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Tetrahydroalstonine

$952

  • Brand : BIOFRON

  • Catalogue Number : BD-P0147

  • Specification : 99.5%(HPLC)

  • CAS number : 6474-90-4

  • Formula : C21H24N2O3

  • Molecular Weight : 352.4

  • PUBCHEM ID : 72340

  • Volume : 25mg

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Catalogue Number

BD-P0147

Analysis Method

HPLC,NMR,MS

Specification

99.5%(HPLC)

Storage

2-8°C

Molecular Weight

352.4

Appearance

Solid

Botanical Source

Structure Type

Alkaloids

Category

SMILES

CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45

Synonyms

IUPAC Name

methyl (1S,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Applications

Anti-lipid-peroxidative principles from Tournefortia sarmentosa PUMID/DOI:DOI:10.1021/np010538y J Nat Prod. 2002 May;65(5):745-7. Using the inhibition of CU2+-induced low-density-lipoprotein (LDL) peroxidation to direct fractionation, four new benzenoids, tournefolal (1), tournefolic acids A (2) and B (3), and B ethyl ester (4), together with salvianolic acid A (5), isosalvianolic acid C (6), lithospermic acid (7), salvianolic acid F (8), and rosmarinic acid (9), were isolated from the stems of Tournefortia sarmentosa. The structures of the new compounds 1-4 were elucidated on the basis of spectral and chemical methods. Furthermore, the anti-LDL-peroxidative activity of the isolated compounds was determined. All isolated compounds exhibited more potent activity than probucol except for salvianolic acid F (8).

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

270.7±30.1 °C

Boiling Point

524.0±50.0 °C at 760 mmHg

Melting Point

227ºC

InChl

InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1

InChl Key

GRTOGORTSDXSFK-DLLGKBFGSA-N

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#:6474-90-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31821696

Abstract

Aim: The aim of this study was to identify and characterize promising endophytes capable of enhancing the content of root alkaloids ajmalicine and serpentine in low alkaloid yielding genotype of Catharanthus roseus cultivar Prabal and the possible mechanisms involved.

Method and result: Of the four strains isolated from alkaloid-rich genotype of C. roseus cultivar Dhawal, endophytic strains CATDLF5 (Curvularia sp.) and CATDLF6 (Choanephora infundibulifera) enhanced serpentine content by 211·7-337·6%, while CATDRF2 (Aspergillus japonicus) and CATDS5 (Pseudomonas sp.) increased the content of ajmalicine by 123·4-203·8% in cultivar Prabal. Upregulated expression of key genes, geraniol 10-hydroxylase, tryptophan decarboxylase and strictosidine synthase involved in terpenoid indole alkaloid (TIA) biosynthetic pathway was observed in endophyte inoculated plants. Upregulated Octadecanoid-derivative Responsive Catharanthus AP2/ERF domain transcription activators like ORCA3 while, and downregulation of transcriptional repressor, ZCTs (Cys2/His2-type zinc finger protein family) enhanced the expression of genes for secondary metabolite production in endophyte-inoculated plants.

Conclusion: The present work concluded that the selected endophytes of C. roseus can enhance the ajmalicine and serpentine contents by modulating the expression of structural and regulatory genes of TIA biosynthetic pathway in root.

Significance and impact of the study: Endophytes can play an important role to enhance in planta content of pharmaceutically important alkaloids in C. roseus and can therefore be useful in reducing the cost of production of important alkaloids.

KEYWORDS

Catharanthus roseus; Ajmalicine; endophytes; serpentine; terpenoid indole alkaloids.

Title

Endophytes enhance the production of root alkaloids ajmalicine and serpentine by modulating the terpenoid indole alkaloid pathway in Catharanthus roseus roots

Author

S Singh 1 2, S S Pandey 1, K Shanker 3, A Kalra 1 2

Publish date

2020 Apr;

PMID

29694031

Abstract

The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2( S)-cathafoline, (+)-akuammiline, and (-)-Ψ-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-Ψ-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof.

Title

Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies

Author

Elias Picazo 1, Lucas A Morrill 1, Robert B Susick 1, Jesus Moreno 1, Joel M Smith 1, Neil K Garg 1

Publish date

2018 May 23

PMID

29406718

Abstract

The medicinal plant Catharanthus roseus accumulates large numbers of terpenoid indole alkaloids (TIAs), including the pharmaceutically important vinblastine, vincristine, ajmalicine, and serpentine. The phytohormone ethylene or methyl jasmonate (MeJA) can markedly enhance alkaloid accumulation. The interaction between ethylene or MeJA in the regulation of TIA biosynthesis in C. roseus is unknown. Here, a metabolomics platform is reported that is based on liquid chromatography (LC) coupled with time-of-flight mass spectrometry to study candidate components for TIA biosynthesis, which is controlled by ethylene or MeJA in C. roseus. Multivariate analysis identified 16 potential metabolites mostly associated with TIA metabolic pathways and seven targeted metabolites, outlining the TIA biosynthesis metabolic networks controlled by ethylene or MeJA. Interestingly, ethylene and MeJA regulate the 2-C-methyl-d-erythritol 4-phosphate (MEP) and acetate-mevalonate (MVA) pathways through AACT and HMGS and through DXS, respectively, to induce TIA biosynthesis in C. roseus. Overall, both nontargeted and targeted metabolomics, as well as transcript analysis, were used to reveal that MeJA and ethylene control different metabolic networks to induce TIA biosynthesis.

Title

Metabolomics Analysis Reveals that Ethylene and Methyl Jasmonate Regulate Different Branch Pathways to Promote the Accumulation of Terpenoid Indole Alkaloids in Catharanthus roseus

Author

Xiao-Ning Zhang 1 2, Jia Liu 3, Yang Liu 3, Yu Wang 3, Ann Abozeid 3 4, Zhi-Guo Yu 1, Zhong-Hua Tang 3

Publish date

2018 Feb 23;