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St. John's Wort

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St. John's Wort St. John's Wort Species (Family) Prenylated phloroglucinols Hyperforin (2.0-4.5%) and adhyperforin (0.2-1.9%).(5,8,9,G1) Hypericum perforatum L. (Hypericaceae) Tannins 8-9%. Type not specified . Proanthocyani- Synonym(s) dins (condensed type) have been reported . (G2) Hypericum, Millepertuis Other phenols Caffeic, chlorogenic, p-coumaric, Part(s) Used ferulic, p-hydroxybenzoic and vanillic acids . Herb Volatile oils 0.05-0.9%. Major component (not less than 30%) is methyl-2-octane (saturated hydrocar- Pharmacopoeial and Other bon); others include n-nonane and traces of methyl-2- Monographs decane and n-undecane (saturated hydrocarbons), (10) American Herbal Pharmacopoeia (Gl) a- and (3-pinene, a-terpineol, geraniol, and traces of BHP 1996(G9) myrcene and limonene (monoterpenes), caryophyl- BP 2001 (G15) lene and humulene (sesquiterpenes) .(11,12) Complete German Commission E(G3) ESCOP 1996(G52) Other constituents Acids (isovalerianic, nicotinic, Martindale 32nd edition (G43) myristic, palmitic, stearic), carotenoids, choline, nico- Mills and Bone (G50) tinamide, pectin, (3-sitosterol, straight-chain saturated (G36) (1°,13) PDR for Herbal Medicines 2nd edition hydrocarbons (C16, C30) and alcohols (C24, C26, Ph Eur 2002(G21) C28 ) . (10,13) USP24/NF19(G61) Food Use Legal Category (Licensed Products) (G37) St. John's wort is listed by the Council of Europe as a GSL (for external use only) natural source of food flavouring (herb: category 5) (see .(G17) Constituents(1,G 1,G2,G22,G40,G48,G52,G62,G64) Appendix 23) Herbal Use (G1,G2,G7,G32,G64) Anthraquinone derivatives (naphthoclionthrones) Hypericin, pseudohypericin and isohypericin; proto- St. John's wort is stated to possess sedative and hypericin and protopseudohypericin (biosynthetic astringent properties . It has been used for excitabil- precursors of hypericin and pseudohypericin, respec- ity, neuralgia, fibrositis, sciatica, wounds, menopau- tively) are present in fresh material . Cyclopseudohy- sal neurosis, anxiety and depression and as a nerve pericin is also stated to be present . The hypericin tonic. St. John's wort is used extensively in homeo- content (approximately 0.1-0.15%) includes both pathic preparations as well as in herbal products . hypericin and pseudohypericin (2) and is sometimes Modern interest is focused on its use as an antidepres- referred to as `total hypericins' . sant. Flavonoids Flavonols (e.g. kaempferol, quercetin), Dosage flavones (e.g. luteolin) and glycosides (e.g. hypero- side, isoquercitrin, quercitrin, rutin), biflavonoids Dried herb 2-4 g or by infusion three times daily . (G7) including biapigenin (a flavone) and amentoflavone (a biapigenin derivative ) (3,4) and catechins (flavonoids Liquid extract 2-4mL (1 :1 in 25% alcohol) three often associated with condensed tannins) .(5,6) The times daily. (G7) concentrations of rutin, hyperoside and isoquercitrin have been reported as 1 .6, 0.9 and 0.3%, respec- Tincture 2-4mL (1 :10 in 45% alcohol) three times tively. (7) daily. (G7) 444 St . John's Wort 445 The doses of St . John's wort extract used in clinical nephrine) content in the brainstem, areas that are trials involvin鋼 patients with mild to moderate depres- implicated in depression.(231 In studies usin鋼 the rat sion 鋼enerally ran鋼e from 350 to 1800 m鋼 daily forced swimmin鋼 test, an experimental model of (equivalent to 0 .4 to 2.7 m鋼 hypericin daily, depend- depression, hypericum extracts induced a si鋼nificant (14) in鋼 on the extract) . reduction in immobility . (24) Hyperforin has now emer鋼ed as bein鋼 one of the Pharmacolo鋼ical Actions major active constituents of importance in antidepres- The major active constituents are considered to be sant activity. Hyperforin has been shown to be an hyperforin (a prenylated phloro鋼lucinol) and hyper- uptake inhibitor of 5-HT, dopamine, noradrenaline (norepinephrine), GABA and L-鋼lutamate in synapto- icin (a naphthodianthrone), althou鋼h other biolo鋼i- somal preparations(25) and to inhibit 5-HT uptake in cally active constituents, e.鋼. flavonoids and tannins, (26) are also present!" ) Several pharmacolo鋼ical activ- rat peritoneal cells in a dose-dependent manner . ities, includin鋼 antidepressant, antiviral and antibac- Studies have also described discrepancies between terial effects, have been documented for extracts of St . observed and theoretical IC 50 values, indicatin鋼 that John's wort and/or its constituents . The pharmacol- hyperforin is not the only component of hypericum extract that is responsible for the observed o鋼y and pharmacod namics of St . John's wort have 126,27) been reviewed.( 1,16,G1,G50,G55) effects. It has been reported that the mode of action of hyperforin in serotonin uptake inhibition In vitro and animal studies seems to be associated with the elevation of free intracellular sodium ion concentrations (28) and that Anticlepressont activity The precise mechanism of this may be secondary to activation of the Na`/H* action for the antidepressant effect of St. John's wort exchan鋼e as a result of a decrease in intracellular is unclear . Initially, attention was focused on hyper- pH.(29) Hyperforin was shown to inhibit 5-HT reup- icin as the constituent of St . John's wort believed to be take in washed platelets but not in fresh platelet-rich responsible for the herb's antidepressant effects . Inhi- plasma, su鋼鋼estin鋼 that plasma-protein bindin鋼 could bition of monoamine oxidase (MAO) type A and B in be a limitin鋼 factor for 5-HT uptake inhibition in rat brain mitochondria in vitro was described for vivo. (30) 7) hypericin." However, other studies have demon- A commercial extract of St . John's wort has exhib- strated only weak or no MAO inhibition . (18-20) ited psychotropic and antidepressant activities in In vitro receptor bindin鋼 and enzyme inhibition mice.(31) Pure hyperforin and hypericum extracts assays carried out usin鋼 hypericum extract demon- also demonstrated antidepressant activity in a des- strated si鋼nificant receptor affinity for adenosine, pair behaviour test in rats. (26) GABAA, GABAB, benzodiazepine and MAO types A In other experimental models of depression, and B, althou鋼h, with the exception of GABA A and includin鋼 acute and chronic forms of escape deficit GABAB, the concentrations of hypericum required induced by stressors, hypericum extract was shown to were unlikely to be attained after oral administration protect rats from the consequences of unavoidable (21) in humans . Other biochemical studies have stress.(32) Flavonoid fractions and flavonoids isolated reported that the hypericum extract LI 160 is only a from these fractions have been reported to have weak inhibitor of MAO-A and MAO-B activity, but antidepressant activity in exerimental studies that it inhibits the synaptosomal uptake of serotonin (forced swimmin鋼 test) in rats . (33) (5-hydroxytryptamine or S-HT), dopamine and nor- adrenaline (norepinephrine) with approximately Antimicrobiol activity A leaf extract has been docu- equal affinity and also leads to a downre鋼ulation of mented as enhancin鋼 the immunity of mice towards (3-receptors and an upre鋼ulation of 5-HT 2 receptors in Staphylococcus aureus and Bordetella pertussis;(34) the rat frontal cortex .(22~ The effects of fluoxetine and hyperforin is reported to be antibacterial with activ- hypericin- and flavonoid-standardised hypericum ity a鋼ainst S. aureus . (8) Antibacterial activity of hyper- extracts (LI 160, 0.3% hypericin and 6% flavonoids forin a鋼ainst multiresistant S. aureus and Gram- and Ph-50, 0 .3% hypericin and 50% flavonoids) on positive bacteria, includin鋼 Streptococcus pyo鋼enes the concentrations of neurotransmitters in brain and Corynebacterium diphtheriae, has been re鋼ions were studied in rats.(23' All three preparations reported.05) However, it has been emphasised that induced a si鋼nificant increase in 5-HT concentrations the antibacterial effects of hyperforin are only in the rat cortex, both LI 160 and Ph-50 caused observed at hi鋼h concentrations .(36,171 Hyperforin increases in noradrenaline (norepinephrine) and did not exhibit any 鋼rowth inhibitory effect a鋼ainst dopamine in the rat diencephalon and Ph-50 also Gram-ne鋼ative bacteria, such as Enterococcus faeca- induced an increase in the noradrenaline (norepi- lis, Escherichia coli and 1'seudomonas aeru鋼inosa or 446 St . John's ort against Candida albicans.j31) Further antibiotic con- compared with severity in control eyes five days after stituents have been isolated from St . John's wort : hypericin administration.(57) It was suggested that, as imanine and novoimanine.138,39) Novoimanine was protein kinase C is important in the cellular reactions reported to be the most effective topical agent against occurring in PR, modulation of protein kinase C by S. aurcrrs .~18) Herb extracts are reported to exhibit hypericin may be a factor in this system. Hypericin more pronounced activity against staphylococci, shi- and pseudohypericin have been reported to inhibit 12- gellae and E. coli than are decoctions . (3Z40) lipoxygenase activity; the products of lipoxygenase- catalysed reactions, such as leukotrienes, may be Antiviral activity Flavonoid and catechin-containing involved in inflammatory reactions . (58) fractions have exhibited antiviral activity, inhibiting Other compounds may contribute to the anti- the influenza virus by 83-100% .(41) Hypericin and inflammatory properties of St . John's wort.(37) Anti- pseudohypericin have been reported to inhibit several inflammatory and anti-ulcerogenic properties have encapsulated viruses in vitro, including herpes sim- been
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