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Helichrysetin

$980

  • Brand : BIOFRON

  • Catalogue Number : AV-C10512

  • Specification : 98%

  • CAS number : 62014-87-3

  • Formula : C16H14O5

  • Molecular Weight : 286.3

  • PUBCHEM ID : 6253344

  • Volume : 5mg

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Catalogue Number

AV-C10512

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

286.3

Appearance

Yellow powder

Botanical Source

Structure Type

Chalcones

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=CC(=C1C(=O)C=CC2=CC=C(C=C2)O)O)O

Synonyms

Helichrysetin/4',6'-dihydroxy-2',4-dimethoxychalcone/2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-/(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one/(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one/2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-/6'-O-methylisosalipurpol

IUPAC Name

(E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Applications

Density

1.4±0.1 g/cm3

Solubility

Apoptosis; Ca Ski; c-Jun N-terminal kinase pathway; helichrysetin

Flash Point

201.0±23.6 °C

Boiling Point

532.0±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

InChl Key

OWGUBYRKZATRIT-QPJJXVBHSA-N

WGK Germany

RID/ADR

HS Code Reference

2914500000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:62014-87-3) 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

29200721

Abstract

BACKGROUND:
Cervical cancer has become one of the most common cancers in women and currently available treatment options for cervical cancer are very limited. Naturally occurring chalcones and its derivatives have been studied extensively as a potential anticancer agent in different types of cancer and helichrysetin is naturally occurring chalcone that possess potent antiproliferative activity toward human cancer cells.

MATERIALS AND METHODS:
Inhibitory activity of helichrysetin was evaluated at different concentrations. Ability of helichrysetin to induce apoptosis and its relation with c-Jun N-terminal kinase (JNK)-mediated mechanism of apoptosis was assessed using flow cytometry and Western blotting.

RESULTS:
Helichrysetin inhibited Ca Ski cells at half maximal inhibitory concentration 30.62 ± 0.38 μM. This compound has the ability to induce DNA damage, mitochondrial membrane disruption, and loss of cell membrane integrity. We have shown that apoptosis was induced through the activation of JNK-mediated apoptosis by DNA damage in the cells then triggering p53-downstream apoptotic pathway with increased expression of pro-apoptotic proteins, Bax and caspase 3, and suppression of Bcl-2 anti-apoptotic protein. DNA damage in the cells also caused phosphorylation of protein ataxia-telangiectasia mutated, an activator of DNA damage response.

CONCLUSION:
We conclude that helichrysetin can inhibit Ca Ski cells through DNA damage-induced JNK-mediated apoptotic pathway highlighting the potential of this compound as anticancer agent for cervical cancer.

SUMMARY:
Helichrysetin induced DNA damage in Ca Ski cellsDNA damage caused JNK-mediated phosphorylation of p53 resulting in p53-mediated apoptosisHelichrysetin is a potential DNA damage inducing agent through JNK activation to kill human cervical carcinoma cells. Abbreviations used: ATM: Ataxia-telangiectasia mutated, DAPI: 4′,6-diamidino-2-phenylindole, DMSO: Dimethyl sulfoxide, FITC: Fluorescein isothiocyanate, IC50: Half maximal inhibitory concentration, JC1-5,5′,6,6′-Tetrachloro: 1′,3,3′-tetraethylbenzimidazolylcarbocyanine, iodide, JNK: c-Jun N-terminal kinase, MMP: Mitochondrial membrane potential, PBS: Phosphate-buffered saline, SRB: Sulforhodamine B, TUNEL: Terminal deoxynucleotidyl transferase dUTP nick labeling.

KEYWORDS

Apoptosis; Ca Ski; c-Jun N-terminal kinase pathway; helichrysetin

Title

Helichrysetin Induces DNA Damage that Triggers JNK-Mediated Apoptosis in Ca Ski Cells.

Author

Fong HY1, Abd Malek SN1, Yee HS1, Karsani SA1.

Publish date

2017 Oct-Dec

PMID

28539058

Abstract

Chalcones are a group of compounds widely distributed in plant kingdom. The aim of this study was to assess the neurite outgrowth stimulatory activity of selected chalcones, namely helichrysetin, xanthohumol and flavokawin-C. Using adherent rat pheochromocytoma (PC12 Adh) cells, the chalcones were subjected to neurite outgrowth assay and the extracellular nerve growth factor (NGF) levels were determined. Xanthohumol (10 μg/mL) displayed the highest (p < 0.05) percentage of neurite-bearing PC12 Adh cells and the highest (p < 0.05) NGF level in the culture medium of xanthohumol-treated cells. While, helichrysetin induced a moderately high numbers of neurite-bearing cells, flavokawin-C did not stimulate neurite outgrowth. This work supports the potential use of xanthohumol as a potential neuroactive compound to stimulate neurite outgrowth.

KEYWORDS

Chalcone; PC12; flavokawin-C; helichrysetin; neurite outgrowth; xanthohumol

Title

The role of chalcones: helichrysetin, xanthohumol, and flavokawin-C in promoting neurite outgrowth in PC12 Adh cells.

Author

Phan CW1,2, Sabaratnam V2,3, Yong WK3, Abd Malek SN2,3.

Publish date

2018 May