receptor ligand (K<sub>i</sub>=4μM) with anxiolytic effects.<ref>{{cite journal|title=Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects|journal=Planta Medica|volume=61|issue=3|pages=213–216|doi=10.1055/s-2006-958058|pmid=7617761|date=June 1995|author=Viola, H; Wasowski, C; Levi de Stein, M; Wolfman, C; Silveira, R; Dajas, F; Medina, JH; Paladini, AC}}</ref> Also has anti-inflammatory, anticancer, cancer-preventing and antioxidant effects.<ref>{{cite journal|title=Anticancer mechanism of apigenin and the implications of GLUT-1 expression in head and neck cancers|journal=Future Oncology|volume=9|issue=9|pages=1353–1364|date=September 2013|pmid=23980682|doi=10.2217/fon.13.84|author=Bao, YY; Zhou, SH; Fan, J; Wang, QY}}</ref><ref>{{cite journal|title=Apigenin: A promising molecule for cancer prevention|journal=Pharmaceutical Research|volume=27|issue=6|pages=962–968|doi=10.1002/mnfr.201200424|pmid=23197449|author=Shukla, S; Gupta, S}}</ref>
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| | [[Catechin]] || 2-4 || 1.8±0.85 || 110 || 8.92 || C<sub>15</sub>H<sub>14</sub>O<sub>6</sub> || 290.27 || ? || ? || ? || ? || ?|| ? || ? || ? || ? || Anticancer, antioxidant, cardioprotective and antimicrobial.<ref>{{cite journal|title=A Review of the Health Effects of Green Tea Catechins in In Vivo Animal Models|journal=The Journal of Nutrition|volume=134|issue=12|pages=3431S-3440S|author=Crespy, V; Williamson, G|url=http://jn.nutrition.org/content/134/12/3431S.full.pdf|format=PDF}}</ref><ref>{{cite journal|title=Beneficial effects of green tea: A literature review|journal=Chinese Medicine|volume=5|issue=1|pages=1–9|doi=10.1186/1749-8546-5-13|url=http://link.springer.com/content/pdf/10.1186/1749-8546-5-13.pdf|format=PDF|pmid=20370896|pmc=2855614|author=Chacko, SM; Thambi, PT; Kuttan, R; Nishigaki, I|date=April 2010}}</ref> Cannabinoid receptor CB<sub>1</sub> ligand.<ref name = Can/>
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| | |
| |-
| |
| | [[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> || ? || ? || Found in higher concentrations in [[Green tea]]. Antioxidant. [[Cannabinoid receptor CB1|CB<sub>1</sub>]] receptor ligand (K<sub>i</sub>=35.7 μM).<ref name = Can>{{cite journal|title=Tea catechins' affinity for human cannabinoid receptors|journal=Phytomedicine|date=January 2010|volume=17|issue=1|pages=19–22|doi=10.1016/j.phymed.2009.10.001|pmid=19897346|author=Korte, G; Dreiseitel, A; Schreier, P; Oehme, A; Locher, S; Geiger, S; Heilmann, J; Sand, PG}}</ref>
| |
| |-
| |
| | [[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 || ? || ? || -<ref>{{cite journal|title=Selective inhibition of the cytochrome P450 isoform by hyperoside and its potent inhibition of CYP2D6|journal=Food and Chemical Toxicology|volume=59|pages=549–553|doi=10.1016/j.fct.2013.06.055|pmid=23835282|date=September 2013|author=Song, M; Hong, M; Lee, MY; Jee, JG; Lee, YM; Bae, JS; Jeong, TC; Lee, S}}</ref> (3.87μM) || ? || ? || ? || ? || ? || ? || Has anti-fungal effects ''in vitro'' (against the plant pathogens [[Pestalotiopsis guepini|P. guepini]] and [[Drechslera]]),<ref>{{cite journal|title=Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated from Camptotheca acuminata|journal=Journal of Agricultural and Food Chemistry|date=January 2005|volume=53|issue=1|pages=32–37|doi=10.1021/jf0484780|pmid=15631505|author=Li, S; Zhang, Z; Cain, A; Wang, B; Long, M; Taylor, J}}</ref> neuroprotective effects via the PI3K/Akt/Bad/BclXL signalling pathway ''in vitro'',<ref>{{cite journal|title=Hyperoside protects primary rat cortical neurons from neurotoxicity induced by amyloid β-protein via the PI3K/Akt/Bad/Bcl(XL)-regulated mitochondrial apoptotic pathway|journal=European Journal of Pharmacology|volume=672|issue=1-3|pages=45–55|doi=10.1016/j.ejphar.2011.09.177|pmid=21978835|date=December 2011|author=Zeng, KW; Wang, XM; Ko, H; Kwon, HC; Cha, JW; Yang, HO}}</ref> anti-inflammatory effects via [[NF-κB]] inhibition ''in vitro'',<ref>{{cite journal|title=Anti-Inflammatory Activity of Hyperoside Through the Suppression of Nuclear Factor-κB Activation in Mouse Peritoneal Macrophages|journal=The American Journal of Chinese Medicine|date=January 2011|volume=39|issue=1|pages=171–181|doi=10.1142/S0192415X11008737|pmid=21213407|author=Kim, SJ; Um, JY; Lee, JY}}</ref> [[Dopamine D2 receptor|D<sub>2</sub> receptor]]-dependent antidepressant-like effects ''in vivo'',<ref>{{cite journal|title=The Anti-Immobility Effect of Hyperoside on the Forced Swimming Test in Rats is Mediated by the D2-Like Receptors Activation|journal=Planta Medica|date=March 2011|volume=77|issue=4|pages=334–339|doi=10.1055/s-0030-1250386|pmid=20945276|author=Haas, JS; Stolz, ED; Betti, AH; Stein, AC; Schripsema, J; Poser, GL; Rates, SM|url=http://lib.kums.ac.ir/documents/10129/71808/334.pdf|format=PDF}}</ref> and [[Glucocorticoid|antiglucocorticoid]]-like effects ''in vitro''.<ref>{{cite journal|title=Antidepressant-like effect of hyperoside isolated from Apocynum venetum leaves: Possible cellular mechanisms|journal=Phytomedicine|volume=19|issue=2|pages=145–149|doi=10.1016/j.phymed.2011.06.029|pmid=21802268|author=Zheng, M; Liu, C; Pan, F; Shi, D; Zhang, Y|date=January 2012}}</ref>
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| | [[Kaempferol]]<ref>{{cite journal|title=MDR- and CYP3A4-mediated drug-herbal interactions|journal=Life Sciences|date=March 2006|volume=78|issue=18|pages=2131–2145|doi=10.1016/j.lfs.2005.12.010|pmid=16442130|author=Pal, D; Mitra, AK}}</ref> || ? || 2.1±0.6 || 107 || 6.44 || C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> || 286.24 || ? || ? || ? || +/-<ref group = Note>Depends on the time frame: short-term administration causes inhibition; long-term causes induction via PXR</ref> || ? || ? || ? || ? || ? || Inhibits the following: inflammation (via [[NF-κB]] and [[STAT1]] inhibition),<ref>{{cite journal|title=Anti-Inflammatory Effects of Flavonoids: Genistein, Kaempferol, Quercetin, and Daidzein Inhibit STAT-1 and NF-κB Activations, Whereas Flavone, Isorhamnetin, Naringenin, and Pelargonidin Inhibit only NF-κB Activation along with Their Inhibitory Effect on iNOS Expression and NO Production in Activated Macrophages|journal=Mediators of Inflammation|date=August 2007|volume=2007|pmid=18274639|pmc=2220047|doi=10.1155/2007/45673|pages=45673|author=Hämäläinen, M; Nieminen, R; Vuorela, P; Heinonen, M; Moilanen, E|url=http://downloads.hindawi.com/journals/mi/2007/045673.pdf|format=PDF}}</ref> cancer, [[histone deacetylase|HDAC]],<ref>{{cite journal|title=Kaempferol, a new nutrition-derived pan-inhibitor of human histone deacetylases|journal=The Journal of Nutritional Biochemistry|volume=24|issue=6|pages=977–985|doi=10.1016/j.jnutbio.2012.07.001|pmid=23159065|date=June 2013|author=Berger, A; Venturelli, S; Kallnischkies, M; Böcker, A; Busch, C; Weiland, T; Noor, S; Leischner, C; Weiss, TS; Lauer, UM; Bischoff, SC; Bitzer, M}}</ref> bacteria, viruses, protozoa and fungi.<ref name = Rev2011>{{cite journal|title=A Review on the Dietary Flavonoid Kaempferol|journal=Mini-Reviews in Medicinal Chemistry|volume=11|issue=4|pages=298–344|doi=10.2174/138955711795305335|pmid=21428901|date=April 2011|author=Calderón-Montaño, JM; Burgos-Morón, E; Pérez-Guerrero, C; López-Lázaro, M}}</ref> It is also known to prevent cardiovascular disease and cancer.<ref name = Rev2011/>
| |
| |-
| |
| | [[Luteolin]] || ? || 2.4±0.65 || 107 || 6.3 || C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> || 286.24 || - || ? || ? || ? || ? || ? || ? || ? || ? || Has anti-inflammatory, anticancer, anti-allergic and antioxidant effects.<ref>{{cite journal|title=Anti-oxidant, anti-inflammatory and anti-allergic activities of luteolin|journal=Planta Medica|volume=74|issue=14|pages=1667–1677|date=November 2008|doi=10.1055/s-0028-1088314|pmid=18937165|author=Seelinger, G; Merfort, I; Schempp, CM}}</ref><ref>{{cite journal|title=Luteolin, a flavonoid with potential for cancer prevention and therapy|journal=Current Cancer Drug Targets|volume=8|issue=7|pages=634–646|doi=10.2174/156800908786241050|pmid=18991571|pmc=2615542|author=Lin, Y; Shi, R; Wang, X; Shen, HM|url=http://www.ncbi.nlm.nih.gov.elibrary.jcu.edu.au/pmc/articles/PMC2615542/pdf/nihms-82233.pdf|format=PDF}}</ref> May also have positive effects on people with [[autism spectrum disorders]].<ref>{{cite journal|title=A case series of a luteolin formulation (neuroprotek®) in children with autism spectrum disorders|journal=International Journal of Immunopathology and Pharmacology|volume=25|issue=2|pages=317–323|pmid=22697063|date=April–June 2012|author=Theoharides, TC; Asadi, S; Panagiotidou, S}}</ref> Potent non-selective competitive inhibitor of [[phosphodiesterase inhibitor|PDE<sub>1-5</sub>]].<ref>{{cite journal|title=Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced [3H]-rolipram from high-affinity rolipram binding sites and reversed xylazine/ketamine-induced anesthesia|journal=European Journal of Pharmacology|date=February 2010|volume=627|issue=1-3|pages=269–275|doi=10.1016/j.ejphar.2009.10.031|pmid=19853596|author=Yu, MC; Chen, JH; Lai, CY; Han, CY; Ko, WC}}</ref>
| |
| |-
| |
| | [[Quercetin]]<ref>{{cite journal|title=Quercetin: A potential drug to reverse multidrug resistance|journal=Life Sciences|date=September 2010|volume=87|issue=11-12|pages=333–338|doi=10.1016/j.lfs.2010.07.004|pmid=20637779|author=Chen, C; Zhou, J; Ji, C}}</ref><ref name = Quer2011>{{cite journal|date=June 2011|title=Quercetin|journal=Alternative Medicine Review|volume=16|issue=2|pages=172–194|issn=10895159|url=http://www.altmedrev.com/publications/16/2/172.pdf|format=PDF|author=Kelly, GS}}</ref> || 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> || ? || ? || Has anti-cancer, anti-inflammatory, anti-allergic, anti-asthmatic, antihypertensive, analgesic, neuroprotective, gastroprotective, anti-diabetic, cardiovascular disease-preventing, antioxidant, antidepressant-like (in rat models of depression), anxiolytic-like, sedative, antimicrobial and athletic performance-promoting effects.<ref name = Quer2011/> Non-selective PDE<sub>1-4</sub> inhibitor that is slightly selective for PDE<sub>3/4</sub> over PDE<sub>1/2</sub>.<ref>{{cite journal|title=Inhibitory effects of flavonoids on phosphodiesterase isozymes from
| |
| guinea pig and their structure–activity relationships|journal=Biochemical Pharmacology|volume=68|issue=10|pages=2087–2094|doi=10.1016/j.bcp.2004.06.030|date=November 2004|pmid=15476679|author=Ko, WC; Shih, CM; Lai, YH; Chen, JH; Huang, HL}}</ref>
| |
| |-
| |
| | [[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 || ? || ? || ? || ? || ? || ? || ? || ? || ? || Has anticancer, cardioprotective, nephroprotective, antioxidant, anti-inflammatory, antidiabetic, procognitive and antilipidaemic effects.<ref>{{cite journal|title=A review on plant-based rutin extraction methods
| |
| and its pharmacological activities|journal=Journal of Ethnopharmacology|volume=150|issue=3|pages=805–817|date=December 2013|doi=10.1016/j.jep.2013.10.036|pmid=24184193|author=Chua, LS}}</ref>
| |
| |-
| |
| | colspan=17 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 || ? || ? || ? || -<ref>{{cite journal|title=Inhibitory effect of caffeic acid and its derivatives on human liver cytochrome P450 3A4 activity|journal=Journal of Medicinal Plants Research|volume=5|issue=15|pages=3530–3536|date=August 2011|author=Jaikang, C; Niwatananun, K; Narongchai, P; Narongchai, S; Chaiyasut, C}}</ref> || ? || ? || ? || ? || ? || Anticancer, hepatoprotective, antibacterial and antioxidant effects reported.<ref>{{cite journal|title=Biological activities and chemical modifications of caffeic acid derivatives|journal=Fudan University Journal of Medical Sciences|volume=38|issue=6|pages=546–552|doi=10.3969/j.issn.1672-8467.2011.06.017|author=Hou, J; Fu, J; Zhang, ZM; Zhu, HL}}</ref>
| |
| | |
| |-
| |
| | [[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 || ? || ? || ? || ? || ? || Antibacterial, anticancer and antioxidant effects have been demonstrated.<ref>{{cite journal|title=Antihypertensive effects and mechanisms of chlorogenic acids|journal=Hypertension Research|volume=35|issue=4|pages=370–374|date=April 2012|doi=10.1038/hr.2011.195|pmid=22072103|author=Zhao, Y; Wang, J; Ballevre, O; Luo, H; Zhang, W}}</ref>
| |
| | |
| |}
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| | |
| {| 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]]. These values are experimental values taken from [http://chemspider.com ChemSpider] and [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgiPubChem] (the access dates are both 13–15 December 2013) where available or, if they are not available approximations are taken from [www.chemaxon.com/download/marvin/for-end-users/ ChemAxon MarvinSketch] 6.1.4 & [http://www.acdlabs.com/resources/freeware/chemsketch/ACDChemSketch]
| |
| |-
| |
| | PSA || [[Polar surface area]] of the molecule in question in square [[angstroms]] (Å<sup>2</sup>). Obtained from [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi PubChem] (the access date is the 13th of December 2013).
| |
| |-
| |
| | 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> || Pharmacokinetic data for ECG comes from a study<ref>{{cite journal|title=Pharmacokinetics of Tea Catechins after Ingestion of Green Tea and (-)-Epigallocatechin-3-gallate by Humans: Formation of Different Metabolites and Individual Variability|journal=Cancer Epidemiology, Biomarkers & Prevention|date=October 2002|volume=11|issue=10 pt 1|pages=1025–1032|pmid=12376503|author=Lee, MJ; Maliakal, P; Chen, L; Meng, X; Bondoc, FY; Prabhu, S; Lambert, G; Mohr, S; Yang, CS|url=http://cebp.aacrjournals.org/content/11/10/1025.full.pdf|format=PDF}}</ref> of its pharmacokinetics after oral administration of green tea.
| |
| |-
| |
| | <sup>b</sup> || Comes from this source.<ref name = JPET2000/>
| |
| |-
| |
| | <sup>c</sup> || Pharmacokinetic data for quercetin comes from a study<ref>{{cite journal|title=Carbon Dioxide Is the Major Metabolite of Quercetin in Humans|journal=The Journal of Nutrition|date=October 2001|volume=131|issue=10|pages=2648–2652|pmid=11584085|url=http://jn.nutrition.org/content/131/10/2648.full.pdf|format=PDF|author=Walle, T; Walle, UK; Halushka, PV}}</ref> using pure oral quercetin, not a SJW extract.
| |
| | |
| |}
| |
| | |
| '''<big>Notes:</big>'''
| |
| | |
| {{reflist|group=Note}}
| |
| | |
| {{collapse bottom}}
| |
| | |
| ==Livestock==
| |
| | |
| ===Poisoning===
| |
| | |
| In large doses, St John's wort is [[poison]]ous to grazing [[livestock]] (cattle, sheep, goats, horses).<ref name="autogenerated1" /> Behavioural signs of poisoning are general restlessness and skin irritation. Restlessness is often indicated by pawing of the ground,[[headshaking]], head rubbing, and occasional hindlimb weakness with knuckling over, panting, confusion, and depression. Mania and hyperactivity may also result, including running in circles until exhausted. Observations of thick wort infestations by Australian graziers include the appearance of circular patches giving hillsides a ‘crop circle’ appearance, it is presumed, from this phenomenon. Animals typically seek shade and have reduced appetite. Hypersensitivity to water has been noted, and convulsions may occur following a knock to the head. Although general aversion to water is noted, some may seek water for relief.
| |
| | |
| Severe skin irritation is physically apparent, with reddening of non-pigmented and unprotected areas. This subsequently leads to itch and rubbing, followed by further inflammation, [[exudation]], and scab formation. Lesions and inflammation that occur are said to resemble the conditions seen in [[foot and mouth disease]]. Sheep have been observed to have face swelling, dermatitis, and wool falling off due to rubbing. Lactating animals may cease or have reduced milk production; pregnant animals may [[Abortion|abort]]. Lesions on [[udder]]s are often apparent. Horses may show signs of [[Anorexia (symptom)|anorexia]], [[Depression (mood)|depression]] (with a comatose state), dilated pupils, and injected [[conjunctiva]].
| |
| | |
| ====Diagnosis====
| |
| | |
| Increased respiration and heart rate is typically observed while one of the early signs of St John's wort poisoning is an abnormal increase in body temperature. Affected animals will lose weight, or fail to gain weight; young animals are more affected than old animals. In severe cases death may occur, as a direct result of starvation, or because of secondary disease or [[Sepsis|septicaemia]] of lesions. Some affected animals may accidentally drown. Poor performance of suckling lambs (pigmented and non-pigmented) has been noted, suggesting a reduction in the milk production, or the transmission of a toxin in the milk.
| |
| | |
| ====Photosensitisation====
| |
| | |
| Most clinical signs in animals are caused by [[Photosensitivity|photosensitisation]].<ref>[http://www.northwestweeds.nsw.gov.au/st_johns_wort.htm#effect_on_animals St John's wort effects on animals]</ref> Plants may induce either primary or secondary photosensitisation:
| |
| *primary photosensitisation directly from chemicals contained in ingested plants
| |
| *secondary photosensitisation from plant-associated damage to the liver.
| |
| Araya and Ford (1981) explored changes in liver function and concluded there was no evidence of ''Hypericum''-related effect on the excretory capacity of the liver, or any interference was minimal and temporary. However, evidence of liver damage in blood plasma has been found at high and long rates of dosage.
| |
| | |
| Photosensitisation causes skin inflammation by a mechanism involving a pigment or photodynamic compound, which when activated by a certain wavelength of light leads to [[Redox|oxidation]] reactions [[in vivo]]. This leads to lesions of tissue, particularly noticeable on and around parts of skin exposed to light. Lightly covered or poorly [[Biological pigment|pigment]]ed areas are most conspicuous. Removal of affected animals from sunlight results in reduced symptoms of poisoning.
| |
| | |
| ==See also==
| |
| * [[Dietary supplement]]
| |
| * [[european Union|EU]] [[Food supplements directive]]
| |
| * [[List of plants poisonous to equines]]
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| | |
| == References ==
| |
| {{Reflist|30em}}
| |
| | |
| ==Further reading==
| |
| *British Herbal Medicine Association Scientific Committee (1983). ''British Herbal Pharmacopoeia''. West Yorkshire: British Herbal Medicine Association. ISBN 0-903032-07-4.
| |
| *{{cite book| author = Müller, Walter| title = St. John's Wort and its Active Principles in Depression and Anxiety| place = Basel|publisher = Birkhäuser| year = 2005| isbn = 978-3-7643-6160-0| url = http://www.springerlink.com/content/gl7841| doi = 10.1007/b137619}}
| |
| | |
| == External links ==
| |
| {{wikispecies|Hypericum perforatum}}
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| {{Commons|Hypericum perforatum}}
| |
| {{refbegin}}
| |
| *{{cite web|author=Barrett S|year=2000 |url=http://www.quackwatch.org/01QuackeryRelatedTopics/DSH/stjohn.html |title=St. John's Wort|work= |accessdate=2009-03-08}}
| |
| *{{cite web|url=http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-stjohnswort.html|title=St. John's wort: MedlinePlus Supplements|publisher=U.S. National Library of Medicine|accessdate=7 October 2009}}
| |
| * [http://www.invasivespeciesinfo.gov/plants/stjohnswort.shtml Species Profile — St. Johnswort (''Hypericum perforatum'')], National Invasive Species Information Center, [[United States National Agricultural Library]]. Lists general information and resources for St John's wort.
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| {{refend}}
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| {{Dietary supplement}}
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| {{Use dmy dates|date=February 2011}}
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| [[Category:Hypericum|perforatum]]
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| [[Category:Flora of Europe]]
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| [[Category:Flora of Estonia]]
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| [[Category:Flora of the United Kingdom]]
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| [[Category:Flora of Lebanon]]
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| [[Category:Garden plants of Europe]]
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| [[Category:Invasive plant species in California]]
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| [[Category:Abortifacients]]
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| [[Category:Antidepressants]]
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| [[Category:Medicinal plants]]
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| [[Category:Monoamine reuptake inhibitors]]
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| [[Category:Plants described in 1753]]
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