[CAS NO. 751-03-1] Obacunone (AI3-37934)

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PRODUCTS SPECIFICATIONS [751-03-1]

Catalog

SLK-S3784

Brand

Selleck

CAS

751-03-1

DESCRIPTION [751-03-1]

Overview

MDL	MFCD00075888
Molecular Weight	454.51
Molecular Formula	C26H30O7
SMILES	C[C@]12[C@]34[C@](O3)(C(=O)O[C@]([C@]4(C)CC[C@@]1([C@]5(C)[C@@](CC2=O)(C(C)(C)OC(=O)C=C5)[H])[H])(C=6C=COC6)[H])[H]

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	2.2002 mL	11.0009 mL	22.0017 mL
5 mM	0.4400 mL	2.2002 mL	4.4003 mL
10 mM	0.2200 mL	1.1001 mL	2.2002 mL
50 mM	0.0440 mL	0.2200 mL	0.4400 mL

Description

Obacunone (AI3-37934, CCRIS 8657), a natural compound present in citrus fruits, has been demonstrated for various biological activities including anti-cancer and anti-inflammatory properties. It significantly inhibits activity in an in vitro enzyme assay with an IC50 value of 28.04 μM; also a novel activator of .

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. 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.

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. 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.

References

[1] Kim J, et al. Biochimie. 2014, 105:36-44.
[2] Shengmei Xu, et al. Protein Cell. 2016, 7(9): 684–688.
[3] Amit Vikram, et al. Appl Environ Microbiol. 2012, 78(19):7012-22.

Synonyms

Oxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,13aS)-

Oxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aαH,4bH,6H)-trione, 1α-(3-furyl)-1,6aα,7,11a,11bα,12,13,13a-octahydro-4bβ,7,7,11aβ,13aα-pentamethyl-

Obacunone

Obacunoic acid, ε-lactone

(1S,3aS,4aR,4bR,6aR,11aR,11bR,13aS)-1-(3-Furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyloxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aH,4bH,6H)-trione

Tricoccin S₃

Oxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, [1S-(1α,3aα,4aS*,4bβ,6aα,11aβ,11bα,13aα)]-

[1S-(1α,3aα,4aS*,4bβ,6aα,11aβ,11bα,13aα)]-1-(3-Furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyloxireno[4,4a]-2-benzopyrano[6,5-g][2]benzoxepin-3,5,9(3aH,4bH,6H)-trione

Obacunoic acid 3,4-lactone

14,15:21,23-Diepoxy-4,4,8-trimethyl-A,D-dihomo-24-nor-4,17-dioxachola-1,20,22-triene-3,7,16-trione

Obakunone