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(-)-Anonaine

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-P0331

  • Specification : 98.0%(HPLC)

  • CAS number : 1862-41-5

  • Formula : C17H15NO2

  • Molecular Weight : 265.31

  • PUBCHEM ID : 160597

  • Volume : 2mg

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Catalogue Number

BD-P0331

Analysis Method

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

265.31

Appearance

Botanical Source

Structure Type

Category

SMILES

C1CNC2CC3=CC=CC=C3C4=C2C1=CC5=C4OCO5

Synonyms

IUPAC Name

(12R)-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene

Applications

Density

1.294g/cm3

Solubility

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

Flash Point

177.1ºC

Boiling Point

444.7ºC at 760mmHg

Melting Point

InChl

InChl Key

VZTUKBKUWSHDFM-CYBMUJFWSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1862-41-5) 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

30303245

Abstract

Objectives: To assess the antiplasmodial activity of the ethanol extract of Xylopia sericea leaves, Annonaceae, often associated with antimalarial use and to perform a bioguided isolation of active compounds.

Methods: Dereplication of ethanol extract by the UPLC-DAD-ESI-MS/MS technique allowed the identification of the major constituents, isolation and identification of alkaloids. The antiplasmodial and cytotoxic activity of the extract, fractions and isolated compounds was evaluated against the chloroquine-resistant W2 strain Plasmodium falciparum and HepG2 cells, respectively.

Key findings: Ethanol extract showed high reduction of parasitemia as well as moderate cytotoxicity (86.5 ± 3.0% growth inhibition at 50 μg/ml and CC50 72.1 ± 5.1 μg/ml, respectively). A total of eight flavonoids were identified, and two aporphine alkaloids, anonaine and O-methylmoschatoline, were isolated. Anonaine disclosed significant antiplasmodial effect and moderate cytotoxicity (IC50 23.2 ± 2.7 μg/ml, CC50 38.3 ± 2.3 μg/ml, SI 1.6) while O-methylmoschatoline was not active against P. falciparum and showed a low cytotoxicity (33.5 ± 1.9% growth inhibition at 50 μg/ml, CC50 274.4 ± 0.5 μg/ml).

Conclusions: Characterization of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS as well as its antiplasmodial activity and the occurrence of anonaine and O-methylmoschatoline in this Xylopia species are reported by the first time.

KEYWORDS

Xylopia sericea; UPLC-DAD-ESI-MS/MS; alkaloids; antiplasmodial activity; cytotoxicity; extract dereplication; flavonoids.

Title

Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS

Author

Douglas Costa Gontijo 1, Geraldo Celio Brandão 2, Maria Fernanda Alves do Nascimento 1, Alaide Braga de Oliveira 1

Publish date

2019 Feb

PMID

29204721

Abstract

Annona muricata Linn or usually identified as soursop is a potential anticancer plant that has been widely reported to contain valuable chemopreventive agents known as annonaceous acetogenins. The antiproliferative and anticancer activities of this tropical and subtropical plant have been demonstrated in cell culture and animal studies. A. muricata L. exerts inhibition against numerous types of cancer cells, involving multiple mechanism of actions such as apoptosis, a programmed cell death that are mainly regulated by Bcl-2 family of proteins. Nonetheless, the binding mode and the molecular interactions of the plant’s bioactive constituents have not yet been unveiled for most of these mechanisms. In the current study, we aim to elucidate the binding interaction of ten bioactive phytochemicals of A. muricata L. to three Bcl-2 family of antiapoptotic proteins viz. Bcl-2, Bcl-w and Mcl-1 using an in silico molecular docking analysis software, Autodock 4.2. The stability of the complex with highest affinity was evaluated using MD simulation. We compared the docking analysis of these substances with pre-clinical Bcl-2 inhibitor namely obatoclax. The study identified the potential chemopreventive agent among the bioactive compounds. We also characterized the important interacting residues of protein targets which involve in the binding interaction. Results displayed that anonaine, a benzylisoquinoline alkaloid, showed a high affinity towards the Bcl-2, thus indicating that this compound is a potent inhibitor of the Bcl-2 antiapoptotic family of proteins.

KEYWORDS

Annona muricata Linn; Antiapoptotic proteins; Apoptosis; Bcl-2 inhibitor; MD simulation; Molecular docking.

Title

Molecular docking studies of bioactive compounds from Annona muricata Linn as potential inhibitors for Bcl-2, Bcl-w and Mcl-1 antiapoptotic proteins

Author

Mohamad Norisham Mohamad Rosdi 1, Shahkila Mohd Arif 2, Mohamad Hafizi Abu Bakar 3, Siti Aisyah Razali 4, Razauden Mohamed Zulkifli 5, Harisun Ya'akob 6 7

Publish date

2018 Jan

PMID

27984920

Abstract

Antimicrobial potential of medicinal plants have been explored extensively these days. This study was carried out to evaluate the antibacterial potential from aerial parts of plant, called ‘Annona senegalensis’ and its constituents. Bioassay guided fractionation led to the isolation of four metabolites, (+)-catechin (1), (-)-anonaine (2), (-)-asimilobine (3) and (+)-nornantenine (4). This is the first report on the isolation of compounds 1, 3 and 4 from this plant. Compounds 2 and 4 showed good activity, whereas 1 and 3 displayed weak inhibition against Streptococcus mutans (ATCC 25175). The results showed that compound 2 and 3 showed significant activity with a minimum inhibition concentration (MIC) of 0.12 and 0.25 mg/mL, respectively. The present study reports for the first time the antibacterial activity of the extract of A. senegalensis and its constituents. As S. mutans is a rather resistant bacteria, the MIC obtained during the present study is significant.

KEYWORDS

Annona senegalensis; Streptococcus mutans (ATCC 25175); alkaloids; antibacterial activity; flavonoids.

Title

Alkaloids from aerial parts of Annona senegalensis against Streptococcus mutans

Author

N Lall 1, N Kishore 1, D Bodiba 1, G More 1, E Tshikalange 1, H Kikuchi 1 2, Y Oshima 1 2

Publish date

2017 Aug