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Isorhynchophylline

$120

  • Brand : BIOFRON

  • Catalogue Number : AV-C10541

  • Specification : 98%

  • CAS number : 6859-01-4

  • Formula : C22H28N2O4

  • Molecular Weight : 384.5

  • PUBCHEM ID : 3037048

  • Volume : 25mg

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Catalogue Number

AV-C10541

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

384.5

Appearance

White crystalline powder

Botanical Source

Uncaria rhynchophylla(Miq.)Miq. ex Havil./Alkaloid from Uncaria and Mitragyna spp. (Naucleaceae)

Structure Type

Indoles

Category

Standards;Natural Pytochemical;API

SMILES

CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O

Synonyms

7-Isorhynchophylline/5-Methoxyindole-3-carboxylic Acid Hydrate/7-Isorhyncophylline/5-Methoxyindole-3-Carboxylic Acid/(16E,20α)-17-Methoxy-2-oxocorynox-16-en-16-carboxylic acid/Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, (αE,3S,6'R,7'S,8'aS)-/Isorhyncophylline/5-methoxyindole-2-carboxylic acid/1H-Indole-3-carboxylic acid, 5-methoxy-/5-Methoxy-1H-indole-3-carboxylic acid

IUPAC Name

methyl (E)-2-[(3S,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Applications

Isorhynchophylline (IRN), an alkaloid isolated from Uncaria rhynchophylla, possesses the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.IC50 value:Target:In vitro: Isorhynchophylline concentration-dependently inhibited the platelet-derived growth factor (PDGF)-BB-induced proliferation of PASMCs. Fluorescence-activated cell-sorting analysis showed that isorhynchophylline caused G0/G1 phase cell cycle arrest [2]. Isorhynchophylline can significantly attenuate the cardiomyocyte hypertrophy induced by AngⅡ [3].In vivo: Isorhynchophylline significantly improved spatial learning and memory function in the D-gal-treated mice. Isorhynchophylline significantly increased the level of glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT), while decreased the level of malondialdehyde (MDA) in the brain tissues of the D-gal-treated mice [1]. Isorhynchophylline prevented monocrotaline induced pulmonary arterial hypertension in rats, as assessed by right ventricular (RV) pressure, the weight ratio of RV to (left ventricular+septum) and RV hypertrophy. Isorhynchophylline significantly attenuated the percentage of fully muscularized small arterioles, the medial wall thickness, and the expression of smooth muscle α-actin (α-SMA) and proliferating cell nuclear antigen (PCNA) [2].

Density

1.4±0.1 g/cm3

Solubility

Antidepressant-like effect; Forced swimming test; Isorhynchophylline; Monoamine neurotransmitter; Reserpine antagonism; Tail suspension test

Flash Point

224.5±23.2 °C

Boiling Point

447.6±25.0 °C at 760 mmHg

Melting Point

114ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:6859-01-4) 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

27900600

Abstract

Isorhynchophylline (IRN), an oxindole alkaloid, has been identified as the main active ingredient responsible for the biological activities of Uncaria rhynchophylla (Miq) Miq ex Havil. (Rubiaceae). Previous studies in our laboratory have revealed that IRN possesses potent neuroprotective effects in different models of Alzheimer’s disease. However, the antidepressant-like effects of IRN are remained unclear. The present study aims to evaluate the antidepressant-like effects of IRN. The antidepressant-like effects of IRN was determined by using animal models of depression including forced swimming and tail suspension tests. The acting mechanism was explored by determining the effect of IRN on the levels of monoamine neurotransmitters and the activities of monoamine oxidases. Intragastric administration of IRN at 10, 20 and 40 mg/kg for 7 days caused a significant reduction of immobility time in both forced swimming and tail suspension tests, while IRN did not stimulate locomotor activity in the open-field test. In addition, IRN treatment antagonized reserpine-induced ptosis and significantly enhanced the levels of monoamine neurotransmitters including norepinephrine (NE) and 5-hydroxytryptamine (5-HT), and the activity of monoamine oxidase A (MAO-A) in the hippocampus and frontal cortex of mice. These results suggest that the antidepressant-like effects of IRN are mediated, at least in part, by the inhibition of monoamine oxidases.

KEYWORDS

Antidepressant-like effect; Forced swimming test; Isorhynchophylline; Monoamine neurotransmitter; Reserpine antagonism; Tail suspension test

Title

Antidepressant-Like Effect of Isorhynchophylline in Mice.

Author

Xian YF1, Fan D2, Ip SP1, Mao QQ1, Lin ZX3.

Publish date

2017 Feb

PMID

22406453

Abstract

Uncaria species (Gouteng in Chinese) have been used as a plant medicine to treat ailments of cardiovascular and central nervous systems. As the main alkaloid constituent of Uncaria species, isorhynchophylline has drawn extensive attention toward antihypertensive and neuroprotective activities in recent years. Isorhynchophylline mainly acts on cardiovascular and central nervous systems diseases including hypertension, brachycardia, arrhythmia, and sedation, vascular dementia, and amnesia. Isorhynchophylline also has effects on anticoagulation, inhibition vascular smooth muscle cell apoptosis and proliferation, anti-multidrug resistant of lung cells, anti-endotoxemic, and antispasmodic. The active mechanisms are related to modulation on calcium ion channel, protection neural and neuroglial cells against β-amyloid(25-35)-induced neurotoxicity and via inducing autophagy. As a candidate drug of several cardiovascular and central nervous systems diseases, isorhynchophylline will attract scientists to pursue the potential related pharmacological effects and its mechanism with new technologies. But relatively few clinical application of isorhynchophylline has been conducted on its pharmacological activities. It requires more in vivo validations and further investigations of antihypertensive and neuroprotective mechanisms of isorhynchophylline.

Copyright ? 2012 Elsevier B.V. All rights reserved.

Title

Isorhynchophylline: A plant alkaloid with therapeutic potential for cardiovascular and central nervous system diseases.

Author

Zhou JY1, Zhou SW.

Publish date

2012 Jun

PMID

30858121

Abstract

AIMS:
Excessive inflammatory response and oxidative stress are considered as important pathogenic factors in the development of acute lung injury. Isorhynchophylline (IRN), a tetracyclic oxindole alkaloid isolated from Uncaria rhynchophylla, possesses anti-inflammatory and anti-oxidant activities. Our study aimed to investigate the effects and potential mechanisms of IRN on lipopolysaccharide (LPS)-stimulated murine alveolar macrophage cell lines MH-S and NR8383.

MAIN METHODS:
CCK-8 assay was used to evaluate the cytotoxicity of IRN and LPS. Inflammatory response was assessed by detecting the mRNA expressions and release of tumor necrosis factor α (TNF-α), interleukin (IL)-1β, IL-6, and plasminogen activator inhibitor-1 (PAI-1) using qRT-PCR and ELISA. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 were examined by qRT-PCR and western blot. Oxidative stress was evaluated by detecting malondialdehyde (MDA) level and the activities of superoxide dismutase (SOD), glutathione peroxidase (GSH-Px) and catalase (CAT). The changes of the toll like receptor (TLR4)/nuclear factor-kappa B (NF-κB)/nod-like receptor protein 3 (NLRP3) inflammasome pathway was detected by western blot.

KEY FINDINGS:
Treatment with LPS or IRN for 24?h showed no cytotoxicity on MH-S and NR8383 cells. IRN pretreatment inhibited LPS-induced production of inflammatory cytokines, expressions of iNOS and COX-2, and oxidative stress in murine alveolar macrophages. Additionally, IRN inhibited LPS-induced activation of TLR4/NF-κB/NLRP3 inflammasome pathway in MH-S cells. Mechanistically, inhibition of TLR4/NF-κB/NLRP3 inflammasome pathway by si-TLR4 suppressed LPS-induced inflammation and oxidative stress in murine alveolar macrophages.

SIGNIFICANCE:
IRN exerted anti-inflammatory and anti-oxidant effects on LPS-stimulated murine alveolar macrophages via inhibition of the TLR4/NF-κB/NLRP3 inflammasome pathway.

Copyright ? 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Acute lung injury; IRN; Inflammatory response; Oxidative stress; The TLR4/NF-κB/NLRP3 inflammasome pathway

Title

Isorhynchophylline exerts anti-inflammatory and anti-oxidative activities in LPS-stimulated murine alveolar macrophages.

Author

Zhou Z1, Su Y2, Fa XE3.

Publish date

2019 Apr 15