Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using β-cyclodextrin as a chiral mobile phase additive

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

doi:10.1016/s0378-4347(96)00359-3

Cited by 61 publications

(42 citation statements)

References 17 publications

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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).…”

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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“…20 Studies on the stereoselective neurotoxicity of TIQs have promoted the development of analytical methods for the determination of TIQ enantiomers. Several HPLC procedures [21][22][23] and a capillary electrochromatographic (CEC) method 24 were reported for the separation of Sal and N-methyl-Sal enantiomers. Gas chromatography-mass spectrometry (GC-MS) has long been used for the quantification of catecholic amines.…”

Section: Introductionmentioning

confidence: 99%

Chiral CE Separation of Dopamine-Derived Neurotoxins

et al. 2005

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An enantiomeric separation of dopamine-derived neurotoxins by capillary electrophoresis has been developed. Tetrahydroisoquinoline (TIQ), dopamine (DA), (R/S)-1-benzyl-TIQ (BTIQ), (R/S)-6,7-dihydroxy-1-methyl-TIQ (salsolinol, Sal), and (R/S)-6,7-dihydroxy-1, 2-dimethyl-TIQ (N-methyl-salsolinol, NMSal) were studied as model compounds. The CE running buffer (50 mM phosphate buffer at pH 3.0) contained 1.5 M urea and 12 mM β-CD as a chiral selector. During separation, the (R)-enantiomers formed more stable inclusion complexes with β-CD, and thus had a longer migration time than their optical antipodes. It was noticed that the recovery rates of these TIQ derivatives were very poor (< 15%) during protein precipitation, a procedure widely used for cleaning up biological samples. The recovery was significantly improved by pre-mixing the sample with a surfactant (e.g., sodium hexanesulfonate or Triton X-100) to reduce the co-precipitation. The present method in combination with electrospray ionization tandem mass spectrometry (ESI-MS/MS) was applied to study samples obtained from in vitro incubation of two catecholamines, dopamine and epinine, with aldehydes forming neurotoxins including (S)-and (R)-NMSal enantiomers. The later is known to induce Parkinsonism in rats.

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“…In the other neural degenerative disease such as Alzheimer disease, elevated b-secretase expression and enzymatic activity was detected in human brains (Yang et al 2003). It is noteworthy that the structure of ADTIQ is similar to neurotoxic salsolinol, and that ADTIQ concentrations in human brains are a hundred to thousand times higher than previously reported salsolinol levels (Deng et al 1997). Salsolinol can specifically affect the nigrostriatal dopamine system and cause a dramatic decline of dopamine level in the substantia nigra of rat (Antkiewicz-Michaluk et al 2000).…”

Section: Discussionmentioning

confidence: 78%

“…They fall into two main categories: the tetrahydroisoquinolines (TIQs) and the bcarbolines. A number of TIQ analogues, including salsolinol, are present in certain foods and beverages (Deng et al 1997), and salsolinol has been considered the most likely neurotoxin candidate for dopamine neurons in this class (Gerlach et al 1998;Naoi and Maruyama 1999). Enzymes involved in the biosynthesis and metabolism of Y. Deng (&) Á Y. Zhang Á Y. Li Á S. Xiao Á D. Song Á H. Qing Á Q. Li School of Life Science, Beijing Institute of Technology, Beijing 100081, China e-mail: deng@bit.edu.cn salsolinol were reported to be possible endogenous factors in the pathogenesis of Parkinson's disease .…”

Section: Introductionmentioning

confidence: 99%

Occurrence and distribution of salsolinol-like compound, 1-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (ADTIQ) in Parkinsonian brains

Deng

Zhang

et al. 2011

J Neural Transm

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Parkinson's disease (PD) arises from the loss of dopaminergic neurons in the substantia nigra. 1-Methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) is well known to cause Parkinsonism in humans with neurotoxicity specific for dopaminergic neurons. The experience with MPTP supports the hypothesis that endogenous or xenobiotic neurotoxins are involved in the pathogenesis of PD in humans. In our study, 1-acetyl-6, 7-dihydroxy-1, 2, 3, 4-tetrahydro-isoquinoline (ADTIQ), a novel compound, was found in frozen human brain tissues. The formation of ADTIQ was demonstrated using dopamine and methylglyoxal under physiological conditions. Methylglyoxal is a by-product of glycolysis. ADTIQ and its precursors, dopamine and methylglyoxal, were detected in different regions of frozen human brains such as the substantia nigra, caudate nucleus, putamen, frontal cortex, and the cerebellum. A significant difference in ADTIQ levels between control and Parkinson's patients was found; for instance, the ADTIQ level in putamen of PD patients was 0.76 ± 0.27 nmol/g compared to 0.10 ± 0.01 nmol/g in control. Our results might indicate that ADTIQ is possibly related to Parkinson's disease.

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Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using β-cyclodextrin as a chiral mobile phase additive

Cited by 61 publications

References 17 publications

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

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

Chiral CE Separation of Dopamine-Derived Neurotoxins

Occurrence and distribution of salsolinol-like compound, 1-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (ADTIQ) in Parkinsonian brains

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