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Songorine

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-S2029

  • Specification : 98%

  • CAS number : 509-24-0

  • Formula : C22H31NO3

  • Molecular Weight : 357.491

  • PUBCHEM ID : 71456946

  • Volume : 20mg

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Catalogue Number

BF-S2029

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

357.491

Appearance

White crystalline powder

Botanical Source

Aconitum carmichaelii

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCN1CC2(CCC(C34C2CC(C31)C56C4CC(=O)C(C5)C(=C)C6O)O)C

Synonyms

(1S,7R,8R,9S,10S,13R,16S)-11-Ethyl-7,16-dihydroxy-13-methyl-6-methylene-11-azahexacyclo[7.7.2.1.0.0.0]nonadecan-4-one/Napellonine/Zongorine/Bullatine G

IUPAC Name

(1R,2R,5R,7R,8R,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.15,8.01,10.02,8.013,17]nonadecan-4-one

Density

1.29

Solubility

Methanol; Acetontrile

Flash Point

201-203ºC

Boiling Point

535.8±50.0 °C at 760 mmHg

Melting Point

201-203ºC

InChl

InChI=1S/C22H31NO3/c1-4-23-10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12-,13+,15-,16-,17+,18?,19-,20+,21+,22+/m1/s1

InChl Key

CBOSLVQFGANWTL-DREQLAFGSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:509-24-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29133056

Abstract

Alkaloids are well-studied secondary metabolites, with recent preclinical studies evidencing that many of them exhibit anti-cancer, anti-depressant, anti-nociceptive, anti-inflammatory, anti-pyretic, anti-platelet, anti-oxidant, and anti-bacterial properties. Aconitum is a genus rich of diverse alkaloids. More than 450 alkaloids have been identified in a variety of species. Songorine is a C20 diterpenoid alkaloid and 12-keto analog of napelline, isolated from Aconitum soongaricum and was associated with a heterogeneous panel of biological functions. However, the bioactivity profile of this natural product has not been reviewed up to now. The present manuscript aims to summarize the most important biological activities associated with songorine administration in preclinical models. The most significant data found in the scientific literature were evaluated in order to summarize the potential clinical utility of songorine in a diverse spectrum of pathologies and conditions. Songorine and its derivatives have many pharmacological effects including anti-arrhythmic, anti-cardiac-fibrillation, excitation of synaptic transmission, anxiolytic effects, anti-nociceptive, anti-inflammatory, anti-arthritis effects, and a regenerative effect in a skin excision wound animal model. Despite its outstanding pharmacotherapeutic potential, songorine has never been tested in clinical trials. Therefore, further evaluation is required to better evaluate its clinical utility.

Copyright © 2017 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Aconitine alkaloid; Aconitum; Multiple pharmacological effects; Songorine

Title

Therapeutic potential of songorine, a diterpenoid alkaloid of the genus Aconitum.

Author

Khan H1, Nabavi SM2, Sureda A3, Mehterov N4, Gulei D5, Berindan-Neagoe I6, Taniguchi H7, Atanasov AG8.

Publish date

2018 Jun 10

PMID

30896826

Abstract

Epithelial ovarian cancer (EOC) is the most frequent cause of cancer‑associated mortality among all types of gynecological cancer. The high recurrence rate and the poor 5‑year survival rate indicate that more effective therapeutic strategies are required. The aim of the present study was to investigate the role and potential mechanisms of songorine in treating EOC. EOC cells were cultured with different concentrations of songorine, following which MTT and flow cytometric analyses were conducted to measure cell viability and apoptosis. Wound healing and Transwell assays were used to detect cell migration and invasion abilities. Furthermore, associated molecules in the glycogen synthase kinase (GSK)‑3β/β‑catenin and B‑cell lymphoma 2 (Bcl‑2)/Bcl‑2‑associated X (Bax) signaling pathways were semi‑quantified by western blotting. Finally, tumor size measurements, pathological observations, western blot analysis and toxicological evaluations were performed in SKOV‑3 tumor‑bearing BALB/c nude mice to investigate the efficacy and safety of songorine. As expected, songorine inhibited EOC cell survival, invasion and migration, promoted EOC cell apoptosis and suppressed mammalian EOC tumorigenic behavior. In particular, GSK3β inhibitor treatment restored the songorine‑induced regulation of the GSK3β/β‑catenin signaling pathway. Furthermore, in the in vitro and in vivo experiments, songorine consistently downregulated the expression of N‑cadherin, vimentin, matrix metalloproteinase (MMP)‑2, MMP‑9, phosphorylated‑GSK3β, β‑catenin and Bcl‑2, and upregulated the expression of E‑cadherin, cleaved caspase‑3, cleaved caspase‑9 and Bax. In conclusion, songorine exerted its anticancer effect through the GSK3β/β‑catenin and Bcl‑2/Bax signaling pathways. These results highlight the potential use of songorine as a novel therapeutic agent for EOC.

Title

Songorine suppresses cell growth and metastasis in epithelial ovarian cancer via the Bcl‑2/Bax and GSK3β/β‑catenin signaling pathways.

Author

Zhang H1, Dong R1, Zhang P2, Wang Y3.

Publish date

2019 May

PMID

12524165

Abstract

Songorine, a diterpenoid alkaloid isolated from the genus Aconitum, was recently found to enhance the excitatory synaptic transmission in rat hippocampus. The mechanism underlying the effects was examined in the present study. The alkaloid at 0.1-300 microM inhibited the specific binding of [(3)H]muscimol to Triton-treated synaptic membranes of rat brain in a concentration-dependent manner (IC(50)=7.06 microM; 95% confidence limits: 3.28-10.84 microM). Scatchard analysis and Lineweaver-Burk double reciprocal plot of [(3)H]muscimol saturation binding data indicate a non-competitive inhibition of the alkaloid on the gamma-aminobutyric acid(A) (GABA(A)) receptor. In acutely dissociated rat hippocampal neurons the alkaloid did not elicit current response, but markedly inhibited the GABA-induced inward current (IC(50)=19.6 microM). The results suggest that songorine is a novel non-competitive antagonist at the GABA(A) receptor in rat brain.

Title

Songorine, a diterpenoid alkaloid of the genus Aconitum, is a novel GABA(A) receptor antagonist in rat brain.

Author

Zhao XY1, Wang Y, Li Y, Chen XQ, Yang HH, Yue JM, Hu GY.

Publish date

2003 Jan 30


Description :

A novel cell membrane affinity sample pretreatment technique for recognition and preconcentration of active components from traditional Chinese medicine PUMID/DOI:28620157 Sci Rep. 2017 Jun 15;7(1):3569. We describe a novel biomembrane affinity sample pretreatment technique to quickly screen and preconcentrate active components from traditional Chinese medicine (TCM), which adopts cell membrane coated silica particles (CMCSPs) as affinity ligands which benefit the biomembrane's ability to maximize simulation of drug-receptor interactions in vivo. In this study, the prepared CMCSPs formed by irreversible adsorption of fibroblast growth factor receptor 4 (FGFR4) cell membrane on the surface of silica were characterized using different spectroscopic and imaging instruments. Drug binding experiments showed the excellent adsorption rate and adsorption capacity of FGFR4/CMCSPs compared with non-coated silica particles. The FGFR4/CMCSPs were used as solid-phase extraction sorbents to pretreat the TCM Aconitum szechenyianum Gay. The resultant FGFR4/CMCSPs exhibited good performance. In addition, high selectivity and recognition ability of the FGFR4/CMCSPs were determined by selectivity experiments. Four alkaloid were screened and identified, one of these alkaloid, Napellonine, showed favorable anti-tumor activity in preliminary pharmacological verification trials including cell proliferation and molecular docking assays. The proposed cell membrane affinity sample pretreatment method is a reliable, effective and time-saving method for fast screening and enriching active compounds and can be extended to pretreat other TCMs as leading compounds resources.