Vindoline - CAS 2182-14-1
Catalog number: B0005-464462
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Molecular Formula:
C25H32N2O6
Molecular Weight:
456.5
COA:
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Chemical Family:
Alkaloids
Description:
Vindoline might contribute to the anti-diabetic effects of Catharanthus roseus, and this natural product may find its more applications in the improvement of β-cell dysfunction and further the potential treatment of type 2 diabetes.
Ordering Information
Catalog Number Size Price Stock Quantity
B0005-464462 50 mg $188 In stock
B0005-464462 100 mg $348 In stock
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Purity:
>98%
Appearance:
Powder
Synonyms:
aspidospermidine-3-carboxylicacid,4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-me; thoxy-1-methyl-,methylester,(2-beta,3-beta,4-beta,5-alpha,12-beta,19-alpha); vindolin; (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl ester; VINDOLINE; Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-; (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl ester; Vindoline Tartrate
MSDS:
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Application:
anti-diabetic
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus.
Giddings LA;Liscombe DK;Hamilton JP;Childs KL;DellaPenna D;Buell CR;O'Connor SE J Biol Chem. 2011 May 13;286(19):16751-7. doi: 10.1074/jbc.M111.225383. Epub 2011 Mar 24.
Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis of putative cytochrome P450 genes in the Catharanthus roseus transcriptome identified candidate genes with expression profiles similar to known terpene indole alkaloid biosynthetic genes. Screening of these candidate genes by functional expression in Saccharomyces cerevisiae yielded a unique P450-dependent enzyme that stereoselectively hydroxylates the alkaloids tabersonine and lochnericine at the 19-position of the aspidosperma-type alkaloid scaffold. Tabersonine, which can be converted to either vindoline or 19-O-acetylhörhammericine, represents a branch point in alkaloid biosynthesis. The discovery of CYP71BJ1, which forms part of the pathway leading to 19-O-acetylhörhammericine, will help illuminate how this branch point is controlled in C.
2.Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H-NMR spectroscopy and multivariate data analysis.
Choi YH;Tapias EC;Kim HK;Lefeber AW;Erkelens C;Verhoeven JT;Brzin J;Zel J;Verpoorte R Plant Physiol. 2004 Aug;135(4):2398-410. Epub 2004 Jul 30.
A comprehensive metabolomic profiling of Catharanthus roseus L. G. Don infected by 10 types of phytoplasmas was carried out using one-dimensional and two-dimensional NMR spectroscopy followed by principal component analysis (PCA), an unsupervised clustering method requiring no knowledge of the data set and used to reduce the dimensionality of multivariate data while preserving most of the variance within it. With a combination of these techniques, we were able to identify those metabolites that were present in different levels in phytoplasma-infected C. roseus leaves than in healthy ones. The infection by phytoplasma in C. roseus leaves causes an increase of metabolites related to the biosynthetic pathways of phenylpropanoids or terpenoid indole alkaloids: chlorogenic acid, loganic acid, secologanin, and vindoline. Furthermore, higher abundance of Glc, Glu, polyphenols, succinic acid, and Suc were detected in the phytoplasma-infected leaves. The PCA of the (1)H-NMR signals of healthy and phytoplasma-infected C. roseus leaves shows that these metabolites are major discriminating factors to characterize the phytoplasma-infected C. roseus leaves from healthy ones. Based on the NMR and PCA analysis, it might be suggested that the biosynthetic pathway of terpenoid indole alkaloids, together with that of phenylpropanoids, is stimulated by the infection of phytoplasma.
3.[Development of new synthetic methods and their application to synthesis of useful compounds].
Tokuyama H Yakugaku Zasshi. 2003 Dec;123(12):1007-21.
Development of novel synthetic methodologies and their application to synthesis of natural products are described. The first topic is about an extension of the scope of our indole synthesis by radical cyclization of o-alkenylphenyl isocyanides. By utilizing this methodology and nitrogenzenesulfonamide chemistry, an efficient total synthesis of hexacyclic aspidosperma indole alkaloid, aspidophytine, was accomplished. As the second generation indole synthesis, we then developed the method by radical cyclization of o-akenylthioanilides. Synthetic utility of this method was fully demonstrated by a total synthesis of iboga alkaloid, catharanthine. Furthermore, a total synthesis of vinca alkaloid, vinblastine through a practical synthesis of vindoline was achieved, in which the stereochemistry of the crucial coupling reaction of two indole fragments could be completely controlled. In addition to the indole chemistry, exceptionally mild transformations of thiol esters to ketones and alkenyl ketones have been developed. Examples of application of the protocols for the synthesis of natural products are also described.
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CAS 2182-14-1 Vindoline

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