(1R,9S)-(-)-β-Hydrastine - CAS 118-08-1
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(1R,9S)-(-)-β-Hydrastine
Catalog Number:
118-08-1
Synonyms:
(1R,9S)-(-)-beta-Hydrastine;Hydrastine base
CAS Number:
118-08-1
Description:
Hydrastine, a natural alkaloid compound, could be used as a dopamine biosynthesis inhibitor.
Molecular Weight:
383.39
Molecular Formula:
C21H21NO6
Quantity:
Milligrams-Grams
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2O
InChI:
InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
InChIKey:
ZCTQGTTXIYCGGC-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 118-08-1 (1R,9S)-(-)-β-Hydrastine

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Reference Reading


1.Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.
Yin SY1, Kim YM, Lee JJ, Jin CM, Yang YJ, Ma JJ, Kang MH, Kai M, Lee MK. Neuropharmacology. 2004 Dec;47(7):1045-52.
The inhibitory effects of (1R,9S)- and (1S,9R)-enantiomers of beta-hydrastine (BHS) on dopamine biosynthesis in PC12 cells were investigated. (1R,9S)-BHS decreased the intracellular dopamine content with the IC50 value of 14.3 microM at 24 h, but (1S,9R)-BHS did not. (1R,9S)-BHS was not cytotoxic at concentrations up to 250 microM towards PC12 cells. In these conditions, (1R,9S)-BHS inhibited tyrosine hydroxylase (TH) activity mainly in a concentration-dependent manner (33% inhibition at 20 microM) and decreased TH mRNA level in PC12 cells. The inhibitory patterns of dopamine content and TH activity by (1R,9S)-BHS showed similar behavioral curves. (1R,9S)-BHS at 10-50 microM also reduced the intracellular cyclic AMP level and Ca2+ concentration. In addition, treatment of L-DOPA at 20-50 microM for 24 h increased the intracellular dopamine content to 198-251% compared with the control in PC12 cells. However, the increase in dopamine levels induced by L-DOPA (20-50 microM) was reduced when L-DOPA was combined with (1R,9S)-BHS (10-50 microM).
2.Effects of hydrastine derivatives on dopamine biosynthesis in PC12 cells.
Kim SH1, Shin JS, Lee JJ, Yin SY, Kai M, Lee MK. Planta Med. 2001 Oct;67(7):609-13.
The effects of hydrastine derivatives on dopamine biosynthesis in PC12 cells were investigated. Treatments of PC12 cells with (1R,9S)-beta-hydrastine hydrochloride [(+)-beta-hydrastine HCl] and (1R,9S)-beta-hydrastine [(-)-beta-hydrastine] showed 50.6 % and 33.1 % inhibition of dopamine content at a concentration of 10 microM for 48 h. However, (1S,9R)-beta-hydrastine [(+)-beta-hydrastine] and hydrastinine hydrochloride did not reduce dopamine content. The IC(50) values of (1R,9S)-beta-hydrastine hydrochloride and (1R,9S)-beta-hydrastine were 9.3 microM and 20.7 microM , respectively. Next, the intracellular mechanisms of (1R,9S)-beta-hydrastine hydrochloride in PC12 cells were investigated. Dopamine content decreased at 6 h and reached a minimal level at 24 h after the exposure of PC12 cells to 20 microM (1R,9S)-beta-hydrastine hydrochloride. Tyrosine hydroxylase (TH) activity was inhibited at 6 h following the treatment with (1R,9S)-beta-hydrastine hydrochloride, and was maintained at a reduced level for up to 36 h in PC12 cells (17 - 27 % inhibition at 20 microM), whereas TH mRNA level was not found to alter for 24 h.
3.Effects of (1R,9S)-beta-hydrastine on l-DOPA-induced cytotoxicity in PC12 cells.
Yin SY1, Lee JJ, Kim YM, Jin CM, Yang YJ, Kang MH, Kai M, Lee MK. Eur J Pharmacol. 2004 Mar 19;488(1-3):71-7.
(1R,9S)-beta-Hydrastine in lower concentrations of 10-50 microM inhibits dopamine biosynthesis in PC12 cells. In this study, the effects of (1R,9S)-beta-hydrastine on L-DOPA (L-3,4-dihydroxyphenylalanine)-induced cytotoxicity in PC12 cells were investigated. (1R,9S)-Hydrastine at concentrations up to 250 microM did not reduce cell viability. However, at concentrations higher than 500 microM it caused cytotoxicity in PC12 cells, as determined with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, TUNEL (terminal deoxynucleotidyltransferase dUTP nick-end labeling) method and flow cytometry. Exposure of PC12 cells to cytotoxic concentrations of (1R,9S)-beta-hydrastine (500 and 750 microM) in combination with L-DOPA (20, 50 and 100 microM) after 24 or 48 h resulted in a significant decrease in cell viability compared with the effects of (1R,9S)-beta-hydrastine or L-DOPA alone, and apoptotic cell death was observed.
4.Effects of (1R,9S)-beta-hydrastine on intracellular calcium concentration in PC12 ce
Yin SY1, Kim YM, Lee JJ, Jin CM, Yang YJ, Park SK, Yoo SK, Lee MK. Biol Pharm Bull. 2007 Aug;30(8):1547-50.
(1R,9S)-beta-hydrastine (BHS) decreases the basal intracellular Ca(2+) concentration ([Ca(2+)](i)) in PC12 cells.(5) This study examined the effects of (1R,9S)-BHS on [Ca(2+)](i) in PC12 cells. (1R,9S)-BHS at 10-100 microM in combination with a high extracellular K+ level (56 mM) inhibited the release of dopamine in a concentration-dependent manner with an IC(50) value of 66.5 microM. BHS at 100 microM inhibited the sustained increase in [Ca(2+)](i) induced by a high K+ level (56 mM), and had an inhibitory effect on the 2 microM nifedipine-induced blockage of the K+ -stimulated sustained increase in [Ca(2+)](i). In addition, (1R,9S)-BHS at 100 microM prevented the rapid and sustained increase in [Ca(2+)](i) elicited by 20 mM caffeine, but did not have an effect on the increase induced by 1 microM thapsigargin, in the presence of external Ca(2+). These results suggest that the active sites of (1R,9S)-BHS are mainly L-type Ca(2+) channels and caffeine-sensitive Ca(2+)-permeable channels in PC12 cells.