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Anisodine hydrobromide

$512

  • Brand : BIOFRON

  • Catalogue Number : BN-O1514

  • Specification : 98%(HPLC)

  • CAS number : 76822-34-9

  • Formula : C17H22BrNO5

  • Molecular Weight : 400.3

  • PUBCHEM ID : 71306882

  • Volume : 100mg

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Catalogue Number

BN-O1514

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

400.3

Appearance

Botanical Source

Structure Type

Category

SMILES

CN1C2CC(CC1C3C2O3)OC(=O)C(CO)(C4=CC=CC=C4)O.Br

Synonyms

anisodinehydrobromide/Benzeneacetic acid, α-hydroxy-α-(hydroxymethyl)-, (1R,2S,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0]non-7-yl ester, hydrobromide (1:1)/(1R,2S,4S,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0]non-7-yl 2,3-dihydroxy-2-phenylpropanoate hydrobromide (1:1)

IUPAC Name

[(1R,2S,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] 2,3-dihydroxy-2-phenylpropanoate;hydrobromide

Density

Solubility

Flash Point

253.2ºC

Boiling Point

495ºC at 760 mmHg

Melting Point

InChl

InChl Key

GJPDCORRBGIJOP-KCVSNGDFSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:76822-34-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29076436

Abstract

Background: Chronic cerebral hypoperfusion is a common pathophysiological state in various cerebrovascular diseases. Anisodine has been reported to exert neuroprotective effects in cerebral ischemia/reperfusion (I/R) animal model. However, it is unclear whether anisodine hydrobromide, the hydrobromide format of anisodine, one of the tropic alkanes alkaloids, exhibits the same neuroprotective effect on chronic cerebral hypoperfusion(CCH) rats. Herein, we tried to unravel these issues.

Methods: CCH model in adult male Sprague-Dawley rats was established by permanent ligation of the bilateral common carotid arteries [two-vessel occlusion (2-VO)] surgery. Rats were randomly divided into six groups: sham, 2-VO, 2-VO + Butyl phthalide and sodium chloride injection (NBP, as positive control group), 2-VO + anisodine hydrobromide (AH)1.2mg/kg, 2-VO +AH0.6mg/kg, 2-VO +AH0.3mg/kg. Cognitive behavior was examined by Morris Water Maze Test. Neuronal survival and apoptosis were evaluated by Nissl staining and Terminal-deoxynucleoitidyl transferase mediated nick end labeling (TUNEL staining). The relative monoamine neurotransmitter (5-hydroxytryptamine (5-HT), norepinephrine (NA)), the content of Ach, the activity of acetylcholin esterase (AchE) were measured in cholinergic system, and the protein expressions of Bcl-2, Bax, p-Akt and p-GSK-3βwere detected by Western blot assay.

Results: The results showed that there is significant memory impairment and a remarkable neuron necrosis and apoptosis, along with the dysfunction of the neurotransmitter systems and central cholinergic system in CCH rats. AH treatment could significantly improve cognitive deficits, while reducing neuron necrosis and apoptosis, apart from increasing the content of 5-HT and decreasing the activity of AchE markedly. Further study revealed that AH could promote the protein expression of Bcl-2, phosphorylation of Akt and GSK-3β, and downregulate the protein of Bax.

Conclusion: AH was demonstrated to ameliorate memory deficits by revising the imbalance of the monoamine neurotransmitter and cholinergic dysfunction. Moreover, AH can attenuate neuronal cell death and apoptosis by activating the Akt/GSK-3βsignaling pathway.

KEYWORDS

Anisodine hydrobromide; apoptosis; cholinergic dysfunction; chronic cerebral hypoperfusion; cognitive deficits; necrocytosis.; neurotransmitter.

Title

Low Dose of Anisodine Hydrobromide Induced Neuroprotective Effects in Chronic Cerebral Hypoperfusion Rats

Author

Dandan Chen 1 2, Cheng Peng 1 2 3, Xiaofang Xie 1 2, Qiuling Chen 1, Han Liu 1, Shiyang Zhang 1, Feng Wan 4, Hui Ao 3

Publish date

2017

PMID

26767288

Abstract

Objective: To establish an HPLC fingerprint of Anisodus tanguticus root for its quality control.

Methods: The analysis was carried out on a Ultimate AQ C18 (250 mm x 4.6 mm, 5 μm) column with the gradient elution of acetonitrile and KH2PO4 buffer soution, whose pH was adjusted to 3.0 with phosphoric acid. The flow rate, column temperature, detection wavelength and injection volume was 1.0 mL/min, 30 degrees C, 210 nm and 10 μL separately. The similarity evaluation and principal component analysis were used to analyze HPLC fingerprint of Anisodus tanguticus root.

Results: HPLC fingerprint of Anisodus tanguticus root was established with 15 common peaks by determining 18 batches of Anisodus tanguticus root samples. Four characteristic peaks, anisodine, scopolamine, anisodamine and anisodamine, were confirmed by comparing their retention time and UV spectrum with standard reference substances. The simiarities of 18 batches of Anisodus tanguticus root were between -0.891 and 0.987. Comprehensive evaluation scores of 18 batches of Anisodus tanguticus root were between -0.85 and 0.89 by principal component analysis.

Conclusion: The established HPLC fingerprint has good precision, repeatability and stability, which can provide more comprehensive information for identification and quality control of Anisodus tanguticus root.

Title

[HPLC Fingerprint of Anisodus Tanguticus Root]

Author

Yun-bin Jiang, Yan Gou, Mao-hua Yuan, Yu-ying Ma, Juan Zhou, Pi-e Wu

Publish date

2015 May

PMID

31514980

Abstract

Current study systematically investigated the interaction of two alkaloids, anisodine and monocrotaline, with organic cation transporter OCT1, 2, 3, MATE1 and MATE2-K by using in vitro stably transfected HEK293 cells. Both anisodine and monocrotaline inhibited the OCTs and MATE transporters. The lowest IC50 was 12.9 µmol·L-1 of anisodine on OCT1 and the highest was 1.8 mmol·L-1 of monocrotaline on OCT2. Anisodine was a substrate of OCT2 (Km = 13.3 ± 2.6 µmol·L-1 and Vmax = 286.8 ± 53.6 pmol/mg protein/min). Monocrotaline was determined to be a substrate of both OCT1 (Km = 109.1 ± 17.8 µmol·L-1, Vmax = 576.5 ± 87.5 pmol/mg protein/min) and OCT2 (Km = 64.7 ± 14.8 µmol·L-1, Vmax = 180.7 ± 22.0 pmol/mg protein/min), other than OCT3 and MATE transporters. The results indicated that OCT2 may be important for renal elimination of anisodine and OCT1 was responsible for monocrotaline uptake into liver. However neither MATE1 nor MATE2-K could facilitate transcellular transport of anisodine and monocrotaline. Accumulation of these drugs in the organs with high OCT1 expression (liver) and OCT2 expression (kidney) may be expected.

KEYWORDS

Anisodine; MATE; Monocrotaline; OCT; Organic cation transporter.

Title

An in Vitro Study on Interaction of Anisodine and Monocrotaline With Organic Cation Transporters of the SLC22 and SLC47 Families

Author

Jia-Yin Chen 1, Jurgen Brockmoller 2, Mladen V Tzvetkov 2, Li-Jun Wang 1, Xi-Jing Chen 3

Publish date

2019 Jul


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