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Catharanthine

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-C2003

  • Specification : 98%

  • CAS number : 2468-21-5

  • Formula : C21H24N2O2

  • Molecular Weight : 336.43

  • PUBCHEM ID : 5458190

  • Volume : 20mg

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Catalogue Number

BF-C2003

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

336.43

Appearance

White crystalline powder

Botanical Source

Catharanthus roseus

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC1=CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC

Synonyms

Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2α,5β,18β)-/Methyl (2α,5β,18β)-3,4-didehydroibogamine-18-carboxylate/Catharanthine Sulphate/catharintine/CatharanthineSulfateBase/catharantine/(2α,5β,6α,18β)-3,4-Didehydroibogamine-18-carboxylic acid methyl ester/Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2a,5b,6a,18b)-/(+)-3,4-Didehydrocoronaridine/Catharanthine/catharanthin/catharinthine/Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2α,5β,6α,18β)-

IUPAC Name

methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

Density

1.3±0.1 g/cm3

Solubility

Methanol

Flash Point

251.1±28.7 °C

Boiling Point

491.5±45.0 °C at 760 mmHg

Melting Point

138-140ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:2468-21-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31115322

Title

[Towards bioproduction of anticancer drugs by yeast].

Author

Courdavault V1, Papon N2, Clastre M1.

Publish date

2019 May

PMID

30256480

Abstract

“The important anticancer drugs, vinblastine, vincristine and analogs, are composed of the monoterpenoid indole alkaloids (MIAs), catharanthine and vindoline, found uniquely in the medicinal plant, Catharanthus roseus. While 26 genes involved in the assembly of these two MIAs are known, two key reactions have eluded characterization to complete the documentation of the vinblastine pathway in this plant species. The assembly of these dimeric MIAs requires O-acetylstemmadenine oxidase (ASO) and a dual function geissoschizine synthase (GS) that reduces cathenamine to form geissoschizine, and that also reduces the ASO product to form a common intermediate for subsequent conversion by four separate hydrolases to catharanthine, tabersonine or vincadifformine, respectively. The in planta role of ASO is supported by identifying a single amino acid-substituted ASO mutant with very low enzyme activity and by virus-induced gene silencing of ASO to produce plants that accumulate O-acetylstemmadenine rather than catharanthine and vindoline found in wild-type (WT) plants. The in planta role of GS is supported by showing that a low GS-expressing mutant accumulating lower levels of catharanthine and vindoline also displays significantly lower tabersonine-forming activity in coupled enzyme assays than in the WT background. Gene expression analyses demonstrate that both ASO and GS are highly enriched in the leaf epidermis where the pathways for catharanthine and tabersonine biosynthesis are expressed. The full elucidation of this canonical pathway enables synthetic biology approaches for manufacturing a broad range of MIAs, including these dimers used in cancer treatment.
© 2018 The Authors The Plant Journal © 2018 John Wiley & Sons Ltd.

KEYWORDS

Catharanthus roseus ; assembly of vinblastine and vincristine; dual-function geissoschizine synthase; gene discovery and function; monoterpene indole alkaloid

Title

Completion of the canonical pathway for assembly of anticancer drugs vincristine/vinblastine in Catharanthus roseus.

Author

Qu Y1, Safonova O1, De Luca V1.

Publish date

2019 Jan

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

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

Publish date

2018 Jun 15


Description :

Catharanthine inhibits nicotinic receptor mediated diaphragm contractions with IC50 of 59.6 μM.Target: nAChRCatharanthine evokes a concentration-dependent attenuation of carbachol responses in the rat ileum preparation, producing rightward curve displacements and decreases in maximal agonist responses. The mixture of serpentine, plus ajmalicine and catharanthine reveals a concentration-dependent inhibitory effect of acethylcholinesterase (AchE), with an IC50 at ca. 2.25 μg/Ml [1]. Catharanthine can induce the self-association of tubulin into linear indefinite polymers with an efficacy that is 75% that of vinblastine or vincristine. Catharanthine binds to tubulin alpha-beta dimer with binding constant of 2.8 mM [2]. Catharanthine stimulates release of amylase from pancreatic fragments and to cause extensive degranulation of pancreatic acinar cells with accumulation of membrane material in the Golgi region. Catharanthine induces a delayed release of Ca2+ from prelabeled pancreatic fragments as compared to bethanechol [3]. Catharanthine inhibits epibatidine-induced Ca(2+) influx in TE671-α, -β, -γ, -δ cells in a noncompetitive manner with similar potencies IC50 of 17 mM-25 mM. Catharanthine inhibits [3H]TCP binding to the desensitized Torpedo AChR with higher affinity compared to the resting AChR. Catharanthine enhances [3H]cytisine binding to resting but activatable Torpedo AChRs, suggesting desensitizing properties [4].