Pharmacological properties of tetrahydronorharmane (Tryptoline)

Rommelspacher, Hans; Kauffmann, Hf; Cohnitz, Christiane Heyck; Coper, H.

doi:10.1007/bf00508615

Cited by 46 publications

(20 citation statements)

References 44 publications

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“…Tryptoline is a natural organic derivative of b-carboline. It is a competitive selective inhibitor of the enzyme monoamine oxidase type A (Teitel and Brossi, 1974;Rommelspacher et al, 1977;Cao et al, 2007;Herraiz, 2008;Movafeghi et al, 2009). The alkaloids used in this study can be divided into two groups: dihydro-b-carbolines (harmaline and harmalol) and aromatic b-carbolines (harmane, harmine).…”

Section: Introductionmentioning

confidence: 99%

Interaction of β-Carboline Alkaloids with RNA

Nafisi

Malekabady

Khalilzadeh

2010

DNA and Cell Biology

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β-Carboline alkaloids are present in medicinal plants such as Peganum harmala L., which have been used as folk medicine in anticancer therapy. Recently, they have drawn attention because of their antitumor activities. Despite considerable interest and investigations on alkaloid-DNA complexes, reports on alkaloid-RNA interaction are very limited. This study is the first attempt to investigate the binding of β-carboline alkaloids (harmine, harmane, harmaline, harmalol, and tryptoline) with yeast RNA. The effect of alkaloid complexation on RNA aggregation and condensation was investigated in aqueous solution at physiological conditions, using constant RNA concentration (6.25 mM) and various alkaloid:polynucleotide (phosphate) ratios of 1:240, 1:160, 1:80, 1:40, 1:20, 1:10, 1:5, 1:2, and 1:1. Fourier transform infrared and UV-visible spectroscopic methods were used to determine the ligand-binding modes, the binding constants, and the stability of alkaloid-RNA complexes in aqueous solution. Spectroscopic evidence showed major binding of alkaloids to RNA with overall binding constants of K(harmine)-RNA = 2.95 × 10⁷ M⁻¹, K(harmane)-RNA = 5.62 × 10⁵ M⁻¹, K(harmaline)-RNA = 7.47 × 10⁵ M⁻¹, K(harmalol)-RNA = 4.32 × 10⁵ M⁻¹, and K(tryptoline)-RNA = 3.21 × 10⁵ M⁻¹. The affinity of alkaloids-RNA binding is in the order of harmine > harmaline > harmane > harmalol > tryptoline. No biopolymer secondary structural changes were observed upon alkaloid interaction and RNA remains in the A-family structure in these complexes.

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Section: Introductionmentioning

confidence: 99%

Interaction of β-Carboline Alkaloids with RNA

Nafisi

Malekabady

Khalilzadeh

2010

DNA and Cell Biology

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“…Tetrahydronorhamane produces pharmacological effects in rats, which are similar to those of serotonin-like drugs and antagonistic to those of dopamine (3). Furthermore it could be established in in vivo and in vitro experiments that tetrahydrpnorharmane inhibits high affinity uptake of serotonin and noradrenaline into a synaptosome-rich fraction from the brain of rats and mice (4,5,6).…”

Section: Introductionmentioning

confidence: 71%

Identification of Tetrahydronorharmane (Tetrahydro-β-carboline) in Human Blood Platelets

Honecker¹,

Coper²,

Fähndrich³

et al. 1980

CCLM

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Summary: The present paper shows that tetrahydronorharmane (tetrahydro-0-carboline) exists in human platelets. The concentration of tetrahydronorharmane in platelets from 10 ml platelet rich plasma was in the range of 9.3 to 25.6 pmol (n=8). Ingestion of tryptamine hydrochloride (n=4) three times daily for three consecutive days and of 19.6 mmol Z)^-tryptophan (n=7) the evening (10 p. m.) before the blood collection did not lead to an increase of tetrahydronorharmane in platelets. Nachweis von Tetrahydronorharman (Tetrahydro-ß-carbolin) in menschlichen Thrombocyten

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“…12. 3 1] and antidopaminergic effects of Tp have been described [41]. Therefore the modulation by different serotonergic agents of the hyperprolactinemic ef fect of Tp cannot be easily interpreted because of the in volvement of multiple biochemical and neurochemical mechanisms in the action of Tp.…”

Section: Discussionmentioning

confidence: 99%

“…Since tryptolines have been shown to affect serotonergic function rather selectively, through inhibition of MAO-A activity [10,12,15,30,31,45] and/or decrease of neuronal 5-HT uptake [2,10,II,15,20,30,41,42], it was of interest to investigate the involvement of hypothalamic 5HT mecha nisms in the endocrine effects of the three compounds. Re cently tryptolines have also been shown to bind to the JHimipramine ('H-IMI) recognition site [23,25] which is lo cated presynaptically on 5HT neurons and is associated with the 5HT uptake molecular complex [24].…”

Section: Discussionmentioning

confidence: 99%

Interaction of Putative Endogenous Tryptolines with the Hypothalamic Serotonergic System and Prolactin Secretion in Adult Male Rats

Ac¹,

Brunello²,

Franzetti³

et al. 1986

Neuroendocrinology

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The effect of 5-methoxytryptoline (5-MeOT), 5-hydroxytryptoline (5-OHT) and tryptoline (Tp), putative endogenous derivatives of the tryptamines, on plasma prolactin (PRL) concentrations has been investigated in the adult male rat. The possible involvement of the hypothalamic serotonergic system has been considered in the mediation of the hormonal effect of the tryptolines. Therefore, plasma PRL levels have been evaluated in rats receiving tryptolines after different pharmacological manipulations of central serotonergic function. Although the three compounds increased the plasma titers of PRL in a dose-dependent manner and enhanced the hypothalamic content of serotonin (5HT), they appear to affect the serotonergic system through different mechanisms. In particular, 5-OHT might act at a presynaptic level, since its hyperprolactinemic effect was antagonized both by the depletion of central 5HT content after p-chlorophenylalanine and by the degeneration of serotonergic terminals after 5,7-dihydroxytryptamine. In contrast, 5-MeOT behaved as if it had a postsynaptic site of action, being counteracted by the serotonergic postsynaptic antagonists metergoline and cyproheptadine. The unsubstituted tetrahydro-β-carboline, Tp, is probably active at both pre- and postsynaptic sites. The enhancing effect of Tp on PRL secretion was antagonized by chronic treatment with p-chlorophenylalanine, while it was also maintained in 5,7-dihydroxytryptamine-lesioned rats. These findings suggest that tryptolines may play a functional role in PRL secretion by interacting with central serotonergic systems through different biochemical mechanisms.

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Pharmacological properties of tetrahydronorharmane (Tryptoline)

Cited by 46 publications

References 44 publications

Interaction of β-Carboline Alkaloids with RNA

Interaction of β-Carboline Alkaloids with RNA

Identification of Tetrahydronorharmane (Tetrahydro-β-carboline) in Human Blood Platelets

Interaction of Putative Endogenous Tryptolines with the Hypothalamic Serotonergic System and Prolactin Secretion in Adult Male Rats

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