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Objective: To identify the phytochemical constituents of Peganum harmala L. (P. harmala) seeds extract by gas chromatography-mass spectrometer (GC-MS) and evaluate their antidepressant activity. Methods: The seeds extract was analyzed by GC-MS to identify their major chemical compounds. The antidepressant activity of P. harmala was demonstrated using the forced swim test and the adrenocorticotropic hormone analysis. After oral administration of the seeds extract and diazepam in rats, the immobility time in the forced swim test was measured and the defecation rate was estimated for all rats. Results: GC-MS analysis showed the presence of indole alkaloids (β-carboline), for exmaple harmaline (48.009%), harmine (38.440%), tetrahydroharmine (8.513%), tetrahydroharman (0.061%) and 6-methoxytetrahydro-1-norharmanone (0.057%) were present in the extract. The results showed that the P. harmala extract (100 mg/kg and 300 mg/kg) were able to reduce the immobility time (80.20 ± 9.01, 46.80 ± 8.53; P < 0.001), the adrenocorticotropic hormone rate (131.33 ± 12.72, 49.72 ± 13.03; P < 0.001) and the defecation rate (1.400 ± 1.342, 0.600 ± 0.548; P < 0.01), respectively. Conclusions: This indicates that the seeds extract can correct the depression and reach the normal state of the treated animals. The results demonstrated that seeds represented a source of indole alkaloids (harmaline, harmine and tetrahydroharmine).

Introduction The Annonaceae family is known as a promising abundant source of secondary metabolites, especially annonaceous acetogenins, terpenoids and isoquinoline-derived alkaloids. Although widely investigated from the phytochemical viewpoint, this family still presents some largely unexplored genera, e.g. the Bocageopsis. Objective To investigate the alkaloid content of Bocageopsis pleiosperma Maas using direct infusion electrospray ionisation ion trap tandem mass spectrometry (ESI-IT-MSn) analysis. Methodology Dichloromethane extracts of aerial parts were subjected to acid–base partitioning to yield the alkaloidal fractions. These fractions were analysed by direct infusion into a (+)ESI-IT-MSn system. The alkaloidal fraction from the leaves was also obtained on a large scale and subjected to chromatographic separation. Results The tentative MSn-based identification of alkaloids in leaves, twigs and trunk bark showed that aporphine alkaloids were restricted to the leaves and twigs, tetrahydroprotoberberine alkaloids were only found in the twigs and trunk bark while benzylisoquinoline alkaloids were found in the leaves, twigs and trunk bark. Chromatographic separation of the leaf alkaloidal fraction yielded the aporphine alkaloids nornuciferine, asimilobine and isoboldine, the β-carboline alkaloid tetrahydroharman and some mixtures containing benzylisoquinoline and aporphine alkaloids, all described for the first time in the Bocageopsis genus. Furthermore, tetrahydroharman has not previously been reported in the Magnoliales order. Conclusion Direct infusion ESI-IT-MSn analysis of alkaloids allowed fast recognition of alkaloidal classes previously reported in the Annonaceae family, aiding the chromatographic step and allowing a selective isolation of compounds previously not identified in the Bocageopsis genus. Copyright © 2015 John Wiley & Sons, Ltd.

A high performance liquid chromatographic method was developed to determine all types of β-carboline alkaloids in medicinal and edible plants. The alkaloids, including internal standards, were purified from plant homogenates by serial extractions after reacting with fluorescamine. The extracts were analysed twice using reversed-phase chromatography with fluorometric detection optimized for each individual analyte. β-Carbolines and tetrahydro-β-carbolines were analysed in the first run, while dihydro-β-carbolines were analysed in the second. The simultaneous separation of harmol, norharman, harman, harmine, harmalol, harmaline, tetrahydronorharman, tetrahydroharman and two internal standards was achieved within 17 min by an isocratic elution. β-Carbolines, dihydro-β-carbolines and tetrahydro-β-carbolines could be quantitatively determined in concentrations of 0.01–50.0 ng/mL. In replicate spiking experiments, the mean recovery was 71–110% and the relative standard deviation was 0.3–10.1% within and between assays. Application of the proposed method has revealed that medicinal plants and dried edible plants contain β-carboline alkaloids at ng/g to µg/g levels. Norharman and harman were distributed in all the tested plants, while harmol and harmalol were found only in some plant species. However, no significant amounts of tetrahydro-β-carbolines were detected in any plant materials tested, suggesting that the oxidation of tetrahydro-β-carbolines to β-carbolines occurs during the drying and/or the storing process. The β-carboline alkaloids may be responsible for the pharmacological effects of certain medicinal plants. Copyright © 1999 John Wiley & Sons, Ltd.

Helicobacter pylori contains alcohol dehydrogenase which oxidizes ethanol to acetaldehyde. In the present study, H . pylori cytosol was incubated in a buffered media at pH 6.0 and 7.4 in the presence of ethanol and tryptamine. Under these conditions, tetrahydroharman (1-methyl-tetrahydro-β-carboline) was produced as a condensation product of tryptamine and acetaldehyde. At pH 6.0, 20.60 ± 5.00% of the added tryptamine was converted to tetrahydroharman, while 27.00 ± 4.80% (mean ± SD) was converted at pH 7.4. Similar reactions between acetaldehyde and other dietary amines seem likely. Such biogenic alkaloids, if formed in vivo , might contribute to the dysphoric effects of alcohol.

1-Methyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid (1-carboxytetrahydroharman, 1-CTHH) has been detected in the brain of rats following intracerebroventricular injection of tryptamine and pyruvic acid. We now report the metabolism of this compound. Following intraperitoneal injection of 1-CTHH into rats, harmalan was found to be the major metabolite besides tetrahydroharman (THH) and harman. A high concentration of THH was measured in the lung while most of harman was found in the urine. Harmalan and THH could be detected in the brain in low concentrations. The products were separated following extraction from tissues by high-performance liquid chromatography (HPLC) on a reversed phase C18-DB column. The identity of the metabolites was confirmed by mass spectrometry (MS) analysis. The results demonstrate the role of 1-CTHH as a precursor of the biologically active compounds harmalan, THH and harman.