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PubMed2000

Quantitative changes of dianthrones, hyperforin and flavonoids content in the flower ontogenesis of Hypericum perforatum.

Samples of Hyperici herba were obtained by harvesting Hypericum perforatum L. in different plant development stages. The relation of flower development phases in the drug's flower fraction was examined. The HPLC method was then employed for the analysis of the content of secondary metabolites in different flower ontogenesis phases. The content of dianthrones, derivatives of quercetin and hyperforin increased from the first bud phases (0.29%, 0.80%, and 2.47%, respectively) to flowers just opened (1.04%, 4.23% and 6.60%, respectively). The content of dianthrones and quercetin glycosides then decreased (in unripe fruits 0.11% and 0.08%, respectively), whereas the amounts of hyperforin increased to 8.07% in fruits. The content of I3,II8-biapigenin increased from 0.21% in small buds to 1.04% in buds just before opening and has then decreased gradually to a value of 0.02% in fruits. Rutin was not detected in the samples.

Anthracenes↗
PubMed2001

Inhibition of interleukin-12 production in lipopolysaccharide-activated mouse macrophages by hpyericin, an active component of Hypericum perforatum.

Hypericin, an active component of Hypericum perforatum, was evaluated for the regulation of interleukin-12 (IL-12) production in mouse macrophages. Hypericin significantly inhibited IL-12 production in lipopolysaccharide-activated macrophages in a dose-dependent manner (IC50 = 1.45 micrograms/ml). Furthermore, hypericin potently inhibited the activation of IL-12 gene promoter, suggesting that hypericin negatively regulated IL-12 production at the transcription level. These results may explain some known biological activities of hypericin including its anti-rheumatic effect.

Animals↗
PubMed2001

Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man.

We have studied the effect of acute and sub-chronic treatments of a formulation of a methanolic extract of hypericum perforatum (HP, also known as St John's wort) on plasma hormones and brain neurotransmitters in healthy human volunteers and rats. Also studied were the effects of equivalent acute doses of two constituents of HP (with respect to LI 160 extract), hypericin and hyperforin in rats. In acute treatment studies in normal volunteers subjects received 9 tablets of the finished product Jarsin 300 and placebo in the pilot study (unblinded) and in the main study (a double blind, balanced order, cross-over design). Results in normal volunteer studies show that HP caused significant increases of salivary cortisol and plasma growth hormone (GH) whereas it decreased plasma prolactin versus placebo. Plasma hormone levels were associated with a rise in plasma hyperforin but not with hypericin, however no significant correlation was found. In the animal studies, acute treatment with LI 160, hyperforin and hypericin all caused significant increases in plasma corticosterone. This was associated with significant increases in brain cortical tissue 5-HT content. The corticosterone responses were attenuated by the 5-HT2 receptor antagonist, ketanserin but not by the 5-HT1A antagonist, WAY-100635. This suggests that the corticosterone responses may be mediated via a 5-HT2 mechanism of action. When sub-chronic and acute treatment using two different doses of LI 160 were compared, plasma corticosterone level were significantly decreased. Thus suggesting a down-regulation or desensitisation of post-synaptic 5-HT2 receptors. Plasma prolactin was significantly reduced by acute treatment with LI 160 and hyperforin treatment but not by hypericin. This was associated with a concomitant rise in brain cortical tissue DA. Both LI 160 and hyperforin treatments decreased the plasma prolactin responses to the DA antagonist, haloperidol, suggesting that this may be associated with a DA-mediated mechanisn of action. When acute and sub-chronic treatments were compared, plasma prolactin responses were increased in the sub-chronically treated animals. The studies when taken together suggest that the LI 160 extract may effect plasma hormonal changes via both 5-HT and DA-mediated mechanisms but do not involve noradrenaline (NA). The data also suggests that hyperforin may be more important than hypericin for effecting these changes following acute treatment. Further studies investigating both acute and sub-chronic effects of these compounds are necessary.

Adult↗
PubMed2001

St. John's wort extract Ze 117 (Hypericum perforatum) inhibits norepinephrine and serotonin uptake into rat brain slices and reduces 3-adrenoceptor numbers on cultured rat brain cells.

Despite almost forty years of widespread use, the mode of action of antidepressant drugs is still largely unknown. There is agreement that these drugs interact with central neurotransmission. Common findings are acute inhibitory actions on reuptake mechanisms for norepinephrine (NE) and for serotonin (5-HT) at presynaptic axons and chronic adaptive effects on neurotransmitter receptors on postsynaptic membranes. In particular, beta-adrenoceptor downregulation has been observed after chronic treatment with most antidepressants in vivo and in cell culture systems. We studied the effectiveness of Ze 117 (St. John's wort) extract (Hypericum perforatum) on NE- and 5-HT-uptake into rat brain slices. Potency and efficacy of the Ze 117 extract were compared with those of tricyclic (TCA) and selective serotonin reuptake inhibitor (SSRI)-type antidepressants. A dose-dependent inhibition was seen on NE and 5-HT uptake into brain slices. The Ze 117 extract was more selective for the uptake of NE than for that of 5-HT. The maximal extent of uptake inhibition by Ze 117 extract was comparable to that of imipramine (IMI), desipramine (DMI) or fluvoxamine for 5-HT, but lower for NE transport, than that of the synthetic antidepressants. Chronic exposure (8 days) of confluent C6-cell cultures to Ze 117 extract resulted in a dose-dependent beta-adrenoceptor downregulation equal to that induced by DMI, a potent TCA. None of these effects could be achieved with either hypericin or hyperforin alone in a relevant dose range. Our results indicate that the St. John's wort extract Ze 117 contains active, but as yet unknown antidepressant principles with effects comparable to those of TCAs.

Animals↗
PubMed2001

In vitro binding studies with two hypericum perforatum extracts--hyperforin, hypericin and biapigenin--on 5-HT6, 5-HT7, GABA(A)/benzodiazepine, sigma, NPY-Y1/Y2 receptors and dopamine transporters.

Interactions between neurotransmitter receptors involved in the pathophysiology of depression, anxiety and ethanol consumption and two extracts (hydromethanolic and lipophilic extracts obtained with hypercritical CO2) from Hypericum Perforatum L or St. John's wort (SJW) and three constituents (hyperforin, hypericin and biapigenin) were evaluated by in vitro binding assays. The two extracts, tested at 10 microg/ml, did not inhibit ligand binding at the following receptors: serotonin 5-HT6 and 5-HT7, benzodiazepine, sigma and neuropeptide Y (NPY) Y1 and Y2 receptors. The hydromethanolic extract, but not the lipophilic extract, interacted with GABA(A) receptors (IC50 5.5 microg/ml), while both interacted with the dopamine (DA) transporters, albeit with high IC50 values (24.5 and 12.9 microg/ml, respectively). Biapigenin (1 microg/ml, 2 microM) inhibited ligand binding at benzodiazepine receptors only (IC50: 2 microM). Hyperforin (1 microg/ml, 2 microM) only inhibited [3H]WIN-35,428 binding to DA transporters, although the IC50 (5 microM) was higher than the IC50 found for inhibition of the synaptosomal DA reuptake (0.8 microM). This finding extended the same observation previously described for the 5-HTergic system to the DAergic system, confirming that the inhibition of monoamine reuptake is due to a different mechanism than that of synthetic antidepressants. Hypericin showed micromolar affinities for both NPY-Y1 and Y2 receptors and for sigma receptors (IC50 3-4 microM). These hypericin activities might be of interest because NPY and sigma receptors have been associated with anxiety disorders, depressive illnesses and ethanol consumption. However, they were present at relatively high hypericin concentrations, and were also light-dependent (i.e. the IC50 values increased when binding assays were carried out in the dark). Thus, our in vitro binding results may suggest that either the pharmacological effects of SJW are due to other molecules than hypericin or hyperforin (other constituents or active metabolites), or that the mechanism of action is different from those that have been considered up to now.

Animals↗
PubMed2001

Hypericum perforatum--a review of clinical studies.

St. John's wort (Hypericum perforatum) has been used as a medicinal herb for over 2000 years. Over the past 2 decades, its application as a plant extract for treating depression has undergone rigorous scientific investigation, and its effectiveness has been shown in studies comparing it with placebo and preference antidepressants. Safety and tolerability studies have revealed that St. John's wort (SJW) preparations have better safety and tolerability profiles than synthetic antidepressants. The indications for St. John's wort preparations comprise patients with mild or moderate depression. Based on the existing literature, limitations to efficacy in more severe cases as well as interactions and contraindications have to be respected.

Antidepressive Agents↗
PubMed2001

A study of the antidepressant activity of Hypericum perforatum on animal models.

The treatment of non-selected depressed patients with a hydro-alcoholic extract of Hypericum perforatum has been reported to have an efficacy similar to that of classical antidepressants. The effects of H. perforatum on three animal depression models have been studied: (a) an acute form of escape deficit (ED) induced by unavoidable stress; (b) a chronic model of ED, which can be maintained by the administration of mild stressors on alternate days; (c) a model of anhedonia based on the finding that repeated stressors prevent the development of appetitive behavior induced by vanilla sugar in satiated rats fed ad libitum. H. perforatum: (i) acutely protects animals from the sequelae of unavoidable stress; (ii) reverts the chronic escape deficit state maintained by repeated stressors and (iii) preserves the animal's capacity to acquire motivated appetitive behavior. Exposure to chronic stress not only induces escape deficit, but also decreases extraneuronal levels of dopamine in the nucleus accumbens shell; both behavioral and neurochemical effects are reverted by long-term treatment with antidepressants. Three-week treatment with H. perforatum reverted the chronic stress effect on extraneuronal dopamine in the nucleus accumbens. A consistent body of data in the literature suggests that, among the components of H. perforatum extract, hyperforin is the compound (or one of the compounds) responsible for the antidepressant activity. We compared the efficacy of the total extract with the efficacy of hyperforin after p.o. administration. In the acute-escape deficit model, hyperforin showed a potency of about ten times that of the total extract in protecting rats from the sequelae of unavoidable stress. Thus, hyperforin appears to be the most likely active component responsible for the antidepressant activity of H. perforatum.

Animals↗
PubMed2002

St. John's wort (Hypericum perforatum)--is it safe during breastfeeding?

Both doctors and patients often treat postnatal depression with herbal preparations derived from St. John's wort. Because these preparations are available to patients as "natural" over-the-counter drugs for depression, they are popularly assumed to be safe. However, no systematic information exists regarding treatment of postnatal depression, infant's safety or pharmacokinetics of hypericum constituents in human breast milk or infant plasma. A mother with post-natal depression was admitted at our service. Her pharmacist had recommended taking a St. John's wort preparation three times a day (Jarsin 300, Lichtwer Pharma AG, Berlin, Germany). Four breast-milk samples (fore and hind milk) during an 18-hour period were analyzed to measure concentration of hypericin and hyperforin. Only hyperforin is excreted into breast milk at a low level, hyperforin and hypericin (two major active components) were below the lower limit of quantification (BLQ: below lower limit of quantification, LQ hypericin: 0.20 ng/ml, LQ hyperforin: 0.50 ng/ml) in this infant's plasma. No side effects were seen in the mother or infant. Before recommending St John's wort for the treatment of depression to women who breastfeed, long-term studies of outcome in infants are needed.

Adult↗
PubMed2002

Antiplatelet and anti-inflammatory constituents and new oxygenated xanthones from Hypericum geminiflorum.

Two new pentaoxygenated xanthones, 2,3-dihydroxy-1,6,7-trimethoxyxanthone (1) and 3,6-dihydroxy-1,5,7-trimethoxyxanthone (2) were isolated from the leaf of Hypericum geminiflorum. The antiplatelet activities of the constituents, 2,6-dimethoxy-p-benzoquinone (3), gemichalcone A (4), gemichalcone B (5), and cycloartocarpin (6), of this plant, were assessed in vitro by determining their inhibitory effects on the aggregation of washed rabbit platelets induced by various inducers. The anti-inflammatory effects of 4 and 5 were assessed in vitro by determining their inhibitory effects on the chemical mediators released from mast cells and neutrophils. Of the compounds tested, 4 exhibited the most potent inhibition of platelet aggregation induced by arachidonic acid (AA) and 4 and 5 strongly inhibited the release of beta-glucuronidase and lysozyme in formyl-Met-Leu-Phe (fMLP)-stimulated rat neutrophils.

Animals↗
PubMed2002

Phenolic compounds from Hypericum perforatum.

During a re-investigation of phenolic compounds from the dried crude drug material of St. John's wort (Hypericum perforatum L.) 22 phenolic compounds were detected by HPLC; 14 of them were quantified using the same system. Twelve phenolic compounds were isolated from the plant material and their structures identified mainly by spectroscopic methods, among them quercetin-3-O-(2"-O-acetyl)-beta-D-galactoside as a new natural product. Cryptochlorogenic acid, protocatechuic acid, 3-O-[Z]-p-coumaroylquinic acid, isoorientin, cyanidin-3-O-alpha-L-rhamnoside, and astilbin were obtained for the first time from this source; the earlier suspected neochlorogenic acid, 3-O-[E]-p-coumaroylquinic acid, mangiferin, miquelianin and guaijaverin were confirmed.

Calibration↗
PubMed2002

Bisxanthones from Hypericum japonicum: inhibitors of PAF-induced hypotension.

The CHCl3-soluble part (HJ) of the MeOH extract from Hypericum japonicum afforded new bisxanthones, jacarelhyperols A (1) and B (2). The structures were elucidated by spectral methods. These compounds and HJ showed significant inhibitory effects against PAF-induced hypotension by an in vivo evaluation method, which can reveal the pharmacological action of the test material.

Animals↗
PubMed2002

Rutin is essential for the antidepressant activity of Hypericum perforatum extracts in the forced swimming test.

It has been shown that aqueous alcoholic extracts of Hypericum perforatum (St. John's wort) are active in the forced swimming test (FST), an animal model for antidepressant activity. In this study, a series of ethanolic and methanolic extracts were investigated and, in almost all cases, the extracts showed strong activity. Only one methanolic research extract had no effect in the in vivo pharmacological experiments. Analytical characterisation using HPLC showed that the inactive extract had a reduced level of the diglycoside flavonoid rutin. Addition of rutin to the inactive extract, to produce a concentration within the normal range, resulted in a strong pharmacological effect comparable to that of the other extracts. First experiments suggest that this re-activation is not dose-dependent, indicating that rutin must be present above a threshold limit. It therefore appears vital that extracts of St. John's wort which are designed for the therapy of depressive disorders should be manufactured using plant material with sufficient amounts of rutin.

Animals↗
PubMed2003

The prototypic antidepressant drug, imipramine, but not Hypericum perforatum (St. John's Wort), reduces HPA-axis function in the rat.

Dysregulation in corticotropin-releasing hormone (CRH) secretion in the hypothalamus-pituitary-adrenal (HPA) axis may be involved in the etiology of major depressive disorder (MDD). Chronic therapy with standard antidepressant drugs, such as imipramine, can downregulate HPA axis function, indicating that the HPA axis may be an important target for antidepressant action. We tested several doses of a standardized commercial preparation of Hypericum perforatum plant extract (popularly known as St. John's Wort), a medicinal herb used for treating mild depressive symptoms, to determine whether it also modulated HPA axis function. Chronic imipramine treatment (daily injections for 8 weeks) of male Sprague-Dawley rats significantly downregulated circulating plasma levels of adrenocorticotropic hormone (ACTH) and corticosterone compared to animals treated with saline. However, chronic St. John's Wort treatment (daily gavage for 8 weeks) had no effect on plasma ACTH or corticosterone, even at the highest doses tested. Our results confirm previous findings that imipramine may have significant peripheral HPA axis-mediated effects. However, our data does not support any role for H. perforatum in modulation of HPA axis function, suggesting that alternative pathways may be involved in mediating its antidepressant effects.

Adrenal Glands↗
PubMed2005

Cytotoxicities of xanthones and cinnamate esters from Hypericum hookerianum.

5-Hydroxy-2-methoxyxanthone (1), 2-hydroxy-3-methoxyxanthone (2), trans-kielcorin (3), 4-hydroxy-3-methoxyphenyl ferulate (4) and 3beta-O-caffeoylbetulinic acid (5) were isolated from Hypericum hookerianum. Compounds 1-5 were tested against the growth of three human tumor cell lines, MCF-7, NCI-H460 and SF-268. Compounds 4 and 5 exhibited significant inhibitory activity effects against all three; GI50 values for 4 were 15.1 +/- 1.6, 18.7 +/- 2.3 and 15.9 +/- 2.7 and for 5 12.2 +/- 2.4, 19.6 +/- 2.3 and 24.3 +/- 2.5. Compound 3 was less active with GI50 values of 55.1 +/- 2.3, 49.7 +/- 3.0 and 40.5 +/- 1.5, while 1 and 2 exhibited only weak effects. Compounds 4 and 5 were moderately effective in influencing the mitogenic response to human lymphocytes to hemoagglutinin, with IC values of 26.1 +/- 3.6 and 40.8 +/- 4.9, respectively.

Antineoplastic Agents, Phytogenic↗
PubMed2006

A pilot randomised, open, uncontrolled, clinical study of two dosages of St John's wort (Hypericum perforatum) herb extract (LI-160) as an aid to motivational/behavioural support in smoking cessation.

There is an association between smoking and depression, yet the herbal antidepressant St John's wort (Hypericum perforatum L.; SJW) herb extract has not previously been investigated as an aid in smoking cessation. In this open, uncontrolled, pilot study, 28 smokers of 10 or more cigarettes per day for at least one year were randomised to receive SJW herb extract (LI-160) 300 mg once or twice daily taken for one week before and continued for 3 months after a target quit date. In addition, all participants received motivational/behavioural support from a trained pharmacist. At 3 months, the point prevalence and continuous abstinence rates were both 18%, and at 12 months were 0%. Fifteen participants (54%) reported 23 adverse events up to the end of the 3-month follow-up period. There was no statistically significant difference in the frequency of adverse events for participants taking SJW once or twice daily (p > 0.05). Most adverse events were mild, transient and non-serious. This preliminary study has not provided convincing evidence that a SJW herb extract plus individual motivational/behavioural support is likely to be effective as an aid in smoking cessation. However, it may be premature to rule out a possible effect on the basis of a single, uncontrolled pilot study, and other approaches involving SJW extract may warrant investigation.

Adolescent↗
PubMed2006

Effect of sub-chronic treatment with Jarsin (extract of St John's wort, Hypericum perforatum) at two dose levels on evening salivary melatonin and cortisol concentrations in healthy male volunteers.

OBJECTIVE: The aim of the present study was to measure the effect of two doses of extracts from Hypericum perforatum (HP), Jarsin, on evening salivary cortisol and NA-mediated melatonin in healthy male volunteers. METHODS: Twenty healthy male volunteers were randomly given a low or high dose of Jarsin for 7 days. Saliva samples for cortisol and melatonin, and overnight urine samples were collected for cortisol and 6-sulfatoxymelatonin and measured by specific radioimmunoassays. RESULTS: Treatment significantly increased salivary cortisol throughout the whole collection period in the low dose group but had no discernable effect in the high dose group. Salivary melatonin was not increased in either dose group following treatment. CONCLUSION: Salivary cortisol was enhanced in the low dose group only and melatonin was not affected by either treatment. We suggest that HP may enhance salivary cortisol via a U-shaped dose-response relationship and that this may be mediated through a 5-HT2 mechanism.

Adult↗
PubMed2000

Effect of antenatal exposure to Saint John's wort (Hypericum) on neurobehavior of developing mice.

OBJECTIVE: We conducted, in a randomized, placebo-controlled manner, behavioral testing on mice offspring exposed antenatally to the herbal antidepressant Saint John's wort (Hypericum ). STUDY DESIGN: A daily dose of Saint John's wort (0.75 mg/g of food consumed), equivalent to that in human beings according to body surface, was chosen because it has been shown to cause an antidepressant effect in adult mice. CD-1 mice were randomly assigned to consume either Saint John's wort (n = 45) or a placebo (n = 45) for 2 weeks before conception and throughout gestation. Behavioral testing consisted of early developmental tasks of geotaxis, separation vocalization, and homing, followed by motor, anxiety, and depression assessments into adulthood. RESULTS: Birth weights of male offspring were less in the Saint John's wort group than in the placebo group (1.68 vs. 1.75 g; P<.01). Offspring in both treatment groups showed no long-term statistical differences in early developmental tasks, locomotor activity, and exploratory behavior throughout development. Performances on a depression task (forced swim) and on anxiety tasks (elevated plus maze as juveniles and adults) revealed no differences between treatment groups. CONCLUSION: Antenatal exposure to a therapeutic dose of Saint John's wort showed no long-term deficits on selected behavioral tasks by developing mice offspring.

Animals↗
PubMed2001

Attractive and defensive functions of the ultraviolet pigments of a flower (Hypericum calycinum).

The flower of Hypericum calycinum, which appears uniformly yellow to humans, bears a UV pattern, presumably visible to insects. Two categories of pigments, flavonoids and dearomatized isoprenylated phloroglucinols (DIPs), are responsible for the UV demarcations of this flower. Flavonoids had been shown previously to function as floral UV pigments, but DIPs had not been demonstrated to serve in that capacity. We found the DIPs to be present in high concentration in the anthers and ovarian wall of the flower, suggesting that the compounds also serve in defense. Indeed, feeding tests done with one of the DIPs (hypercalin A) showed the compound to be deterrent and toxic to a caterpillar (Utetheisa ornatrix). The possibility that floral UV pigments fulfill both a visual and a defensive function had not previously been contemplated. DIPs may also serve for protection of female reproductive structures in other plants, for example in hops (Humulus lupulus). The DIPs of hops are put to human use as bitter flavoring agents and preservatives in beer.

Animals↗