Epibrassinolide

Names

[ Name ]:
Epibrassinolide

[Synonym ]:
CH09964 EPIBRASSINOLIDE
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-3H-benzo[c]indeno[5,4-e]oxepin-3-one
1,6-Dioxacyclodeca-3,8-dien
(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one
24-Epicastasterone
3.24-EPIBRASSINOLIDE
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
(2a,3a,5a,22R,23R,24S)-2,3,22,23-Tetrahydroxy-B-homo-7-oxaergostan-6-one
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethylheptan-2-yl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
EPI BRASSINOLIDE
24-EPIBRASSINOLIDE
2α,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one
cis,cis-1,6-Dioxa-3,8-cyclodecadien
1,6-dioxa-cyclodeca-3,8-diene
4-Epicastasterone
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethylheptan-2-yl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-on
(2α,3α,5α,22R,23R,24S)-2,3,22,23-Tetrahydroxy-B-homo-7-oxaergostan-6-one
2a,3a,22,23-Tetrahydroxy-24-methyl-B-homo-7-oxa-5a-cholestan-6-one
Epibrassinolide(24-Epibrassinolide)
Brassinolide(epibrassinolide,Homobrassinolide)
BRASSINOLIDE(BR)
2,4-Epibrassinolide
3H-Benz[c]indeno[5,4-e]oxepin-3-one, 10-[(1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-, (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-
3H-Benz[c]indeno[5,4-e]oxepin-3-one, 10-[(1S,2R,3R,4R)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-, (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-
.(22R,23R,24R)-2
Brassinolide
Epibrassinolide
24-(R)-EPIBRASSINOLIDE
brassinosteroid

Biological Activity

[Description]:

Epibrassinolide is a natural brassinosteroid (BR) derivative, is a plant regulator with a similar structure to mammalian steroids. Epibrassinolide is a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Natural Products >> Steroids

[Target]

Plant growth regulator, Apoptosis inducer[1]

[In Vitro]

Epibrassinolide (EBR) is a biologically active compound of the brassinosteroids, steroid-derived plant growth regulator family. Cells are incubated with various doses (0-100 μM) of Epibrassinolide for 24 or 48 h and cell viability is determined by MTT assay. Epibrassinolide induced cell viability loss in dose- and time-dependent manner compared to untreated samples in LNCaP and DU145 prostate cancer cells. Increasing concentrations of Epibrassinolide is more effective on LNCaP cell viability loss than DU145 cells suggesting that androgen-dependent cells are more sensitive to Epibrassinolide than androgen-independent prostate cancer cells. In further experiments, 25 μM Epibrassinolide is selected due to its moderate cytotoxic effect on both cell lines. The effect of Epibrassinolide treatment is examined on cell proliferation by counting the cell number within 96 h. A higher and earlier inhibition of cell proliferation is observed in LNCaP than DU145 cells[1].

[Cell Assay]

LNCaP (CRL-1740) and DU145 (CRL-2698) human prostate cancer cell lines are used. PNT1a normal prostate epithelial cell line is used. Cells are grown in RPMI 1640 medium, supplemented with 10 % fetal bovine serum, 10,000 U penicillin/mL and 10 mg streptomycin/mL. Cells are cultured at 37°C in a humidified 5 % CO2 incubator (HERA cell 150). Cells are seeded overnight and then treated with the desired drug concentrations. Cells are seeded at 1×104 density per well in 96-well plates and exposed to various concentrations of Epibrassinolide for 24 and 48 h. 10 μL MTT dye (5 mg/mL) is added to each well and cells are kept at 37°C for 4 h. The resulting formazan crystals are solubilized in 200 μL DMSO. The density of the solubilized formazan is read at 570 nm spectrophotometrically[1].

[References]

[1]. Obakan P, et al. Activation of polyamine catabolic enzymes involved in diverse responses against epibrassinolide-induced apoptosis in LNCaP and DU145 prostate cancer cell lines. Amino Acids. 2014 Mar;46(3):553-64.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
633.7±55.0 °C at 760 mmHg

[ Melting Point ]:
256°C

[ Molecular Formula ]:
C₂₈H₄₈O₆

[ Molecular Weight ]:
480.677

[ Flash Point ]:
202.3±25.0 °C

[ Exact Mass ]:
480.345093

[ PSA ]:
107.22000

[ LogP ]:
3.12

[ Vapour Pressure ]:
0.0±4.2 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
−20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
22-36/37/38

[ Safety Phrases ]:
22-36/37/39-45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Organ-specific effects of brassinosteroids on stomatal production coordinate with the action of Too Many Mouths.

J. Integr. Plant Biol. 57(3) , 247-55, (2015)

In Arabidopsis, stomatal development initiates after protodermal cells acquire stomatal lineage cell fate. Stomata or their precursors communicate with their neighbor epidermal cells to ensure the "on...

Conifer somatic embryogenesis: improvements by supplementation of medium with oxidation-reduction agents.

Tree Physiol. 35 , 209-24, (2015)

A major barrier to the commercialization of somatic embryogenesis technology in loblolly pine (Pinus taeda L.) is recalcitrance of some high-value crosses to initiate embryogenic tissue (ET) and conti...

Proteomic Analysis of Microtubule Interacting Proteins over the Course of Xylem Tracheary Element Formation in Arabidopsis.

Plant Cell 27 , 2709-26, (2015)

Plant vascular cells, or tracheary elements (TEs), rely on circumferential secondary cell wall thickenings to maintain sap flow. The patterns in which TE thickenings are organized vary according to th...