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6-Acetonyldihydrochelerythrine

$1,030

  • Brand : BIOFRON

  • Catalogue Number : AV-C10434

  • Specification : 98%

  • CAS number : 22864-92-2

  • Formula : C24H23NO5

  • Molecular Weight : 405.5

  • PUBCHEM ID : 185516

  • Volume : 5mg

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Catalogue Number

AV-C10434

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

405.5

Appearance

Yellow powder

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)CC1C2=C(C=CC(=C2OC)OC)C3=C(N1C)C4=CC5=C(C=C4C=C3)OCO5

Synonyms

1-(1,2-Dimethoxy-12-methyl-12,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl)acetone/1-[(13s)-1,2-dimethoxy-12-methyl-12,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]propan-2-one/2-Propanone, 1-[(13S)-12,13-dihydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]-/1-[(13S)-1,2-Dimethoxy-12-methyl-12,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]acetone/2-Propanone, 1-((13S)-12,13-dihydro-1,2-dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridin-13-yl)-/1-(1,2-Dimethoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-13-yl)-propan-2-one/2-Propanone, 1-(12,13-dihydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl)-

IUPAC Name

1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]propan-2-one

Applications

Density

1.3±0.1 g/cm3

Solubility

Flash Point

314.1±30.1 °C

Boiling Point

595.7±50.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

VGTQLFWIJIABSU-SFHVURJKSA-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#:22864-92-2) 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

25066282

Abstract

6-Acetonyldihydrochelerythrine (1), a benzophenanthridine alkaloid, isolated from the methanol extract of Zanthoxylum capense, displayed potent cytotoxic activity in human HCT116 and SW620 colon carcinoma cells, to a higher extent than 5-fluorouracil (5-FU), the cornerstone chemotherapeutic agent in colon cancer. Cytotoxicity of 1 was evaluated by MTS, lactate dehydrogenase (LDH), and Guava ViaCount assays. Interestingly, 1 significantly induced cytotoxicity in both cell lines, leading to a significant increase in LDH release, as compared to 5-FU. Further, Guava ViaCount flow cytometry assays demonstrated that 1 significantly increased cell death, as shown by the presence of a significantly higher population of apoptotic cells in both cell lines, as compared to cells exposed to 5-FU. Furthermore, evaluation of nuclear morphology by Hoechst staining of 1-treated HCT116 and SW620 cells confirmed flow cytometry results, demonstrating a marked induction of apoptotic cell death by 1, again to a further extent than that elicited by 5-FU. In addition, immunoblot analysis to ascertain the molecular events triggered by 1 exposure was performed. The results show that 1 exposure reduced the steady-state expression and activation of the pro-survival proteins ERK5 and Akt and increased the steady-state expression of p53 in both HCT116 and SW620 cells. Changes in ERK5 or Akt activation can be ascertained by evaluating the ratio of p-ERK5/ERK5 or p-Akt/Akt. In addition, exposure to 1 reduced expression of XIAP, Bcl-XL, and Bcl-2, while increasing the cleavage of poly(ADP-ribose) polymerase in both cell lines. Collectively, the data indicate that 6-acetonyldihydrochelerythrine (1) is a potent inducer of apoptosis in HCT116 and SW620 cell lines, highlighting its potential relevance in colon cancer.

Title

6-Acetonyldihydrochelerythrine Is a Potent Inducer of Apoptosis in HCT116 and SW620 Colon Cancer Cells.

Author

Mansoor TA1, Borralho PM1, Luo X1, Mulhovo S2, Rodrigues CM1, Ferreira MJ1.

Publish date

2014 Aug 22