Vindorosine | CAS:5231-60-7 | Manufacturer ChemFaces

Vindorosine

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Description:

Vindorosine has blood vessel relaxation effect, possible underlying mechanisms involving the inhibition of Ca(2+) entry via L-type Ca(2+) channels in vascular smooth muscles.

Targets:

Calcium Channel | Sodium Channel

In vivo:

Planta Med. 2014 Dec;80(18):1672-7.

Antagonism of Ca2+ influx via L-type Ca2+ channels mediates the vasorelaxant effect of Catharanthus roseus-derived vindorosine in rat renal artery.[Pubmed: 25340466]

The present study examined possible cellular mechanisms for the relaxation of rat renal arteries induced by Vindorosine extracted from C. roseus.
METHODS AND RESULTS:
Intrarenal arteries were isolated from 200-300 g male Sprague-Dawley rats and treated with different pharmacological blockers and inhibitors for the measurement of vascular reactivity on a Multi Myograph System. Fluorescence imaging by laser scanning confocal microscopy was utilized to determine the intracellular Ca(2+) level in the vascular smooth muscles of the renal arteries. Vindorosine in micromolar concentrations relaxes renal arteries precontracted by KCl, phenylephrine, 11-dideoxy-9α,11α-epoxymethanoprostaglandin F2α, and serotonin. Vindorosine-induced relaxations were unaffected by endothelium denudation or by treatment with the nitric oxide synthase inhibitor N (G)-nitro-L-arginine methyl ester hydrochloride, the guanylyl cyclase inhibitor 1H-[1, 2, 4]oxadiazolo[4,3-a]quinoxalin-1-one, the cyclooxygenase inhibitor indomethacin, or K(+) channel blockers such as tetraethylammonium ions, glibenclamide, and BaCl2. Vindorosine-induced relaxations were attenuated in the presence of 0.1 µM nifedipine (an L-type Ca(2+) channel blocker). Vindorosine also concentration-dependently suppressed contractions induced by CaCl2 (0.01-5 mM) in Ca-free 60 mM KCl solution. Furthermore, fluorescence imaging using fluo-4 demonstrated that 30 min incubation with 100 µM Vindorosine reduced the 60 mM KCl-stimulated Ca(2+) influx in the smooth muscles of rat renal arteries.
CONCLUSIONS:
The present study is probably the first report of blood vessel relaxation by Vindorosine and the possible underlying mechanisms involving the inhibition of Ca(2+) entry via L-type Ca(2+) channels in vascular smooth muscles.

Vindorosine Description

Source:	The herbs of Catharanthus roseus (L.) G. Don
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

J Am Chem Soc. 2010 Sep 29;132(38):13533-44.

Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues.[Pubmed: 20809620]

METHODS AND RESULTS:
Concise asymmetric total syntheses of vindoline (1) and Vindorosine (2) are detailed based on a unique intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles inspired by the natural product structures.Implementation of the approach for the synthesis of 1 and Vindorosine required the development of a ring expansion reaction to provide a 6-membered ring suitably functionalized for introduction of the Δ(6,7)-double bond found in the core structure of the natural products.
CONCLUSIONS:
Two unique approaches were developed that defined our use of a protected hydroxymethyl group as the substituent that controls the stereochemical course of the cycloaddition cascade.

Product Name	Vindorosine
Price:
CAS No.:	5231-60-7
Catalog No.:	CFN98853
Molecular Formula:	C₂₄H₃₀N₂O₅
Molecular Weight:	426.5 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The herbs of Catharanthus roseus (L.) G. Don
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Vasorelaxation Compound Library Alkaloids Compound Library Sodium Channel Inhibitor Library Calcium Channel Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.3447 mL	11.7233 mL	23.4467 mL	46.8933 mL	58.6166 mL
5 mM	0.4689 mL	2.3447 mL	4.6893 mL	9.3787 mL	11.7233 mL
10 mM	0.2345 mL	1.1723 mL	2.3447 mL	4.6893 mL	5.8617 mL
50 mM	0.0469 mL	0.2345 mL	0.4689 mL	0.9379 mL	1.1723 mL
100 mM	0.0234 mL	0.1172 mL	0.2345 mL	0.4689 mL	0.5862 mL

CFN97570	Scholaricine	99694-90-3	356.4	C₂₀H₂₄N₂O₄
CFN98205	11-Hydroxytabersonine	22149-28-6	352.4	C₂₁H₂₄N₂O₃
CFN98338	Ervamycine	27773-39-3	366.5	C₂₂H₂₆N₂O₃
CFN89194	Echitovenidine	7222-35-7	436.55	C₂₆H₃₂N₂O₄
CFN89203	Echitoveniline	72855-79-9	548.63	C₃₁H₃₆N₂O₇
CFN98799	Vandrikidine	50656-92-3	382.5	C₂₂H₂₆N₂O₄
CFN98853	Vindorosine	5231-60-7	426.5	C₂₄H₃₀N₂O₅
CFN98083	Vindoline	2182-14-1	456.5	C₂₅H₃₂N₂O₆
CFN90926	Vindolinine	5980-02-9	336.43	C₂₁H₂₄N₂O₂
CFN98256	Scandine	24314-59-8	350.4	C₂₁H₂₂N₂O₃