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Liriodenine

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BN-O1526

  • Specification : 98%(HPLC)

  • CAS number : 475-75-2

  • Formula : C17H9NO3

  • Molecular Weight : 275.3

  • PUBCHEM ID : 10144

  • Volume : 5mg

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Catalogue Number

BN-O1526

Analysis Method

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

275.3

Appearance

Yellow powder

Botanical Source

This product is isolated and purified from the barks of Liriodendron chinense (Hemsl.) Sarg.

Structure Type

Category

SMILES

C1OC2=C(O1)C3=C4C(=C2)C=CN=C4C(=O)C5=CC=CC=C53

Synonyms

Spermatheridin/Oxoushinsunine/8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one/8H-1,3-Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one/8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one (9CI)/8H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one/Liriodenine/Ushinsunine,oxo/Spermatheridine/Micheline B/Oxoushinsunin

IUPAC Name

Density

1.5±0.1 g/cm3

Solubility

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

Flash Point

275.0±21.5 °C

Boiling Point

531.0±19.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

MUMCCPUVOAUBAN-UHFFFAOYSA-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#:475-75-2) 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

30453785

Abstract

A new aporphine glycoside, (-)-anolobine-9-O-β-D-glucopyranoside was isolated from the twigs of pawpaw (Asimina triloba) along with 7 known alkaloids including five aporphine alkaloids (anolobine, nornuciferine, norushinsunine, liriodenine, and lysicamine), a proaporhine alkaloid (stepharine), and a tetrahydrobenzylisoquinoline alkaloid (coclaurine). Among these compounds, nornuciferine, lysicamine, stepharine, and coclaurine are reported for the first time from this plant. The structure of the new compound was elucidated by spectroscopic methods, including 1 D, 2 D NMR, and HRESI-MS. The absolute configuration of compounds 1, 2, 7 and 8 was determined by CD experiment.

KEYWORDS

Annonaceae; NMR; alkaloids; anolobine-9-O-β-D-glucopyranoside; aporphine.

Title

Isoquinoline Alkaloids From Asimina triloba.

Author

Taghreed A Majrashi 1 2 3, Fazila Zulfiqar 1, Amar G Chittiboyina 1, Zulfiqar Ali 1, Ikhlas A Khan 1 2

Publish date

2019 Oct;

PMID

28821607

Abstract

Eupolauridine and liriodenine are plant-derived aporphinoid alkaloids that exhibit potent inhibitory activity against the opportunistic fungal pathogens Candida albicans and Cryptococcus neoformans However, the molecular mechanism of this antifungal activity is unknown. In this study, we show that eupolauridine 9591 (E9591), a synthetic analog of eupolauridine, and liriodenine methiodide (LMT), a methiodide salt of liriodenine, mediate their antifungal activities by disrupting mitochondrial iron-sulfur (Fe-S) cluster synthesis. Several lines of evidence supported this conclusion. First, both E9591 and LMT elicited a transcriptional response indicative of iron imbalance, causing the induction of genes that are required for iron uptake and for the maintenance of cellular iron homeostasis. Second, a genome-wide fitness profile analysis showed that yeast mutants with deletions in iron homeostasis-related genes were hypersensitive to E9591 and LMT. Third, treatment of wild-type yeast cells with E9591 or LMT generated cellular defects that mimicked deficiencies in mitochondrial Fe-S cluster synthesis including an increase in mitochondrial iron levels, a decrease in the activities of Fe-S cluster enzymes, a decrease in respiratory function, and an increase in oxidative stress. Collectively, our results demonstrate that E9591 and LMT perturb mitochondrial Fe-S cluster biosynthesis; thus, these two compounds target a cellular pathway that is distinct from the pathways commonly targeted by clinically used antifungal drugs. Therefore, the identification of this pathway as a target for antifungal compounds has potential applications in the development of new antifungal therapies.

KEYWORDS

drug action; infectious disease; iron-sulfur protein; small molecule; yeast.

Title

Two Plant-Derived Aporphinoid Alkaloids Exert Their Antifungal Activity by Disrupting Mitochondrial Iron-Sulfur Cluster Biosynthesis

Author

Siddharth K Tripathi 1, Tao Xu 1, Qin Feng 1, Bharathi Avula 1, Xiaomin Shi 2, Xuewen Pan 2, Melanie M Mask 3, Scott R Baerson 3, Melissa R Jacob 1, Ranga Rao Ravu 1, Shabana I Khan 1 4, Xing-Cong Li 1 4, Ikhlas A Khan 1 4, Alice M Clark 1 4, Ameeta K Agarwal 5 6

Publish date

2017 Oct 6;

PMID

27886649

Abstract

A combined experimental and theoretical DFT study of the structural, vibrational and electronic properties of liriodenine is presented using B3LYP function with 6-311G (2d, p) basis set. The theoretical geometry optimization data were compared with the X-ray data for a similar structure in the associated literature, showing similar values. In addition, natural bond orbitals (NBOs), HOMO-LUMO energy gap, mapped molecular Electrostatic Potential (MEP) surface calculation, first and second order hyperpolarizabilities were also performed with the same calculation level. Theoretical UV spectrum agreed well with the measured experimental data, with transitions assigned. The molecular electrostatic potential map shows opposite potentials regions that forms hydrogen bonds that stabilize the dimeric form, which were confirmed by the close values related to the CO bond stretching between the dimeric form and the experimental IR spectra (1654cm-1 for the experimental, 1700cm-1 for the dimer form). Calculated HOMO/LUMO gaps shows the excitation energy for Liriodenine, justifying its stability and kinetics reaction. Molecular docking studies with Candida albicans dihydrofolate reductase (DHFR) and Candida albicans secreted aspartic protease (SAP) showed binding free energies values of -8.5 and -8.3kcal/mol, suggesting good affinity between the liriodenine and the target macromolecules.

KEYWORDS

Aporphine alkaloid; DFT; FT-IR; Hyperpolarizabily; Molecular docking; UV-VIS.

Title

Spectroscopic Investigation, Vibrational Assignments, HOMO-LUMO, NBO, MEP Analysis and Molecular Docking Studies of Oxoaporphine Alkaloid Liriodenine

Author

Renyer A Costa 1, Priscilla Olliveira Pitt 2, Maria Lucia B Pinheiro 2, Kelson M T Oliveira 3, Kahlil Schwanka Salome 4, Andersson Barison 4, Emmanoel Vilaca Costa 2

Publish date

2017 Mar 5;


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