DEGUELIN Chemical Properties

Melting point:

85-87 °C(lit.)

alpha 

D27 -97.2° (c = 0.2 in benzene)

Boiling point:

560.1±50.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: >10 mg/mL

form 

solid

color 

white to yellow

optical activity

[α]/D -70 to -80°, c = 0.2 in methanol

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

DX1500000

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

DEGUELIN Usage And Synthesis

Description

Rotenoids, deriving from the flavonoid family of compounds, act as chemopreventive agents that inhibit NADH:ubiquinone oxidoreductase activity and suppress phorbol ester-induced ornithine decarboxylase (ODC) activity. The rotenoid compound deguelin, originally isolated from the bark of M. sericea (Leguminosae) to be used as an insecticide and fish poison, has chemopreventive and chemosensitizing effects in models of skin, mammary, colon, and lung carcinogenesis. Deguelin inhibits cell growth (IC₅₀ = <10-8 M), blocks PI3K/Akt activation, suppresses COX-2 expression, and induces apoptosis in premalignant and squamous human bronchial epithelial (HBE) cells without affecting normal HBE cells. At 6 mg/kg, deguelin induces Parkinson’s disease-like symptoms in rats after six days of subcutaneous infusion and therefore may also serve as a useful model for Parkinson’s disease research.

Uses

antineoplastic, antiviral, insecticide, ornithine decarboxylate inhibitor

Uses

(?)-Deguelin has been used as:

• a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
• an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
• an analytical standard in high-performance liquid chromatography (HPLC)

Uses

Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers.

Definition

ChEBI: Deguelin is a rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. It has a role as an apoptosis inducer, an antineoplastic agent, a plant metabolite, an angiogenesis inhibitor, an antiviral agent, a mitochondrial NADH:ubiquinone reductase inhibitor, an anti-inflammatory agent and an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor. It is a member of rotenones, an aromatic ether, an organic heteropentacyclic compound and a diether.

Biological Activity

Anticancer and antiviral agent; chemopreventive and pro-apoptotic. Inhibits phorbol ester-induced ornithine decarboxylase and NADH:ubiquinone oxidoreductase activities (IC 50 values are 11 and 6.9 nM respectively). Inhibits PI 3-kinase and reduces pAkt levels in pre-malignant and malignant human bronchial epithelial cells. Active in vivo .

Biochem/physiol Actions

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.

target

FAK | ROS | Caspase | Akt | ERK | PARP | EGFR | p53 | p21 | MMP(e.g.TIMP) | PKC | PI3K | MEK | NOS | COX | JNK | p38MAPK | ROCK | NF-kB | p65 | VEGFR

References

1) Chun et al. (2003), Effects of deguelin on the phosphatidylinositol 3- kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells; J. Natl. Cancer Inst., 95 291 2) Kang et al. (2012), Deguelin, an AKT Inhibitor, Down-Regulates NFκB Signaling and Induces Apoptosis in Colon Cancer Cells and Inhibits Tumor Growth in Mice; Dig. Dis. Sci.,?57 2873 3) Lee et al. (2004), Molecular mechanisms of deguelin-induced apoptosis in transformed human bronchial epithelial cells; Biochem. Pharmacol., 68 1119 4) Ito et al. (2004), Cancer chemopreventive activity of rotenoids from Derris trifoliata; Planta Med., 70 8

DEGUELIN(522-17-8)Related Product Information

• NS-398
• Indometacin
• Piroxicam
• (S)-(+)-Ibuprofen
• Saw Palmetto P.E
• Heartleaf Houttuynia P.E.
• Meloxicam
• Elm bark extract
• Rotenone
• N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE
• Equol
• DEGUELIN
• 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE
• 1-(2,4-Dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone
• 2,5-DIMETHOXYPHENYLACETONE
• METHYLEUGENOLGLYCOL
• 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE
• (2,4,5-TRIMETHOXYPHENYL)ACETALDEHYDE