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PubMed1982

Consumption of poisonous plants (Senecio jacobaea, Symphytum officinale, Pteridium aquilinum, Hypericum perforatum) by rats: chronic toxicity, mineral metabolism, and hepatic drug-metabolizing enzymes.

Effect of dietary tancy ragwort (Senecio jacobaea), comfrey (Symphytum officinale), bracken (Pteridium aquilinum) and alfalfa (Medicago sativa) on hepatic drug-metabolizing enzymes in rats were measured. Tansy ragwort and bracken increased (P less than 0.05) the activity of glutathione transferase and epoxide hydrolase. Comfrey and alfalfa increased (P less than 0.05) the activity of aminopyrine N-demethylase. Feeding bracken or St. John's wort (Hypericum perforatum) in conjunction with tansy ragwort did not influence chronic toxicity of tansy ragwort as assessed by rat survival time. Dietary tansy ragwort resulted in increased (P less than 0.05) hepatic copper levels; the other plants did not affect copper levels. The results do not suggest any major interaction in the toxicity of tansy ragwort with bracken or St. John's wort.

Animals↗
PubMed1999

Neuroendocrine evidence for dopaminergic actions of hypericum extract (LI 160) in healthy volunteers.

BACKGROUND: We studied the effect of a single dose of a formulation of a methanolic extract of Hypericum perforatum (HP), also known as St. John's wort, on plasma concentrations of growth hormone (GH), prolactin (PRL), and cortisol (CORT) in 12 healthy male volunteers. METHODS: Subjects received 9 tablets of the finished product Jarsin 300 and placebo in a double-blind, balanced-order, cross-over design. RESULTS: Following HP relative to placebo, there was a significant increase in plasma GH and a significant decrease in plasma PRL. Plasma CORT levels were unchanged. CONCLUSIONS: Taken together with data from animal experimental studies, the findings suggest that this dose of HP may increase some aspects of brain dopamine function in humans.

Adult↗
PubMed1997

Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L.

The biosynthesis of xanthones was studied in cell cultures of Hypericum androsaemum L. We have detected a new benzophenone synthase, for which the preferred substrate is benzoyl-CoA, itself supplied by 3-hydroxybenzoate:coenzyme A ligase. The stepwise condensation of benzoyl-CoA with three molecules of malonyl-CoA, catalyzed by benzophenone synthase, yields 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by benzophenone 3'-hydroxylase, a cytochrome P450 monooxygenase. These biosynthetic steps, leading to the formation of 2,3',4,6-tetrahydroxybenzophenone, represent an alternative pathway to that recently proposed for cell cultures of Centaurium erythraea [Peters et al., Planta (1997) in press].

Acyl Coenzyme A↗
PubMed1994

An antifungal gamma-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense.

A new gamma-pyrone (hyperbrasilone), three known xanthones (1,5-dihydroxyxanthone, 5-hydroxy-1-methoxyxanthone and 6-deoxyjacareubin) and betulinic acid have been isolated from a dichloromethane extract of stems and roots of Hypericum brasiliense. Their structures were established by spectroscopic methods (UV, EI-MS, 1H and 13C NMR) and that of the gamma-pyrone was confirmed by X-ray crystallography. Hyperbrasilone and the xanthones were all antifungal against Cladosporium cucumerinum, while the three xanthones showed differing degrees of inhibition of monoamine oxidase A and B.

Animals↗
PubMed2001

Benzopyrans from Hypericum polyanthemum.

From the aerial parts of Hypericum polyanthemum Klotzsch ex Reichardt (Guttiferae), three chromenes, 6-isobutyryl-5,7-dimethoxy-2,2-dimethyl-benzopyran; 7-hydroxy-6-isobutyryl-5-methoxy-2,2-dimethyl-benzopyran and 5-hydroxy-6-isobutyryl-7-methoxy-2,2-dimethyl-benzopyran were isolated. Their structures were determined by NMR spectroscopic analyses.

Benzopyrans↗
PubMed2001

Benzophenone O-glucoside, a biogenic precursor of 1,3,7-trioxygenated xanthones in Hypericum annulatum.

Two benzophenones, hypericophenonoside (1) and annulatophenone (2) were isolated from the methanol extract of the herb of Hypericum annulatum. The structures of the benzophenones were established as 2'-O-beta-D-glucopyranosyl-2,4,5',6-tetrahydroxy benzophenone (1) and 2,3',5',6-tetrahydroxy-4-methoxybenzophenone (2) based on spectral and chemical evidence. Hypericophenonside is the second benzophenone O-glycoside found in nature. Acid and enzymatic hydrolysis of (1) led directly to the formation of 1,3,7-trihydroxyxanthone (gentisein). This fact confirmed the hypothesis that some xanthones could be formed in plants by dehydration of 2,2'-dihydroxybenzophenones, and the intermediate precursors appear to be benzophenone O-glycosides ortho to the carbonyl function.

Benzophenones↗
PubMed2002

Two benzophenone O-arabinosides and a chromone from Hypericum annulatum.

Two benzophenone O-arabinosides, annulatophenonoside (1) and acetylannulatophenonoside (2) were isolated from the methanol extract of the herb of Hypericum annulatum. The structures of the benzophenones were established as 2-O-alpha-L-arabinofuranosyl-3',5',6-trihydroxy-4-methoxybenzophenone (1) and 2-O-alpha-L-3"-acetylarabinofuranosyl-3',5',6-trihydroxy-4-methoxybenzophenone (2) based on spectral and chemical evidence. A chromone, 5,7-dihydroxy-3-methylchromone (3) was isolated from the chloroform extract. Although it has been previously synthesized it is encountered in a plant source for the first time. Co-occurrence of the two new benzophenone O-arabinosides along with the biogenetically related 1,5,7-trihydroxy-3-methoxyxanthone was not found.

Benzophenones↗
PubMed1998

Oxidation products of hyperforin from Hypericum perforatum.

The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by means of 2D NMR methods is reported. The products had the same 1-(2-methyl-1-oxopropyl)-2,12-dioxo-3,10 beta-bis(3-methyl-2-butenyl)-11 beta-methyl-11 alpha-(4-methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0(4,8)]-3-dodec ene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-l-hydroxyethyl group in the 6 beta-position, whereas the other compound (a hemiacetal, C32H46O5), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6 alpha- and 6 beta-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.

Anti-Bacterial Agents↗
PubMed1998

Xanthones from Hypericum japonicum and H. henryi.

From the aerial part of Hypericum japonicum, one new xanthone glycoside, 1,5-dihydroxyxanthone-6-O-beta-D-glucoside, one novel dimer xanthone, bijaponicaxanthone, and the first natural prenylated xanthone, 1,3,5,6-tetrahydroxy-4-prenylxanthone, were isolated together with the four known xanthones, 1,5,6-trihydroxyxanthone, isojacereubin, 6-deoxyisojacareubin and 4',5'-dihydro-1,5,6-trihydroxy-4',4',5'-trimethylfurano (2',3':4,5) xanthone. five previously known xanthones, kielcorin, cadensin, 1,7,-dihydroxyxanthone, 1,5-dihydroxy-4-methoxyxanthone and 1,2,5-trihydroxyxanthone were also found in the dichoromethane extract of the stems and leaves of H. henryi. Their structures were elucidated by spectroscopic and chemical methods. Some of the compounds from H. japonicum were found to exert an interesting coagulant activity in an in vitro test. The chemotaxonomic value of xanthones is discussed briefly.

Animals↗
PubMed2001

Antibacterial spectrum of Hypericum hookerianum.

The antibacterial activity of the chloroform, acetone and methanol extracts of Hypericum hookerianum leaves and stems was evaluated. All extracts showed antibacterial activity against six different gram-positive and gram-negative bacteria, the methanol extracts exhibiting the maximum inhibitory activity at 400 microg/ml.

Anti-Bacterial Agents↗
PubMed1997

Determination of naphthodianthrones in plant extracts from Hypericum perforatum L. by liquid chromatography-electrospray mass spectrometry.

The determination of the naphthodianthrone constituents in extracts of dried blossoms of Hypericum perforatum L. by combined HPLC-electrospray mass spectrometry is described. Hypericin (1), pseudohypericin (2) and their precursor compounds produce intensive negative quasi-molecular ions by deprotonation provided a non-acidic eluent system is used in the HPLC separation. From the [M-H]- ions formed in the electrospray ionization process characteristic daughter ion spectra can be obtained by collisional activation which have been studied by tandem mass spectrometry.

Anthracenes↗
PubMed1999

Efficacy of an Hypericum perforatum (St. John's wort) extract in preventing and reverting a condition of escape deficit in rats.

The treatment of unselected depressed patients with an hydro-alcoholic extract of Hypericum perforatum has been reported to have an efficacy similar to that of classical antidepressants. In the present report, the effects of H. perforatum were studied on three animal models of depression: (i) an acute form of escape deficit (ED) induced by an unavoidable stress; (ii) a chronic model of ED, which can be maintained by the administration of mild stressors on alternate days; (iii) a model of anhedonia based on the finding that repeated stressors prevent the development of an appetitive behavior induced by vanilla sugar in satiated rats fed ad libitum. H. perforatum acutely protected animals from the sequelae of unavoidable stress; such an effect was partially prevented by the administration of SCH 23390 or (-)-pindolol. Moreover, H. perforatum reverted the ED maintained by repeated stressors and preserved the animal's capacity to learn to operate for earning a positive reinforcer. It was concluded that H. perforatum contains some active principle(s) endowed with antidepressant activity.

Acute Disease↗
PubMedDate not supplied

Antimicrobial and cytotoxic activity of rottlerin-type compounds from Hypericum drummondii.

Hexane extracts of Hypericum drummondii showed significant activity against the Gram-positive bacteria Staphylococcus aureus, Bacillus subtilis, and the acid-fast bacterium Mycobacterium smegmatis in an agar well diffusion assay. Employing bioassay-directed fractionation procedures, four new rottlerin-type compounds (drummondins A, B, C[1-3], and F [4]) were isolated and identified by spectral and physical characterization. The antimicrobial activity of these compounds was comparable to or greater than that demonstrated by streptomycin and generally correlated with cytotoxic activity determined with cultured P-388, KB, or human cancer cell lines (breast, colon, lung, melanoma). No cell-type selectivity was observed. In addition, two known compounds, albaspidins A-A [5] and P-P [6], were isolated and structured characterized. Neither demonstrated appreciable antimicrobial or cytotoxic activity.

Anti-Bacterial Agents↗
PubMedDate not supplied

New antimicrobial filicinic acid derivatives from Hypericum drummondii.

Bioactivity-guided fractionation of the hexane extract of the stems and leaves of Hypericum drummondii has afforded four new filicinic acid derivatives: drummondin D, isodrummondin D, drummondin E, and drummondin F. The structures of these compounds were established by spectroscopic methods. All compounds possessed strong antibiotic activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis and the acid fast bacterium Mycobacterium smegmatis.

Acetophenones↗
PubMed1999

A new chalcone, xanthones, and a xanthonolignoid from Hypericum geminiflorum.

A new prenyl chalcone, gemichalcone C (1), was isolated from the heartwood and root of Hypericum geminiflorum. Three new xanthones-6, 7-dihyroxy-1,3-dimethoxyxanthone (2), 4-hydroxy-1, 2-dimethoxyxanthone (3), and gemixanthone A (4)-and four known xanthones were isolated from the leaves and stems of the same plant.

Carbohydrate Sequence↗
PubMed1998

Significance of genetic and environmental aspects in the field cultivation of Hypericum perforatum.

Agronomical and biochemical parameters of seven Hypericum perforatum (St. John's wort) accessions grown at three experimental sites in Switzerland were followed over a two year period (1995-1996). Significant effects of environmental (= site) and genetic factors (= accession) on flowering dates, plant length, and plant dry matter production (= plant yield) were observed in both years; rankings of sites and accessions with regard to plant yield were similar in both years despite the fact that the first year crop contributed only a minor part to the overall yield of both years together. Maximum dry matter production per year reached 159 dt/ha for the total plant and 54 dt/ha for the flowering segment (i.e. the pharmaceutically relevant, upper segment of the plants comprising the majority of flowers). HPLC analysis of the constituents covered eight secondary metabolites (amentoflavone, biapigenin, hyperforin, hypericin, hyperosid, pseudohypericin, quercetin, rutin). Generally, secondary metabolite contents were significantly lower in the first year of cultivation ranging from 12% (hyperosid) to 83% (hyperforin) of the contents measured in the 1996-crop. Significant genetic effects on the production of all tested secondary metabolites (except biapigenin) were observed in 1996 whereas environmental effects appeared to be less distinct (except for amentoflavone and pseudohypericin). In conclusion, genetic factors strongly affected plant yield as well as secondary metabolite content in H. perforatum cultivation; the availability of genetically superior plant material next to improved agrotechnological methods therefore is supposed to become a key factor for successful future field production.

Chromatography, High Pressure Liquid↗