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PubMed2002

Determination of flavonoids in Hypericum perforatum by HPLC analysis.

AIM: To establish an HPLC method for simultaneous determination of four flavonoids in Hypericum perforatum L., ruitn, hyperin, avicularin and quercetin. METHODS: C18 column was used, the chromatography was carried out with a linear gradient program. The mobile phase was A: H2O (pH 3.0-3.5 adjusted with phosphoric acid) and B: acetonitrile, at flow rate of 1.0 mL.min-1, peaks were detected at 254 nm. RESULTS: The linear range of rutin was 1.376-8.256 micrograms.mL-1 (gamma = 0.9999), hyperin 3.160-18.960 micrograms.mL-1 (gamma = 0.9996), avicularin 0.968-5.808 micrograms.mL-1 (gamma = 0.9998) and quercetin 0.776-4.656 micrograms.mL-1 (gamma = 0.9993). The average recovery of rutin was 97.8%, RSD 4.8% (n = 3), hyperin 100.7%, RSD 3.7% (n = 3), avicularin 97.3%, RSD 0.8% (n = 3) and quercetin 100.5%, RSD 4.4% (n = 3). All of RSDs of precision were less than 2% (n = 5), reproducibilities less than 3%. CONCLUSION: The method is simple, effective and feasible. It can be used to determine flavonodis in Hypericum perforatum.

Calibration↗
PubMed2003

Dissolution, solubility and cooperativity of phenolic compounds from Hypericum perforatum L. in aqueous systems.

The dissolution in water of phenolic constituents of St. John's wort (Hypericum perforatum L.) from a medicinal tea and a coated tablet formulation showed different dissolution profiles. In general, the flavonoid glycosides were well dissolved, followed by flavonoid aglycones and hypericin while hyperforin was only detectable at a very low level. Interestingly, hypericin exhibited much better extraction and dissolution rates than the similarly lipophilic hyperforin. When determining the octanol/water partition coefficient it became obvious that the solubility of pure hypericin in water increased upon addition of some phenolic constituents typical for Hypericum extracts. Most effective in solubilizing hypericin was hyperoside (hyperin, quercetin 3-O-beta-D-galactoside) which increased the concentration of hypericin in the water phase up to 400 fold in this model.

Anthracenes↗
PubMed2003

[Determining the quantity of hypericin in medicinal materials and asepsis seedings of Hypericum perforatum by HPLC].

OBJECTIVE: To establish the method of determining the quantity of hypericin in Hypericum perforatum and determine the quantity of the hypericin in defferent medicinal materials and asepsis seedings which grow in defferent environment. METHOD: The specimen is extracted with methanol--Pyridine (9:1) ultrasound extraction. Chromatographic assay is performed on a hypersily ODS2 (4.6 mm x 150 mm, 5 microm) column. The mobile phase is composed of methanol -1.56% dihydric natrium phosphate hydrogen natrium solution (shift solution's acidity to 2.1 with phosphoric acid)--ethyl acetate (4:1.9:1), velocity of flow is 1 mL x min(-1); column temperature is 35 degrees C; the detection wavelength is 590 nm. RESULT: A satisfactory seperaration between hypericin and impurity. The calibration curve is linear over the range of 0.0524-0.2620 microg for hypericin (r = 0.9998). The average recovery of hypericin is 97.50%. CONCLUSION: The quantity of hypericin in Hypericum perforatum has something to do with the genetic factor, environment factor, growing period and dry means. The method of determining the quantity of hypericin can be regarded as the method of controling the quantity of medicinal materials.

Anthracenes↗
PubMed2005

Bone marrow necrosis: a rare complication of herbal treatment with Hypericum perforatum (St. John's wort).

A 22-year-old man presented with fever and ulceration of the oral mucosa. The patient had pharyngeal and esophageal candidiasis. For the 3 weeks prior to presentation, he had been taking approximately 1000 mg/day of flowering herbs (Hypericum perforatum L, known as St. John's wort) for treatment of depression. A complete blood count on the first day of hospitalization showed agranulocytosis and normocytic anemia. His condition worsened, and he developed progressive dysphagia. A bone marrow biopsy on day 3 revealed bone marrow necrosis. After the diagnosis was established (day 3 of hospitalization), treatment with granulocyte colony-stimulating factor 48 U/day, intravenous immunoglobulin 400 mg/kg, and amphotericin B 100 mg/day was initiated. The patient did not respond, and died within one week of the diagnosis. This cases suggests that Hypericum species may lead to severe hematologic toxicity, with conditions involving bone marrow necrosis.

Adult↗
PubMed2004

Continuation and long-term maintenance treatment with Hypericum extract WS 5570 after successful acute treatment of mild to moderate depression--rationale and study design.

Unipolar major depression is often a chronic disease that may require lifelong prophylaxis. Recovery from an acute episode is followed by 4-6 months of relapse prevention. After that, long-term maintenance treatment is administered to avoid recurrence. We present the rationale and design of an ongoing double-blind, randomized, placebo-controlled trial investigating the efficacy of Hypericum extract WS 5570 in relapse prevention in recurrent unipolar depression. An estimated sample of 425 adults with recurrent, mild to moderate major depression (ICD-10 and DSM-IV criteria), > or = 3 previous episodes (last 5 years) and a total score > or = 20 points on the 17-item Hamilton Rating Scale for Depression (HAMD) will be included. After a one-week wash out patients receive 3 x 300 mg/day WS 5570 single-blind for 6 weeks. Responders are randomized to 26 weeks of double-blind continuation treatment with 3 x 300 mg/day WS 5570 or placebo. Patients completing continuation treatment without relapse enter 52 weeks of doubleblind maintenance treatment, where those treated with WS 5570 are re-randomized to 3 x 300 mg/day WS 5570 or placebo. The primary outcome measure is the time to relapse during continuation treatment (HAMD > or = 16, clinical diagnosis of depression, or premature treatment termination for inefficacy). Hypericum extract, with its favourable tolerability profile, could be an interesting option for long-term prophylaxis. The trial was designed according to current consensus and guidance. Notably, it includes long-term prophylactic treatment with the same drug and the same therapeutic dose applied during acute treatment, uses well-defined outcome measures and provides a clear distinction between relapse and recurrence.

Acute Disease↗
PubMed1998

Hypericum perforatum inhibits the binding of mu- and kappa-opioid receptor expressed with the Semliki Forest virus system.

The effects of Hypericum perforatum extracts on in vitro [3H]naloxone binding to the human mu- and rat kappa-opioid receptors were studied in chinese hamster ovary (CHO) cells using the Semliki Forest virus (SFV) expression system. Binding of [3H]naloxone to the mu- and kappa-opioid receptor was inhibited in the presence of Hypericum extracts showing IC50 values of approximately 25 and 90 micrograms/ml, respectively. In contrast, extracts of Valeriana officinalis did not inhibit binding to the mu-opioid receptor. Also, single constituents of H. perforatum like the flavonoids quercetin and kaempferol and the glycosilated flavonoid quercitrin did not inhibit [3H]naloxone binding to the mu-opioid receptor up to a concentration of 10 microM. The present in vitro data may suggest a new possible mechanism for the anti-depressant effect of H. perforatum.

Animals↗
PubMed1999

Biochemical activities of extracts from Hypericum perforatum L. 1st Communication: inhibition of dopamine-beta-hydroxylase.

Extracts from the herb "St. John's wort" (Hypericum perforatum L.) are used for the treatment of mental depression, nervousness, sleeplessness and for their wound healing, diuretic and antirheumatic properties. As one biochemical mechanism for depression lack of catecholamine neurotransmitters has been discussed. The results of this investigation show that alcoholic extracts from Hypericum perforatum L. on the basis of total hypericin content inhibit dopamine-beta-hydroxylase with an IC50 of 0.1 mu mol/l; pure commercial hypericin inhibits with an IC50 of 21 mu mol/l. Enzymes involved in the synthesis of dopamine from tyrosine, namely tyrosinase and tyrosine decarboxylase, are not influenced by hypericin at concentrations from 1 up to 10 mu mol/l.

Anthracenes↗
PubMed1999

Biochemical activities of extracts from Hypericum perforatum L. 2nd Communication: inhibition of metenkephaline- and tyrosine-dimerization.

Extracts from the herb "St. John's wort" (Hypericum perforatum L.), besides other activities such as wound healing, antigout, antirheumatic and diuretic properties, are widely used to counteract neurological disorders such as depressive situations, nervousness and sleeplessness. The characteristic and leading component in these extracts, the dianthraquinone hypericin, is very likely not to represent the main active principle mediating the desirable effects. Thus, standardization of the drug is no longer based on the quantification of total hypericin and since several years simply the determination of dry matter content is in use instead. As biochemical background of depression the lack of catecholamine neurotransmitters or decreased beta-endorphins such as methionine- or leucine-enkephalins have to be envisaged. This communication reports on the inhibition of myeloperoxidase-catalyzed dimerization of enkephalins by Hypericum extracts. The substitution for enkephalins by tyrosine and for myeloperoxidase by horseradish peroxidase may represent a simple and inexpensive biochemical model reaction of pathological events during the manifestation of depressive events suitable for drug standardization.

Anthracenes↗
PubMed1999

Biochemical activities of extracts from Hypericum perforatum L. 3rd Communication: modulation of peroxidase activity as a simple method for standardization.

Alcoholic extracts from the herb "St. John's wort" (Hypericum perforatum L.) are widely used to counteract depressive situations, where the question on the mainly active principle is still under discussion. Thus, standardization of the drug on the basis of dry matter has been chosen instead of the popular leading component, hypericin. Inhibition of myeloperoxidase-catalyzed dimerization of enkephalins by Hypericum extracts has recently been reported. This method is based on the separation and quantification of enkephalin dimers by HPLC. In order to simplify this assay myeloperoxidase could be substituted by the cheaper horseradish peroxidase and the enkephalins by the amino acid tyrosine without loss of significance. In this communication we represent a more rapid photometric method based on peroxidase-catalyzed indole acetic acid oxidation suitable for quick, simple and economic drug standardization.

Chromatography, High Pressure Liquid↗
PubMed1998

Solubilized hypericin and pseudohypericin from Hypericum perforatum exert antidepressant activity in the forced swimming test.

It has been shown recently that the fraction IIIc of a crude extract of Hypericum perforatum, (St. John's wort) that contained both hypericin (1) and pseudohypericin (2), was remarkably active in the rats forced swimming test (FST) after Porsolt. However, neither of the naphthodianthrones isolated from this fraction were sufficiently effective when administered suspended in water. The solubility of 1 and 2 is remarkably increased in the presence of a fraction containing procyanidins, especially procyanidin B2, which is present also in the active Hypericum fraction IIIc. The cooperative effect of procyanidins significantly increased the in vivo effects of 1 and 2, which exhibited inverted U-shaped dose response curves, in the FST. The anti-immobility effect of solubilized 1 and 2 was antagonized by the dopamine antagonist sulpiride. These data indicate that naphthodianthrones are antidepressant constituents of H. perforatum and suggest that the dopaminergic system is involved in their action.

Animals↗
PubMed1997

Testing the antidepressant effects of Hypericum species on animal models.

This paper summarizes the antidepressant effects of certain Hypericum species on animal models. Although there are many drugs in clinical use for the management of human depression, most of the antidepressant drugs have undesirable side effects, some of which may limit the daily life of patients, and therefore, more specific agents with lesser side effects are necessary as a new therapeutic modality for the rational treatment of depression. In our laboratory, we observed antidepressant activity with the alcoholic extract of H. calycinum whose effects on the central nervous system of mice are almost equal to the extract prepared from St. John's wort, H. perforatum. Other species, H. hyssopifolium ssp. elongatum var. elongatum seems to have no antidepressant activity. From these data, it can be concluded that at least some of Hypericum species may have a potential use for the treatment of depression.

Animals↗
PubMed1999

Hypericum in seasonal affective disorder (SAD).

Volunteers from the membership of the SAD Association took part in a postal survey, before and after eight weeks' treatment with Hypericum (Kira), using an 11-item rating scale. The maximum score is 44 and the mean score in 168 patients using Kira alone was 21.3. This fell to 13 at endpoint (p < 0.001). The corresponding figures for 133 patients using Kira + light therapy were 20.6 and 11.8, respectively (p < 0.001). In both groups, there was significant improvement in anxiety, loss of libido and insomnia. There were no significant between-group differences on any measure except that improvement in sleep was greater in the Kira + light group (p < 0.01). On the results of this survey, Hypericum would appear to be an effective treatment for SAD.

Analysis of Variance↗
PubMed1999

Isolation, purity analysis and stability of hyperforin as a standard material from Hypericum perforatum L.

In 1996 131.5 million daily doses of preparations containing extracts of Hypericum perforatum L. were prescribed in Germany for treating mild to moderately severe depressive disorders. New pharmacological and clinical results focus on hyperforin as the main active ingredient of the drug. Hyperforin (C35H52O4) is one of the main components (2-4%) of the dried herb Hypericum perforatum L. It was isolated after six consecutive steps: extraction of deep-frozen blossoms (-20 degrees C) with n-hexane by means of an Ultra Turrax at room temperature; separation of lipophilic substances on a silica gel column; purification of the relevant fraction by preparative HPLC; evaporation of the mobile phase under reduced pressure; removal of the remaining water by freeze-drying; and storage of hyperforin at -20 degrees C under nitrogen. The identity and purity of the isolated substance were determined by high-performance thin-layer chromatography (HPTLC), high-performance liquid chromatography (HPLC) with diode-array and ultraviolet detection (DAD and UV), Fourier-transformed infrared (FTIR) and proton nuclear magnetic resonance (1H NMR) spectroscopy, and liquid chromatography coupled with positive-ion electrospray-ionization tandem mass spectrometry (LC-ESI(+)-MS-MS). By use of these methods the purity of hyperforin was shown to be >99.9%. Peroxides present at each step of the isolation were detected by titration and by means of Merckoquant analytical peroxide test-strips. Elimination of the peroxides and stabilization of hyperforin was achieved by consistent protection from oxidation-the mobile phases were protected by use of ascorbic acid; evaporation and freeze-drying were performed under nitrogen; and the mobile phase used for preparative HPLC was sparged with helium. Stability testing was performed by HPLC-the samples were stored at -30 degrees C in a normal atmosphere and at -20, 4, and 20 degrees C in a normal atmosphere or under nitrogen. Results were compared with those obtained after storage under liquid nitrogen (-196 degrees C). Because of its high sensitivity to oxidation, hyperforin was more stable under nitrogen under all test conditions. There was no statistically significant difference between results obtained after 8 months at -20 degrees C under nitrogen or at -30 degrees C under a normal atmosphere and those from the reference sample stored under liquid nitrogen (-196 degrees C). Despite this, because of the tendency of hyperforin to degrade, long-term storage at -70 degrees C under nitrogen is recommended.

Bridged Bicyclo Compounds↗
PubMed1995

[Treatment of depressive symptoms with a high concentration hypericum preparation. A multicenter placebo-controlled double-blind study].

In a multicenter, placebo-controlled double-blind trial, the effect on depression (ICD 10 F 32.1) of treatment with an innovative highly concentrated hypericum preparation was investigated. The study contained 97 outpatients who received 100 to 120 mg of the hypericum extract bid. The course of the illness was assessed with the Hamilton Depression Scale (HAMD), the von Zerssen Depressivity Scale (D-S) and the Clinical Global Impression Scale (CGIS). Treatment resulted in an appreciable improvement in the symptoms of depression, and the 70% response rate (n = 43), corresponded to that of chemical antidepressants. The preparation also showed an anxiolytic effect. The substance was extremely well tolerated, and no side-effects were reported by any of the patients.

Administration, Oral↗
PubMed2002

Effect of Hypericum perforatum (St John's wort) in major depressive disorder: a randomized controlled trial.

CONTEXT: Extracts of Hypericum perforatum (St John's wort) are widely used for the treatment of depression of varying severity. Their efficacy in major depressive disorder, however, has not been conclusively demonstrated. OBJECTIVE: To test the efficacy and safety of a well-characterized H perforatum extract (LI-160) in major depressive disorder. DESIGN AND SETTING: Double-blind, randomized, placebo-controlled trial conducted in 12 academic and community psychiatric research clinics in the United States. PARTICIPANTS: Adult outpatients (n = 340) recruited between December 1998 and June 2000 with major depression and a baseline total score on the Hamilton Depression Scale (HAM-D) of at least 20. INTERVENTIONS: Patients were randomly assigned to receive H perforatum, placebo, or sertraline (as an active comparator) for 8 weeks. Based on clinical response, the daily dose of H perforatum could range from 900 to 1500 mg and that of sertraline from 50 to 100 mg. Responders at week 8 could continue blinded treatment for another 18 weeks. MAIN OUTCOME MEASURES: Change in the HAM-D total score from baseline to 8 weeks; rates of full response, determined by the HAM-D and Clinical Global Impressions (CGI) scores. RESULTS: On the 2 primary outcome measures, neither sertraline nor H perforatum was significantly different from placebo. The random regression parameter estimate for mean (SE) change in HAM-D total score from baseline to week 8 (with a greater decline indicating more improvement) was -9.20 (0.67) (95% confidence interval [CI], -10.51 to -7.89) for placebo vs -8.68 (0.68) (95% CI, -10.01 to -7.35) for H perforatum (P =.59) and -10.53 (0.72) (95% CI, -11.94 to -9.12) for sertraline (P =.18). Full response occurred in 31.9% of the placebo-treated patients vs 23.9% of the H perforatum-treated patients (P =.21) and 24.8% of sertraline-treated patients (P =.26). Sertraline was better than placebo on the CGI improvement scale (P =.02), which was a secondary measure in this study. Adverse-effect profiles for H perforatum and sertraline differed relative to placebo. CONCLUSION: This study fails to support the efficacy of H perforatum in moderately severe major depression. The result may be due to low assay sensitivity of the trial, but the complete absence of trends suggestive of efficacy for H perforatum is noteworthy.

Adult↗
PubMed2005

[Effect of Hypericum perforatum extract on in vitro labelling of blood elements with technetium-99m and on biodisponibility of sodium pertechnetate in Wistar rats].

PURPOSE: To evaluate the effect of a hiperico extract (Hypericum perforatum) on the labeling of blood elements with technetium-99m (99mTc) and in the bioavailability of the radiopharmaceutical sodium pertechnetate in Wistar rats. METHODS: Blood (heparinized) withdrawn from Wistar rats is incubated with a hiperico extract, with a stannous cloride and with 99mTc, as sodium pertechnetate (99mTcONa). Plasma (P) and cells (C) are isolated by centrifugation. Samples of P and C are also precipitated with trichloroacetic acid (TCA 5%) and soluble (FS-P; FS-C) and isoluble (FI-P; FI-C) fractions are separated. In the bioavailability analysis, the extract or NaCl 0.9% solution is administrated into Wistar rats (gavage) during 15 days. Sodium pertechnetate was administered and after 10 min, the animals are sacrificed, the organs were isolated, the radioactivity determined in a well counter, and the percentages of radioactivity per gram (%ATI/g) in the organs are calculated. RESULTS: The hiperico extract decreasedsignificantly (P < 0.05) the %ATI in the cells, cellular insoluble fraction and plasma insoluble fraction. The biodistribution was significantly (P < 0.01) decreased in bone, muscle and thyroid and significantly (P < 0.05) increased in pancreas. CONCLUSION: The analysis of the results indicates that in studied extract should have substances that should oxidize the stannous ion, reducing the fixation of the 99mTc on the erythrocytes and plasma and cellular proteins. Moreover, it could produce metabolic alterations with influence in the uptake of the radiopharmaceutical 99mTcO4Na in bone, muscle, pancreas and thyroid.

Animals↗
PubMed2000

High performance liquid chromatography/electrospray mass spectrometry of Hypericum perforatum extracts.

Hypericum perforatum L. (St. John's Wort) is a widely distributed herbaceous perennial plant which has been well known as a medicinal plant since antiquity. In recent years, H. perforatum has received increasing attention for the treatment of depression and other neuralgic disorders. The main constituents of H. perforatum extract include flavonoids, naphthodianthrones, phloroglucinols, essential oils and xanthones. The present work reports the analysis of naphthodianthrones and phloroglucinols in H. perforatum extracts by means of high performance liquid chromatography (HPLC) coupled simultaneously to a diode array detector (DAD) and electrospray mass spectrometry (ESI-MS). Hypericin, pseudohypericin, hyperforin and adhyperforin were separated and identified on the base of their on-line UV and mass spectra. Quantitative analysis of hypericin derivatives in different extracts of H. perforatum using DAD and MS detectors was performed. In addition, direct infusion ESI-MS of H. perforatum extracts was applied to obtain rapid mass fingerprints of constituents present in the sample.

Chromatography, High Pressure Liquid↗
PubMed2000

Screening for the antidepressant activity of some species of Hypericum from South Brazil.

The crude methanol extracts of three species of the genus Hypericum (H. brasiliense, H. caprifoliatum and H. myrianthum) native to South Brazil were evaluated for the antidepressant activity according to the forced swimming test, a classical animal model for antidepressant drug screening. Among the species studied, only H. caprifoliatum showed activity. Thus, this plant was fractionated with solvents in increasing polarity (petroleum ether; petroleum ether: chloroform (1:1); chloroform and methanol). The petroleum ether fraction was the only one which demonstrated antidepressant activity at a dose of 270 mg/kg/day (i.p.). The chemical analyses showed that this fraction is rich in phenolic compounds, mainly of the phloroglucinol type.

Analysis of Variance↗