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Cedrelone

$1,280

  • Brand : BIOFRON

  • Catalogue Number : BN-O1626

  • Specification : 98%(HPLC)

  • CAS number : 1254-85-9

  • Formula : C26H30O5

  • Molecular Weight : 422.5

  • PUBCHEM ID : 21596358

  • Volume : 5mg

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Catalogue Number

BN-O1626

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

422.5

Appearance

Powder

Botanical Source

This product is isolated and purified from the barks of Cedrela toona

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C(=O)C=CC2(C1=C(C(=O)C3(C2CCC4(C35C(O5)CC4C6=COC=C6)C)C)O)C)C

Synonyms

(13α,14β,15β,17α)-17-(3-Furyl)-6-hydroxy-4,4,8-trimethyl-14,15-epoxyandrosta-1,5-diene-3,7-dione/(1S,2aR,3aR,3bR,9aR,9bR,11aS)-1-(Furan-3-yl)-5-hydroxy-3b,6,6,9a,11a-pentamethyl-2,2a,6,9a,9b,10,11,11a-octahydronaphtho[1',2':6,7]indeno[1,7a-b]oxirene-4,7(1H,3bH)-dione/Androsta-1,5-diene-3,7-dione, 14,15-epoxy-17-(3-furanyl)-6-hydroxy-4,4,8-trimethyl-, (13α,14β,15β,17α)-/14,15,21,23-diepoxy-6-hydroxy-4,4,8-trimethyl-24-nor-chola-1,5,20,22-tetraene-3,7-dione/Dihydrocedrelon/(13α,14β,15β,17α)-17-(furan-3-yl)-6-hydroxy-4,4,8-trimethyl-14,15-epoxyandrosta-1,5-diene-3,7-dione/14,15,21,23-Diepoxy-6-hydroxy-4,4,8-trimethyl-24-nor-chola-1,5,20,22-tetraen-3,7-dion

IUPAC Name

(1R,2R,4R,6S,7S,10R,11R)-6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadeca-12,16-diene-14,18-dione

Density

1.3±0.1 g/cm3

Solubility

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

Flash Point

307.1±30.1 °C

Boiling Point

584.2±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C26H30O5/c1-22(2)17(27)7-9-23(3)16-6-10-24(4)15(14-8-11-30-13-14)12-18-26(24,31-18)25(16,5)21(29)19(28)20(22)23/h7-9,11,13,15-16,18,28H,6,10,12H2,1-5H3/t15-,16+,18?,23?,24-,25?,26?/m0/s1

InChl Key

OQMUOVSEPOBWMK-MFNRWJBWSA-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#:1254-85-9) 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

31424680

Abstract

PURPOSE:
Glioma is one of the most aggressive types of human cancers and responsible for considerable mortality across the globe. Moreover, the development of drug resistance and lack of efficient drug options form the major hurdle in the treatment of gliomas. Herein, the anticancer potential of Cedrelone was examined against temozolomide-resistant glioma cells.

METHODS:
The proliferation rate of malignant glioma cells was assessed by CCK-8 cell counting assay. Autophagy was detected by electron microscopy. Apoptotic cell death was revealed by propidium iodide (PI) staining. Cell cycle analysis was performed by flow cytometry. Protein expression was determined by immuno blotting.

RESULTS:
The results showed that Cedrelone could considerably inhibit the proliferation of glioma cells. The anticancer activity of Cedrelone against the U87 malignant glioma cells was found to be due to induction of apoptosis. The Cedrelone-triggered apoptosis was also linked with alteration in the apoptosis-related protein expression. It also caused increase of reactive oxygen species (ROS) and decline of mitochondrial membrane potential (MMP). Additionally, Cedrelone could also trigger G2/M cell cycle arrest of U87 cells. Furthermore, it was found that Cedrelone could inhibit the ERK/MAPK signalling pathway in the temozolomide-resistant malignant glioma cells.

CONCLUSIONS:
These results indicate that Cedrelone could inhibit the growth of temozolomide-resistant malignant glioma in vitro and may be used for the development of chemotherapy against this disease.

Title

Antitumor activity of Cedrelone in temozolomide-resistant human glioma cells is accompanied by mitochondrial mediated apoptosis, inhibition of angiogenesis, cell cycle disruption and modulation of ERK/MAPK signalling pathway.

Author

Cao Y1, Zhang L, Wang Y

Publish date

2019 May-Jun

PMID

31857088

Abstract

Cedrelone is a limonoid isolated from the plant Trichilia catigua (Meliaceae). Previous studies have demonstrated that cedrelone (1) has several damaging effects on triple negative breast tumor (TNBC) cell line MDA-MB-231. In this work we investigated two new derivatives of cedrelone, the acetate (1a) and the mesylate (1b), to examine whether their effects are improved in comparison to the lead molecule. Cedrelone acetate (1a) was the most cytotoxic compound on TNBC cells and was chosen for additional analyses in traditional two-dimensional (2D) monolayer cultures and three-dimensional (3D) assays. In 2D, 1a induced cell cycle arrest, apoptosis and inhibited essential steps of the metastasis process of the MDA-MB-231 cells, in vitro. Moreover, 1a was able to revert the malignant phenotype of the T4-2 cells in 3D. These effects were concomitant with the downregulation of EGFR, β1-integrin and phospho-Akt, which could have resulted in a decrease of NFκB levels and MMP9 activity. These results suggest that 1a could be used as an important model for the design of a new drug to be applied in cancer treatment and be further studied in vivo for its antitumor and antimetastatic effects.

KEYWORDS

3D cell culture; Breast cancer; Cancer; Limonoid; Natural products

Title

Acetylation of cedrelone increases its cytotoxic activity and reverts the malignant phenotype of breast cancer cells in 3D culture.

Author

Becceneri AB1, Fuzer AM2, Popolin CP2, Cazal CM3, Domingues VC4, Fernandes JB4, Vieira PC5, Cominetti MR2.


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