We Offer Worldwide Shipping
Login Wishlist

Rhynchophylline

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-R2004

  • Specification : 98%

  • CAS number : 76-66-4

  • Formula : C22H28N2O4

  • Molecular Weight : 384.47

  • PUBCHEM ID : 5281408

  • Volume : 20mg

In stock

Quantity
Checkout Bulk Order?

Catalogue Number

BF-R2004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

384.47

Appearance

White crystalline powder

Botanical Source

Uncaria rhynchophylla,Uncaria macrophylla,Uncaria hirsuta

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

Methyl-(7β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat/Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate/Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate/Mitrinermine/Rhyncophylline/mitrinermin/Methyl (2E)-2-[(3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-1,2,2',3',6',7',8',8a'-octahydro-5'H-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyacrylate/Methyl (7β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate/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-, methyl ester, (αE,3S,6'S,7'S,8'aS)-/methyl (7β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate/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-, methyl ester, (αE,3R,6'R,7'S,8'aS)-/Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-2',3',6',7',8',8'a-hexahydro-2-hydroxy-α-(methoxymethylene)-, methyl ester, (αE,3R,6'R,7'S,8'aS)-/rhynchophyllin/RHYNCHOLPHYLLINE

IUPAC Name

methyl (E)-2-[(3R,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

Density

1.2±0.1 g/cm3

Solubility

Methanol; Acetontrile; Acetone; DMSO

Flash Point

293.0±30.1 °C

Boiling Point

560.8±50.0 °C at 760 mmHg

Melting Point

216°; mp 197-199° (Ban et al., loc. cit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:76-66-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29476799

Abstract

In the past few years, ketamine, a noncompetitive NMDA antagonist, has been widely abused worldwide as a new type of synthetic drug, severely affecting the physical and mental health of ketamine abusers. Previous studies have suggested that rhynchophylline can alleviate drug abuse and reverse the conditioned place preference caused by the abuse. MicroRNAs (miRNAs) are important factors regulating gene expression and are involved in the drug addiction process. The hippocampus is a critical area in the brain involved in causing drug addiction. However, the hippocampal miRNA expression profile and the effects of rhynchophylline on miRNA expression during ketamine abuse have not been reported. Thus, this study analyzed the hippocampal miRNA expression profile during ketamine-dependence formation and the effects of rhynchophylline on the differential expression of miRNAs induced by ketamine. The results of microarray analysis suggested that the expression levels of miR-331-5p were significantly different among three groups (the control, ketamine, and ketamine + rhynchophylline groups). miR-331-5p levels were significantly decreased in the ketamine model group and were upregulated in the ketamine + rhynchophylline group. Bioinformatics analysis of miR-331-5p and the 3′ UTR of nuclear receptor related 1 protein (Nurr1) identified binding sites and showed downregulation, and the overexpression of miR-331-5p in hippocampal tissues showed that miR-331-5p is a negative transcription regulatory factor of Nurr1. Interestingly, we found that the downstream protein of Nurr1, brain-derived neurotrophic factor (BDNF), showed identical expression trends in the hippocampus as Nurr1. However, the transcription of the protein upstream of Nurr1, cyclic adenosine monophosphate response element-binding protein (CREB), did not show any significant differences between the ketamine group and the ketamine + rhynchophylline group. However, after rhynchophylline intervention, p-CREB showed significant differences between the ketamine and the ketamine + rhynchophylline groups. In summary, miR-331-5p is a key regulatory factor of Nurr1, and rhynchophylline can participate in the process of resistance to ketamine addiction through the miR-331-5p/Nurr1/BDNF pathway or inhibition of CREB phosphorylation.

Copyright © 2018 Elsevier Inc. All rights reserved.

KEYWORDS

BDNF; CREB; Ketamine addiction; Nurr1; Rhynchophylline; miRNA

Title

Effects of rhynchophylline on the hippocampal miRNA expression profile in ketamine-addicted rats.

Author

Li C1, Tu G2, Luo C1, Guo Y3, Fang M1, Zhu C1, Li H1, Ou J1, Zhou Y1, Liu W1, Yung KKL4, Mo Z5.

Publish date

2018 Aug 30

PMID

29951541

Abstract

Eighteen Sprague-Dawley rats were randomly divided into three groups: ketamine group, rhynchophylline group, and ketamine combined with rhynchophylline group (n = 6). The rats of two groups received a single intraperitoneal administration of 30 mg/kg ketamine and 30 mg/kg rhynchophylline, respectively, and the third group received combined intraperitoneal administration of 30 mg/kg ketamine and 30 mg/kg rhynchophylline together. After blood sampling at different time points and processing, the concentrations of ketamine and rhynchophylline in rat plasma were determined by the established ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method. Chromatographic separation was achieved using a UPLC BEH C18 column (2.1 mm × 50 mm, 1.7 μm) with carbamazepine as an internal standard (IS). The initial mobile phase consisted of acetonitrile and water (containing 0.1% formic acid) with gradient elution. Multiple reaction monitoring (MRM) modes of m/z 238.1 → 179.1 for ketamine, m/z 385.3 → 159.8 for rhynchophylline, and m/z 237.3 → 194.3 for carbamazepine (IS) were utilized to conduct quantitative analysis. Calibration curve of ketamine and rhynchophylline in rat plasma demonstrated good linearity in the range of 1-1000 ng/mL (r > 0.995), and the lower limit of quantification (LLOQ) was 1 ng/mL. Moreover, the intra- and interday precision relative standard deviation (RSD) of ketamine and rhynchophylline were less than 11% and 14%, respectively. This sensitive, rapid, and selective UPLC-MS/MS method was successfully applied to pharmacokinetic interaction study of ketamine and rhynchophylline after intraperitoneal administration. The results showed that there may be a reciprocal inhibition between ketamine and rhynchophylline.

Title

Pharmacokinetic Interaction Study of Ketamine and Rhynchophylline in Rat Plasma by Ultra-Performance Liquid Chromatography Tandem Mass Spectrometry.

Author

Chen L1, You W1, Chen D1, Cai Y1, Wang X2, Wen C3, Wu B3.

Publish date

2018 May 23

PMID

32047439

Abstract

The increase of blood pressure accelerates endothelial progenitor cells (EPCs) senescence, hence a significant reduction in the number of EPCs is common in patients with hypertension. Autophagy is a defense and stress regulation mechanism to assist cell homeostasis and organelle renewal. A growing number of studies have found that autophagy has a positive role in repairing vascular injury, but the potential mechanism between autophagy and senescence of EPCs induced by hypertension has rarely been studied. Therefore, in this study, we aim to explore the relationship between senescence and autophagy, and investigate the protective effect of rhynchophylline (Rhy) on EPCs. In angiotensin II (Ang II)-treated EPCs, enhancing autophagy through rapamycin mitigated Ang II-induced cell senescence, on the contrary, 3-methyladenine aggravated the senescence by weakening autophagy. Similarly, Rhy attenuated senescence and improved cellular function by rescuing the impaired autophagy in Ang II-treated EPCs. Furthermore, we found that Rhy promoted autophagy by activating AMP-activated protein kinase (AMPK) signaling pathway. Our results show that enhanced autophagy attenuates EPCs senescence and Rhy rescues autophagy impairment to protect EPCs against Ang II injury.

Copyright © 2020 Lin, Zhang, Li, Ji, Chen, Li and Li.

KEYWORDS

autophagy; endothelial progenitor cells; hypertension; rhynchophylline; senescence

Title

Rhynchophylline Attenuates Senescence of Endothelial Progenitor Cells by Enhancing Autophagy.

Author

Lin L1, Zhang L2, Li XT3, Ji JK4, Chen XQ4, Li YL5,6, Li C1,5.

Publish date

2020 Jan 28


Description :

Rhyncholphylline, an alkaloid isolated from Uncaria, shows potent inhibition of lipopolysaccharide (LPS)-induced NO production in rat primary microglial cells.IC50 value:Target:In vitro: Rhyncholphylline effectively suppresses release of proinflammatory cytokines in LPS-activated microglial cells and the underling molecular mechanism for the inhibition of microglial activation; Attenuated LPS-induced production of proinflammatory cytokines such as TNF-α and IL-1β as well as NO in mouse N9 microglial cells [1]. Rhynchophylline exerts it protective action against ischemia-induced neuronal damage by preventing NMDA, muscarinic M1, and 5-HT2 receptors-mediated neurotoxicity during ischemia [3].In vivo: The neuroprotective effect of rhynchophylline was investigated in a stroke model. Following pMCAO, rhynchophylline treatment not only ameliorated neurological deficits, infarct volume and brain edema, but also increased claudin-5 and BDNF expressions (p < 0.05). Moreover, rhynchophylline could activate PI3K/Akt/mTOR signaling while inhibiting TLRs/NF-κB pathway [2].