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At least 19 recordsLinked to original sources
PubMed1997

Salsolinol and norsalsolinol in human urine samples.

The tetrahydroisoquinoline alkaloids salsolinol and norsalsolinol were found in human urine samples in concentrations ranging from 0.1 to 29.5 ng/ml. Great interindividual variation was found in urine levels of these alkaloids in a collection of chronic alcoholics and in a group of nonalcoholics. Thus, levels of the individual alkaloids are insufficient markers for distinguishing between alcoholics and nonalcoholics. However, by using the concentration ratio of norsalsolinol and salsolinol, the so-called dopamine-aldehyde adduct ratio (DAAR), significant differences between alcoholics (median 1.3) and nonalcoholics (median 0.6) were detected. This concentration ratio could serve as a marker for the processor state of the dopaminergic system.

Alcoholism↗
PubMed1979

[Chemical mechanism of the effect of alcohol].

The formation of tetrahydro-isoquinoline alkaloids in human and animal metabolisms subsequent to alcohol consumption is reported. The spectrum of identified products ranges from simple structures such as salsolinol to the complicated skeleton of protoberberines. These substances, hitherto found exclusively in plants, interfere with the biosynthesis, biodegradation and neurotransmission of the structurally closely related biogenic amines from which they are formed, and thus affect the vegetative nervous system.

Acetaldehyde↗
PubMed1976

Potentiation of ethanol narcosis by dopamine- and l-DOPA-based isoquinolines.

The isoquinolines, salsolinol and 3-carboxysalsolinol, prolong ethanol-induced narcosis in mice. Pretreatment with carbidopa increases the effect of 3-carboxysalsolinol but not of salsolinol. These results suggest that ethanol sleeping-time potentiation by l-LOPA may involve a partial conversion to the isoquinoline in vivo. A central depressant action of salsolinol or the 3-carboxy analogue is suggested.

Alkaloids↗
PubMedDate not supplied

[Pharmacologic study of dopamine catabolites on the contractility of isolated guinea pig myocardium].

Tetrahydroisoquinolines (TIQs) are alkaloids originated as natural catabolic derivatives of catecholamines (CAT). Dopamine, under special circumstances, condenses with aldehydes to produce tetrahydropapaveroline (THP), salsolinol (SOL) and salsoline (SAL). We investigated the inotropic activity of THP, SOL and SAL on the isometric contractility of papillary muscles isolated from guinea pigs hearts and compared their actions to those corresponding to adrenaline (A) and isopropylarterenol (ISO). In order to analyze their combined effects, TIQs and A were applied simultaneously. THP, SOL and SAL produced positive inotropic effects as beta receptor agonists; their actions were antagonized with propranolol. The inotropic efficacy of TIQs compared to that of catecholamines, is: CAT = 1; SAL = 0.32; THP = 0.47 and SOL = 0.32. Their middle effective dose (DE50), indicates an order of potency of: ISO = SAL greater than A = THP greater than SOL. Combination of THP or ISO with A produces an additive effect; however, SAL behaves as a partial agonist, meaning that it produces an antagonistic, non-competitive type effect on the inotropic action of adrenaline. Chemical structure of TIQs shows significant relationship with their pharmacological activity on ventricular myocardium, similar to that of catecholamines. The influence of the methoxyl group attached to C-7 in SAL, as the only difference with SOL which instead has a hydroxyl group in that position, deserves special mention; such structural difference provides to SAL bigger inotropic efficacy and potency, as well as beta adrenergic antagonistic activity. The results of the present paper emphasize the biological significance of active catabolites from catecholamines as are the tetrahydroisoquinoline compounds.

Animals↗
PubMed1982

Dopamine-derived tetrahydroisoquinolines. Novel inhibitors of dihydropteridine reductase.

Dopamine-derived tetrahydroisoquinolines, such as 3',4'-deoxynorlaudanosolinecarboxylic acid, higenamine-1-carboxylic acid, higenamine, and salsolinol, inhibit human liver dihydropteridine reductase noncompetitively with Ki values ranging from 1.5 to 90 microM. The enzyme is also inhibited noncompetitively by dopamine (Ki = 6 microM) and aminopterin (Ki = 100 microM) but uncompetitively by phenylpyruvic acid (Ki = 6.5 mM). These alkaloids may alter monoamine metabolism in mammals by inhibiting dihydropteridine reductase.

Alkaloids↗
PubMed2004

[Asymmetric reactions based on activation and structure control of molecule--asymmetric reaction of lithiated nucleophiles].

The methodology we developed relies on an external chiral coordinating reagent that forms a deaggregated chelate complex with organolithium reagents. Under the positive control of a chiral dimethyl ether of stilbenediol 4, an asymmetric conjugate addition reaction of organolithium reagents with unsaturated imines and esters proceeded successfully to yield the corresponding addition products with reasonably high stereoselectivity. The sense of stereochemistry is predictable based on a coordination model. The methodology has been extended to a catalytic asymmetric 1,2-addition reaction of organolithium reagents with imines. An enantiotopic group differentiating the opening of cyclohexene oxide with organolithium was also mediated by a chiral ligand. The asymmetric Horner-Wadsworth-Emmons reaction of phosphonates and Peterson reaction of alpha-silylester with 4-substituted cyclohexanone were another successful extension of the methodology. A three-component reagent of lithium ester enolate, lithium amide, and chiral diether reacts with imines to afford beta-lactam with reasonably high enantioselectivity. Tridentate aminoether ligands were also shown to affect the catalytic asymmetric addition of lithium ester enoaltes to imines, giving beta-lactams with high enantioselectivity. Asymmetric conjugate addition of lithium amide to enoates was mediated by a chiral diether ligand to give the beta-aminoester with high yield and enatioselectivity. The methodology has been successfully applied to an asymmetric synthesis of biologically potent compounds. Dihydrexidine, a promising anti-Parkinsonism candidate, and salsolidine, a representative isoquinoline alkaloid, have been synthesized using asymmetric addition reactions of organolithium reagents as the key steps.

Antiparkinson Agents↗
PubMed2004

[Studies on the alkaloids from Salsola collina Pall].

AIM: To study the chemical constituents of Salsola collina Pall.. METHODS: Compounds were isolated by silica gel column chromatography. IR, MS, 1HNMR, 13CNMR, HMQC, HMBC, DEPT were used for the structural identification. RESULTS: Two amide alkaloids were obtained. They were identified as N-transferuloyl-3-methyldopamine (I), (10bS)-1,2,3,5,6, 10b-hexahydropyrrolo [2,1-a]-8,9-dihydroxyisoquinoline-3-one (II). CONCLUSION: Compound I was isolated from this genus for the first time. Compound II is a new compound named salsoline A.

Molecular Structure↗
PubMed1999

A systematic regional study of dopamine and dopamine-derived salsolinol and norsalsolinol levels in human brain areas.

Dopamine and the dopamine-derived tetrahydroisoquinoline alkaloids salsolinol and norsalsolinol were measured by high-performance liquid chromatography with electrochemical detection in 15 regions of the human brain. The regional distribution of dopamine in 32 brains was similar to previous reports with highest concentrations in the basal ganglia, especially in the striatum, followed by the substantia nigra and the hypothalamus. Significant amounts of salsolinol and norsalsolinol were only found in these dopamine-rich areas, whereas in the other regions no alkaloids were detected. These findings suggest that the concentration of the substrate dopamine may determine the alkaloid level during in vivo formation.

Adult↗
PubMed1993

Dopamine-derived tetrahydroisoquinolines and Parkinson's disease.

The daily urinary excretion of salsolinol, 1,2-dehydrosalsolinol, and norsalsolinol, as free, glucuronide, and sulfate, has been measured in parkinsonian patients and age-matched controls in an attempt to examine whether the determination of dopamine-derived alkaloids in urine may be used as a marker of the decrease in brain dopamine levels associated with the disease. In contrast with a preliminary study where the daily urinary excretion of total salsolinol was significantly higher in young controls than in parkinsonians, in the present study no difference was found between parkinsonian patients and controls concerning salsolinol and norsalsolinol excretion. However, the urinary excretion of total 1,2-dehydrosalsolinol was significantly higher in the control group, owing to a statistically significant increase in its excretion as sulfate in this group. Further studies appear to be necessary to establish whether 1,2-dehydrosalsolinol, salsolinol, and/or any other dopamine-derived alkaloid may serve for the detection of subjects with dysfunctions of the dopaminergic system.

Aged↗
PubMed1993

Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines.

The in vivo effects of dopamine-derived alkaloids, 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines, salsolinols, and their N-methylated derivatives on a dopaminergic cell model, clonal rat pheochromocytoma PC12h cells, were examined by culture in the presence of various concentrations of the agents. The effects were evaluated in comparison with those by 1,2,3,4-tetrahydroisoquinoline and its N-methylated derivatives. Among 1,2,3,4-tetrahydroisoquinolines, only N-methylisoquinolinium ion had cytotoxic effect on PC12h cells. In general, 6,7-dihydroxyisoquinolines had more potent cytotoxic effect than N-methylisoquinolinium ion, and they reduced protein amounts of PC12h cells at 100 microM and 1 mM concentration. The specific activity of tyrosine hydroxylase, the rate-limiting enzyme in dopamine biosynthesis, decreased with these isoquinolines at concentrations lower than those required to reduce the protein amount. The toxicity of N-methylated derivatives seems to be more potent than non-methylated isoquinolines. Salsolinols were proved to be accumulated in the mitochondrial fraction of the cells after 3 days in culture. N-methyl-1,2,3,4-tetrahydroisoquinoline depleted ATP from PC12h cells and it was prevented by preincubation with an inhibitor of type-A monoamine oxidase, clorgyline. These results indicate that N-methylated and oxidized derivatives of dopamine-derived alkaloids may be potent dopaminergic neurotoxins similar to 1-methyl-4-phenylpyridinium ion in the human brain and may induce Parkinson's disease after long years of accumulation.

Animals↗
PubMedDate not supplied

[Interaction of various tetrahydroisoquinoline alkaloids with opiate receptors in the rat hypothalamus and midbrain].

Using the method of competitive displacement of 3H-labelled naloxone, (D-ala2)-met enkephalinamide or (D-ala2)-D-leu-enkephalin by salsolinol, 1-methyl-6-hydroxy-1, 2, 3, 4-tetrahydro-beta-carboline or 1-methyl-6-methoxy-1, 2, 3, 4-tetrahydro-beta-carboline from opiate receptors, it was shown that the alkaloids studied were capable to cause specific interactions with rat hypothalamus and midbrain however, exhibiting distinctly less affinity as compared with morphine or its analogs. The sodium ratios, determined from the effective doses of the tetrahydroisoquinoline alkaloids corresponding to the alkaloid concentrations, which induce 50% displacement of 3H-naloxone from the opiate receptors in the presence or absence of 100 mM NaCl, have been found to be 0.75 for salsolinol and 3.6 for beta-carbolines studied. The data obtained suggest that salsolinol, similar to naloxone, is a "pure" morphine antagonist, whereas the beta-carbolines studied may be classified with the agonist-antagonist type. A considerable decrease in the affinity of mu-type opiate receptors has been found in presence of salsolinol in the incubation medium. The possible mechanisms of pharmacological action of the alkaloids and their relation to development of alcohol dependence and tolerance are discussed.

Alcoholism↗
PubMed2005

Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics.

BACKGROUND: Dopamine (DA)-derived tetrahydroisoquinolines (TIQs) are discussed as neurochemical factors of addiction processes in alcoholism. In a prospective study, the regional distribution of DA, (R)-salsolinol (SAL), and (S)-SAL, as well as norsalsolinol (NorSAL) was examined systematically in a large collective of human brain samples obtained by autopsy. METHODS: The material comprises 44 brains of alcoholics and 47 controls with 6 standardized specimens in each case. The analytes were determined after solid-phase extraction and enantioselective derivatization using gas chromatography-mass spectrometry. RESULTS: Levels of DA, (R/S)-SAL, and NorSAL in alcoholics did not differ significantly from those of the control group. A relationship between alcohol consumption and SAL formation could not be proved. Topical differences and no ubiquitous occurrence were encountered. Significant amounts of (R)-SAL and (S)-SAL as well as NorSAL only were found in DA-rich areas of the basal ganglia, whereas in other regions of the brain, no TIQs were detected. Especially in the nucleus caudatus, the concentrations of DA, SAL, and NorSAL decreased significantly with rising age. CONCLUSION: These findings do not support the hypothesis that one of the SAL enantiomers or NorSAL is involved in the genesis of alcoholism. However, they suggest that the concentration of the substrate DA may determine the alkaloid level during in vivo formation. The revealed data can serve as reference for other studies in humans concerning the cause of alcoholism or other neurodegenerative diseases with the involvement of TIQs.

Adult↗
PubMed1999

Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline and salsolidine by amine N-methyltransferase A from bovine liver.

Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline (7-hydroxy-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) and salsolidine (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) by amine N-methyltransferase A isolated from bovine liver is reported. Incubation with S-adenosylmethionine as cosubstrate revealed that in case of isosalsoline, an endogenous tetrahydroisoquinoline alkaloid, the (+)-(R)-enantiomer, is preferentially methylated, whereas in the case of salsolidine the (-)-(S)-enantiomer is preferentially methylated. The results were obtained by using two independent methods, namely a radioassay and HPLC following separate incubation experiments.

Animals↗