Determination of the (R)- and (S)-enantiomers of salsolinol and N-methylsalsolinol by use of a chiral high-performance liquid chromatographic column

Deng, Yulin; Maruyama, Wakako; Dostert, P.; Takahashi, Tsutomu; Kawai, Maki; Naoi, Makoto

doi:10.1016/0378-4347(95)00136-7

Cited by 54 publications

(34 citation statements)

References 20 publications

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“…Using the microdialysis technique it was shown that the MPTP-like Nmethyl-(R)-salsolinol is formed in the rat brain by N-methylation of the R- (Maruyama et al, 1992). Both of these enantiomers were also found predominantly in the human brain (Deng et al, 1995).…”

Section: Tetrahydroisoquinolinesmentioning

confidence: 99%

Animal models of Parkinson's disease: An empirical comparison with the phenomenology of the disease in man

Gerlach

Riederer

1996

J. Neural Transmission

442

221

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Animal models are an important aid in experimental medical science because they enable one to study the pathogenetic mechanisms and the therapeutic principles of treating the functional disturbances (symptoms) of human diseases. Once the causative mechanism is understood, animal models are also helpful in the development of therapeutic approaches exploiting this understanding. On the basis of experimental and clinical findings. Parkinson's disease (PD) became the first neurological disease to be treated palliatively by neurotransmitter replacement therapy. The pathological hallmark of PD is a specific degeneration of nigral and other pigmented brainstem nuclei, with a characteristic inclusion, the Lewy body, in remaining nerve cells. There is now a lot of evidence that degeneration of the dopaminergic nigral neurones and the resulting striatal dopamine-deficiency syndrome are responsible for its classic motor symptoms akinesia and bradykinesia. PD is one of many human diseases which do not appear to have spontaneously arisen in animals. The characteristic features of the disease can however be more or less faithfully imitated in animals through the administration of various neurotoxic agents and drugs disturbing the dopaminergic neurotransmission. The cause of chronic nigral cell death in PD and the underlying mechanisms remain elusive. The partial elucidation of the processes underlie the selective action of neurotoxic substances such as 6-hydroxydopamine (6-OHDA) or 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), has however revealed possible molecular mechanisms that give rise to neuronal death. Accordingly, hypotheses concerning the mechanisms of these neurotoxines have been related to the pathogenesis of nigral cell death in PD. The present contribution starts out by describing some of the clinical, pathological and neurochemical phenomena of PD. The currently most important animal models (e.g. the reserpine model, neuroleptic-induced catalepsy, tremor models, experimentally-induced degeneration of nigrostriatal dopaminergic neurons with 6-OHDA, methamphetamine, MPTP, MPP+, tetrahydroisoquinolines, beta-carbolines, and iron) critically reviewed next, and are compared with the characteristic features of the disease in man.

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Section: Tetrahydroisoquinolinesmentioning

confidence: 99%

Animal models of Parkinson's disease: An empirical comparison with the phenomenology of the disease in man

Gerlach

Riederer

1996

J. Neural Transmission

442

221

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“…Sal has an asymmetric centre at C1 and exists as (R)-and (S )-enantiomers (Deng et al 1997). In humans, reports have shown that (R)-enantiomer of Sal can only be detected (Deng et al 1995), whereas others indicated that the enantiomer ratio of (R)-/(S )-Sal was approximately 2 (Musshoff et al 2000). In previous studies, the concentration of (R)-Sal was found to be higher than the (S )-Sal, depicting the presence of such biosynthetic enzyme in etiology of disease.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic condensation of dopamine and acetaldehyde: a salsolinol synthase from rat brain

et al. 2011

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Salsolinol (1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline; Sal) is structurally similar to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, which is supposed to have a role in the development of Parkinson-like syndrome in both human and non-human subjects. In the human brain, the amount of (R)-enantiomer of Sal is much higher than (S )-enantiomer, suggesting that a putative enzyme may participate in the synthesis of (R)-salsolinol, called (R)-salsolinol synthase. In this study, the (R)-salsolinol synthase activity in the condensation of dopamine and acetaldehyde was investigated in the crude extracts from the brains of Sprague Dawley rats. Identification of the enzymatic reaction products and enzyme activity detection were achieved by HPLC-electrochemical detection. The discovery of this enzyme activity in rat's brain indicates the natural existence of (R)-salsolinol synthase in the brains of humans and rats, and it is distributed in most brain regions of rat with higher activity in soluble proteins extracted from striatum and substantia nigra.

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“…the retention factors decreased with increasing MeOH content. In summary, the optimal mobile phase selected was a mixture of 0.1 m phosphate buffer (pH 5.2)-MeOH = 98:2 (v/v), which resulted in a similar resolution to that reported by Deng et al (1995).…”

Section: Direct Separation Of 1-and 3-substituted Tiq Enantiomersmentioning

confidence: 74%

“…1, 6,7-Dihydroxy-1-methyl-Tiq (salsolinol); 2, 1-methyl-Tiq; 3, 3-methyl-Tiq; 4, 6,7-dimethoxy-1-methylTiq (salsolidine); and 5, 6,7-dimethoxy-3-methyl-Tiq. (Liu et al, 2000) or HPLC method (Deng et al, 1995;Baum and Rommelspacher, 1994;Rommelspacher et al, 1995;Stammel and Thomas, 1993;Zhang et al, 2004a,b). However, to the best of our knowledge, no attempts have yet been made to separate the enantiomers of salsolinol analogs on the different types of CSPs developed in the past decade.…”

Section: Introductionmentioning

confidence: 99%

Comparison of column performances in direct high‐performance liquid chromatographic enantioseparation of 1‐ or 3‐methyl‐substituted tetrahydroisoquinoline analogs. Application of direct and indirect methods

Péter

Mamiro

Ilisz

et al. 2005

Biomedical Chromatography

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The enantioseparability of 1- or 3-methyl-substituted tetrahydroisoquinolines was investigated by direct and indirect high-performance liquid chromatography. Alpha- and beta-cyclodextrin-, macrocyclic glycopeptide- and cellulose-based chiral columns and isothiocyanate- and Sanger-type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, beta-cyclodextrin-, vancomycin- and teicoplanin-containing macrocyclic glycopeptide-based columns appeared to be most suitable; of the CDAs, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution.

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Determination of the (R)- and (S)-enantiomers of salsolinol and N-methylsalsolinol by use of a chiral high-performance liquid chromatographic column

Cited by 54 publications

References 20 publications

Animal models of Parkinson's disease: An empirical comparison with the phenomenology of the disease in man

Animal models of Parkinson's disease: An empirical comparison with the phenomenology of the disease in man

Enzymatic condensation of dopamine and acetaldehyde: a salsolinol synthase from rat brain

Comparison of column performances in direct high‐performance liquid chromatographic enantioseparation of 1‐ or 3‐methyl‐substituted tetrahydroisoquinoline analogs. Application of direct and indirect methods

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