482-68-8

Usage

Uses

Used in Pharmaceutical Industry:
SARPAGINE is used as a pharmaceutical compound for its potent effects on the cardiovascular system. Its ability to lower blood pressure makes it a valuable candidate for the development of drugs targeting hypertension.
Used in Research and Development:
SARPAGINE is used as a research compound for studying its pharmacological properties and potential applications in various therapeutic areas. Its specificity and low toxicity make it an attractive molecule for further investigation and development of novel therapeutic agents.
Used in Drug Delivery Systems:
Similar to gallotannin, SARPAGINE could potentially be incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. The development of novel drug delivery systems, such as organic and metallic nanoparticles, could improve the efficacy of SARPAGINE in treating specific conditions.

References

Bodendorf, Eder., Naturwis<., 40, 342 (1953)

InChI:InChI=1/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-/t12-,15?,17-,18-/m0/s1

Upstream product

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• 1428381-59-2 (6S,11aS,E)-9-ethylidene-2-methoxy-6,8,9,10,11a,12-hexahydro-6,10-methanoindolo-[3,2-b]quinolizin-11(5H)-one 
• 2149-40-8 (+)-10-methoxyvellosimine 
• 522-47-4 10-methoxynormacusine B 
• 1443744-07-7 3-(((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-5-methoxy-2-(trimethylsilyl)-1H-indole 
• 16381-42-3 ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 21987-25-7 5-methoxy-3-methyl-1H-indole 
• 168143-70-2 tert-butyl 5-methoxy-3-methyl-1H-indole-1-carboxylate 
• 168143-74-6 1-tert-butyloxycarbonyl-3-bromomethyl-5-methoxyindole 
• 600135-92-0 (3S,6R)-6-(1-tert-butyloxycarbonyl-5-methoxy-3-indolyl)-methyl-3,6-dihydro-3-isopropyl-2,5-diethoxypyrazine 
• 104-94-9 4-methoxy-aniline 
• 600135-94-2 3-(((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-5-methoxy-1H-indole 
• 1443744-09-9 (R)-ethyl 2-(benzylamino)-3-(5-methoxy-1H-indol-3-yl)propanoate 

Relevant academic research and scientific papers

Nature-inspired stereospecific total synthesis of P-(+)-dispegatrine and four other monomeric sarpagine indole alkaloids

All five: The first total synthesis of the C2-symmetric indole alkaloid 1 involved a late-stage thallium(III) acetate-mediated intermolecular oxidative coupling to construct the C9-C9' bond with complete regio- and stereocontrol. The formation of a single atropodiastereomer in this critical step arises from internal asymmetric induction. The first total synthesis of four other monomeric sarpagine indole alkaloids is also described. Copyright

Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P -(+)-dispegatrine and six other monomeric indole alkaloids

The first regio- and stereocontrolled total synthesis of the bisphenolic, bisquaternary alkaloid (+)-dispegatrine (1) has been accomplished in an overall yield of 8.3% (12 reaction vessels) from 5-methoxy-d-tryptophan ethyl ester (17). A crucial late-stage thallium(III) mediated intermolecular oxidative dehydrodimerization was employed in the formation of the C9-C9′ biaryl axis in 1. The complete stereocontrol observed in this key biaryl coupling step is due to the asymmetric induction by the natural sarpagine configuration of the monomer lochnerine (6) and was confirmed by both the Suzuki and the oxidative dehydrodimerization model studies on the tetrahydro β-carboline (35). The axial chirality of the lochnerine dimer (40) and in turn dispegatrine (1) was established by X-ray crystallography and was determined to be P(S). Additionally, the first total synthesis of the monomeric indole alkaloids (+)-spegatrine (2), (+)-10-methoxyvellosimine (5), (+)-lochnerine (6), lochvinerine (7), (+)-sarpagine (8), and (+)-lochneram (11) were also achieved via the common pentacyclic intermediate 16.

Deoxysarpagine hydroxylase--a novel enzyme closing a short side pathway of alkaloid biosynthesis in Rauvolfia.

Microsomal preparations from cell suspension cultures of the Indian plant Rauvolfia serpentina catalyze the hydroxylation of deoxysarpagine under formation of sarpagine. The newly discovered enzyme is dependent on NADPH and oxygen. It can be inhibited by typical cytochrome P450 inhibitors such as cytochrome c, ketoconazole, metyrapone, tetcyclacis and carbon monoxide. The CO-effect is reversible with light (450 nm). The data indicate that deoxysarpagine hydroxylase is a novel cytochrome P450-dependent monooxygenase. A pH optimum of 8.0 and a temperature optimum of 35 degrees C were determined. K(m) values were 25 microM for NADPH and 7.4 microM for deoxysarpagine. Deoxysarpagine hydroxylase activity was stable in presence of 20% sucrose at -25 degrees C for >3 months. The analysis of presence of the hydroxylase in nine cell cultures of seven different families indicates a very limited taxonomic distribution of this enzyme.

CHARACTERISTICS OF VELLOSIMINE REDUCTASE, A SPECIFIC ENZYME INVOLVED IN THE BIOSYNTHESIS OF THE RAUWOLFIA ALKALOID SARPAGINE

A plant enzyme - vellosimine reductase - has been isolated from Rauwolfia cell suspension cultures.This new enzyme has been purified (110-fold) and characterized.The reductase is a specific enzyme of the sarpagine pathway catalyzing the NADPH dependent conversion of vellosimine into 10-deoxysarpagine.The latter alkaloid is the immediate biogenetic precursor of sarpagine as shown by its high in vivo incorporation rate (86percent) into sarpagine.

VELLOSIMINE REDUCTASE. A SPECIFIC ENZYME INVOLVED IN THE CELLFREE BIOSYNTHESIS OF SARPAGINE TYPE ALKALOIDS.

Vellosimine reductase is a substrate and cofactor specific enzyme which catalyzes the NADPH-dependent reduction of vellosimine (4) forming 10-deoxy-sarpagine type alkaloids.