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Tabersonine

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-T2007

  • Specification : 98%

  • CAS number : 4429-63-4

  • Formula : C21H24N2O2

  • Molecular Weight : 336.43

  • PUBCHEM ID : 20485

  • Volume : 20mg

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Catalogue Number

BF-T2007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

336.43

Appearance

Off-White crystalline powder

Botanical Source

root bark of Voacanga africana Stapf

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC

Synonyms

(-)-Tabersonine/TABERSONINE/Methyl (5α,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate/methyl 2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate/Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5α,19α)-

IUPAC Name

methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate

Density

1.3±0.1 g/cm3

Solubility

Chloroform; Ethyl Acetate

Flash Point

249.4±28.7 °C

Boiling Point

488.7±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1

InChl Key

FNGGIPWAZSFKCN-ACRUOGEOSA-N

WGK Germany

RID/ADR

HS Code Reference

2934990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:4429-63-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30006510

Abstract

The jerantinine family of Aspidosperma indole alkaloids from Tabernaemontana corymbosa are potent microtubule-targeting agents with broad spectrum anticancer activity. The natural supply of these precious metabolites has been significantly disrupted due to the inclusion of T. corymbosa on the endangered list of threatened species by the International Union for Conservation of Nature. This report describes the asymmetric syntheses of (-)-jerantinines A and E from sustainably sourced (-)-tabersonine, using a straight-forward and robust biomimetic approach. Biological investigations of synthetic (-)-jerantinine A, along with molecular modelling and X-ray crystallography studies of the tubulin-(-)-jerantinine B acetate complex, advocate an anticancer mode of action of the jerantinines operating via microtubule disruption resulting from binding at the colchicine site. This work lays the foundation for accessing useful quantities of enantiomerically pure jerantinine alkaloids for future development.

Title

Sustainable Syntheses of (-)-Jerantinines A & E and Structural Characterisation of the Jerantinine-Tubulin Complex at the Colchicine Binding Site.

Author

Smedley CJ1, Stanley PA2, Qazzaz ME2, Prota AE3, Olieric N3, Collins H2, Eastman H2, Barrow AS1, Lim KH4, Kam TS5, Smith BJ1, Duivenvoorden HM1, Parker BS1, Bradshaw TD2, Steinmetz MO3,6, Moses JE7.

Publish date

2018 Jul 13;

PMID

29746822

Abstract

Sepsis caused by Gram-negative bacteria is one of major causes for the progression of acute lung injury (ALI) with limited treatment and effective medicines. Tabersonine is an indole alkaloid mainly isolated from Catharanthus roseus, and a potential drug candidate for treatment of cancer and Alzheimer’s disease (AD), however, its anti-inflammatory effect has not been revealed. In this study, we reported that tabersonine ameliorated lipopolysaccharides (LPS)-induced ALI in vivo and inhibited LPS-mediated macrophage activation in vitro. By using murine ALI model, we found that tabersonine significantly attenuated LPS-induced pathological injury in the lung. Tabersonine also inhibited LPS-mediated neutrophil infiltration, elevation of MPO activity and the production of TNF-α, IL-6 and IL-1β. Furthermore, tabersonine inhibited LPS-induced the production of pro-inflammatory mediators such as iNOS, NO and cytokines by suppressing NF-κB and p38 MAPK/MK2 signaling cascades. Tabersonine reduced the K63-linked polyubiquitination of TRAF6. Taken together, these results suggested that tabersonine has anti-inflammatory activities in vitro and in vivo, and is a potential therapeutic candidate for the treatment of ALI/ARDS.

Copyright © 2018 Elsevier Inc. All rights reserved.

KEYWORDS

Acute lung injury; Inflammation; NF-κB; TRAF6; Tabersonine; p38

Title

Tabersonine attenuates lipopolysaccharide-induced acute lung injury via suppressing TRAF6 ubiquitination.

Author

Zhang D1, Li X2, Hu Y3, Jiang H4, Wu Y5, Ding Y6, Yu K7, He H8, Xu J9, Sun L10, Qian F11.

Publish date

2018 Aug;

PMID

29724909

Abstract

Vinblastine, a potent anticancer drug, is produced by Catharanthus roseus (Madagascar periwinkle) in small quantities, and heterologous reconstitution of vinblastine biosynthesis could provide an additional source of this drug. However, the chemistry underlying vinblastine synthesis makes identification of the biosynthetic genes challenging. Here we identify the two missing enzymes necessary for vinblastine biosynthesis in this plant: an oxidase and a reductase that isomerize stemmadenine acetate into dihydroprecondylocarpine acetate, which is then deacetoxylated and cyclized to either catharanthine or tabersonine via two hydrolases characterized herein. The pathways show how plants create chemical diversity and also enable development of heterologous platforms for generation of stemmadenine-derived bioactive compounds.

Copyright © 2018 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.

Title

Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle.

Author

Caputi L1, Franke J1, Farrow SC1, Chung K1, Payne RME1, Nguyen TD1, Dang TT1, Soares Teto Carqueijeiro I2, Koudounas K2, Duge de Bernonville T2, Ameyaw B1, Jones DM1, Vieira IJC3, Courdavault V4, O'Connor SE5.

Publish date

2018 Jun 15


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