Obacunone

Catalog No.S3784

Obacunone Chemical Structure

Molecular Weight(MW): 454.51

Obacunone, a natural compound present in citrus fruits, has been demonstrated for various biological activities including anti-cancer and anti-inflammatory properties. It significantly inhibits aromatase activity in an in vitro enzyme assay with an IC50 value of 28.04 μM; also a novel activator of Nrf2.

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Biological Activity

Description Obacunone, a natural compound present in citrus fruits, has been demonstrated for various biological activities including anti-cancer and anti-inflammatory properties. It significantly inhibits aromatase activity in an in vitro enzyme assay with an IC50 value of 28.04 μM; also a novel activator of Nrf2.
Targets
Nrf2 [2]
()
Aromatase [1]
(Cell-free assay)
28.4 μM
In vitro

Obacunone is strongly inhibited MCF-7 cell proliferation without affecting non-malignant breast cells. Treatment with obacunone increases apoptosis by upregulating expression of the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl2, as well as inducing G1 cell cycle arrest. In addition, obacunone significantly inhibits aromatase activity in an in vitro enzyme assay. Exposure of MCF-7 breast cancer cells to obacunone down-regulates expression of inflammatory molecules including nuclear factor-kappa B (NF-kB) and cyclooxygenase-2 (COX-2). Obacunone inhibits COX-2 and NF-kB by activation of the p38 mitogen-activated protein kinase (MAPK). Obacunone is reported as a glutathione S-transferase (GST) enzyme inducer as well as a neuroprotective agent acting by induction of heme oxygenase-1 via the p38 MAPK pathway[1]. Obacunone is a novel activator of Nrf2 by decreasing Nrf2 ubiquitination and increasing its stability. It can effectively protect cells from oxidative stress by activating the Nrf2 pathway. Obacunone could induce the expression of the ARE-dependent luciferase gene in a dose-dependent manner[2].

In vivo The systemic administration of obacunone strongly inhibits bleomycin-induced lung fibrosis in mice. Obacunone can inhibit cancer proliferation and has some therapeutic effects on cardiovascular diseases[2]. In vitro and animal studies suggests that obacunone and a few other limonoids may have potential anticarcinogenic activity against certain types of cancers. A 500-mg/kg (of body weight) dose of obacunone per day is well tolerated and does not have adverse effects in rats, indicating a low toxicity[3].

Protocol

Cell Research:[1]
+ Expand
  • Cell lines: Human breast cancer (MCF-7) and non-malignant immortalized breast epithelial (MCF-12F) cell lines
  • Concentrations: 12.5, 25, 50,100 and 200 μM
  • Incubation Time: 24, 48, and 72 h
  • Method: The MCF-7 cells are cultured in DMEM medium containing 10% (v/v) fetal bovine serum, 200 U/mL penicillin G, and 200 mg/mL streptomycin. The MCF-12F cells are cultured in a 1:1 mixture of DMEM and Ham's F12 medium with 20 ng/mL of epidermal growth factor (EGF),100 ng/mL cholera toxin, 0.01 mg/mL insulin, 500 ng/mL hydrocortisone, and 5% (v/v) chelextreated horse serum, and then the cells are incubated at 37℃ with 5% CO2. To evaluate the anti-proliferate effects of obacunone, viability of the MCF-7 and MCF-12F cells are measured using the tetrazolium MTT reduction assay. The MCF-7 or MCF-12F cells (1×104/well) are seeded into a 96-well plate and allowed to adhere overnight. Cells are treated with different concentrations (12.5, 25, 50,100 and 200 μM) of either obacunone or OG and incubated for 24, 48, and 72 h. Tamoxifen, a well-known anti-estrogen drug used for breast cancer therapy, is used as a positive control. After the various time points, 10 ml of the MTT (5 mg/mL) reagent are added to each well and incubated for 2h at 37℃. After 2h incubation, the medium is removed and 200 ml of DMSO is added to dissolve the purple formazan. The absorbance is measured by an ELISA microplate reader at 570 nm.
    (Only for Reference)
Animal Research:[2]
+ Expand
  • Animal Models: Eight-week-old B6 mice
  • Formulation: corn oil
  • Dosages: 10 mg/kg
  • Administration: i.p.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 90 mg/mL (198.01 mM)

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 454.51
Formula

C26H30O7

CAS No. 751-03-1
Storage powder
in solvent
Synonyms N/A

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Aromatase Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID