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α-Santonin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-S3001

  • Specification : 98%

  • CAS number : 481-06-1

  • Formula : C15H18O3

  • Molecular Weight : 246.3

  • Volume : 25mg

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Catalogue Number

BF-S3001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

246.3

Appearance

powder

Botanical Source

Structure Type

Terpenoids

Category

SMILES

CC1C2CCC3(C=CC(=O)C(=C3C2OC1=O)C)C

Synonyms

IUPAC Name

Density

1.18g/cm3

Solubility

DMSO : 62.5 mg/mL (253.76 mM; Need ultrasonic)

Flash Point

189.7ºC

Boiling Point

423.4ºC at 760mmHg

Melting Point

172-173 °C(lit.)

InChl

InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1

InChl Key

XJHDMGJURBVLLE-BOCCBSBMSA-N

WGK Germany

RID/ADR

HS Code Reference

2932900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:481-06-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31101800

Abstract

BACKGROUND Sesquiterpene lactones have gained tremendous attention owing to their potent anticancer properties. The main focus of this study was to evaluate the anticancer effects of a naturally occurring sesquiterpene lactone, santonin, against human breast cancer SK-BR-3 cells. MATERIAL AND METHODS Cell counting kit 8 assay was used for the determination of cell viability. Apoptosis was detected by DAPI (4′,6-diamidino-2-phenylindole) and annexin V/propidium iodide (IP) staining. Flow cytometry was used for cell cycle analysis and western blotting was used for the estimation of protein expression. RESULTS Results showed that santonin exerts significant anti-proliferative effects on the SK-BR-3 breast cancer cells in a concentration dependent manner. Santonin showed an IC₅₀ of 16 µM against SK-BR-3 cells. DAPI staining showed that santonin caused DNA fragmentation in the SK-BR-3 cells, which is indicative of apoptosis. Annexin V/PI staining showed that apoptotic cell percentage increased up to 34.32% at 32 µM concentration of santonin. Santonin also caused an increase in the expression of Bax, caspase-3, and caspase-9, and a decrease in the expression of Bcl-2. Santonin also caused the arrest of the SK-BR-3 cells at the G2/M phase of the cell cycle and suppressed the expression of cyclin A and B1. Finally, santonin could also block the Raf/MEK/ERK pathway in breast cancer cells. CONCLUSIONS The findings of this study suggest the potential for the naturally occurring sesquiterpene lactone santonin in breast cancer treatment and also suggest that it could be developed as a promising anticancer agent.

Title

Naturally Occurring Sesquiterpene Lactone-Santonin, Exerts Anticancer Effects in Multi-Drug Resistant Breast Cancer Cells by Inducing Mitochondrial Mediated Apoptosis, Caspase Activation, Cell Cycle Arrest, and by Targeting Ras/Raf/MEK/ERK Signaling Pathway

Author

Zhiqiang Wu 1 2, Chenchen Wang 1 3, Mingzhu Huang 1 3, Zhonghua Tao 1 3, Wangjun Yan 1 2, Yiqun Du 1 3

Publish date

2019 May 18

PMID

31082765

Abstract

α-Santonin, a sesquiterpene lactone isolated from Artemisia Santonica, possesses diverse bioactivities including antioxidant, anti-inflammation, immunosuppressive, anti-roundworm, anti-malaria, etc. However, its bioactivities are not satisfactory and need to be further optimized. Thus, many α-santonin derivatives were synthesized on the basis of rings A, B and C for the discovery of new analogues with prominent bioactivities. Herein, we reviewed and discussed the related synthetic methodologies, diverse bioactivities and structure-activity relationships (SAR) of α-santonin derivatives

KEYWORDS

Bioactivities; Derivatives; Structure-activity relationship; Synthetic strategies; α-Santonin.

Title

Structure-activity relationship and synthetic methodologies of α-santonin derivatives with diverse bioactivities: A mini-review

Author

Jiangming Wang 1, Siyuan Su 1, Shangzhe Zhang 1, Shiyang Zhai 1, Ruilong Sheng 2, Wenhui Wu 1, Ruihua Guo 3

Publish date

2019 Aug 14

PMID

30813573

Abstract

The [3 + 2] cycloaddition (32CA) reaction of an α-santonin derivative, which has an exocyclic C⁻C double bond, with p-bromophenyl nitrile oxide yielding only one spiroisoxazoline, has been studied within the molecular electron density theory (MEDT) at the MPWB1K/6-311G(d,p) computational level. Analysis of the conceptual density functional theory (CDFT) reactivity indices and the global electron density transfer (GEDT) account for the non-polar character of this zwitterionic-type 32CA reaction, which presents an activation enthalpy of 13.3 kcal·mol-1. This 32CA reaction takes place with total ortho regioselectivity and syn diastereofacial selectivity involving the exocyclic C⁻C double bond, which is in complete agreement with the experimental outcomes. While the C⁻C bond formation involving the β-conjugated carbon of α-santonin derivative is more favorable than the C⁻O one, which is responsible for the ortho regioselectivity, the favorable electronic interactions taking place between the oxygen of the nitrile oxide and two axial hydrogen atoms of the α-santonin derivative are responsible for the syn diastereofacial selectivity.

KEYWORDS

[3 + 2] cycloaddition reactions; diastereofacial selectivity; molecular electron density theory; nitrile oxides; regioselectivity; α-santonin.

Title

A Molecular Electron Density Theory Study of the Chemoselectivity, Regioselectivity, and Diastereofacial Selectivity in the Synthesis of an Anticancer Spiroisoxazoline derived from α-Santonin

Author

Luis R Domingo 1, Mar Rios-Gutierrez 2, Nivedita Acharjee 3

Publish date

2019 Feb 26;


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